The Most Dangerous Form of Action
I've watched this pattern destroy quarterly results. Month one: sales rep misses target, has a good excuse, you let it slide. Month two, closer but still a miss. Month three, more meetings but no closed deals. Just like that, your quarter is gone. I've seen this happen with smart, experienced managers who convince themselves they're being patient when they're really just living in denial.
I was there myself. The problem wasn't that I was patient. The problem was I had no thesis to be patient about. I was being a rabbit.
When I started managing larger teams, while getting deeper into my role and obsessing over execution, I picked up a short book called “The Art of Execution” by Lee Freeman-Shor. It's mainly about investing. I was getting into that at the same time. The writer is an investment manager observing his top-performing fund managers and categorizing how they handle winning and losing positions. But what I discovered was something far more useful: a framework for understanding why smart people make terrible decisions when faced with deteriorating situations.
What I didn't expect was how directly this investing framework would transform my approach to operational leadership. The insight that changed everything wasn't about markets. It was about the psychology of doing nothing.
The Five Archetypes of Execution
Freeman-Shor studied how elite investors, people who should know better, responded when their positions started losing value. What he found wasn’t a spectrum of competence. It was a taxonomy of fear, discipline, and conviction. Five distinct patterns emerged, and only two of them consistently made money.
The framework splits into two scenarios: how you handle what’s failing, and how you handle what’s working. Both reveal more about your judgment than you’d like to admit.
When Things Go Wrong: Three Ways to Lose
The Rabbits freeze. When a position drops 10%, they hold. At 20%, they hold. At 30%, they’re still holding, paralyzed by the hope that patience will be rewarded. The math works against them: a 20% loss requires a 25% gain just to break even. A 50% loss needs a 100% surge. Rabbits tell themselves they’re being rational, long-term thinkers. They’re actually just afraid to admit they were wrong.
In business, rabbit behavior is everywhere. The struggling market that keeps getting “one more quarter.” The underperforming channel that’s been “about to turn around” for six months. The process everyone knows is broken but no one wants to redesign. That sales rep. Rabbits don’t lack intelligence—they lack the courage to cut their losses.
The Assassins act fast. When a position drops 20%, they sell. No emotion, no second-guessing, no hoping for a rebound. They limit the damage and redeploy capital elsewhere. They miss some recoveries, sure. But they also avoid catastrophic losses, and they free up resources to chase better opportunities.
In organizations, Assassins are the leaders who kill projects early when the data turns negative. Who restructure teams at the first sign of dysfunction. Who pivot strategies the moment market signals shift. They’re not always right, but they’re never stuck.
The Hunters do something counterintuitive: when a position drops, they buy more. But not recklessly—they only double down when their original thesis still holds, when the fundamentals haven’t changed, when they have genuine conviction that the market is wrong. It’s disciplined contrarianism. High risk, