The trouble started shortly after I bought my truck.

To give my wife extra space in the driveway, I parked slightly off to the side. Within a week, a small pool of water appeared beneath my tire. My stepdad - the kind of guy who once disassembled a microwave just to prove it could be done - took one look and said it was a damaged main water line. Standard residential pipes run about a foot deep in a straight line up to the house. We needed to dig on the left side of the meter.

One problem: the water was pooling six feet to the right.

Dig where the pipe should be, he said. You won’t find anything by the driveway.

An hour in the brutal Arizona August heat and a three-foot hole later: nothing but dirt. My wife, watching from the garage, suggested I dig where the water actually was. I explained - patiently (condescendingly) - why that made no sense.

I eventually relented, just to prove her wrong.

Less than five minutes in: water line.

A corner-cutting installer had swapped copper for cheap PVC, routed it around the meter to hide the switch, and buried it so shallow that my truck cracked it in the first week. My stepdad’s expertise described a world where the contractor had done his job honestly. It had no answer for the one where he hadn’t.

I stood there, soaked, three feet deep in the wrong hole, looking at my wife standing over the right one. That gap between where I was sure the problem was and where it actually was has stayed with me longer than any leak.

Sometimes, our inability to plug a leak stems from our confidence in where the pipe should be.

Subscribe now

Hidden Pipes

Revenue doesn’t just appear. It flows through a system of pipes you’ve built, inherited, or duct-taped together over time. When performance breaks down, the leak is always somewhere in that flow: pipeline, conversion, retention, pricing, etc.

The challenge isn’t that we ignore leaks. It’s that we look for them in the places our experience says they should be. Even if we’re aware of the existence of corner-cutting contractors, we don’t account for that existence if we haven’t personally experienced it.

The most dangerous blind spots are the ones your expertise has built for you.

Two Ways to Miss

I once watched a business unit work through a stretch of declining website performance.

Week after week, the finance lead pointed at the same culprit: a recent rebrand. He had a chart showing the traffic drop lined up perfectly with the new site launch. The data was clear. The timing was obvious.

The COO kept shutting it down. “Stop talking about the rebrand. It’s not the rebrand.”

The COO had led the rebranding effort himself. He’d followed best practices, done everything right, and his confidence in having done everything right left no room for what the data was plainly showing. Traffic drops after a website redesign are well-documented - common enough that entire SEO playbooks exist for managing them. He wasn’t unfamiliar with the concept, but his confidence in the team’s execution had ruled it out as a risk.

That’s one way to miss. You won’t look at where the water is.

But the finance lead had his own problem. He found the pool of water…and then he kept pointing at it. Week after week. Meeting after meeting. “It’s the rebrand” became a recurring agenda item, each time with an updated chart that showed what the previous one had already shown, as if re-proving the diagnosis was the same thing as making progress.

How much of the decline was attributable to the rebrand versus other factors? What was the expected recovery timeline as rankings stabilized? What levers could they pull in the meantime? He hadn’t touched any of these. He’d found the leak and was standing over it, pointing, waiting for someone else to pick up a shovel.

That’s the second way to miss. You find the water, but you refuse to dig.

One person wouldn’t look at where the water was. The other wouldn’t stop pointing at it long enough to pick up a shovel. Both failures felt productive. Neither one fixed the leak.

In most organizations, when a team is stuck on a problem, they’re stuck in one of these two ways.

Busy Wrong

Full effort. Wrong problem.

This is the more dangerous of the two traps, because it’s the one that feels the most like progress.

The team has identified a problem and is executing against it with real energy. Shovels are moving. Dirt is flying. Meetings have action items. Dashboards are being tracked. The only issue is that the pipe is somewhere else entirely.

Me digging a three-foot hole on the wrong side of the meter was Busy Wrong. My stepdad had a clear diagnosis, a clear action plan, and total conviction in both. The problem wasn’t effort or commitment. It was that his expertise had pointed him to where the pipe should have been rather than where it actually was.

This plays out constantly. A sales team underperforms for two quarters in a row. Leadership reviews recent deal closures and lands on a diagnosis: a lack of discounting discipline.

Junior reps giving away margin, sloppy deal economics. The data support it. Everyone in the room has seen this movie. So the team launches a crackdown: new approval workflows, pricing guardrails, weekly deal desk reviews.

But if pipeline coverage is running at 2x when it should be 4x, the real problem is volume, not rate. Even perfect discounting discipline doesn’t close deals that aren’t in the funnel. The team has spent a quarter building infrastructure around the wrong problem while the actual crack - a collapsing top of funnel - continues to expand.

Undisciplined discounting is real. But it’s a drip. Insufficient pipeline is the leak.

This is the operational cousin of what I explored in Confident… and Completely Wrong: the gap between how sure we feel and how sure we should be. In that piece, the risk was analytical - fast thinking that skips the slow work of questioning our own conclusions. Busy Wrong is what happens when that same overconfidence gets operationalized. You don’t just think you know where the pipe is. You’ve deployed a team to go dig there.

The way out of Busy Wrong is a single question, asked before you commit more resources: if we fixed this completely tomorrow, would the number that matters actually move?

If the answer is clearly yes, you’re not Busy Wrong. Keep digging.

If the answer is uncertain, stop. Go back to the diagnosis. The instinct will be to keep executing because pausing feels like losing momentum. It’s not. A week spent verifying your diagnosis is almost always cheaper than a quarter spent solving the wrong problem.

The hardest part of escaping Busy Wrong is that it requires someone in the room to slow down a team that feels productive. Nobody wants to be the person who says, “I think we’re digging in the wrong place” when everyone else is breaking a sweat putting in effort. But that’s exactly the moment the question earns its keep.

Broken Record

Right answer. No shovel.

If Busy Wrong is dangerous because it mimics progress, Broken Record is insidious because it mimics contribution.

The team has the correct diagnosis. Sometimes painfully, obviously correct. And they keep re-presenting it because identifying a problem feels like solving one. The finding gets escalated, re-shared, and updated with fresh data that confirms what the old data already showed. Meanwhile, the actual lever sits unassigned, and the pipe keeps leaking.

The finance lead in the rebrand story was a Broken Record. He was right. He was right every single week. And being right, week after week, didn’t recover a single dollar of lost traffic.

Broken Record persists for a specific reason: the person who finds the leak usually isn’t the person who owns the lever. The finance team can identify the traffic decline, but the fix lives in marketing or product. So the finding gets re-presented, because re-presenting it is the only move available to the person holding the data. Each repetition is an implicit plea - will somebody please do something about this? - disguised as an update.

And every week, the finding gets re-presented without a plan attached, and the cost compounds. I’ve written before about Decision Debt as the hidden cost of deferred action. Broken Record is one of the most common ways organizations accumulate it. The diagnosis exists. The lever doesn’t. And each week of inaction both delays the fix and, more importantly, narrows the options available for fixing it.

The way out of Broken Record behavior is to convert the diagnosis into a decision. Before the finding gets presented one more time, it needs three things:

• A number. Quantified revenue or cash impact. Not directional. Not “material.” A number.

• A horizon. How long until this drains the well? Weeks? Quarters? The time horizon changes everything about urgency.

• A lever with a name next to it. Not a workstream. Not a taskforce. A specific action and a person who owns it.

Without a number, horizon, or lever, you haven’t picked up the shovel yet. You’re simply pointing.

The finance lead had the data. What he didn’t have was a story that translated “here’s what’s broken” into “here’s what it’s costing us, here’s what recovers on its own, here’s what we need to go fix, and here’s who’s fixing it.”

Pick Up the Shovel

Here’s what should have happened in that weekly performance meeting.

The finance lead was right about the leak. The COO was right that pointing at it wasn’t going to fix it. The move nobody made was to do both things at once: name the problem, size it, and decide what to do about it.

The rebrand is driving half of our traffic decline. That’s $1M in weekly pipeline impact. $500K recovers on its own over six weeks. Here are three levers for the rest, and here’s the gap we still need to close.

That’s how you plug the damn leak.

My stepdad and I eventually got there. We stopped arguing about where the pipe should have been, walked to where the water actually was, and started digging. Five minutes. That’s all it took once we stopped letting expertise tell us where to look.

The next time you’re in a review and the conversation feels stuck - the same problem resurfacing, the same debate going nowhere - ask yourself which trap you’re in.

Are you Busy Wrong? Putting full effort behind the wrong problem? If you fixed this tomorrow, would the number actually move?

Or are you a Broken Record? Right answer, but no shovel? Can you put a number on it, a timeline under it, and a name next to the lever?

Dig where the water is. Not where it should be.

Subscribe now

Share

It was 11 pm on a Tuesday, and I was standing in the walk-in cooler of a Texas BBQ-themed restaurant chain, counting celery.

This was early in my career - audit days - where I was questioning why I needed a Master’s degree and a CPA to do what I was asked to do. That day, another office needed a body to do an inventory observation, and I was the body. I didn’t know the client, didn’t know their systems, didn’t know anyone on the engagement team. Just the guy with the clipboard, lamenting not following directions to purchase non-slip shoes.

But when the restaurant handed me their final inventory sheet, the numbers didn’t match. By a lot. I flagged it to the restaurant staff, and to my surprise, they weren’t concerned - apparently, their system broke recipes into component ingredients, so the counts would always look off. I documented the variances, noted the limitations, and sent the package to the engagement team.

The following Monday, I got a call from the senior on the engagement. It was…not friendly.

I was told, in so many words, that I must have done it wrong. I was the only person across all inventory observations to report variances - and if one count failed, they’d have to expand the sample size. A costly endeavor for the client and a massive headache for the audit team.

The easy thing to do, the expected thing to do, was to concede that I’d misunderstood something.

I didn’t. I couldn’t.

As you’d expect, I felt pressure to conform here. I’ve never felt so exposed as I did in this moment when no one had heard of this system quirk that I had seen firsthand. Ultimately, I didn’t want to sign my name to something I knew was wrong.

I said, “Call the restaurant. We had a long conversation about this. This is how their system works.”

A couple of days later, I got a second call. This one was conciliatory. The senior had done more digging, and not only was I right - that’s exactly how the system worked - but no one on the audit team or the inventory counts had known about it.

Let that sit for a second. Every other auditor who did an inventory count at this chain encountered the same discrepancy. And every single one of them either missed it or decided it wasn’t worth the hassle of reporting it.

The variance itself was immaterial. Nobody was going to restate earnings over celery. But if you can’t hold your ground over a vegetable, good luck when the stakes are real.

Sooner or later, you’ll have to pick your hill.

Subscribe now

When restraint fails

If you’ve been reading this newsletter, you know I’m a broken record about restraint.

WAIT before you speak. Don’t try to wrestle every gator if your goal is to cross the SWAMP. Use a Light Touch. Say “Yes, And” instead of playing Dr. No. The whole operating system I’ve built is designed to keep finance leaders from overplaying their hand.

That restraint is an investment. Every battle you don’t fight, every gator you ignore, every moment you let someone else take the spotlight - it all builds political and social capital that makes you a trusted voice in the room.

But capital that never gets deployed isn’t an asset. If you never leverage the credibility you’ve built, you’re leaving value on the table. There’s a line where a light touch shifts from education to abdication. Where you’re so focused on “picking your battles,” you avoid all of them. Where diplomacy becomes complicity.

We’ve all heard the expression: “Is this the hill you want to die on?” It’s usually rhetorical - a polite way of saying drop it. And most of the time, that’s the right call.

But how do you know when it isn’t? How do you decide whether this it the time to let it go or dig in?

You need a framework for that. One that’s designed to talk you off the hill at every step - because most things that feel important aren’t existential. But the ones that survive? Those you can’t let go.

• H — How Deep Does It Go? → Tests the decision (is the precedent bigger than it looks?)

• I — Is My Read Right? → Tests you (are you confident enough to spend capital on this?)

• L — Level of Conviction → Tests your resolve (what cost are you willing to endure?)

• L — Lack of a Parachute → Tests your options (can you negotiate a safer path first?)

H — How deep does it go?

If this decision became a permanent, unwritten policy - if every department did the equivalent of this, every quarter, forever - would you still be okay with it?

This is the SWAMP test on steroids. SWAMP asks whether something is worth your voice. The H asks whether something is worth your capital.

The most dangerous decisions don’t look dangerous. They look small.

• A marketing team runs a test campaign without ROI guardrails.

• A product leader hires a contractor outside the approved headcount process.

• A sales team offers a one-time discount that quietly becomes permanent.

The dollar amount is a rounding error, but the precedent isn’t. When unaccountable spend goes unchallenged, every department learns that accountability is optional. When process gets sidestepped and nobody pushes back, the entire planning cycle becomes performative.

Think back to the celery. The variance was immaterial, but an audit process where people don’t report findings fails the extrapolation test immediately.

This test cuts through the noise. You’re not asking, “Is this $50K spend a problem?” You’re asking, “Am I okay with every department running unaccountable test budgets indefinitely?”

If the answer is yes - or even “eh, probably” - this isn’t your hill. You have bigger swamps to cross.

If no, keep going.

I - Is my read right?

Am I sure enough to risk my hard-earned capital?

H tests the decision. I tests you.

It’s tempting to skip this step. You’ve done the extrapolation, you can see where this is heading, and the pattern is obvious. But as I wrote in Confident and Completely Wrong, the most dangerous form of confidence is the kind that doesn’t know it’s wrong. We overvalue the information we have and discount what we can’t see. The gap between how sure we feel and how sure we should be is a chasm you want to avoid falling into.

This is where you apply the BET framework from Slaying the Seven. On a scale of 1 to 10, how confident are you in your read of this situation? And remember: you can’t use seven.

If you’re an 8 or above, you’ve done the work. You’ve sought out the disconfirming evidence, stress-tested your assumptions, and you still believe this is headed somewhere bad. Move to the next letter.

If you’re a 6 or below, stop. Your conviction isn’t strong enough to spend capital on. That doesn’t mean you’re wrong…it means you need more information before you bet everything. Flag the risk, document your concerns, and keep watching. The hill will still be there if your read turns out to be right.

The worst possible outcome isn’t dying on a hill. It’s dying on the wrong hill - and burning the credibility you’ll need when the right one comes along.

L - Level of conviction

What level of misery am I willing to endure to be right about this?

I asked whether you’re right. This L asks whether it matters enough to you personally, because those are not the same thing.

You can be certain a decision is wrong and still decide it’s not worth your career. And that’s okay. Not every correct read deserves your capital.

But when it does - when the stakes match the conviction - you need to know what you’re signing up for. Because dying on a hill isn’t a dramatic speech in a boardroom. It’s a sustained campaign of being the person who won’t let this go. And that has a real cost on you and your reputation.

• Bet Your Comfort. You’re willing to be the annoying one in the room for a few weeks. You’ll keep raising it, absorb the eye rolls, and accept being temporarily unpopular. You’re not losing sleep; you’re just losing a little goodwill.

• Bet Your Capital. You’re willing to burn real political equity. Relationships will be strained. You’re trading influence on future issues for leverage on this one. This is where your Light Touch disappears, and you become, temporarily, the heavy hand.

• Bet Your Seat. You’re willing to lose the job over this. Not because you want to, but because staying silent would compromise something you can’t live with.

The gut check is simple: Does your willingness to endure match the severity of what H and I told you?

• If the precedent is org-wide and your read is an 8, but you’re only willing to bet your comfort, you haven’t found your hill. You’ve found something you wish someone else would fight.

• If you’re ready to bet your seat over something where the precedent is shallow and your confidence is shaky? That might be ego driving the bus, not conviction.

L - Lack of parachute

Before you sacrifice yourself, propose the tripwire.

Most “hills to die on” dissolve when you reframe them. You don’t need to block the decision. You need to demand a contingency.

“I’ll support this if we agree on the tripwire that tells us it’s not working, and the exit plan if it doesn’t.”

This is the “Yes, And” of high-stakes disagreements. You’re not Dr. No or the blocker - you’re the de-risker. The person who says “yes, with a parachute.”

Think about the marketing spend example. Instead of blocking the test: “Let’s run it. But let’s agree that if we don’t see X return by Q3, we pull the budget and reallocate. And let’s define X now, not when the results are in.”

If the org accepts the tripwire, you don’t need to sacrifice yourself. You’ve built a mechanism to catch the problem early - a circuit breaker that protects the org without requiring you to go to war.

But if they refuse? If the response is “just trust us” or “we’ll evaluate when we get there,” that is the signal. An org that won’t agree to a reasonable off-ramp has already decided the destination. They don’t want anyone pulling the emergency brake.

That’s your hill.

Running up that hill

The framework is designed to be reductive.

• Most things fail at H — they’re not that deep when you extrapolate.

• Of the survivors, most fail at I — your read isn’t as solid as it feels.

• Of what’s left, most fail at the first L — your resolve doesn’t match the cost.

• And many of the rest dissolve at the second L when you propose a tripwire.

HILL helps you distinguish when to fight and when not to. It’s the difference between a leader who picks every battle and a leader who picks the right ones.

Think back to that walk-in cooler in Texas. The celery didn’t matter. What mattered was the willingness to say: this is what I found, and I’m not changing it because it’s inconvenient.

Whether you’re a staff auditor pushing back on a senior or a CFO pushing back on a CEO, the question is the same: Is this the one?

All that restraint you’ve been practicing? That’s how you build the capital. The WAIT tests. The SWAMP filters. The light touch. Every time you held back when it wasn’t worth it, you were earning the credibility to be heard when it is.

The goal isn’t to die on hills. The goal is to be the kind of leader whose judgment is so trusted that when you finally say, “This is the one,” the room stops.

So build the capital. And when HILL tells you it’s time - spend it. Don’t let that one go.

Before You Go

If you’re reading this, you’re either part of the early crew who took a chance on an unknown newsletter or you’re new, and someone you trust sent this your way. Either way, thank you. I appreciate all of your feedback and support.

If you found value in this post, the best way to support this work is to share it with someone who’s dealing with the same challenges. Send them the post, or just send them to cfoframeworks.com to subscribe.

Share

Subscribe now

It started raining here in Phoenix the other day - a minor miracle.

My daughter, who is four, was thrilled. My son, who is one, was ambivalent. And my wife, whose age will remain undisclosed, was confused.

That’s weird. The weather app said a 30% chance of rain, but I didn’t think it would actually happen. This is the first time it’s ever been right.
- My lovely, very smart, anonymously aged wife

Weather forecasts, like any forecast, aren’t particularly intuitive. We see “30% chance of rain” and conflate it with “not going to happen” rather than “if we had ten days with these exact conditions, it would rain on three of them.”

Thinking probabilistically requires us to imagine alternative timelines, a difficult feat in and of itself. But when we have to commit to a forecast, it becomes even more difficult because, at the end of the day, we either meet the objective or we miss. Just look at how wildly inconsistent we are in interpreting probabilistic language!

The gap between what people say and what they mean is where forecasts go to die. But the good news is that we can coach those around us to close that gap. This not only helps us get better inputs into our outlook for the company, but it also helps them see what’s around the corner and proactively react to it!

Regardless of the forecasting maturity you’re dealing with, I have a solution that will help you. Below is the B.E.T Framework for better probabilistic thinking.

Subscribe now

B. Ban the seven

We should all fear the number seven. (And, yes, it was physically painful not to make a “Why was six afraid of seven?” joke here.)

For beginners, a good basic framework for forecasting is asking someone to express their confidence on a scale of 1 to 10, with 1 being never gonna happen, and 10 being guaranteed.

BUT, and this is a big but, when people are uncertain, they’ll use seven as a hedge. It’s high enough to look like you’re trying, but low enough to let them opt out if it fails.

My old COO was relentless about this. During budget sign-offs, he’d go around the room and ask everyone on the team - not just the VPs - how confident they were on a scale of 1-10, and you could not use 7.

This forced you into a binary. You’re either:

• 8 or above - effectively fully committed, or

• 6 or below - implicitly flagging a risk that you’ll have to make explicit

If you said 8-10, you were on the hook. If you were missing your commitments in April, you would be reminded about your confidence score if you tried to insinuate that the goal was really more of a stretch goal.

If you said six or below, the meeting stopped until you and your team identified what data point or resource was needed to get you to an 8.

Kill the seven, and you kill the safety of the hedge.

One caveat: none of this works without psychological safety. If people fear punishment for a low confidence score, they’ll just game the system with eights. The goal is honest signal, not performative certainty. Build the trust first, then build the muscle.

E. Expose the stakes

In Thinking in Bets, Annie Duke argues that the most honest question in the world is: "Wanna bet?" As soon as you put a price on an opinion, the brain shifts from "selling" to "processing."

If you’ve graduated from binary, but the team is still struggling with distinguishing a 75% confident floor vs a 95% confidence floor, you can start to dip your toes into probabilistic thinking by getting your team to make these kinds of bets.

I saw this play out firsthand when a colleague of mine ran his forecast reviews with a payscale pinned to the wall.

• Bet your paycheck (Level 1): You’re pretty sure.

• Bet your bonus (Level 2): You’re confident.

• Bet your job (Level 3): You’re certain. This is the hill you’re willing to die on.

One quarter, a sales leader said he’d “bet his bonus” on hitting a stretch pipeline target. Two months later, when the pipe was soft, my colleague pulled up the bet. The conversation wasn’t adversarial – it was clarifying. The leader had to articulate what had changed, not just wave his hands at “market conditions.” That’s the power of the bet: it creates a reference point that makes revisionism harder.

When you ask a sales leader, "Would you bet your bonus on that Q4 revenue forecast?", the posture of the conversation changes instantly. A bonus payout is far more tangible than a percentage, and because it’s relative to the individual, you can get a sense of their confidence based on how much they’re willing to commit.

T. Train the range

If your team is ready for more nuance than betting on portions of their take-home pay, the final step is to teach people what “95% confidence” actually looks like.

Most people are wildly overconfident in their own uncertainty. They think “95% sure” means “I’m really sure,” but it actually means that if you make 20 predictions, you should only be wrong once.

To train this muscle, run a Range-Finder Drill.

Ask your team to provide a range (a lower and upper bound) for 20 items they couldn’t possibly know exactly, like the length of the Nile River or the year Harvard was founded.

If your team is properly calibrated, they should get 19 out of 20 right. If they only get 10 right, they’ve just proven their “confidence” is a guess.

Try one right now: What year was the first iPhone released?

If you said your 95% confidence range was 2005–2009, you’d be right – it was 2007. But if you said 2006–2008, that’s a tighter range that reflects more confidence than most people actually have.

If you need some examples, you can check out the calibration questions in How to Measure Anything, which I’ve excerpted here.

This drill builds the mental muscle of setting wide enough ranges to account for the things they don’t know. And, in turn, when you’ve seen them develop this muscle, you can have confidence in their 95% confidence outcome.

Going all in

Precision is a muscle you have to build, not an innate trait.

If you want your team to be better forecasters, you have to stop letting them hide in the middle ground.

When this works – when your team has killed the hedge, learned to put skin in the game, and calibrated their ranges – you stop getting hopes dressed up as commitments. You start getting leverage where someone says, “I’m a six on this,” and everyone in the room knows exactly what that means and what to do about it.

If you don’t teach your team how to bet, don’t be surprised when your forecast leaves you standing in the rain.

Thanks for reading CFO Frameworks! Subscribe for free to receive new posts and support my work, and leave me a comment to let me know what you think.

Leave a comment

Subscribe now

“Do you consider yourself lucky?”

This was, by far, my favorite interview question I’ve ever been asked. It’s deceptively simple, but it reveals a great deal. Is the candidate optimistic or pessimistic? Do they appreciate the role others (and even the universe) have played in their lives, or do they believe everything is a result of their individual effort?

I said yes then, and I suspect that was a big reason I got the job. Sometimes, we get lucky.

But luck is a fickle strategy.

This is my first post in a while because my luck recently ran out. First, I threw my back out. Then, my one-year-old son needed surgery on both of his legs. Thankfully, both of us are on the mend.

This forced pause gave me time to reflect. Luck gets you in the door, but systems keep you there.

If you're new here, this post is your map. If you've been here since January, it's a reminder of how far we've come.

New to CFO Frameworks? Start Here

If you joined recently: Welcome. We started with 10 readers in January. Most of you joined in the last quarter, which means you’ve got a year’s worth of frameworks waiting in the archive. Consider this your orientation.

Three posts to start with:

1. Wait for It - How to speak up when it matters, and shut up when it doesn’t.

2. The ABCs of Partnership - How to get off the sidelines and into ever decisive huddle.

3. Less is More - How to add by subtraction.

Been here from the beginning? You know where we’ve been. Skip ahead to What’s Next to help shape where we’re going.

What I Learned by Writing This Newsletter

Early in my career, I thought finance leadership was about being right. Build the perfect model, present the data, and watch people comply. I was…insufferable.

I wasn’t a leader; I was a barrier. The “Dr. No” who killed momentum. The analyst who presented data like a stampeding elephant without regard for the story. I realized that while our education teaches us how to build the model, it rarely teaches us how to get people to listen to it.

Writing this newsletter forced me to articulate what I’d learned the hard way: nobody cares about your model if they don’t understand the story. Nobody implements your recommendation if they don’t trust the relationship. Excellence in finance is 20% technical, 80% behavioral.

That insight became FRAME—Focus, Relationships, Analysis, Messaging, and Execution. It’s not a methodology. It’s a mental model for how effective finance leaders actually operate.

Over the past year, we’ve built a library of tactics using this structure. Here’s your guide to what matters most.

Share CFO Frameworks

The FRAME Library: Your Guide to the Archive

F — Focus (Prioritization)

The core problem: We waste time on trivial decisions while avoiding strategic ones. Urgency masquerades as importance, and even great teams drift off course.

Start here if you’re new:

• Break Free from the Bike Shed - Why we obsess over $28 lunch charges instead of $28M strategic decisions, and how to apply the Law of Triviality to reclaim your focus

• Gravity Wells - The prioritization frameworks that help anchor teams to core priorities before the day begins, with a toolkit for diagnosing what’s pulling you off course

The practical takeaway: Before your next meeting, ask “Is this a bike shed?” If you’re spending energy disproportionate to the decision’s impact, you’ve found one. Name it, then redirect.

R — Relationships (Influence)

The core problem: We think our job is to be the brake pedal, but our real job is to build the business up, not break people down. We try to be the hero who fixes everything, creating teams that depend on us rather than own their outcomes.

Start here if you’re new:

• No More Dr. No - How to use “Yes, And” to validate goals while pivoting to trade-offs, transforming from blocker to strategic partner

• A Light Touch - How to gauge Task-Relevant Maturity so you know when to be hands-on and when to step back and let your team own the outcome

The practical takeaway: Next time someone asks for more budget, resist the immediate “no.” Try: “Yes, that sounds like an important initiative... and we’ll need to figure out what to cut to fund it. Let’s talk through the trade-offs together.”

A — Analysis (Data & Insight)

The core problem: We rely on “System 1” thinking - fast, intuitive - which gives us an illusion of understanding. We design for the “average” and end up serving no one.

Start here if you’re new:

• Confident... and Completely Wrong - How to develop Story Sense: when an explanation feels too complete, pause and think “maybe”

• One Size Fails All - Why designing for the average (like the 1950s Air Force cockpit) ensures you fit no one, and why you need to disaggregate your data to find excellence in the edges

The practical takeaway: Next time you see an average that “tells the story,” dig one level deeper. Break it down by segment, cohort, or time period. The most important insights are usually hiding in the variation.

M — Messaging (Communication)

The core problem: We present raw data to the “Rider” (logic) but ignore the “Elephant” (emotion). We use vague terms like “innovation” or “strategy” that mean different things to everyone - Black Hole Words - that guarantee misalignment.

Start here if you’re new:

• The Numbers Will Speak for Themselves (They Won’t) - How to use the STORY framework (Set the stage, Treasure/Obstacle, Resolution) to bridge the gap between analysis and action

• The Montoya Matrix - How to convert Black Hole Words into Binding Words with precise, measurable definitions that align teams

The practical takeaway: Before your next presentation, write down your key message as a story: What’s at stake (Set the stage)? What opportunity or problem exists (Treasure/Obstacle)? What are we going to do about it (Resolution)? Build your slides around that narrative.

E — Execution (Operations)

The core problem: Every short-term workaround acts like a credit card swipe against your future agility—what I call Decision Debt. And urgency without autonomy creates chaos, not speed.

Start here if you’re new:

• Decision Debt: The Hidden Cost of Every (In)Action - How to SCAN your environment to identify “Invisible Drift” and standardize before the debt compounds

• Fast is Fragile - How to build Smooth Operators by giving them the “envelope” (the mission) instead of just the task list

The practical takeaway: Identify one workaround your team has been living with for more than 90 days. That’s Decision Debt. This week, either standardize it (make it official) or eliminate it (stop the bleeding).

What’s Next?: The Psychology of Finance

We started with 10 readers. Within a year, we crossed 200. Over 150 of you joined in the last eight months.

That growth means I’m hearing new questions - less about “how do I build the model” and more about “how do I get people to listen to it.” Less technical, more human.

That’s leading me into Year Two’s focus: The Psychology of Finance. The behavioral dynamics that separate good finance leaders from great ones.

I’m currently researching three deep dives for January. If one of these hits close to home, hit reply and let me know—I’d love to prioritize what helps you most:

• Meeting Fatigue - Why most meetings suck, how to fix yours, and when to just decline the invite altogether.

• Hills to Die On - How to pick which conflicts actually matter and how to navigate them without burning bridges or your reputation.

• Ambition vs. Burnout - How to be strategic about your career trajectory instead of just grinding harder and hoping for the best.

Your input directly shapes what I write. If there’s a different “soft skill” struggle keeping you up at night, I want to hear about it.

Before You Go

If you’re reading this, you’re either part of the early crew who took a chance on an unknown newsletter or you’re new, and someone you trust sent this your way. Either way, thank you. This only works if it’s useful.

If you found value in this post, the best way to support this work is to share it with someone who’s dealing with the same challenges. Send them the post, or just send them to cfoframeworks.com to subscribe.

Here’s to Year Two, and to building systems that outlast our luck.

Leave a comment

I finally had it - the mythical seat at the table. Even better, the Senior Director of Operations pulled me aside to encourage me to contribute more.

Your voice is important in that room. We need to hear it more.

Don’t have to tell me twice.

Feeling the rush of relevance, I went into next week’s staff meeting guns ablazing. I was correcting minor revenue differences in real time, critiquing slide formatting, and offering a crash course on what the CFO expected of us whenever anyone inhaled.

Thankfully, that same Ops leader pulled me aside again.

Love the passion, Taylor. Could use fewer…interjections.

Welp, shit.

I suspect I’m not alone in traveling this predictable path. If we’re not careful, we can lose the influence we earn by conflating requests for clarity with commentary.

If we’re not careful, we can talk ourselves out of our job.

The Talk-Trap Curve

Hitting the sweet spot of speaking up enough is tough. At any one time, we can inhabit one of three spots on a Talk-Trap Curve.

• Invisible: You stay quiet, hoping the data speaks for you. Inevitably, you get feedback that you are too quiet. If you fail to address this, someone else will take your seat.

• Insufferable: You find your voice (and your confidence!) but overshoot, treating every pause or minor difference as an RFP for your opinion. If you fail to address this, someone else will take your seat.

• Influential: You choose your battles, time insights perfectly, and raise the room’s business acumen.

The climb from invisible to influential is steep; the slide to insufferable is greased.

Why? Loss aversion. Two of the three spots on the curve are in danger of losing their seat at the table altogether!

We fear losing the trust of the team - missing the one comment that averts financial disaster - so we overcompensate and comment on everything.

To compensate for this, we need to think of our voice as scarce capital. We should deploy it where the Return on Conversation (ROC) is highest.

The Art of Iaido

In the Japanese art of iaido, a swordsman trains to win with one flawless draw-and-cut. Flailing blades are for amateurs; masters make a single motion count. A dojo elder once told his students,

Every extra swing is a confession you planned poorly.

Finance voice works the same way. You can slash at every slide—or stand poised, waiting for the precise moment where one insight ends the debate.

What we need is a framework to help us decide when to speak up vs shut up.

Actually, one may not be enough. Like in iaido, there’s more than on disciplined move you can master.

The three mini-frameworks ahead are your iaido kata: disciplined moves that turn fewer words into bigger wins.

Mini-Framework #1 - WAIT Test

Why Am I Talking?

Before you weigh in, think about what the end-goal is. Ask yourself “Why am I talking?”

1. Add signal - new data, pattern, or trade-off that should be considered but isn’t.

2. Protect value - surface a material risk in time to act.

3. Advance decision - get the group from debate to commit.

If one or more apply, speak up. Otherwise, it’s best to stay on mute.

The filter question:

“Is what I’m about to say worth stepping into the spotlight for?”

Mini-Framework #2 - SWAMP Test

I’m here to cross the swamp, not wrestle every alligator.

It’s tempting to correct the record - to make sure what’s being said or done is right. But the reality is, our value isn’t in what’s right but rather what’s valuable. What moves the ball forward.

Said another way, it’s not worth burning your social capital on minor squabbles.

If you get one or more “yes” answers - grab the mic. If not - holster it. These are the definition of low ROC disputes.

The filter question:

“Will this actually help us cross the swamp - or am I just fighting another gator?”

Mini-Framework #3: The Radio Tower Rule

Assuming you’ve decided not to WAIT and you’re not just wrestling gators, it’s time to decide how to deliver the clarity the team needs from you.

Imagine your message as a radio broadcast. Most finance people transmit way too much data: endless detail, hedged explanations, and multiple caveats.

That’s not communication; that’s noise.

Your real value isn’t your accuracy - it’s your clarity.

Be a signal tower, not a weather station. Deliver one strong, clear message. Stop transmitting when you’ve made your point. Let it land.

When to use it: Once you’ve decided your contribution is necessary, ensure it’s short, memorable, and actionable.

The filter question:

“What’s the single most important thing I want everyone to remember?”

Bonus Framework - Count to Ten

I once attended a forensic accounting training where the instructor dropped this nugget:

People hate silence. When someone stops talking, silently count to ten. More likely than not, the person you’re interviewing will add more color just to fill the silence.

Ten seconds of silence is an eternity in a live discussion. Our instinct, especially when we’re sitting in the Insufferable spot, is to fill that silence with our voice. Don’t.

Count to ten. See if anyone else chimes in. You may learn something new. You may see others step up to challenge the team, saving you the effort.

Embrace the discomfort and let the silence do your talking.

Putting it together

Let’s recap:

• 💡 WAIT Test: Speak selectively.

• 🐊 Swamp Test: Don’t chase every detail.

• 📡 Radio Tower Rule: Deliver clear, concise messages.

• 🔟 Count to Ten: Give others the opportunity to step in before you do.
  
  

Getting to Influential isn’t about talking less - it’s about ensuring what you say gets heard. It’s about knowing your role isn’t measured by how many words you say, but by how much clarity you add.

The CFO’s superpower isn’t their intelligence. It’s their ability to increase everyone else’s.

There’s an old story about a village by a river.

One day, a child is spotted floating downstream, struggling to stay above water. A villager dives in to save them — just in time. But then another child appears. And another. Soon, the entire village is working around the clock to pull children from the river.

They become faster, more coordinated, even heroic.

Until someone finally asks:

“Who’s throwing them in upstream?”

Most companies operate like that village.

Growth initiatives flow in with urgency and ambition — each one well-intentioned, but often half-baked. The burden of defining success, aligning systems, and managing execution falls downstream to operations.

Ops scrambles to measure. To instrument. To fix. They swim harder. They build rafts. They get faster. But they’re still in the river.

It feels productive. It feels responsive. But it’s fast…and Fast is Fragile.

There’s a better way. The solution isn't to slow down; it's to get smarter about how and when we move.

Be quick. Don’t hurry.

The best operators move fast, but only after they’ve filtered well. They don’t optimize chaos. They prevent it.

The Framework: Raise the Gate

A three-part model for upstream filtration — to protect your systems, your teams, and your outcomes.

1. Raise the Gate

Only fund what clears the bar.

Before an initiative earns a green light, it should be able to answer a few simple questions:

• What problem are we solving?

• Who owns the outcome?

• How will we measure success?

• What systems or teams are impacted?

If a proposal can’t clear that bar, it doesn’t move forward.

Most failed projects didn’t die in execution. They died the moment we said yes without asking enough.

Think of the countless products launched with fanfare and met with crickets, or the improvement initiatives that only served to set the team further back, all because the core problem and desired outcome weren't clearly defined upfront.

2. Instrument Before Impact

No metrics, no motion.

Measurement isn’t a cleanup job. It’s a launch requirement.

If you can’t define success, align on KPIs, and build the instrumentation before go-live, the initiative isn’t ready. Full stop.

Because if you don’t know what good looks like, you can’t tell whether you’re getting closer to it. Like launching a marketing campaign without tracking the source of leads, leaving you to guess whether it was effective.

Every measurement is both a snapshot and a signal — it tells you where you are and helps you decide what matters.

Shipping without observability doesn’t make you agile.
It makes you blind — and too confident to know it.

3. Constrain by Capacity

Burnout isn’t a badge.

Operational bandwidth isn’t infinite. It’s a fixed asset, and one of your most fragile.

If you don’t protect it, your team will look busy but finish nothing.

When too much flows through at once, quality drops, accountability blurs, and learning is impossible.

Every initiative you add is a bet. And every bet spreads your attention thinner.

The real risk isn’t doing too little — it’s starting too much and finishing none of it well. Less beats more.

Limit concurrent work. Prioritize ruthlessly. Build in time to regroup, refine, and repair.

When everything flows through, everything breaks eventually.

Common Pitfalls

These are the reflexes that kill clarity before you even begin:

“But We Need to Move Fast!”
Speed without clarity is just motion. You’ll ship more — and finish less.
The fastest way to get somewhere meaningful is to know where not to go.

“We’ll Figure Out Metrics Later.”
That’s not agility. That’s amnesia.
If you don’t define success upfront, you’ll rationalize failure after the fact.

“Everyone Else Is Doing It.”
FOMO isn’t a strategy.
Most of the initiatives that appear fast from the outside are quietly failing from the inside.
Execution is a visibility game — don’t trust the surface.

“This Will Slow Us Down.”
Yes. That’s the point.
Constraints slow you down at the start, so you don’t stall out in the critical execution phase.

The prep you resist now is the rework you regret later.
Raise the gate — or drown in do-overs.

💼 A Tool to Raise the Gate

Want to bring this thinking into your org?

I’ve created a Strategic Initiative Proposal Template that reflects these same principles — problem clarity, ownership, instrumentation, and constraint.

You can download it here: 👉 Strategic Initiative Template

It’s built to help your team say yes only when the initiative is truly ready — and say not yet with clarity, not confusion.

Making the Shift

The village didn’t build a better rescue system. It went upstream.

And what once felt like chaos became quiet.

You can only swim against the current for so long before you drown. You can’t solve downstream what should have been stopped upstream.

The best operators don’t just move faster — they design better flow.
They don’t rescue. They filter.
They raise the gate.

And once the gate is in place, everything changes:

• Fewer emergencies

• Clearer metrics

• More work that actually finishes

It starts with a single move:

• Pick one team that’s overwhelmed.

• Trace the noise back to its source.

• Apply the filter before the flood.

Need help?
Use this proposal template to set the bar.
Make clarity the cost of entry.

You don’t need to say yes fåster.
You need to say yes later — and better.
Start upstream.

“I just don’t see myself here in a year’s time.”

I was floored. It was my first review cycle with a high-performing manager I’d hired, and there she was telling me that she didn’t care for the job. She loved the people and her business partners, but her scope and responsibilities were much narrower than what she had been promised.

And it was my fault.

In my effort to shield her from the aspects of the job that could make her miserable, I had inadvertently protected her from challenges and, consequently, from any growth.

I thought I was being helpful. I was wrong.

Peter Drucker, the father of modern management, once gave Jim Collins a perspective-shifting challenge. Collins was agonizing over leaving his faculty position at Stanford, worried about survival and success. Drucker cut through his anxiety with a single, penetrating question:

“It seems to me you spend a lot of time worrying how you will survive,” said Peter. “You will probably survive.”

He continued, “And you seem to spend a lot of energy on the question of how to be successful. But that is the wrong question.”

He paused, then like the Zen master thwacking the table with a bamboo stick: “The question is: how to be useful!”

It’s deceptively simple. Being useful sounds straightforward, even mundane. But when we dig deeper, we discover that true usefulness isn’t about what we accomplish—it’s about what we enable in others. And that’s where most of us get it wrong.

The temptation is to equate usefulness with personal achievement.

If I accomplish more, I’ll be useful.

If I stand out, I’ll be useful.

If I make my mark, I’ll be useful.

But real usefulness rarely works that way, especially as you take on greater responsibility. The more senior you become, the less the job is about what you accomplish, and the more it’s about what you enable in others. And that shift—from doing to enabling—is where many of us get it wrong.

The Usefulness Trap

The challenge of being useful, especially in leadership, is that it feels like it should be simple.

See a problem, solve a problem. Notice a gap, fill a gap. Help where help is needed.

But anyone who's tried to mentor a junior colleague, manage a team, or even help a friend knows that it's rarely that straightforward. I learned this lesson the hard way early in my career, watching a senior leader try to "help" his team by staying late every night to review and polish their models. Six months later, the team's output had decreased - they'd learned to wait for his improvements rather than develop their own skills.

We've all been there, haven't we? Watching someone struggle with a problem we know how to solve, itching to jump in and fix it. Or maybe we're on the other side, grinding our teeth as someone offers well-meaning but unhelpful advice from the sidelines.

It’s easy to get this wrong, even with the best intentions. In fact, most failed attempts at being useful fall into a handful of predictable traps:

• The Hero jumps in to solve every problem, working nights and weekends to keep projects on track. They're the first to volunteer and the last to leave. But their relentless helpfulness creates a vacuum - when they're out sick, the whole team grinds to a halt. They've become so essential that they're actually harmful.

• The Oracle dispenses wisdom from on high, offering profound insights without ever getting their hands dirty. "Have you considered approaching this from a different angle?" they ask, before floating away to their next meeting. Their advice might be sound, but without practical support, it's just philosophy.

• The Servant says yes to every request, maintaining an ever-growing to-do list of other people's priorities. They're everyone's favorite colleague until they burn out, leaving dozens of half-finished projects in their wake.

• The Taskmaster believes in tough love, pushing people toward their potential whether they're ready or not. "I'm just trying to help you grow," they explain, as another teammate updates their resume.

• The Cheerleader offers endless encouragement but no substantive support. "You've got this!" they declare, while you're drowning in problems they could actually help solve.

Each of these postures can feel useful—even wise—in the moment. But as I’ve written before, confident and completely wrong leadership is one of the easiest traps to fall into.

Each archetype represents a different way of getting the balance wrong - doing too much, too little, or the wrong kind of help entirely.

And here's the cruel irony: the more determined we are to be useful, the more likely we are to fall into these traps. Our very intensity pushes us toward extremes.

We need a more nuanced approach. A light touch.

A Light Touch

What we need isn't more effort or better intentions - we need a completely different approach. Instead of force, we need finesse. We need what I call a "light touch."

Think of teaching someone to ride a bike - it's all about finesse. Push too hard, and they'll speed out of control. Let go too soon, and they'll fall. But find that sweet spot - a gentle hand ready to steady but not control - and they're flying down the street on their own in no time.

That same balance applies in leadership, coaching, and life. And surprisingly, one of the best illustrations I’ve seen doesn’t come from a business book or management guru. It comes from Futurama.

In Godfellas, Bender (the robot) becomes the god of a tiny civilization that develops on his body after colliding with an asteroid as he hurls through space.

The civilization grows and thrives under Bender's care, but he eventually realizes that being a god is not as easy as it seems. In his attempts to heed his worshippers’ prayers, he ultimately wins the affection of some but disillusions others. This bifurcation of the populace horrifies him, and when asked to favor a side between the factions, he refuses.

[Spoiler] Ultimately, the two groups kill each other in an all-out war. [Spoiler]

Bender then encounters a cosmic entity (who may or may not be God), and they discuss the challenges of placating their followers.

Bender: You know, I was God once.

God Entity: I saw. You were doing very well, until everyone died.

Bender: It was awful. I tried helping them. I tried not helping them. But in the end, I couldn’t do them any good.

We can all relate here…well, maybe not with the being a god part, but this struggle between our intentions to help and the ramifications of our intervention is a very human (or robot) issue. In our pursuit of usefulness, we can do more damage than good.

And here, finally, is where we get a semblance of a framework to help us.

God Entity: If you do too much, people get dependent on you. And if you do nothing, they lose hope. You have to use a light touch, like a safecracker or a pickpocket.

Bender: Or a guy who burns down a bar for the insurance money!

God Entity: Yes, if you make it look like an electrical thing. When you do things right, people won't be sure you've done anything at all.

To be clear, I’m not equating usefulness to godliness. Nor am I advocating adopting the mindset of a safecracker, pickpocket, or insurance fraudster.

But this is, at its core, the skill great leaders master: knowing how to help without creating dependence, and when to step back to foster real growth.

The underlying lesson is balance - not too much intervention as to invite dependence, not too little as to breed hopelessness. Usefulness is a sweet spot in which our presence is felt but not focal. When our efforts are appreciated but have no claim on the successful outcome, we’ve done things right.

Go back to the Jim Collins story at the top. Peter’s contribution wasn’t heavy-handed (“You should write best sellers for a living!”) or aloof (“You’ll be happy no matter what you do…now get out of my office.”) Peter used a light touch, challenging Jim’s thinking without telling him how to think.

All of this feels intuitive. Why don’t we do this more often?

What often gets in the way of this model is our ego. Regardless of where we are in our careers or lives, we rarely feel like we have the luxury to shrug off receiving credit. The tangible accomplishments we can put our name to feel better than the accomplishments of others that we influenced. The items in our personal wins column make us feel safe. Who gets credit matters, doesn’t it?

Maybe not. In this model of usefulness, what you accomplished may not be clear, but your influence on the environment will be undeniable.

Think of it this way: Nobody buys a jersey with the coach’s name on the back, but nobody denies the impact of a great coach on the team.

Perhaps it’s easier to see an example. Let’s look at one of the most successful coaches in Silicon Valley history.

The trillion-dollar coach

Bill Campbell may be the most famous person you’ve never heard of.

He was integral to the success of companies like Google, Apple, Amazon, Twitter, and Facebook. His success in coaching these companies’ leaders to build world-class organizations earned him the title of Trillion-Dollar Coach.

Look at a sample of Bill’s leadership principles and see what you notice about his approach.

1. Your title makes you a manager; your people make you a leader. Accrue respect, don’t demand it.

2. It’s the people. The well-being and success of her people is the top priority of any manager. Great people flourish in an environment that liberates and amplifies that energy. Managers create this environment through support, respect, and trust.

3. Best ideas, not consensus. The manager’s job is to run a decision-making process, ensuring all perspectives are heard and considered. If necessary, break ties to make the decision.

4. Don’t stick it in their ear. Offer stories and help guide people to the best decisions for them. Don’t tell them what to do.

5. Be the evangelist for courage. Believe in people more than they believe in themselves.

Bill mastered the concept of a light touch. He supported people - pushed them - but never so much that they grew dependent on him. He intuitively shifted between intervening when needed, supporting when it counted, and stepping back when others were ready to lead.

The focus was always on others - he focused on those he coached so they could focus on those they led. You can’t tie a single accomplishment of these businesses to Bill, yet his impact was felt.

Excellent teams at Google had psychological safety (people knew that if they took risks, their manager would have their back). The teams had clear goals, each role was meaningful, and members were reliable and confident that the team’s mission would make a difference…[Bill] went to extraordinary lengths to build safety, clarity, meaning, dependability, and impact into each team he coached.

When you do things right, you tap into the innate potential of those around you and elevate them to a level never thought possible. Standing back and looking at the whole picture, it will be impossible to decipher how much of the impact was from your coaching versus their execution. And that’s what you want because it doesn’t matter who gets the credit.

When you worry less about who gets credit, the opportunity for impact is limited by how many people you can be useful to.

That’s the posture of the light touch: helping in a way that fosters growth, not dependence. But putting this into practice requires more than good intentions—it takes constant calibration. We need to be deliberate about how and when we offer help.

How to be useful

So how do we know when to lean in - and when to let go?

A light touch doesn’t mean doing nothing. And it certainly doesn’t mean taking control. It means calibrating your involvement to meet the moment, providing just enough support to help others succeed without making them dependent on you.

One of the clearest ways I’ve found to think about this comes from Andy Grove, former CEO of Intel. Grove described leadership posture as a function of “Task-Relevant Maturity.”

The idea is simple: how you manage someone should depend on how capable and confident they are in a given area, not how senior or skilled they are.

When task-relevant maturity (TRM) is low—someone is new to a task or domain—you need to be more hands-on. As TRM builds, you shift to supporting: offering guidance without taking control. And when TRM is high, the best thing you can do is step away and give ownership.

The art of the light touch is mastering that shift. Not doing too much or too little—but adjusting how you help, so others grow stronger and more capable over time.

Here are a few ways to apply this in your own leadership - shifting your posture as others grow in task-relevant maturity:

1. Focus on what you enable, not what you accomplish.
   When TRM is low, it’s tempting to jump in and drive outcomes yourself. But from the start, focus on building capability. Shared accomplishments have more impact than solo heroics. Those who put the team on the right path are remembered, while those who cling to defensible control often stall.

2. Be clear on what, flexible on how.
   As TRM builds, resist the urge to dictate process. Define what success looks like, but leave space for the team to figure out how to get there. This less beats more approach fosters ownership and intrinsic motivation - the real drivers of growth.

3. Shift your posture over time.
   Your primary job is to help people become more effective so that they no longer need your intervention. Pay attention to where each person is on the TRM curve, and adjust accordingly. Intervene when necessary—support when helpful. Step away when ready. That’s the light touch.

Mastering the shift is the essence of a light touch. It’s what separates leaders who create capable, empowered teams from those who unknowingly foster dependence or disengagement.

Even small gestures can have an outsized impact. The real art lies in knowing when to intervene, when to support, and when to step away—adjusting your posture as others grow in capability.

Master that shift, and you won’t just be successful. You’ll be useful.

Next Steps

Take a moment to evaluate your current leadership approach:

1. How many decisions did you make last week that others could have made?

2. When was the last time you let someone struggle through a problem you could have solved?

3. What percentage of your team's success required your direct intervention?

The answers will tell you if you're developing capability or dependency.

Next Steps:

• Choose one project where you're currently heavily involved

• Identify one aspect you can step back from this week

• Document what happens when you do

Remember: The goal isn't to do less - it's to enable more.

When you master the light touch, you create leaders, not followers. You build capability, not dependency. And most importantly, you become truly useful, not just busy.

The question isn't whether you can help. It's whether you can help in a way that makes your help increasingly unnecessary.

Ready to share this?

If this resonated, I’d love it if you shared it. I hope more leaders learn to lead with a light touch—and leave stronger teams behind them.

Share

And, if you haven’t already, please subscribe to never miss a post!

Subscribe now

And, finally, check out my interview with Glenn on the FP&A Today Podcast here:

In my interview with Glenn Hopper on the FP&A Today Podcast, we discussed how to transform Finance teams into strategic partners. I hinted at the answer there, but I wanted to take the time to fully develop the playbook.

As finance leaders, we face a unique paradox: we have unprecedented visibility into every aspect of the business, yet we're often the last to be invited into strategic conversations. While other departments chase growth and innovation, we're cast as the responsible parent, expected to say "no" and protect the bottom line. Our position gives us the perfect vantage point to drive value, but our reputation as scorekeepers keeps us stuck on the sidelines.

We have to earn our spot on the field through partnership.

But not just any partnership. Finance leaders face unique challenges in building trust: we're expected to be both watchdog and advisor, to maintain control while enabling growth, to say "no" while finding ways to say "yes." Success requires a delicate balance of oversight and enablement that most partnership advice fails to address.

In this article, we'll explore "The ABCs of Partnership," a framework specifically designed for finance leaders who need to maintain control while building trust. These principles will help you transform from gatekeeper to strategic partner without compromising your essential oversight role. Whether you're a CFO looking to increase your strategic impact or a finance manager trying to build better business relationships, these battle-tested approaches will help you navigate the unique tensions finance leaders face in building partnerships.

Subscribe now

Aim to Assist

As finance professionals, we're trained to focus on controls, compliance, and risk management. These are essential responsibilities, but they can trap us in a reactive stance - waiting to say "no" to bad ideas rather than helping shape good ones. The most effective finance partners flip this dynamic by asking a simple question before every interaction: "How can I be useful here?"

Consider two finance leaders reviewing the same out-of-budget marketing request:

• Leader A focuses on policy: "This exceeds your quarterly budget by 20%."

• Leader B focuses on being useful: "What outcomes are you targeting? Let me help you build a business case that justifies this investment."

Both leaders maintain financial oversight, but Leader B's approach transforms a potential conflict into an opportunity for partnership. They're not just enforcing rules - they're helping their partner succeed within those rules.

The key is to step back and ask yourself, "Am I being useful?" If that feels unnatural, here are a few other ideas to maintain an aim to assist the business:

• Look for friction points. Some friction between finance and business partners is inevitable and even healthy - we need controls and oversight. But unnecessary friction often signals an opportunity to be more useful. For example, if your approval process consistently causes last-minute fire drills, that's a friction point you can solve by getting involved earlier in planning cycles. Or if business partners frequently challenge your allocations, perhaps the methodology needs to be more transparent or better aligned with how the business operates.

• Start with "why". When a sales leader requests a higher commission rate, they're not really asking about compensation - they're trying to solve for growth or retention. When product wants to increase their AWS spend, they're thinking about customer experience, not infrastructure costs. By understanding these underlying "whys," finance can shift from reactive approval to proactive problem-solving. Instead of just saying yes or no to the specific request, we can help shape solutions that achieve the business goal while maintaining financial discipline.

• Challenge your assumptions. As finance professionals, we're trained to think in binary terms: compliant or non-compliant, over or under budget, approved or rejected. But most business decisions live in the grey area. Instead of defaulting to "no" when a request exceeds budget, ask "what would have to be true for this to make sense?" Maybe it's finding offsetting savings elsewhere, phasing the investment differently, or building in success-based triggers. The goal isn't to abandon financial discipline, but to find creative ways to enable good business decisions within our control framework.

Build Clear Boxes

Finance departments are often seen as the ultimate "black box" - mysterious places where business requests go in and seemingly arbitrary decisions come out. Budget submissions disappear into a void, only to emerge months later as approved or rejected. Allocation methodologies remain opaque until they show up on P&Ls. Planning assumptions stay hidden until they become constraints.

These black boxes create friction not because partners disagree with our decisions, but because they don't understand how we make them. The irony? We're following rigorous processes and clear principles - we just haven't made them visible to others.

Here are a few ways to apply clear-coating:

• No grand reveals. Classic storytelling suggests the best way to tell a story is to build up to a conclusion, a grand reveal, that rewards the audience with the coveted "aha!" moment. The reverse is true in Business Partnering. When a Marketing VP asks about their Q2 forecast, their heart stops if you open with "Well, let me walk you through our methodology..." They're wondering if they're about to hear bad news. Instead, start with "You're tracking 5% ahead of plan, and here's why..." Then, if they're interested in the details, you can explain how your forecasting model works. This builds trust by showing you understand their priorities while maintaining the rigor of your analysis.

• Make complex models accessible. Your FP&A model might span 20 tabs with complex macros and lookup tables, but your business partners don't need to see that engine room. What they need is a dashboard that shows them what drives their numbers. For example, when Sales asks about commission forecasts, give them a simple input template that mirrors how they think about their business: pipeline stages, close rates, average deal sizes. Behind the scenes, your model can do the heavy lifting, but they see only what's relevant to their decisions.

• Turn black box processes into decision trees. Instead of keeping approval criteria mysterious, show partners exactly how decisions get made. If someone wants to hire above budget, don't just say, "It needs CFO approval." Share the decision tree: "If the role generates revenue within 6 months, it goes to the VP. If it's longer or doesn't have a direct revenue impact, it needs the CFO's sign-off. If it's strategic and above $X, it goes to the CEO." This doesn't reduce your control - it just helps partners make better requests.

The key isn't to eliminate every black box - some complexity in finance is necessary and valuable. The goal is to make our processes clear enough that partners trust our decisions even when they don't get the answer they wanted.

Close the Loop

Every month, finance teams produce mountains of reports: P&Ls, variance analyses, KPI dashboards. But here's the painful truth: most of these reports don't drive action. They sit unread in inboxes or get skimmed during meetings without changing decisions.

Why? Because we're answering the wrong question. Our partners don't just need to know if they're over or under budget - they need to know what to do about it. They don't just want to see this month's metrics - they want to understand what those metrics mean for their decisions.

In short, to elevate information to insights, we must emphasize the "so what."

Here are three ways to close this loop between information and action:

• Connect metrics to decisions. When Engineering is 20% over their cloud spend budget, don't just report the variance. Connect it to choices: "At this burn rate, we'll need to either reduce development environments by 30% or cut planned feature work to stay within the annual budget. Here are three specific ways to optimize spend without impacting velocity..." This transforms the report from an FYI to a decision framework.

• Make trends actionable. Instead of just noting that customer acquisition costs are rising, show what's driving the increase and what it means: "CAC has increased 40% due to lower conversion rates in paid channels. At current trends, we'll exhaust our Q3 marketing budget by August. Here are the specific campaigns driving the increase, and here's how adjusting our channel mix could bring costs back in line while maintaining growth targets."

• Focus on futures, not just facts. Monthly business reviews shouldn't just recap what happened - they should shape what happens next. Rather than ending with "Marketing missed their pipeline targets," close the loop: "Marketing's current program mix is generating 30% less pipeline than needed for Q4 targets. Based on our campaign attribution analysis, shifting budget from events to digital could close this gap. Here's the specific reallocation we'd recommend..."

Default to "Yes, And"

Every finance leader knows this moment: A product team excitedly presents their new initiative. The ROI looks promising, the strategy is sound, but... it wasn't in the budget. The old you would have stopped there: "Sorry, no budget." But that response doesn't just kill the idea - it kills future collaboration. Next time, they'll try to work around finance instead of with us.

The irony? Finance teams often say "no" to protect the business, but this reflexive response actually creates more risk. When teams stop bringing ideas to finance early, we lose our chance to shape initiatives before they become problems. We become a roadblock to avoid rather than a partner to engage.

Here's how to change this dynamic without compromising financial discipline:

• Replace "No" with "Yes, and..." When the Sales team wants to double their headcount mid-year, don't start with budget constraints. Start with: "Yes, it’s important to avoid being understaffed going into the summer months, and to get approval, we’d need to show a 3-month payback period. What if we phased the hiring to match pipeline growth? Let's model out different scenarios." This keeps the conversation focused on solutions while maintaining financial guardrails.

• Turn constraints into catalysts. When Marketing proposes an unbudgeted campaign, don't reject it outright. Instead: "Yes, this could work, and we'd need to find the budget elsewhere. I noticed your events program is under-delivering - could we reallocate from there? That would let us test this new approach without increasing overall spend."

• Make trade-offs explicit. When Engineering requests more cloud spend, frame it as a choice: "Yes, we can increase the infrastructure budget, and we'd need to offset it somewhere. Would you rather reduce contractor spend or delay the office expansion? Let's look at the impact of each option." This transforms budget discussions from yes/no decisions into strategic choices.

Eliminate Ambiguity

"We need more data before we can make that decision."

It's finance's reflexive response to uncertainty - asking for more information, more analysis, more proof. But this instinct often masks a deeper truth: we usually have enough data to act. We just don't want to take the risk of being wrong.

The real skill isn't gathering more data - it's making confident decisions with the information we already have. Our job isn't to eliminate every uncertainty through analysis, but to help the business take smart risks with the insights already available.

Here's how to turn develop a bias for action:

• Start with what you know, then bound what you don't. When evaluating a new market entry, don't get lost in the unknowns. Start with, known costs. Then build ranges for uncertainties: "Our TAM is $500M. At 2-5% penetration (based on similar launches), that's $10-25M revenue. Even at the low end, with our 40% margin, we'd hit ROI targets." This transforms abstract uncertainties into concrete scenarios.

• Put numbers on paper. When debating expansion plans, don't let discussions stay theoretical. Draft a simple model with explicit assumptions: "Here's version 1 - I assumed X% growth, Y% margins, and Z% overhead. What looks wrong?" Having something concrete to critique is more productive than endless speculation. The model will be wrong, but it makes the discussion specific and actionable.

• Define the decision threshold. In technology investments, it's tempting to endlessly refine estimates. Instead, name your criteria up front: "We need 25% IRR to proceed. Given what we know about costs and benefits, what would have to be true about adoption rates to hit that threshold?" This focuses analysis on what matters for the decision, not theoretical perfection.

The goal isn't to eliminate every uncertainty - it's to identify which unknowns actually matter for the decision at hand, and to make those unknowns concrete enough to act on.

Conclusion

Every finance leader faces the same fundamental challenge: How do we maintain necessary control while building true partnership? The old model - where finance focuses solely on protecting the business through rigid controls and endless analysis - creates the illusion of safety while actually increasing risk. When partners view us as obstacles, they work around us. When we demand perfect information, we miss opportunities to shape decisions early.

The ABCs offer a different path. Being useful rather than just being right. Making our processes transparent instead of mysterious. Turning reports into action drivers rather than historical records. Finding ways to say "yes, and" instead of defaulting to "no." And most importantly, having the courage to act on the information we have rather than hiding behind requests for more data.

This isn't just about being a better partner - it's about being a more effective guardian of the business. Because true financial leadership isn't about controlling every decision - it's about building the trust and frameworks that help the business make better decisions on its own.

Ready to share this?

If you found it helpful, forward it to your team or peers. Great finance leaders spread clarity, not chaos.

Share

And, if you haven’t already, please subscribe to never miss a post!

Subscribe now

And, finally, check out my full interview with Glenn here:

The pessimist sees difficulty in every opportunity. The optimist sees opportunity in every difficulty.
— Winston Churchill

"This will never work," my CEO declared, staring at our proposed compensation overhaul. "I understand we need changes, but this is a bridge too far."

His reaction wasn't surprising. We weren’t just tweaking our incentive structure — we were eliminating renewal incentives altogether, violating two decades of "common sense." Our analysis showed these incentives weren't just inefficient — they were actively harmful. Sales reps were offering unnecessary discounts to pull forward renewals that would have happened anyway, destroying value and damaging customer relationships in the process.

The data was clear, but challenging deeply held beliefs is never easy. Data alone doesn’t inspire change.

Six months later, that "radical" idea had become obvious in hindsight. We saved millions. Customer satisfaction scores rose. Retention improved. And the same executives who defended the old system now wondered why we hadn’t made the change sooner.

What changed wasn’t the data — it was how we saw the problem. Instead of fixating on what might go wrong, we asked what would need to go right. That simple shift — from risk avoidance to opportunity pursuit — became a repeatable approach to every major decision that followed.

It wasn’t just optimism. It was strategy.

Subscribe now

Experience is a Double-Edged Sword

Experience is a double-edged sword: it makes you both wise and cynical.

As discussed in The Dangers of Playing It Safe, the formula for delivering superior results is unconventionality and accuracy.

Success has a certain gravitational pull. Successful teams often default to pattern recognition over pattern breaking. Their experience, once their greatest asset, slowly becomes a liability.

Said another way, success breeds skepticism. Anything that deviates from what’s proven is a threat; thus, successful organizations will spend more time debating new ideas than decoupling from outdated norms.

This explains one of the most persistent paradoxes in business: why companies that optimize well often fail to innovate. They listen to their best customers. They refine what works. And in doing so, they miss the weak signals that point to what's next.

That’s where upstarts thrive. Unburdened by legacy beliefs, they see value where others see noise. They don’t need to unlearn. They just need to see the good.

The Blumhouse Model

No one embodies this mindset better than Jason Blum. His company, Blumhouse Productions, has made some of the most profitable films of all time:

• Paranormal Activity, his first film, generated $193 million worldwide on a budget of $15 thousand.

• Sinister generated $87 million on a budget of $3 million.

• Insidious grossed over $99 million on a budget of $1.5 million.

• Get Out grossed $255 million on a budget of $4.5 million, not to mention an Academy Award for Best Original Screenplay.

What’s surprising is Blumhouse’s breakout films were those that every other major studio discarded. Blumhouse was the studio of last resort.

Most of the successful movies we’ve done, no one else wanted to do. Nobody wanted to make The Purge, which was floating around three years. No one wanted to make The Gift, when it was a script called Weirdo. Nobody wanted Paranormal Activity, even after it was finished. Almost all our success stories are like that.

What does Blum see that others miss?

Filmmaking is primarily a numbers game. There’s more supply than you can ever fulfill, so you must thin the herd of spec scripts and rough cuts to find the winners. As a result, movie studio executives rely on their experience of what doesn’t work to filter what comes across their desks.

And that’s the mistake.

Blum wasn’t filtering for flaws. He was spotting the spark — the thing in the script or vision that had potential. Where others saw risk, he saw connection.

The longer you are in the business, the more material comes your way. It becomes easy after a while to get lazy and dismiss everything as garbage. You have to find a way to focus on areas that show promise. Every script is a work in progress — it’s a blueprint for something else.

Seeing the good isn’t enough, though. All creative endeavors carry risk, even the ones with promise. To be truly successful, Blumhouse uses the financial constraints of the budget and contracts to limit the downside.

In big movies, interests are not aligned between those above the line [actors, director, producers, writers] and the financier, because above the line gets paid whether the movie works or not. The financier only makes money if the movie works, and that fundamentally sets up a contentious relationship. What I love about low-budget movies is my interests and the director’s interests and the actors’ interests are aligned. No one makes money unless the movie works, and that informs every creative decision.

In short, Blum started by seeing the good. He then engineered every aspect of the business to capture upside without overexposing downside:

• Low-budget production

• Profit-sharing instead of big fixed fees

• Release decisions based on test screenings

This wasn’t blind optimism or luck. It was calculated risk, with incentives and constraints built in.

A system, not a gamble.

The SEE Framework: A Model for Opportunity-Oriented Leadership

Blum’s approach is more than a Hollywood anomaly — it’s a transferable model that applies just as well to comp overhauls, product bets, GTM shifts, or bold org changes.

S — Spot the Spark

Start by asking: What would make this work? Train your eye to find the signal inside the noise. Most ideas fail not because they’re bad, but because no one sees the good early enough to nurture it.

E — Engineer the Edges

Set boundaries. Use constraints — budget, incentives, scope — to reduce risk and focus creativity. The goal isn’t to eliminate risk. It’s to shape it.

E — Experiment for Exposure

Don’t debate hypotheticals — test and learn. Pilot ideas in low-stakes settings and scale based on what works. This turns vision into evidence.

Helping Others SEE

Optimism might not make you successful, but pessimism will ensure you’re not.
- Shane Parrish

Even if you spot the spark, you’ll often need to help others see it too. That means recognizing resistance as a feature, not a bug. Most skepticism comes from experience, not ignorance.

Here’s how to bring others along:

1. Start with Their Wisdom. Honor the logic behind the current model before proposing a new one.

2. Build the Bridge. Show how the new approach extends strengths rather than invalidates them.

3. Make It Safe. Lower the stakes. Pilot. Test. Invite skepticism into the process, not outside of it.

Final Thought

The SEE framework isn’t about blind faith — it’s about structured belief. It’s how you place smarter bets, pursue unconventional upside, and create environments where good ideas can survive long enough to prove themselves.

You don’t need to believe every idea will work. But if you never train yourself — or your team — to SEE the good, you’ll never find the few that change everything.

Spot the spark. Engineer the edges. Experiment for exposure. That’s how optimists win.

Ready to share this?

If you found it helpful, forward it to your team or peers. Great finance leaders spread clarity, not chaos.

Share

And, if you haven’t already, please subscribe to never miss a post!

Subscribe now

Every action you take — and every decision you defer — creates leverage. It either multiplies your opportunities or magnifies your risks. The latter accumulates over time, creating significant drag as “what is” limits “what could be.” Just ask the American railway companies of the 1830s.

England and America built their first modern railways within a year of each other: the Liverpool and Manchester Railway (1830) and the Mohawk & Hudson Railway (1831). Each set the space between the rails (i.e., the rail gauge) at 4 feet 8 1⁄2 inches.

As railroads proliferated throughout the 1830s and 1840s, so too did the variety of gauge sizes. Few based their selection solely on engineering criteria. In some cases, it was a matter of familiarity, aligning the gauge with the width of the transportation lanes the railway was replacing. In others, it was a strategic decision, fending off competitors or neighboring nations from connecting to their rails.

This made things complicated. By the 1870s, America utilized over twenty different gauges varying anywhere from five to seven feet. Left to their own devices, the railways had created a transportation network that would force passengers and cargo to switch trains at each junction. Something had to be done.

The Americans tried everything except addressing the root cause. They built adjustable wheels, modified tracks, and even used cranes to lift entire train cars between different gauges. Each solution worked just well enough to avoid facing the real problem: the lack of standardization.

So many innovations, so little progress. After years of working around the problem, the writing was on the wall. As long as the railways were allowed to set their own gauges, long-distance train travel was neither safe nor efficient. Gauge standardization was the only solution.

During the Transcontinental Railroad development in 1869, railways were torn up and replaced with the standard 4 feet 8 1⁄2 inches gauge first installed over 30 years ago. The change was expensive but not nearly as disruptive as expected. Standardization enabled an unparalleled focus on a singular solution. Focus brought efficiencies, as exemplified by Louisville and Nashville’s replacement of a combined ~2,000 miles of track within one day.

As impressive as this was, it wasn’t revolutionary. The British came to the same conclusion more than 20 years earlier. As the Americans toiled with solutions to a problem they created, the British solved the problem at its source by enacting the Railway Regulation Act, which defined the same 4 feet 8 1⁄2 inches gauge as standard, banning all others.

The American approach is a stark reminder of how our past decisions can shape our trajectories. Each decision creates a commitment that reduces our option pool. Each commitment acts as a form of leverage; it can amplify our outcomes either positively or negatively.

Much like debt.

Decisions as Debt

The parallels between financial and decision debt are striking:

• Like a mortgage, some decisions fund transformative growth

• Like credit card debt, others trap us in cycles of inefficiency

• Like leverage ratios, there's a tipping point where flexibility becomes fragility

• Like compound interest, the cost of deferring hard choices grows exponentially

The key is knowing which decisions are investments and which are indulgences.

Starting a company. Going to graduate school. Buying a home. These potentially life-changing events would be largely unattainable if they were only available to those who had the cash in hand. It is when the cost outweighs the benefits of our outstanding commitments that we get into trouble.

In finance, this is known as debt overhang. Think of it as a borrowing black hole, where the debt burden looms so large that it consumes all available resources. Even if a golden opportunity presents itself, there’s no way to pursue it, as every incremental resource generated is needed to fund the obligation. The commitment becomes a condemnation. Debt becomes a four-letter word.

Our decisions work in much the same way. Just as the American railways' initial gauge choices seemed rational but created mounting infrastructure debt, organizations today face similar crossroads.

Every commitment creates constraints - the question is whether those constraints will focus or fragment our efforts.

Take technology standardization. Like Britain's early gauge regulation, a well-planned standard can create powerful efficiencies. Microsoft's decision to standardize Windows development on .NET in 2002 enabled rapid innovation. But contrast this with IBM's commitment to mainframes in the 1980s - what began as a strength became a constraint that nearly crippled the company during the PC revolution.

The key is distinguishing between constraints that create leverage and those that create liability. Amazon's "two-pizza team" rule deliberately constrains team size to enhance productivity, much like how standardized rail gauges enabled faster and more efficient transportation. Yahoo's pre-2013 office-only policy, on the other hand, mirrors the fragmentation of American railways: a constraint that seemed logical but ultimately limited growth and innovation.

This bifurcation process is easier said than done. All decisions should be viewed in context, meaning one shouldn’t shy away from reversing course on what was a good decision in the past.

Consider 1Password, which didn’t take outside funding until (too) late in the game:

Brett: Do you look back and you can clearly see that at certain points there would have been benefits if you chose to raise capital?

Jeff: Hindsight being 20/20, I would've raised capital earlier. You can get to a point where you're proud of things you should no longer be proud of. Maybe said a better way the things that you're proud of can inhibit you…once you've been bootstrapped for 10 years and everybody's like, wow, you've grown this, great company, all bootstrapped, how impressive is that, that becomes becomes your identity.

…If we had had marketing and go-to market and like real marketing, if we had been more mature earlier, that would've helped us…

The choice to be bootstrapped became a badge of honor, and the badge of honor became a constraint. The team had to overcome the (perceived) negative of taking on outside capital to accelerate their growth, because they recognized that growth would be inefficient in the short term.

Decisions are force multipliers because they focus our resources. Just like debt consumes a percentage of future earnings, decision debt consumes future opportunities that otherwise would’ve been available to us if we’re not careful.

If we make the right choices, the payoff is massive. If not, we fall behind to the point where we may never catch up.

The Hidden Patterns Behind Decision Debt

Decision overhang is dangerous because it’s a gradual process. Think of each decision as a swipe of a credit card - a series of individually small purchases can put us into the same bind as a singular, massive one. Keeping our decision debt manageable requires that we:

1. Reflect on how past decisions affect us today and

2. Remember what decisions were made.

To make this distinction, it helps to think about decisions across two dimensions:

• Awareness (Was the decision made deliberately or accidentally?): The American railways didn't intend to create a fragmented network - it emerged from many local decisions. Britain, in contrast, deliberately standardized their gauge early. The difference between intentional choices and unconscious patterns often determines whether we can manage their consequences.

• Impact (Does the decision create focus or fragmentation?): Some constraints, like Amazon's two-pizza team rule, channel energy in productive directions. Others, like IBM's mainframe commitment, scatter resources across incompatible efforts. The key is distinguishing between decisions that concentrate power and those that dissipate it.

These dimensions create four distinct patterns:

Invisible Drift (Most Dangerous)

• What it looks like: Multiple teams solving the same problem differently

• Example: Different business units building their own billing systems.

• Response: Stop the bleeding, then standardize

Quick Fixes (Most Common)

• What it looks like: Temporary patches that quietly become permanent.

• Example: Manual reporting workarounds that never get automated.

• Response: Set hard deadlines for cleanup and systemization.

Happy Accidents (Most Overlooked)

• What it looks like: Productive patterns you didn't plan

• Example: Teams naturally adopt an efficient project rhythm without formal training.

• Response: Spot it early. Codify and scale what’s working.

Strategic Standard (Most Valuable)

• What it looks like: Clear constraints that speed up alignment and execution.

• Example: Britain’s early nationwide railway gauge regulation.

• Response: Strengthen the standard. Build momentum around it.

Turning the Tide: How to SCAN for Decision Debt

Warning Signs Your Decision Debt is Becoming Dangerous:

• More than 20% of resources maintaining workarounds

• Three different solutions to the same problem

• Rising coordination costs between teams

• Increasing resistance to change

• Growing backlog of "temporary" fixes

The good news? Like financial debt, decision debt can be restructured. The SCAN framework helps you move from reactive to strategic decision-making.

When we think about our decisions in this way, we can determine which ones continue to serve us and which hold us back. Decision debt is inevitable, but decision overhang is not.

The path forward is clear: we must become active managers of our decision debt. This means developing a systematic way to SCAN our environment:

Spot Patterns

Like the early signs of railway incompatibility, decision debt often reveals itself through daily friction:

• Multiple departments building similar tools ("We needed our own version")

• Increasing time spent on workarounds ("It's just temporary")

• Rising coordination costs between teams

• Resistance to standardization ("Our case is different")

Warning Signs:

• More than 20% of team time spent on maintenance

• Three or more solutions to the same problem

• Regular exceptions to standard processes

• Growing backlog of "technical debt"

Categorize Deliberately

Ask these questions to identify which pattern you're dealing with:

• Quick Fix: "Was this meant to be temporary?"

• Invisible Drift: "How many ways do we do this?"

• Strategic Standard: "Does this constraint speed us up?"

• Happy Accident: "What's working well without formal structure?"

Key Questions for Teams:

• "If we started fresh, would we make this choice again?"

• "Are we solving symptoms or root causes?"

• "What patterns emerged naturally vs. by design?"

Assess Systematically

Measure the real cost of your decision patterns:

• Time Cost: Hours spent maintaining multiple solutions

• Opportunity Cost: Innovation prevented by maintenance

• Coordination Cost: Effort required to keep teams aligned

• Future Cost: Growing difficulty of eventual changes

Prioritization Matrix:

• High Impact/Low Effort: Address immediately

• High Impact/High Effort: Plan strategic resolution

• Low Impact/Low Effort: Fix opportunistically

• Low Impact/High Effort: Accept or deprecate

Navigate Strategically

Choose your approach based on pattern type:

For Quick Fixes:

• Set firm timelines for permanent solutions

• Build replacement into regular sprint cycles

• Get stakeholder buy-in for short-term pain

• Document current state to prevent recurrence

For Invisible Drift:

• Map all current approaches

• Calculate total maintenance cost

• Pilot standardization with willing teams

• Create clear migration paths

For Strategic Standards:

• Document what makes them effective

• Spread adoption through demonstration

• Measure and share positive impact

• Build supporting infrastructure

For Happy Accidents:

• Study why they work well

• Formalize best elements

• Scale gradually with monitoring

• Maintain flexibility in implementation

Getting Started

1. Choose one area showing warning signs

2. Map current state using the framework

3. Pick one high-impact, achievable change

4. Set clear metrics for success

5. Review progress monthly

Common Pitfalls:

• Trying to fix everything at once

• Focusing on symptoms over causes

• Neglecting stakeholder buy-in

• Forgetting to measure baseline state

The Cost of Waiting

The American railways eventually standardized their gauge, but only after decades of costly workarounds. Their story offers a sobering reminder: the interest on decision debt compounds daily.

Every month you delay addressing systematic problems, you pay a premium in:

• Lost opportunities

• Wasted resources

• Declining morale

• Competitive disadvantage

Take Action Now:

1. Map your current decision debt using the framework above

2. Choose one high-impact area to address

3. Set clear metrics for progress

4. Review and adjust monthly

5. Share your learnings

The question isn't whether we'll accumulate decision debt - we will. The question is whether we'll manage it systematically or let it manage us.

Ready to share this?

If you found it helpful, forward it to your team or peers. Great finance leaders spread clarity, not chaos.

Share

And, if you haven’t already, please subscribe to never miss a post!

Subscribe now

In 1899, President McKinley had a problem.

The Spanish-American War was underway. The U.S. needed to coordinate with General García, leader of the Cuban insurgents. But García was deep in the jungle. No known address. No phone. No map.

McKinley summoned an officer.

"Where exactly is García?" he asked. The officer paused. "I'd need a proper map, some men, maybe a telegraph line set up first."

He summoned another.

"Should I wait for written orders?" the second asked. "And who’s in charge once I get there? Do we know if García will even cooperate?"

Excuses. Bureaucracy. Delay.

Finally, someone said, “Send Rowan.”

Lieutenant Andrew Rowan took the envelope, saluted, and left. No hesitation. No clarifying questions. No follow-ups. Weeks later, he emerged—mission accomplished.

That simple act of execution became a phenomenon. The essay A Message to Garcia sold 40 million copies. It was handed out in factories, classrooms, and even the Russian army. A parable of action over analysis.

As leaders, we face our own "García moments" daily. The board needs revised projections by morning. The CEO wants to understand acquisition implications before markets open. Auditors require documentation that seems buried in the jungle of legacy systems.

In these moments, we don't just need speed—we need something more fundamental.

Rowan didn’t move fast. He moved without friction.

The contrast between Rowan and the other officers wasn’t about intelligence or dedication. It was about something more elusive:

Autonomy paired with urgency.

Because in modern finance organizations, we’ve designed systems that produce far more hesitation than heroics.

The Real Problem with “Urgency”

We’ve taught our teams to value speed.

• Respond quickly.

• Escalate early.

• Move fast.

But urgency without autonomy creates chaos.

• More updates, fewer decisions.

• More pressure, less progress.

• More noise, less clarity.

The result? Slack pings. Dashboard proliferation. People hustling without moving forward.

Fast alone is fragile.

This isn’t just a people problem—it’s a system problem. Our workflows, approval chains, and communication norms often reward responsiveness over results.

We don’t need more hustle. We need smarter systems and better operators.

Subscribe now

The Smooth Operator Matrix

A simple 2x2 to help diagnose how your team responds to pressure:

• 💤The Waiter: Needs direction at every step. Delivers only when told. Likely to ask, “Do we have a template?”

• 🔥The Firefighter: High urgency, low clarity. Constant motion, but usually sideways.

• 🔨The Tinkerer: Smart, independent, but too removed from real priorities. Polishes tools no one needs.

• 🚀The Smooth Operator: Knows the mission. Doesn’t need hand-holding. Escalates only when stuck. Think: Rowan.

This is a cousin to the Eisenhower Matrix. Where that framework helps prioritize tasks based on urgency and importance, this one diagnoses how work gets done. It's not about what gets done first—it's about how well it gets executed under pressure.

How to Build a Team and System of Rowans

If you want more Smooth Operators, you have to lead differently—and redesign your environment. Here’s how:

1. Start with Clarity

Give them the envelope.

Not just "analyze churn," but "help us understand if we're losing high-LTV users before renewal—and what to do about it."

Clarity turns passive receivers into active drivers. It transforms anxiety into action.

For People:

• Anchor work in business outcomes, not tasks

• Eliminate ambiguity around the "why"

• Share context early—then step back

For Systems:

• Make briefings concise and goal-oriented

• Document intent alongside deliverables

• Encourage outcome framing over project scoping

2. Grant Decision Rights

Let them move.

Rowan didn't email for approvals halfway through the jungle. Your team shouldn't need five sign-offs to launch a dashboard.

Define what they own. And what they don’t need to ask about.

For People:

• Explicitly delegate decision boundaries

• Normalize escalation after action, not before

• Audit what work is blocked and why

For Systems:

• Build default approval thresholds

• Streamline workflows in tools (e.g., Slack, Jira, Asana)

• Limit synchronous bottlenecks to true exceptions

3. Create Execution Space

Get out of the way.

This means fewer check-ins, fewer alignment meetings, fewer status docs. Trust doesn’t scale through visibility. It scales through outcomes.

For People:

• Protect maker time for deep work

• Swap recurring syncs for async updates

• Trust is built by not hovering—start there

For Systems:

• Use tools that reinforce async over real-time

• Eliminate redundant status checks

• Encourage visibility through progress, not presence

4. Frame Urgency with Purpose

Not everything is García-level.

Use urgency selectively. When something really matters, explain why. Not “we need this now,” but “this unlocks a decision on $2M of spend.”

People run harder when they know where the finish line is—and why it matters.

For People:

• Align on what’s truly urgent vs simply fast

• Highlight business impact with every deadline

• Urgency without clarity leads to burnout

For Systems:

• Triage requests based on business value

• Time-box reactive cycles

• Keep the Eisenhower Matrix visible when setting priorities

Closing Reflection

Message to Garcia became a global sensation not because Rowan moved quickly—but because he moved with direction and autonomy.

Your best people want that same clarity. That same trust.

They don’t want the checklist. They want the envelope.

Build the system. Empower the people.
Find your Rowans.
Give them the mission.
Let them deliver the message.

Ready to share this?

If you found it helpful, forward it to your team or peers. Great finance leaders spread clarity, not chaos.

Share

In Season 5 of Parks and Recreation, Ron Swanson and April Ludgate find themselves in Chris Traeger's management seminar. As the discussion turns to motivation and productivity, distinct positions are taken between the three characters:

Ron: "There are only three ways to motivate people: money, fear, and hunger."

Chris: "Oh, I disagree. What about encouragement, appreciation, and smiles? When people feel supported, they literally explode with productivity!"

April: "Can you guys just figure out which is better and tell me so we can leave?"

Regardless of your familiarity with these characters, I bet you can relate to at least one of their approaches. The carrot vs. stick debate plays out in workplaces everywhere. And like April, many of us are just trying to get through it without arguing management theory.

But what if the debate misses the point entirely? What if something essential has been left out - a single missing piece? One that could just click into place.

Let Go of My LEGOs

Imagine someone offered to pay you to build LEGO models. Not a lot, mind you - a few dollars for the first one and a little less for each subsequent unit - but hey, you've played with LEGOs as a kid for free so you're certainly moving up in the world.

After meeting with the researcher, you take your LEGO kit and get to work. It's not too complicated - it takes you about ten minutes to build the 40 piece set. Once you're done, you hand the completed model to the researcher, who then asks if you'd like to build another. Sure, why not? Each time you agree to build one more, you're given an identical new LEGO model to build. If you're anything like the average Harvard undergrad who participated in this study, 11 models have accumulated on the desk before you decided to take your money and leave.

Score one for Ron Swanson. Here‘s a job to be done, and you pay someone to do it for you. Money talks, right?

Imagine the same scenario with one slight twist. After you complete the first model and tell the researcher you'll do another, you take your new LEGO set to your desk, and that's when you notice that the researcher is disassembling what you just built. When you're done and offer to do a third, the researcher hands you the box with your first model. As you return to your seat, the researcher deconstructs your second LEGO set to be ready for you should you do a fourth. When you finally call it quits, the researcher's desk is clear of all but the last model you completed, which she begins to deconstruct.

Piece. By. Piece.

So what? LEGOs aren't intended to survive the test of time. Surely, you went into this knowing your hard work wouldn't be preserved in the university trophy case for all to see. The endgame is the same, with the second scenario being far more practical for the poor researcher who had to watch you play with LEGOs.

Here's the thing - that slight twist makes a world of difference. If you were put into the second scenario (the Sisyphus condition), you would have built 32% fewer LEGO models, and your payout would be 20% less than your peers in the first (the Meaningful condition). This is striking. The study described above was conducted with Harvard undergraduates, individuals who, presumably, are smart enough to know that the LEGO models would return to the box. Yet the Sisyphus participants were less productive and, therefore, earned less than their statistically identical peers whose only distinction was being spared observing the deconstruction of their work.

If money talks, it was merely a whisper in this case. Meaning, or the lack of it, spoke louder.

The pointlessness of the task sapped the students' motivation, causing them to disregard the earning opportunity afforded them by the incentive structure. As intuitive as they are, the productivity theories posed by Ron and Chris fail to explain this.

Meaning, it turns out, matters deeply.

If removing meaning can crush motivation this dramatically, what happens when we add it? For answers, let's look at one of the most metrics-driven environments possible: call centers.

Subscribe now

Call Me, Maybe?

There are a lot of thankless jobs out there, but that of the university development fundraiser has to be near the top of the list. Cold-calling alumni and asking for donations can be a grueling task. Most calls will go straight to voicemail, and when they don’t, more often than not, you probably wish they did.

Metrics matter, particularly how much money you bring in. The industry has an abundance of Chris Traegers, with their relentless attempts to boost employee satisfaction, and Ron Swansons, with their laser-like focus on incentives and performance minimums. For managers, it can be challenging to cut through the noise as the sheer volume of rewards and punishments can crowd out any other motivation. How can meaning possibly make a difference in an environment like this?

Adam Grant, now of the Wharton School, designed an experiment to find out. A sample of thirty-nine fundraiser callers was split into three groups:

1. The Interpersonal Contact Condition, who spent five minutes interacting with a student who benefited from the scholarships their work funded

2. The Letter Control Condition, who read a letter from such a student and discussed it within the team for five minutes

3. The Control Condition, who received no interaction with the scholarship beneficiaries

I'm sure you can guess where this is going. Those in the first condition vastly outperformed the other two. Here's what you probably didn't expect: the productivity gained from that five-minute conversation had a lasting impact. A month after the interaction, students in the Interpersonal Contact Condition were bringing in 2.71 times more money than what they had brought in before the intervention. Five minutes of meaning equated to productivity lifts for a month. That‘s one hell of an ROI.

Dismissing this as purely academic would be a mistake. Results like those above have been replicated elsewhere (see further reading), but the signs that meaning matters extend beyond university research labs. The business benefits, but so do the employees. In a 2018 survey, 80% of respondents reported they would rather have a boss who cared about them finding meaning and success in work than receive a 20% pay increase. I wouldn't recommend such a pitch in the next annual review, but it gives you a sense of how critical this is.

Money talks, but meaning motivates.

Meaning Makes It Work

Chris and Ron devise an experiment to decide whose management theory is best. The rules are simple: each has a stack of folders to be filed and go about putting their techniques to work on the hapless Jerry Gergich. Chris uses inspiration, and Ron uses intimidation. The results are unsurprising: more of Ron's folders were put away, but most were filed incorrectly. It's ultimately declared a draw, with the real winner being April, who pitted the two against each other while she achieved her goal of leaving the seminar altogether.

After what we've discussed above, a draw feels appropriate. The task was pointless, and the techniques employed were attempts to externally influence rather than internally motivate. None of this is to say that carrots and sticks don't work - they do. But like any good LEGO set, it's not how many pieces you have but how they fit together.

There's an old story about three bricklayers working on a cathedral. When asked what they're doing, the first says "I'm laying bricks." The second replies "I'm building a wall." But the third looks up with pride and declares "I'm building a cathedral that will lift people's spirits for generations."

Same task, different meanings. And as our LEGO builders and call center workers showed us, that difference transforms everything about how people approach their work.

This insight runs counter to our intuition. Left to our own devices, we'll default to carrots and sticks because the theories are more pervasive, which in turn makes it easier. Less risky. What manager would want to be left holding the bag because they shifted from PIPs to customer meet and greets? But that's a false choice. Meaning doesn't replace other motivators—it amplifies them. The challenge is helping every builder—whether working with plastic bricks or stone ones—see their own cathedral taking shape.

So how do leaders put this insight into practice without seeming manipulative or naive? The key is understanding that meaning isn't about grand missions or inspirational speeches.

As leaders, we can help our teams find meaning by:

1. Connect work to impact: Create opportunities, even brief ones, for employees to see how their work affects others. This could be as simple as sharing customer testimonials or having team members from different departments explain how they use each other's work. Help them see how their bricks form the cathedral.

2. Protect meaning: Be vigilant about practices that inadvertently strip meaning from work. When projects change direction or get cancelled, take time to explain why the work still mattered and what was learned.

3. Let meaning multiply: Don't abandon traditional motivators—enhance them. Use meaning as the foundation that makes your incentives, recognition, and feedback more effective.

The debate between carrots and sticks misses the point entirely. You can't motivate someone to care. You can only help them understand why they should.

That's the true power of meaning. It doesn't add to motivation—it transforms the very nature of work itself. When people understand why their effort matters, they don't need to be pushed or pulled. The joy of building something that matters is motivation enough.

Further Reading

Predictably Irrational: The Hidden Forces That Shape Our Decisions

• Written by the lead researcher of the LEGO study (Dan Ariely), this book covers his vast research on how we behave doesn't often jive with our intuition.

Give and Take: Why Helping Others Drives Our Success

• Written by the lead researcher of the Call Center study (Adam Grant), this book compiles his research on the success of those who focus on others.

There’s a Zen Buddhist story about an old farmer who earned his livelihood by dutifully working his crops with the help of his two closest companions: his horse and his son.

One day, a storm damaged part of the stable, and the horse broke free and ran away. Upon hearing the news, his neighbors checked in on him. “Such bad luck,” they offered.

“Maybe,” replied the farmer.

The next morning, the horse returned, accompanied by three wild mares. The neighbors couldn’t believe their eyes. “How wonderful!” they exclaimed.

“Maybe,” replied the farmer.

The following day, the son was thrown off one of the new mares' back, breaking his leg in the process. The neighbors again visited to offer their sympathies. “Such misfortune,” they murmured.

“Maybe,” replied the farmer.

The next day, soldiers came to the village to conscript young men into the army. After seeing the son was unable to walk due to his broken leg, they decided to leave the boy behind. “How fortunate!” the neighbors said.

“Maybe,” replied the farmer.

Definitely, Maybe

At first glance, this seems like a simple story about patience or suspended judgment. But there's a more unsettling insight hiding in plain sight: The neighbors' greatest failure wasn't their hasty judgment - it was their complete blindness to their own blindness. They weren't just wrong; they were wrong about how much they could be wrong.

This meta-blindness - the gap between what we know and what we think we know - isn't just some ancient parable. It's actively shaping how we process information and make decisions right now.

To understand why we so often miss the bigger picture - like the farmer's neighbors did - we need to understand how our minds process information and make judgments. This is where Nobel Prize-winning psychologist Daniel Kahneman's research provides crucial insights.

In his book, Thinking Fast and Slow, Nobel Prize-winning psychologist Daniel Kahneman detailed two modes of thinking. System 1 is like an overeager assistant, jumping in with quick answers based on patterns and past experience. System 2 is the careful analyst, stepping back to examine assumptions and consider alternatives. The trouble is, System 1 doesn't just act quickly - it actively prevents us from realizing when we should slow down and let System 2 take over.

Here's how this creates meta-blindness: When System 1 jumps to a conclusion, it doesn't just give us an answer - it gives us an illusion of understanding. We don't just make quick judgments; we become convinced those judgments are thorough and complete.

Consider how this plays out in a typical business meeting: Someone presents a new product idea, and within minutes, executives nod along, asking about implementation details. Their System 1 has already classified this as a "good idea" based on a few familiar patterns, and now they're rushing to execution. What's fascinating isn't just the speed of their judgment - it's their complete unawareness of all the crucial questions they haven't asked:

• What customer problem does this actually solve?

• Why hasn't this been done before?

• What assumptions are we making about our capabilities?

• What don't we know about the competitive landscape?

The executives aren't just making a quick decision—they've become blind to the possibility that there might be more to consider. Their System 1 has given them not just an answer but an illusion of complete understanding.

Consider how this plays out in everyday decisions: When we evaluate a job candidate based on a one-hour interview, we don't just make quick judgments - we forget how much we can't possibly know from that brief interaction. When we assess a company's performance from quarterly numbers, we don't just analyze the data - we forget about all the crucial context we can't see. This isn't just rushed judgment; it's a fundamental blindness to the limits of our knowledge.

This is precisely how the farmer's neighbors fell into their trap. It wasn't just that they rushed to judgment about each event—it was that their System 1 thinking made them blind to the possibility of future developments. They weren't just wrong; they were convinced they had the complete picture each time.

What makes this meta-blindness even more dangerous is how our minds work to preserve it. Through what psychologists call motivated reasoning, we don't just jump to conclusions - we actively defend our blindness to alternatives.

Consider how the neighbors would have reacted if someone had suggested they might be missing part of the picture. With the son's broken leg, they wouldn't just have disagreed - they would have marshaled evidence to prove their perspective was complete: the boy's pain, the medical costs, the lost labor. All true facts, carefully selected to maintain their illusion of complete understanding.

We do this constantly in our own lives, and the pattern is always the same: The more someone challenges our incomplete picture, the more energy we invest in proving it's complete.

Take a simple domestic dispute: Your partner asks why you left dirty dishes in the sink. Watch how quickly meta-blindness takes hold:

First, System 1 jumps to your defense with what feels like a complete explanation: you were rushing to a meeting, you had to file taxes, you were putting out fires at work. These reasons feel thorough and justified.

Then meta-blindness deepens: Not only do you become convinced your explanation is complete, but you start gathering evidence to prove it. You recall how your partner left their shoes in the hallway last week, how they forgot to buy groceries last month. Your mind isn't just defending your actions - it's actively building a case for why your perspective is the only one that matters.

The truth hiding in plain sight? You could have done the dishes. But acknowledging this would require seeing what System 1 is working so hard to hide: that your "complete" understanding is anything but complete.

Subscribe now

The Illusion of Context

Let’s go back to the story of the farmer with the concepts we just learned in mind, and you’ll notice how the narrative dictates our interpretation:

1. We judge the story as told, focusing on external events rather than individual actions. What if the story began with details about how neglectful the farmer was in his day-to-day duties. The stables weren’t adequately maintained, and proper precautions were rarely, if ever, taken. When a minor storm blows through the town, it’s no wonder the neglected fence falls apart, and the horse gets out. Furthermore, a boy trying to ride a wild mare the day after he randomly appeared on the property feels short-sighted. The broken leg feels obvious.
   
   In this version, the neighbors’ reactions feel justified, if not passive-aggressive, and the lesson shifts to one about how preventative measures and precautions can save you a lot of pain.
   
   
   This pattern plays out daily in business decisions. A product launch fails, and we immediately blame poor execution. A star employee quits, and we attribute it to compensation. A merger disappoints, and we point to integration issues. In each case, we risk focusing on the immediate narrative while missing the deeper systemic forces at play - just as the neighbors missed the broader pattern of events unfolding around the farmer.
   

2. We judge the story based on the time horizon it dictated. The story ends on a high note - the son avoids going to war, and the old farmer tripled his horses. Even though it implies that more events will follow, we walk away feeling inspired.But what if the story ended with the son’s broken leg? The parable becomes a cautionary tale about taking in wild mares your runaway horse made friends with, and the broader lesson about fate and patience seems far less pertinent.
   
   The neighbors’ meta-blindness wasn't just about missing future events; it was about being blind to the very possibility of contextual relevance.
   
   Consider the Glass-Steagall Act's repeal in 1999. When the 2008 financial crisis unfolded, most analysis focused on immediate causes: greedy bankers, irresponsible borrowers, complex derivatives. What was harder to see - what we were blind to seeing - was how the removal of Depression-era banking safeguards had created the very conditions for these immediate causes to emerge. We weren't just missing historical context; we were blind to the importance of historical context itself.
   
   Alternatively, what if the other boys drafted into the military went on to have successful careers, seeing the world and reaching the upper echelons of society no farmer would ever dream of? The lesson loses its luster if we focus on the fate of a boy whose only companions are horses (one who doesn’t seem to care for him too much) and an emotionless father who seems incapable of celebrating anything positive in his life.

In short, our preference for low-effort decisions and emotional justifications causes us to overvalue the information available to us and discount (or discard) the unknown. It’s not that we don’t appreciate the value of incremental information; we don’t realize there’s anything left to gather to inform our opinion.

This layered meta-blindness - about information, context, and time - creates a particularly dangerous form of confidence. We don't just miss what we don't know; we become structurally incapable of recognizing there's more to know.

The Story Sense Framework: Breaking Through Meta-Blindness

What made the farmer different wasn't his patience or wisdom - it was his systematic resistance to the illusion of complete understanding. His "maybe" wasn't just a placeholder response; it was a tool for maintaining awareness of what he couldn't see.

This is what separates great decision-makers from merely experienced ones: they've developed what we might call "Story Sense" - a structured approach to recognizing and resisting meta-blindness.

Like any skill, Story Sense can be developed through practice. The key is learning to recognize the warning signs of meta-blindness: when understanding feels too complete, when consensus forms too quickly, when complexity suddenly seems simple.

Here are three tools to break through meta-blindness:

1. Scene Detection: Spotting the Frame's Edge

   • First reaction: "What am I seeing?"

   • Meta-blindness check: "What might I be trained not to see?"

   • System 2 prompt: "What would make my current understanding incomplete?"
     

   When the neighbors saw a broken leg, they thought they saw everything relevant. The farmer's "maybe" wasn't about what might happen next - it was about acknowledging the limits of what he could currently see.
   

2. Speaker Awareness: Finding the Blind Spots

   • First reaction: "Who's telling this story?"

   • Meta-blindness check: "What might their perspective naturally hide?"

   • System 2 prompt: "What other perspectives would tell this differently?"
     

   Our meta-blindness often comes pre-installed with the perspectives we trust. The neighbors weren't just interpreting events - they were trapped within their community's shared way of seeing.
   

3. Sequence Recognition: Breaking Time's Frame

   • First reaction: "Where are we in this story?"

   • Meta-blindness check: "What timeframes am I ignoring?"

   • System 2 prompt: "How might future context change everything?"
     

   The farmer's genius wasn't patience - it was his resistance to the illusion that any moment is truly complete. Each "maybe" was a reminder that time itself shapes understanding.

Breaking Free from Meta-Blindness: A Daily Practice

The tools above aren't just analytical frameworks - they're practices for breaking free from the comfortable prison of perceived understanding. Here's how to put them to work:

1. Start with Triggers
   Watch for these warning signs of meta-blindness:

   • When consensus forms too quickly

   • When explanations feel too complete

   • When complexity suddenly seems simple

   • When objections seem obviously wrong
     

2. Build New Habits

   • Before important meetings, write down what you think you know for certain

   • After key decisions, list what information you might be blind to

   • During discussions, actively look for perspectives that could break your frame

   • When reviewing results, consider what longer timeframes might reveal
     

3. Ask Better Questions
   Replace:

   • "What's the solution?" with "What might make this problem incomplete?"

   • "Who agrees?" with "What perspective are we all missing?"

   • "What's the impact?" with "How might future context change our understanding?"
     

Return one final time to our farmer. His "maybe" wasn't just wisdom - it was a warning. A reminder that every story we think we understand completely is actually teaching us something about our own blindness.

When his horse ran away, the neighbors saw misfortune.
When it returned with companions, they saw triumph.
When his son broke his leg, they saw tragedy.
When the army passed by, they saw luck.

But the farmer saw something far more important: the edge of his own understanding.

That's the real power of "maybe" - not as a hedge against uncertainty, but as a lens for seeing our own meta-blindness. Because the most dangerous story isn't the one we get wrong. It's the one we think we completely understand.

Next time you're absolutely certain about something, pause.

Say "maybe."

And watch as your certainty dissolves into possibility.

"We need more."

It's the first response of every struggling team. More headcount to handle the load. More features to stay competitive. More processes to prevent mistakes. More meetings to stay aligned.

More. More. More.

But here's the cruel irony of growth: The more we add to fix our problems, the more problems we create to fix.

Let me show you what I mean.

In a recent leadership workshop, I presented this challenge:

Imagine you are a manager at this Circle K location and have been tapped to address the escalating number of robberies occurring. Like most convenience stores, the cash on hand makes your store a target for petty criminals, and the crime rate is hurting your employees, customers, and bottom line. Also, like most convenience stores, margins are thin, so you don’t have unlimited capital to solve the issue.

Take a moment to consider your solution. How would you address this problem?

If you're like most leaders, you're falling into one of three traps that catch even the most sophisticated organizations:

• Costly deterrents (e.g., higher security monitoring, hiring on-site security, etc.),

• Cheap but unreliable preventative controls (e.g., employees keep a firearm under the register, ask local police to stop by more often, etc.), or

• Acknowledgment that robberies happen and focus on the aftermath (e.g., training employees on how to handle the situation, higher-definition cameras to catch perpetrators, etc.).

There’s nothing inherently wrong with these ideas, but none of them feel quite right. You may have noticed a theme to the buckets - they all add something. Added security. Added police presence. Added training.

We’re operating in a constrained environment (again, margins are thin), yet we can’t help but invest in adding something to remove the problem. What we so often overlook is removing something from the equation.

Take a look at that picture of the storefront again. Did you notice that advertisements obscure all of the windows? Gee, I wonder why criminals see your store as an easy target.

This may sound like a silly example, but it’s based on a program launched by the police in Canada called Clear Zone. The basic premise is simple - providing visibility directly into a store and the front counter from the street deters criminals because they know it's more likely they'll get caught. Launched in 2013, it reduced robberies by 18%…and, most importantly, it cost the stores virtually nothing.

The owner of this Circle K removed posters from the far left window to see the cash register from the street.

Our default mode to add is not exclusive to convenience store owners. Behavioral scientist Leidy Klotz designed a series of experiments with lego structures to showcase how we often overlook removing something to improve it (emphasis mine).

Behavioral Scientist

In one study, recently published in Nature, we challenged participants to modify a sandwich-like structure made from Legos so that it was strong enough and high enough to hold a masonry brick above the head of a stormtrooper figurine. Each participant received a structure consisting of parallel horizontal Lego panels connected by a vertical column that narrowed to only one block wide where it connected to the top panel. We asked participants to:

“Improve this project so that it can hold a brick above the storm trooper’s head without collapsing.”

And we offered an incentive:

“You will earn one dollar if you successfully complete this task. Each piece you add costs ten cents.”

The best solution is to remove the single block forming the thin part of the column. The top panel can then be attached to the larger section of the column, which stabilizes the structure and still leaves enough clearance to avoid the storm trooper getting squashed by the masonry brick.

Subtracting one block was the fastest way to solve the problem. Plus, only subtracting allowed participants to earn the full dollar.

And yet participants were still more likely to add than subtract. This was evidence that people add to their detriment—at least when trying to modify a Lego structure so that it can hold a brick safely above the head of a stormtrooper.

The full paper is fascinating, but you get the point. Only when prompted to consider subtraction did anyone consider removing a brick to stabilize the structure. Otherwise, people focused on adding bricks despite the cost.

This reveals something profound about our thinking: We equate addition with progress and subtraction with loss. Even when subtraction is clearly better—cheaper, simpler, more elegant—our instinct is to build up rather than pare down.

Subscribe now

The Hidden Costs of Addition

The problem with an addition mindset is that it attempts to solve with scale rather than sense. This bias toward more creates mounting complexity that slowly suffocates organizations:

1. Complexity Debt: Each addition—whether it's a new process, feature, or role—creates hidden maintenance costs that compound over time. Like technical debt in software, this complexity debt slowly suffocates innovation and agility.

2. Resource Dilution: When we consistently solve problems by adding resources, we spread our attention and energy ever thinner. More meetings, more reports, more initiatives—each new addition divides our focus further.

3. Solution Bloat: Adding becomes our default response, even when subtraction would be more effective:

   • When productivity drops, we add another collaboration tool instead of removing unnecessary meetings

   • When deadlines slip, we add more checkpoints instead of simplifying the process

   • When sales decline, we add more features instead of removing friction

In most cases, these efforts are not only allowed but celebrated. As discussed in The Dangers of Playing it Safe, doing more is a good cover for when nothing is going well. Sure, times are tough, but look at their effort…or so the thinking goes. Ultimately, these strategies delay the inevitable, but that doesn’t negate the attractiveness of the tactic.

The key to all of this is to remember that subtraction isn’t about doing more with less but removing what doesn’t meaningfully move you forward. Paradoxically, only by removing things that would otherwise diffuse our efforts can we ultimately end up with more.

When things aren’t adding up, start subtracting.

How to Make Subtraction Your Default Strategy

When asked how he created his masterpiece David, Michelangelo responded by saying, “It's simple. I just removed everything that is not David.”

This is the essence of subtraction—seeing what doesn't belong and having the courage to remove it.

Here's how to teach yourself to see the solution waiting to be revealed by subtraction:

First, Change Your Questions. The hardest part isn't the removing—it's knowing what to remove. Start by replacing the questions that trigger our addition bias:

Then, Make It a Practice. Subtraction requires discipline:

• Before discussing things you could add, list three things you could eliminate

• When reviewing plans, count the ratio of additions to subtractions

• Look for places where a series of recent additions have created complexity over time

Finally, Make It Visible. Subtraction often goes unnoticed—which is exactly why it needs celebration:

• When a team eliminates three unnecessary meetings, celebrate that win

• When someone simplifies a process from twelve steps to three, tell that story

• When a product succeeds by removing features, make it a case study

The truth is, subtraction isn't about having less—it's about making room to do more. And in a world obsessed with more, the ability to subtract might be your most valuable skill.

Sometimes, the most powerful solution isn't hidden behind what's missing—it's hiding behind what's already there. Like a window obscured by advertisements, or a LEGO structure one brick too heavy, your next breakthrough might not need anything new.

It might just need less.

Share CFO Frameworks

When asked about his remarkable physical transformation for It's Always Sunny in Philadelphia, Rob McElhenney offered a simple explanation:

Look, it's not that hard. All you need to do is lift weights six days a week, stop drinking alcohol, don't eat anything after 7pm, don't eat any carbs or sugar at all, in fact just don't eat anything you like, get the personal trainer from Magic Mike, sleep nine hours a night, run three miles a day, and have a studio pay for the whole thing over a six to seven month span. I don't know why everyone's not doing this. It's a super realistic lifestyle and an appropriate body image to compare oneself to.

Rob McElhenney's sardonic description reveals an uncomfortable truth about efficient growth: it's neither efficient nor sustainable. His "perfect" transformation required unsustainable precision, resource abundance, and single-minded focus.

Sound familiar? It should. This is exactly how we talk about corporate growth in 2025. Just optimize everything. Eliminate all waste. Grow efficiently. All as if perfect execution alone could guarantee sustainable growth.

But McElhenney's transformation worked precisely because it was unsustainable - a focused sprint of growth that required extraordinary resources (studio backing), extreme discipline (strict regimen), and singular focus (no competing priorities).

The tech industry's current upheaval shows what happens when we chase this impossible standard of sustainable efficiency. During the zero interest rate period (ZIRP), companies had abundant capital but lacked discipline. Now they're swinging to the opposite extreme - cutting 260,000 jobs in 2023 alone in pursuit of perfect efficiency. Both approaches miss a fundamental truth: growth isn't always meant to be efficient.

While the broader economy has remained stable, tech companies are wrestling with a fundamental reset in how they think about growth. The conventional wisdom points to two factors:

1. Companies overbuilt during COVID, misreading temporary demand spikes as permanent shifts

2. Capital now has a real cost, forcing harder choices about which projects to pursue

But this explanation misses something deeper. The real story isn't about mistakes but the fundamental nature of growth itself.

Any organism or organization facing rapid change has three options:

1. Get Large - Build aggressively to capture the opportunity, accepting that growth will be messy

2. Get Lean - Preserve resources and efficiency, risking missed opportunities

3. Maintain - Wait for more clarity, knowing the choice will eventually be forced

During COVID, tech companies that chose to "Get Large" weren't ignoring efficiency - they were acknowledging that explosive growth is inherently inefficient. Those who tried to "Get Lean" preserved their resources but watched competitors capture market share they'll never recover.

This tension creates a natural cycle: periods of aggressive, inefficient growth followed by necessary consolidation and refinement. The companies that get in trouble aren't the ones who grow messily - they're the ones who don't recognize when it's time to shift between these phases.

This creates a deeper strategic challenge. As we discussed in The Dangers of Playing It Safe, following the crowd guarantees average results. The real opportunities come from taking non-consensus positions - deliberately choosing a different path than your peers.

But here's the paradox: when growth opportunities appear, everyone faces the same pressures to "Get Large." Choosing to "Get Lean" requires the courage to look wrong while others grow. Choosing to grow requires accepting inefficiency while others optimize.

So the question isn't whether to grow efficiently - it's how to navigate these cycles with intention rather than being pushed around by them.

The companies that chose to "Get Large" during COVID weren't necessarily wrong. The e-commerce shift was real - they just overestimated its magnitude. But here's the key insight: their real mistake wasn't growing too fast, but failing to recognize when it was time to shift gears.

This points to a crucial truth about growth: the problem isn't that growth is inefficient - it's that we keep trying to make it efficient.

When you try to grow "efficiently," you end up neither truly growing nor truly efficient. It's like trying to gain muscle while staying lean - the physics don't (naturally) work that way. You either starve the muscles you’re trying to build, or you’re so focused on growth that you don’t notice most of what you’ve gained is fat.

This brings us to the core insight: when you commit to getting large, you will inevitably get too large. It's not a mistake - it's physics. Growth requires experimenting with new approaches, entering new markets, trying new strategies. Some of these bets will work perfectly. Many won't. But these "inefficiencies" aren't failures - they're the necessary cost of learning what works.

Getting more than you bargained for in times of growth isn't a function of greed or poor judgment - it's just how growth works. In nature, in bodybuilding, and yes, in business.

This points to a crucial distinction that most companies miss: the difference between trying to grow efficiently and managing growth efficiently.

Growing efficiently means attempting to eliminate waste during periods of expansion - a recipe for stunting your growth. Managing growth efficiently means embracing the natural cycle between periods of aggressive growth and strategic consolidation.

The key isn't to avoid inefficiency - it's to get better at shifting between these phases with intention.

Subscribe now

The Natural Rhythm of Growth

At its core, growth follows a simple formula: combine stimulus with supply. A muscle grows when stressed and fed. A business grows when opportunity meets resources.

But here's where most growth strategies go wrong: they try to optimize this formula for efficiency, as if the right balance of inputs could eliminate waste. This fundamentally misunderstands how growth works.

Consider competitive bodybuilding - perhaps the most scientific approach to intentional growth we have. Yes, it's technically possible to build muscle while staying lean, just as McElhenney showed. But it requires unsustainable levels of precision, resource abundance, and single-minded focus. Most athletes, like most companies, can't maintain that perfect balance indefinitely.

Instead, most successful bodybuilders embrace a different approach: deliberate cycles of growth and refinement. During bulking phases, they accept some fat gain as the cost of building muscle. During cutting phases, they accept some muscle loss as the price of getting lean. The art isn't in avoiding these trade-offs, but in managing them strategically.

This cycling approach works because it acknowledges two fundamental barriers to sustained efficient growth:

1. Aversion to bloat. Nature abhors a vacuum, and humans abhor waste. In any growth endeavor, we’re hyperaware of external signals that we are (or could be) failing. If we fail to realize some level of waste is expected, we could starve the growth in our efforts to eliminate the excess. In our muscle building example, we tend to undermine our gains because we fear adding fat to pursue muscle. This fear of fat causes us to undereat, creating a caloric deficit, which means our body can't adequately feed the growth we're working towards.

2. Capacity for precision. We tend to confuse the abundance of data available to us with the precision in which we can wield it. Data is naturally messy, and our over-reliance on what numbers say compounded by our inability to consider alternative interpretations of the output tends to result in surprises. For example, our muscle growth model presupposes you know (1) how many calories you burn and (2) how many calories you consume. Unfortunately, standard tools such as fitness trackers and food labels are notoriously imprecise, with error rates of up to 90 percent and 20 percent per FDA guidelines, respectively.

Most competitive bodybuilders have turned these limitations into advantages. Instead of fighting the inefficiencies inherent in growth, they plan for them. Their approach is elegantly simple:

During bulking cycles, they:

• Target steady weight gain (0.5-1 pound per week)

• Accept that this includes both muscle and fat

• Adjust course based on real results, not theoretical targets

• Focus purely on growth, knowing they can refine later

During cutting cycles, they:

• Switch completely to fat loss mode

• Accept some muscle loss as inevitable

• Use the same measured approach to minimize losses

• Time these phases around competition schedules

The key insight isn't just that they cycle - they fully commit to each phase rather than trying to optimize for everything at once.

The Growth Cycle in Practice

This pattern of intentional expansion followed by strategic refinement isn't unique to bodybuilding - it's fundamental to how growth works in any domain:

• Innovation: Consider Nvidia's dominance in AI. They didn't achieve it through careful efficiency - they overbuilt GPU capacity for crypto, accepting massive waste. When that market collapsed, they had the scale ready for the AI boom. Their "inefficiency" became their advantage.
  

• Marketing: As Rory Sutherland notes, effectiveness often requires inefficiency. Wedding invitations sent by mail are "wasteful" compared to email, but that very inefficiency makes them effective. The goal isn't to minimize cost but to maximize impact.
  

• Careers: 's J-Curves vs. Stairs framework shows how the most successful careers alternate between risky growth spurts (the J-Curve) and periods of consolidation (the Stairs). Like bodybuilders cycling between bulking and cutting, professionals need both phases to achieve sustained growth.

Making Growth Cycles Work in Practice

Mastering these growth cycles means first accepting a counterintuitive truth: not every part of your business should be efficient at the same time. Just as bodybuilders can't simultaneously maximize muscle growth and minimize fat across their entire body, companies can't optimize every division at once.

This creates a fundamental challenge: how do you know which parts of your business should be lean and which should be large? The answer lies in understanding where each division sits in terms of its growth potential and current profitability:

Managing across these quadrants requires three key capabilities:

Portfolio Balance

• Maintain a mix of bulking and cutting initiatives

• Fund growth experiments with optimization gains

• Be willing to drop what isn't working to fuel what is

• Accept that peak performance is temporary

Measurement Systems

• Track both efficiency metrics (unit economics, margins) and growth metrics (market share, ARR growth) across all areas

• In bulking zones, allow some efficiency trade-offs to enable growth but maintain minimum performance thresholds

• In cutting zones, pursue efficiency gains that don't fundamentally compromise growth potential

• Watch for signals that it's time to shift phases

Resource Flexibility

• Create distinct but flexible pools for growth and optimization initiatives

• Build appropriate buffers - larger for growth experiments, tighter for efficiency projects

• Keep some resources mobile to support phase transitions

• Maintain optionality without sacrificing commitment to current priorities

The art isn't in perfecting any one phase - it's in managing the transitions between them. Like a bodybuilder cycling between bulking and cutting, success comes from knowing when to shift gears and having the courage to commit fully to each phase.

Conclusion: The Courage to Grow

Don't fret, baby, we're simply growing.
- 8105, Moving Mountains

What we're seeing in today's tech industry isn't a failure of growth strategy - it's a natural part of the growth cycle. The challenge isn't that companies grew inefficiently during ZIRP, or that they're cutting too aggressively now. The challenge is that we keep trying to eliminate these cycles rather than master them.

The path forward requires three shifts in how we think about growth:

1. Accept the Physics - Growth will always generate some waste. The goal isn't to eliminate inefficiency but to make it productive.

2. Embrace the Rhythm - Like bodybuilders alternating between bulking and cutting, companies need to intentionally shift between expansion and optimization.

3. Focus on Timing - The key skill isn't growing efficiently - it's recognizing when to shift between phases. Get this right, and the inefficiencies become investments in your next phase of growth.

The companies that will thrive aren't those pursuing perfect efficiency. They're the ones learning to dance between these phases with intention, understanding that sustainable growth isn't about avoiding waste - it's about turning today's inefficiencies into tomorrow's advantages.

Call me a safe bet, I’m betting I’m not

I’m glad that you can forgive

Only hoping as time goes, you can forget

-Brand New, The Boy Who Blocked His Own Shot

One of the great ironies of life is we have a strong tendency to play it safe, even if it costs us the win.

In boardrooms and budget meetings, we make choices that seem prudent and wise: spreading resources evenly to avoid risk, maintaining systems that "still work," and preserving structures that have "always worked."

Each careful choice helps us avoid failure. And each careful choice guarantees we'll never achieve excellence.

The issue stems from a cognitive bias called loss aversion, where the pain of loss is felt twice as intensely as an equivalent gain. This psychological quirk makes us excellent at avoiding downside but terrible at capturing upside.

Imagine finding $20 on the street only to have it blown out of your hands by a strong gust of wind. Economically, you’re in no worse a spot than before you found the money, but you feel worse because it feels like you lost $20 ($20 gain - $40 loss).

When triggered, this predilection for avoiding a loss causes us to conflate safety with success. While the two can lead you to the same choice, they aren’t synonymous.

The safe choice is nestled in averages. As the old saying goes, there’s safety in numbers, so when threatened, we look to conform to what most people would do in our shoes. There’s little, if any, upside to be had because we’re seeking the herd's protection rather than leading the pack.

That’s not to say there isn’t value in using common sense. Sometimes adequate is sufficient. This gets us in trouble when there’s dissonance between what we want and the behaviors we exhibit. When we want to be great but we deliver average.

This psychological dynamic creates a predictable pattern in professional decision-making, one that Howard Marks, co-founder of Oaktree Capital Management, captured perfectly in his memo "Dare to Be Great." His simple framework reveals why the safest path so often leads to mediocrity:

His overarching point is that superior results require a synthesis of unconventionality and accuracy, as payoffs can only be high when a select few are particularly prescient. This is effectively the Pareto principle in action - 20% of the activity will deliver 80% of the results.

What goes unnoticed, though, is how appealing the bottom two quadrants are. Sure, you can’t be elite by following the consensus, but delivering average on a consensus position is defensible. It’s safe. If you aim to maintain the status quo, you’re better off sticking with the like-minded masses rather than venturing outside the box with the non-consensus few.

Finance leaders face this same dynamic daily. Whether it's sticking with legacy systems despite their inefficiencies, maintaining conventional reporting structures that blur accountability, or spreading resources evenly across initiatives rather than betting on breakthrough opportunities - the "safe" choice often feels easier to defend than the bold one that could deliver extraordinary results.

To see how this plays out in practice, consider NFL play-calling. Winning in the NFL is hard, but you can improve your odds by keeping the opposing offense off the field. When faced with converting a short-yardage situation where success means keeping possession of the ball, having the quarterback (QB) run behind the offensive line has resulted in a first down 84% of the time over the last five years. There are few guarantees in life, but with those odds, it’s about as close as you’ll come in a game of skill.

And yet, coaches have only used that formation 10% of the time.

What’s happening here? Nine times out of ten, NFL coaches call a play with a significantly lower success rate than the QB sneak. One could argue that the play is so effective because it’s used infrequently, but it’s hard to imagine a play-calling strategy with a higher mix of QB sneaks wouldn’t result in a net increase in first downs.

In these high-pressure moments, it’s doubtful that the coach doesn’t want to win. Here, loss aversion is likely still in play, but it’s not the game they’re worried about; it’s their job.

The quarterback is arguably the most valuable player on the field, and putting them in harm’s way is a good way to get put on the hot seat. The sneak is significantly safer than a dropback pass where the quarterback is exposed to open-field or blindside hits where injury risks are significantly higher. However, it’s not statistics that stand out in our minds; it’s frequency. If your quarterback gets hurt on a common play, the masses will consider it an unfortunate event but a risk of the game. But if someone gets hurt on a play rarely seen, it’s easier to blame the play call than probability.

In other words, conventional failure preserves your career. Unconventional failure ends it.

Running with the herd is easier than leading the pack when your livelihood is on the line.

Perhaps the most unsettling truth about safety is this: it’s appealing not because it prevents failure but because it spares us from having to explain our failures.

A failed consensus choice comes with a built-in alibi - everyone else would have done the same thing. But a failed unconventional choice? That requires justification, defense, explanation. We optimize for accountability, not outcomes.

This is why great leaders aren't just comfortable being wrong - they're comfortable being wrong in ways that no one else would dare to be wrong. They understand that the path to extraordinary results requires extraordinary mistakes.

The point is this: if your goal is above-average results, you can't get there by chasing safety. Yet that's exactly what we do - through increasingly sophisticated forms of avoidance that we mistake for strategy.

The Three Illusions: How Safety Undermines Excellence

These patterns are subtle but devastating. They feel like prudent management but systematically destroy the possibility of excellence:

• The Illusion of Balance - We spread resources evenly across priorities, calling it "comprehensive" or "strategic," which is an implicit preference for activity over outcomes. We guarantee we'll be great at nothing when we try to be good at everything. Real impact requires the courage to choose what matters most. Excellence demands concentration.
  

• The Illusion of Certainty - We gather more data, build more models, seek more validation. But excellence lives at the edge of uncertainty, where data runs out and judgment begins. Analysis should inform our leaps forward, not justify our standstill. Every datapoint that delays action is a shield against excellence.
  

• The Illusion of Discovery- We launch initiatives under the banner of "learning and discovery," stating unequivocally “we’re going to learn” but without any specific hypothesis to prove wrong. This isn't science; it's structured wandering. We can always claim success because we never committed to what success looks like. Excellence requires the courage to be precisely wrong, not vaguely right.

The Right Risks

Excellence isn't about eliminating risk but choosing the right ones. Start by identifying one "safe" choice in your organization that's holding you back. Perhaps it's a legacy system everyone curses but no one replaces, a meeting everyone attends but no one values, or a process that protects reputations but destroys results.

Then ask yourself: What would excellence look like here? Not adequacy, not industry standard - excellence. Between your vision and current reality lies the cost of caution.

Playing it safe isn't playing to win. It's just a respectable way to lose.

"Shoot for the moon. Even if you miss, you'll land among the stars."

We love these inspiring calls to aim high. But sometimes reaching your destination is worse than missing it entirely – when you get exactly what you asked for but not what you needed.

This is precisely what happened in 1999 with NASA's Mars Climate Orbiter. Built by the best minds from NASA's Jet Propulsion Laboratory (JPL) and other collaborating institutions, it carried state-of-the-art instruments to map the Martian atmosphere and surface. Together, they embarked on a journey that was supposed to add a new chapter in space exploration.

Then, the $125 million probe crash-landed on Mars.

The crash was attributed to the units of measurement used by different teams: Lockheed Martin engineers were using the imperial system (pounds-force), while NASA's team used the metric system (newtons). Beyond the failure to align on measurement, there were several instances where one or both teams failed to course correct. NASA scientists noticed that the Orbiter was drifting off course almost immediately, but managers demanded that the worriers and doubters "prove something was wrong."

Despite constant measurement and a clear vision of where they wanted to land, NASA allowed the probe to shift 100 kilometers off course at the end of its 500-million-kilometer voyage--more than enough to hit the planet's atmosphere and be destroyed accidentally.

The problem here was not the error; it was the failure of NASA's systems engineering, and the checks and balances in our processes, to detect the error. That's why we lost the spacecraft.- Edward Weiler, NASA Associate Administrator for Space Science

Even the most capable teams can get pulled off course. The difference between success and failure isn't in the size of the deviation—it's in how quickly you detect it.

Like spacecraft encountering gravity wells in space, teams face invisible forces that can gradually pull them farther and farther from their intended path. The deviation starts small, almost imperceptible, but compounds over time.

Our trajectory is subject to the gravitational pull of other ideas, projects, and priorities. Steering the ship requires immense focus, and that focus must be on the right things.

Consider Blockbuster, which promised shareholders a digital future while doubling down on physical stores. Or Blackberry, which promised customers the best mobile experience while clinging to outdated keyboards. Or Kodak, which saw the digital future coming but promised investors they'd protect the film business instead.

The tragedy isn't just making the wrong choice—it's faithfully executing it right into obsolescence.

Prioritization is a superpower — one that can differentiate high-performing individuals and teams. More importantly, prioritization is a superpower that can be learned.

To be good prioritizes, we first have to learn why we suck at it in the first place.

The Forces That Pull Us Off Course

Every gravity well starts with a gentle pull. It's barely noticeable at first—just a slight tug away from your intended course. But the closer you get, the stronger it becomes until breaking free requires more energy than you might have.

Here are the five gravity wells that capture even the best teams:

• The Path of Least Resistance: We naturally gravitate toward easy, visible work instead of crucial challenges. It's not laziness—it's human nature to prefer immediate progress over tackling complex problems. However, this tendency leads teams to postpone the very challenges that could make or break their success.

• The Planning Fallacy: We consistently take on more than we can deliver. This isn't just optimism—it's a systematic underestimation of what it takes to execute well. When everything is a priority, nothing truly is.

• The Urgency Illusion: We react to what feels urgent rather than what's truly important. The constant ping of emails and messages creates a false sense of urgency that hijacks our attention from meaningful work.

• The Perfectionist's Dilemma: We treat every task as equally important, investing the same level of effort regardless of strategic value. This isn't about having high standards—it's about failing to distinguish where those high standards matter most.

• Shiny Object Syndrome: We constantly pivot to the next big thing, abandoning established priorities for novel initiatives. This isn't just a distraction—it's a systematic undervaluation of consistent execution in favor of new possibilities.

These patterns act like gravity wells: subtle at first but increasingly powerful as you drift closer. What makes them particularly dangerous is how they masquerade as virtues: responsiveness, ambition, thoroughness, adaptability. By the time you realize you're caught in their pull, breaking free requires tremendous energy.

Breaking Free: Your Navigation Systems

Willpower won't save you from the pull of gravity wells. But the right frameworks will.

1. The Monkey and the Pedestal

X Blog

The big idea: Escape the gravity well of easy wins by tackling make-or-break challenges first.

Why we need it: If your goal is to teach a monkey to recite Shakespeare on a pedestal, the last thing you should do is build the pedestal! Yet teams are constantly pulled toward these visible but inconsequential tasks, drifting further from what really matters.

When to use it: Large, complex projects with multiple dependencies or uncertain futures.

Learn more: Google X Blog.

2. Can/Should Matrix

The big idea: Break free from the gravity well of misaligned capabilities and priorities.

Why we need it: Teams often get caught between two forces: the pull of what they can do easily and the attraction of perfect but impossible solutions. This framework helps chart a course between these extremes, keeping teams focused on what's both achievable and valuable. When caught in this well, teams either chase everything they're capable of doing or get paralyzed by perfect solutions they can't execute.

The Can/Should Matrix thus does two things:

1. It reminds us that the top of our list should always be what we can and should do (Boxes 2, 3, and 5).

2. It forces us to identify how to unlock capabilities preventing us from what we should do (e.g., what shifts Box 1 to 2 or 3?).

When to use it: Mid- to long-term team goals.

Learn more: The Beautiful Mess - Can Do vs. Should Do

3. The Eisenhower Matrix

The big idea: Escape the gravity well of false urgency by segmenting your to-do list based on importance and urgency.

• Delegate tasks that are urgent but don't require your expertise

• Delete tasks that don't add measurable value and distract from core tasks

• Do urgent tasks that have material consequences if not completed timely

• Schedule tasks that aren't urgent but usher in long-term goals

Why we need it: The constant pull of "urgent" tasks creates one of the strongest gravity wells teams face. Each urgent request adds to the gravitational force, pulling teams further from what's truly important. We know intellectually what matters most, but the immediacy of urgent tasks creates an almost irresistible attraction.

Imagine a manager with an Exec Team presentation tomorrow, an upcoming team-building activity in a month, a backlog of emails, and Slack messages from various colleagues throughout the day. What typically happens is the emails and Slack messages continue to demand the manager’s attention, meaning she dedicates less time to the Exec Team presentation (Urgent/Important) and the Team-Building activity (Not Urgent/Important), such that what matters most gets rushed.

Using the Eisenhower Matrix, the manager can box out time to focus on what matters and batch unimportant tasks like emails and Slack messages.

When to use it: Personal task lists.

Learn more: Invest Your Time Intentionally with the Eisenhower Matrix (Forbes)

4. The LNO Framework

The big idea: Break free from the perfectionist's gravity well by strategically investing effort where it matters most.

Why we need it: The perfectionist's gravity well is particularly deceptive because it masquerades as excellence. Each task becomes equally weighted, pulling teams into spending precious energy on low-impact work. The closer you get to this well, the harder it becomes to distinguish between necessary quality and diminishing returns.

Shreyas, the creator of this framework, uses this example of a Product Manager’s to-do list to emphasize how the time allocation changes once you think about leverage.

Before LNO:

After LNO:

When to use it: Daily / Weekly tasks.

Learn more: Shreyas’s Tweetstorm.

5. Big Rocks

The big idea: Resist the gravitational pull of constant change by anchoring to your core priorities. If you start filling your time with sand and pebbles (minor tasks and secondary responsibilities), you won't have room for the big rocks (your most important priorities).

Why we need it: The stronger a team's momentum becomes around new initiatives, the harder it is to maintain orbit around what truly matters. Like a spacecraft using a planet's gravity to maintain its trajectory, teams need fixed points—their "big rocks"—to stay on course.

Consider this a longer-term version of the Eisenhower Matrix. The concept is similar - what’s important should be prioritized over what’s unimportant - but you swap out Urgency for Impact (or leverage if you want to think about this in conjunction with LNO). The biases are the same — we tend to focus on what’s recently come across our desk or what conversation has sparked on Slack — but being intentional about what matters allows us to keep these new ideas in perspective.

When to use it: Long-term team goal planning.

Learn more: The Seven Habits of Highly Effective People, Steven Covey.

Conclusion

Most teams don't fail because they choose the wrong destination—they fail because they get caught in gravity wells along the way. What starts as a slight deviation compounds until escape requires more energy than they have left.

The most dangerous part? Each gravity well masquerades as a virtue: urgency disguises itself as responsiveness, perfectionism as excellence, and novelty as innovation. By the time teams realize they're caught, breaking free requires more energy than most have left to give.

That's why great teams need both awareness and tools. They need to recognize these gravity wells for what they are, and they need navigation systems to plot a course through them.

No one is immune to these gravitational pulls. But with the right tools and enough practice, we can learn to detect them early and chart a clear course.

Every priority is a promise to overcome these forces. Make fewer, but give each one enough fuel to escape.

On July 26, 1945, the Allied leaders issued the Potsdam Declaration to Japan—surrender unconditionally or face "prompt and utter destruction." When asked for Japan's response, Prime Minister Kantarō Suzuki told reporters it was one of mokusatsu.

The translation Washington received—"ignore with silent contempt"—triggered outrage. Within ten days, the atomic bomb fell on Hiroshima.

This may be the most tragic misunderstanding in history. The word mokusatsu, derived from "silence," has two distinct meanings. While the inflammatory translation was technically correct, there was a far less provocative interpretation:

"No comment."

While not universally accepted, this latter meaning is widely cited as Suzuki's intention—he was buying time while his government debated the surrender terms.

The translator could have noted this ambiguity. Suzuki could have been more precise. Instead, a single word's dual meaning helped trigger catastrophe.

While few modern miscommunications end in warfare, the business world faces its own costly battles over meaning. A single misaligned term in a strategic plan can waste millions in resources, derail critical projects, or destroy valuable partnerships. Just ask the CFO who approved what they thought was an 'incremental' investment in a new product line, only to discover that while corporate defined 'incremental' as net-new revenue to the company, the division meant revenue that was incremental to their P&L - even if it cannibalized other divisions. Or consider the transformation project where 'run-rate savings' meant something entirely different to Finance (cost reductions achieved in-year) versus Operations (theoretical savings once all changes were fully implemented), leading to a painful earnings miss and some difficult board conversations.

The challenge isn't just about precision - it's about detecting misalignment before it creates chaos.

Subscribe now

What makes these misalignments particularly dangerous is their invisibility. When we encounter completely foreign terms, we naturally seek clarification. But the deceptively familiar phrases—the ones we think we understand—create the deepest chasms of miscommunication. Like a fault line hidden beneath seemingly solid ground, these semantic gaps can remain undetected until they rupture.

These chasms are everywhere in business language, hiding in plain sight. Take a typical strategic planning meeting where everyone nods along to the need for more "innovation." To the CTO, this means investing millions in quantum computing research. To the Head of Product, it means A/B testing different button colors. To the CFO, it means finding clever ways to reduce costs. Three executives leave the room, each confident they're aligned, each heading in radically different directions.

These semantic gaps—what Molly Graham aptly calls "black hole words"—are treacherous because they create an illusion of alignment while masking fundamental disagreements. Like their celestial namesakes, they have massive hidden gravity, pulling resources and effort into an invisible void. But not all misaligned terms are equally dangerous.

Even attempts at precision can fall prey to misalignment. An HBR survey of 1,700 professionals revealed that common probability terms carry wildly different meanings: "highly likely" meant anything from a 50% to 90% chance of success. When millions of dollars hang on such assessments, this variance isn't just semantic—it's existential.

Probability terms are just the beginning. Words like "strategic," "agile," and "customer-centric" have become so stretched and distorted that they've lost any shared meaning. Yet executives continue to build plans around them, like architects trying to measure with elastic rulers.

This raises a crucial question: why do some ambiguous terms create mere confusion while others trigger catastrophe?

Like Inigo Montoya's famous observation about misused words, we need a way to identify terms that don't mean what we think they mean. Let's call it the Montoya Matrix—a tool for mapping language along two critical dimensions:

• Alignment: Do people share the same definition?

• Impact: How much damage can confusion cause?

When we plot terms along these axes, four distinct quadrants of business language emerge:

The Montoya Matrix helps us identify and manage these quadrants, each with its own characteristics and risks:

• Black Hole Words are the most dangerous—terms like "innovation" or "strategy" can derail entire projects when different interpretations collide. Their gravity pulls in multiple meanings while creating an illusion of alignment. These words appear precise enough to build plans but contain hidden chasms of misunderstanding that only become visible when it's too late.

• Binding Words, by contrast, create clarity through precise, enforced definitions. When someone says "board approval" or "EBITDA margin," there's little room for interpretation. These terms often have formal definitions or legal consequences—like "material disclosure" in SEC filings.

• Buzzwords like "synergy" or "thought leadership" create noise but rarely affect outcomes. Everyone knows these terms are more decoration than substance—no one has ever lost sleep over conflicting definitions of "paradigm shift." Their vagueness is so obvious that they function more as corporate wallpaper than decision-making tools.

• Baseline Words provide the foundation for basic coordination—terms like "fiscal year" or "signed contract" that mean exactly what everyone thinks they mean. These terms rarely cause problems because they're either backed by clear external standards or so fundamental that misalignment would make basic business impossible.

Understanding these quadrants reveals why some organizations thrive while others stumble over their words. In healthy environments, teams actively convert Black Hole Words into Binding Words. In toxic ones, people learn to hide behind comfortable vagaries—using ambiguity as a shield.

Like any diagnostic tool, the Montoya Matrix isn't just for identification—it's for action. Here's how to use it:

1. Identify Your Black Holes: Audit your organization's most important documents—strategic plans, OKRs, and project charters. Circle terms that could mean different things to different stakeholders. Pay special attention to words that appear frequently in high-stakes decisions.

2. Convert to Binding Words: For high-impact terms, create explicit definitions with measurable components. If "customer satisfaction" matters to your business, define exactly how it will be measured and tracked. Make these definitions visible and reference them consistently.

3. Eliminate Buzzwords: Replace vague terms with specific, measurable language. "Drive innovation" becomes "launch new products in specific markets." "Improve efficiency" becomes "reduce specific process times by defined percentages."

4. Build on Baseline: Ground complex concepts in commonly understood terms. Rather than asking "Are we aligned on the strategy?" (a Black Hole invitation), ask "What specific metrics will show we're succeeding?" Rather than "significant opportunity," define the actual revenue or cost numbers you're targeting.

The mokusatsu incident shows us that even small linguistic gaps can have massive consequences. While modern business stakes may not reach the level of atomic warfare, they're still profound—failed products, broken partnerships, destroyed careers. Each time we let a Black Hole Word pass unchallenged or hide behind comfortable buzzwords, we risk our own small-scale catastrophe.

The solution isn't perfect precision—it's purposeful clarity. Know which words matter most, define them explicitly, and build the courage to ask, "What exactly do you mean by that?"

The cost of clarity is the momentary discomfort of asking hard questions. The cost of ambiguity is the lasting pain of acting on wrong answers.

Subscribe now

Share

Leave a comment

Early in my career, I earned the unfortunate nickname “Dr. No.”

Some form of this moniker is pervasive for gatekeeper organizations, bordering on the banal. Finance is no exception.

Chief No Officer. The Office of No. The No It All. Ok…the last one is pretty funny, but you get the gist.

It’s understandable why this stereotype exists. Resources are scarce, the allocation of which creates a natural (arguably healthy!) tension between Operations and Finance. If you think of the business as a car, the two operate as the gas and brake pedals, respectively, with the intention that the tandem creates a smooth ride - not too fast, not too slow.

Perceived through this lens, it is expected - predestined, even - that Finance has to say “no” a lot. Otherwise, the car will continue to speed up, eventually careening off the proverbial fiscal cliff.

In practice, stepping on the gas and breaks in quick succession (if not simultaneously!) is anything but smooth. Ideally, the brakes are only applied in emergencies or transition points. You don't have to rush to slow down if you’re conscious about when to speed up!

As a recovering no-aholic, I discovered that the solution to this problem came from an unexpected place: improvisational theater. By adapting their techniques, I developed a response framework that preserves Finance's role as a partner and financial steward while breaking free from the "Dr. No" stereotype.

The key? Starting with "yes."

Yes, And

In the early days of improvisational theater, performers often tried to one-up each other with clever quips or jokes. This competition undermined the scene, with performers losing confidence in each other and audiences losing interest. Anyone who has watched Michael Scott's painful attempts at improv on The Office has seen this dynamic in action—the constant need to be the star kills the collaborative spirit that makes scenes work.

In the 1950s, a group of performers known as The Second City experimented with a different approach. Rather than competing to be the funniest individuals, they focused on how to be the funniest group. Rejecting each others’ ideas on stage was killing momentum, but simply saying “yes” wasn’t enough to build momentum as the onus to develop the scene reverted to one individual. The best scenes were those that leveraged all of the talents on stage.

This insight led to the development of “Yes, And,” where performers would accept and, most importantly, build on each other’s ideas instead of trying to outdo them. The intent is not to develop every idea but to maximize momentum by focusing energy on building upon each other rather than tearing each other down. Often, the words “yes, and” aren’t even uttered - the new information is implicitly accepted and built upon.

As you watch the scene above, notice how ideas are treated as abundant rather than scarce. Not every concept is expanded upon - many are acknowledged and allowed to fade away - but the duo never stops to debate what’s been added to the scene. This is the real power of Yes, And - the performers leverage each other’s contributions in linguistic judo to move towards an aligned objective.

Now that we understand what Yes, And is, let’s turn our attention to how leveraging it will disqualify you from winning the “No”bel prize.

The V/C Response Framework

When presented with an idea, we effectively have two decision spectrums to factor into our response: validation (V) and collaboration (C).

• Validation (no → neutral → yes) reflects the degree to which someone feels heard, irrespective of the approval outcome.

• Collaboration (conflict → neutral → collaborate) reflects the effort to build towards a desired outcome, irrespective of the degree to which the proposed idea factors into that equation.

The key to the point above is that the quality of the response is not based on the decision but on the presentation. How we respond is just as important as what we say. This framework suggests that we can make someone feel heard and valued, even if their suggestion is rejected.

In How to Castrate a Bull, NetApp co-founder Dave Hitz describes how he leverages this framework to defend unpopular decisions.

Let’s say you have decided to pursue Plan A. As a manager, it is part of your job to defend and explain that decision to folks who work for you. So when someone marches into your office to explain that Plan A sucks, and that Plan Z would be much better, what do you do?

My old instinct was to listen to Plan Z, say what I didn’t like about it, and to describe as best as I could why Plan A was better. Of course, the person has already seen these same arguments in the e-mail I sent announcing the decision, but since they didn’t agree, they must not have heard me clearly, so I’d better repeat my argument again, right? I can report that this seldom worked very well.

It works much better if I start out by agreeing: “Yep. Plan Z is a reasonable plan. Not only for the reasons you mentioned, but here are two more advantages. And Plan A—the plan that we chose—not only has the flaws that you mentioned, but here are three more flaws.” The effect of this technique is amazing. It seems completely counterintuitive, but even if you don’t convince people that your plan is better, hearing you explain your plan’s flaws—and their plan’s advantages—makes them much more comfortable.

Yes, And is not about agreeing with someone. It’s a technique to recognize the value of and encourage participation in the ideation process. It’s a belief that we’re at our best when moving forward rather than stopping or looking backward.

The Four Response Types (And Only One That Works)

Picture this: You're in a meeting, and someone pitches an idea. At that moment, you have four ways to respond.

Three will mark you as Dr. No.

One will transform you into a trusted partner.

Let's dissect them:

Looking at the quadrants, it becomes clear why more than half of common responses effectively translate to "no":

• "Yes, But..."—The Performer. As Jon Snow wisely notes in Game of Thrones, "Everything before the word 'but' is horseshit." This response masquerades as support while delivering rejection. It's like starting a breakup with "You're amazing, but..." Everyone knows what's coming, and that initial "yes" makes it worse. Try this: Strip out the "yes" and see if your message changes. Spoiler alert: it won't.

• "No, But..."—The Hedger This is the corporate equivalent of "I'm not sure I can make it to your party." It's a “no” disguised in maybes and caveats. When we lead with "No, but," we're either unsure of our authority or trying to soften the blow. Either way, we're eroding trust. Better to be clear than wishy-washy.

• "No, And..."—The Hijacker This response comes in two equally problematic flavors; both stem from ego and kill collaboration faster than a Game of Thrones wedding.

  • The Opportunist: "No to your idea, and let me tell you about my completely unrelated agenda!"

  • The Supreme Leader: "No to your feature X, because my feature Y is clearly superior!"

• "Yes, And..."—The Builder. Finally, the response that changes everything. This isn't about rubber-stamping every idea. It's about saying, "I hear you," and "Let's see what's possible." When you respond with "Yes, and," you're not approving the specific request—you're approving the collaboration.

Think of it like improv comedy: The best scenes happen when performers build on each other's ideas rather than competing for the spotlight. "Yes, and" keeps the momentum going while steering toward better solutions.

To help ground the theory, let’s apply it to an everyday use case. Imagine a business partner approached you for approval to throw an unbudgeted, expensive year-end party to celebrate the team’s efforts throughout the year. This matters a lot to the team, and there is no question that the budget cannot absorb this incremental spend. Which response do you believe will be best received?

1. Yeah…that sounds like a good idea, but we can’t afford it.

2. We don’t have that in the budget, but you’re welcome to follow up with the CEO to see if he’s willing to take that hit to the P&L.

3. We can’t afford it (followed by a bah-humbug for good measure).

4. We don’t have that in the budget, and candidly, I’m not sure we should be throwing a celebration when our gross margins have eroded over the last three quarters.

5. That sounds like something the team would appreciate, and given how we’re pacing on the P&L, we’ll have to figure out a way to fund it.

Unless you take distinct pleasure in disappointing others, #5’s Yes, And is the winner here. The same message is delivered in all instances (we don’t have the budget), but the response validates the requestor and shifts the discussion to how to do what they want within the current constraint environment. By inviting the requestor into the process, the question is reframed from “can I spend this money” to “what am I willing to give up to have this party.” This is no longer a yes/no question; it’s a trade-off question.

Poof, no more Dr. No.

Why This Matters

The shift from "Dr. No" to "Yes, And" isn't just about making Finance more likable—it fundamentally transforms how organizations make decisions and allocate resources. When Finance leads with "No," three harmful patterns emerge:

1. Shadow Spending - Teams learn to hide expenses or fragment them into smaller, under-the-radar purchases.

2. Decision Paralysis - People stop bringing ideas forward, creating a culture of risk aversion.

3. Us vs. Them - The organization splits into camps: those who "make things happen" and those who "prevent things from happening."

In contrast, when Finance leads with "Yes, And," we see:

• Better Ideas - When people help shape a solution rather than defend against objections, they invest more deeply in its success. Instead of working around constraints, they work with them.

• Earlier Influence - By being seen as an enabler rather than a barrier, Finance gets a preview of initiatives while they're still forming. This early seat at the table means more opportunity to shape direction, not just approve or deny.

• Stronger Partnerships - Teams stop viewing Finance as the department of "no" and start seeing us as collaborative problem-solvers. This trust leads to more transparent discussions about challenges and constraints.

Most importantly, this approach preserves what matters: financial discipline. We're not saying yes to everything—we're creating an environment where constraints breed creativity rather than frustration.

Tips on How to Say Yes, And

While simple in concept, mastering "Yes, And" requires deliberate practice and a shift in mindset. Here are specific techniques to help you break free from the "No It All" reputation:

• Seek the Why before the Why Not. When your sales leader proposes hiring three new reps in a hiring freeze, resist the urge to say, "We can't afford it." Instead, understand the underlying need: "We're losing deals because we can't cover our territories." Now you have a foundation to build upon: "I see how coverage gaps hurt revenue. What if we reallocated our most experienced reps to high-value accounts and hired one strategic SDR to support them?"

• Lead with Questions, Not Answers. When you're struggling to find the good, get curious: "Help me understand what problem this solves?" or "What would success look like?" Often, the real opportunity isn't in the initial proposal but in the underlying need.

• Ban the But. Our brains are wired to forget everything before the word "but." That seemingly harmless conjunction erases any goodwill built by your initial agreement. Eliminate it from your response template, and watch how andnaturally creates bridges instead of walls: "That's an innovative approach, and here's how we could make it work within our budget constraints."

• Build the Chain. Each And should invite another. Picture a product launch discussion: "Yes, we could accelerate the timeline, and if we reallocate Q3 marketing spend..." which leads to "Yes, and we could start pre-sales earlier..." which leads to "Yes, and that would give us customer feedback before full launch..." Watch how momentum builds as each person adds their link to the chain.

The Final Yes

Breaking free from being Dr. No isn't just about changing how we speak—it's about transforming how we think about our role in the organization. Finance professionals aren't here to say no; we're here to help find the way to yes. When we lead with curiosity instead of judgment, with collaboration instead of control, we become true partners in building the business.

The next time you feel that reflexive "no" rising to your lips, pause. Seek the why before the why not. Ask questions before giving answers. Ban the but. Build the chain. You might find that the best way to protect the business isn't by being Dr. No—it's by being Dr. Know-How-To-Make-It-Happen.

In December 1914, Ernest Shackleton faced a leader's nightmare. His ship Endurance was trapped in Antarctic pack ice, slowly being crushed. Twenty-seven men stranded. No radio. No rescue coming. Just vast ice fields stretching to every horizon, with temperatures plunging below -20°F.

For many leaders, such chaos would have meant paralysis. But Shackleton did something remarkable: He turned clarity into momentum. First, he gathered unvarnished facts: 1,200 miles from safety, six months of food, and zero chance of rescue. This clear sight led to focused action: salvaging supplies, building ice camps, and maintaining morale. Each move revealed new possibilities, and each success built confidence until they had enough momentum to attempt what seemed impossible: a journey across 800 miles of the world's most treacherous seas.

Through seventeen months of relentless effort, this momentum carried every single crew member to safety. They survived brutal storms, navigated treacherous seas, and crossed unmapped mountains. But more remarkably, they proved something vital about leadership: clarity, properly applied, creates unstoppable momentum.

While few of us will face Antarctic challenges, we all encounter moments that demand this same transformation of clarity into momentum. Whether navigating a career transition, leading through change, or launching a venture, the fundamental question remains: How do you turn clear sight into unstoppable progress?

The answer lies in three frameworks that work together as a momentum-building system. Think of them as both navigation tools and parts of a powerful flywheel:

• The Strategic Lens converts observation into action.

• The Sphere of Influence aligns action with your level of influence.

• The Uncertainty Map guides you on how confidently to advance.

These frameworks serve two vital functions:

1. As individual frameworks, they help you move skillfully through uncertain territory.

2. As a flywheel, they generate momentum that makes each turn more potent than the last.

Like a physical flywheel, this system takes initial effort to start turning. But once in motion, it creates compound benefits:

• Clear sight reveals where to focus

• Focused action expands your influence

• Smart navigation reveals new opportunities

• Each turn builds momentum for the next

Let's start with your first push: seeing reality with absolute clarity. This initial framework—which Shackleton used on the ice—converts raw observation into actionable insight.

1. The Strategic Lens - Seeing Reality Without Filters via the 3 What’s

When chaos strikes, our instinct is to act immediately. This is what makes Shackleton's first moments on the ice remarkable—instead of rushing to action, he forced himself to see the situation exactly as it was, not as he wished it to be.

The Strategic Lens framework builds this discipline into three deceptively simple questions (the 3 What’s):

While straightforward on the surface, answering them with candor often requires pushing past our natural biases and defense mechanisms. Further, it requires us to push beyond what feels like a natural finish line - explaining what happened - to convert it into a compensating response.

Key Principles

• Ruthlessly separate facts from interpretations—be skeptical of answers that begin with “I think,” “I assume,” or “I would expect.”

• Question your assumptions, especially those that make you comfortable—many issues arise from systemic causes, not individual actions.

• Let data, not hopes, drive decisions—not everything is measurable, but if we're willing to disaggregate our existing views, we tend to have more signals than we believe. 

• Focus your strategic response on the impact, not the problem—you don’t need to solve the challenge you identify in raw reality to improve things. 

• Establish feedback loops to assess your understanding—your initial analysis of the situation may change as more information becomes available!

The power of this framework lies in its bias to action. Success arises from the courage to recognize reality instead of holding onto what we hope is true, prioritizing the construction of a future over the chronicling of the past.

2: Spheres of Influence - Focus Your Energy via the 3 C’s

Understanding reality is crucial, but it can also be paralyzing. When Shackleton assessed his situation on the ice, he saw dozens of problems: food shortages, crew morale issues, weather conditions, and navigation challenges. The key to his success wasn't just seeing clearly—it was knowing where and how to exert influence effectively.

This second framework helps you avoid two common traps:

• Overreaching where you lack influence

• Underutilizing the influence you have

Think of your influence extending across three distinct but interconnected spheres (the 3 C’s):

Key Principles

• Start with what's directly within your control—when everything feels overwhelming, the smallest action within your control can create momentum.

• Build influence through demonstrated competence—your sphere of influence grows naturally when you execute well in your control zone.

• Let go strategically, not in defeat—releasing what you can't control isn't surrender; it's a deliberate choice to focus your energy where it matters.

• Treat your spheres as dynamic, not fixed—what you can't influence today might become controllable tomorrow, and vice versa.

• Focus on leverage points, not complete solutions—small actions in the right places often have more impact than grand gestures in the wrong ones.

The power of this framework lies not in controlling everything but in understanding where and how to apply influence effectively. Success often comes from knowing which sphere you're operating in and choosing the right approach for each.

3: The Uncertainty Map - Navigating via the 3 Knowns

After Shackleton assessed his situation and focused his energy, he faced the navigator's eternal question: How do we move forward when we can't see the whole path? Like any skilled explorer, he knew different territories demanded different approaches. You sprint across the open ground but move cautiously through the fog.

The Uncertainty Map is your navigation tool for unknown territory. Just as a physical map helps you choose your path and pace, this framework helps you:

• Know where you stand (What territory are you in?)

• Choose your approach (How should you move here?)

• Spot the dangers and opportunities ahead

• Adjust your speed and commitment to match the terrain

Key Principles

• Build from what you know for certain—verified facts create a foundation for exploring unknowns.

• Convert unknowns into experiments where possible—many "uncertainties" can be tested with small, low-risk actions.

• Distinguish between what you can't know yet and what you can't know at all—timing might be uncertain, but underlying patterns rarely are.

• Use uncertainty as a guide, not a barrier—gaps in knowledge often point to your next strategic opportunity.

• Update your map as territories shift—what was unknowable yesterday might be explorable today.

The strength of this framework lies not in removing uncertainty but in navigating it wisely. Success is achieved by engaging with the unknown rather than being immobilized by it, transforming uncertainty from an obstacle into a guide.

The Clarity Flywheel: Where the Magic Happens

The real power of these frameworks emerges when they work together. Like a flywheel in engineering, the system gains momentum with each turn: facts revealed through your Uncertainty Map strengthen your Strategic Lens, influence gained through focused action expands your Sphere, and clarity about what you can control helps you navigate uncertainty more confidently.

Let's see how this cycle created unstoppable progress in one of history's greatest survival stories.

The Flywheel in Action: Shackleton's Journey

The power of the Clarity Flywheel becomes evident when we trace how Shackleton used all three frameworks in sequence, with each turn building on the last:

First Turn: Initial Crisis (January 1915)

When the Endurance first became trapped, Shackleton immediately began collecting hard data. Through careful celestial navigation, he fixed their position at 69°5'S, 51°30'W. He established a rigorous system of ice observations and supply inventories, creating a clear picture of their situation. This raw data (Strategic Lens) guided his first critical decisions about transforming the ship into a winter station.

With this clarity, he focused his influence where it mattered most: the ship's immediate operation. He reorganized the crew into a three-watch system, maintaining the discipline of a working vessel despite their immobility. Every man had duties, from meteorological observations to caring for the dogs, creating a sphere of productive activity within their ice-locked world.

Most importantly, Shackleton began methodically tracking what they could and couldn't know. While they could measure the ice's thickness and monitor its pressure on the ship, the duration of their entrapment remained unknowable. This acceptance of uncertainty helped him prepare the crew for a long wait while avoiding false promises about quick escape.

Second Turn: Ship's Abandonment (October 1915)

By October, new facts demanded attention. The ship's timbers were cracking under increasing ice pressure, and their position had shifted significantly with the drifting pack ice. Shackleton's careful observations showed the Endurance was doomed, leading to his order to abandon ship on October 27th.

This brutal reality clarified his sphere of control: they needed to create a viable camp on the ice. He focused the crew's energy on salvaging every useful item from the ship—from food stores to planks that could shelter their supplies. The organized routines established during their months on the ship proved crucial, as the crew efficiently transformed their situation from ship-based to camp-based survival.

Their uncertainty map evolved too. While they now knew with certainty they would need to escape by other means, they could begin exploring the movement patterns of the ice floe that became their home. This knowledge would prove crucial in the months ahead.

Third Turn: Escape Planning (April 1916)

After months of careful observation, Shackleton had accumulated crucial data about their drift and the changing ice conditions. Through regular navigation checks, he knew they had moved hundreds of miles north with the current. The warming spring temperatures were beginning to break up the pack ice—both an opportunity and a threat.

His sphere of influence now focused intensely on preparing for their escape by sea. Every man was assigned to specific boats, and they practiced launching procedures and emergency protocols. The crews were carefully balanced, with the most experienced sailors distributed among the three boats.

Their uncertainty map had evolved significantly. While they knew their position and had good data about prevailing currents, the conditions they would face in the open ocean remained unknown. Shackleton used this knowledge to make his boldest decision: rather than attempting to reach the closer but desolate Antarctic continent, they would aim for the whaling stations of South Georgia, where help was certain if they could reach it.

Each turn of the flywheel had built upon the last, transforming overwhelming chaos into actionable decisions. The frameworks didn't eliminate the danger—the most harrowing part of their journey still lay ahead—but they provided a method for moving forward when the situation seemed impossible.

Your Turn: Start Your Flywheel

Theory becomes powerful when put into practice. Here's how to begin:

The 90-Minute Clarity Sprint

Block out 90 uninterrupted minutes with a blank notebook and your most pressing challenge in mind.

First 30: Strategic Lens

• List 10 pure facts about your situation

• Challenge each: "How do I know this is true?"

• Circle the 3 most surprising facts

Next 30: Sphere of Influence

• Draw your three circles

• Map what you control, what you can influence, and what to release

• Choose one high-leverage action from your control zone

Final 30: Uncertainty Map

• Note 3 certainties you can build upon

• Identify 2 unknowns you could investigate this week

• Spot 1 opportunity worth exploring

Maintain Momentum

Schedule two weekly check-ins:

• Monday (15min): Choose one action and one uncertainty to investigate

• Thursday (15min): Review what you learned and plan your next move

Avoid Common Traps

• Don't wait for perfect information—start with what you know

• Focus on what you can influence now, not everything that needs fixing

• Turn unknowns into experiments rather than obstacles

Your First Turn

Every unstoppable force starts with a single push:

Your momentum begins with 90 minutes this week.

Not with solving everything.
Not with perfect clarity.
Just 90 minutes of honest observation, focused action, and intelligent navigation.

Book that time now. Create your space. Gather your tools. Give yourself the gift of momentum.

Remember:

• The first turn is the hardest

• Each turn makes the next one easier

• Momentum, once built, becomes unstoppable

The leaders we admire aren't smarter or braver.
They've just learned to turn clarity into momentum.
Now it's your turn.

Your flywheel awaits. Time to push.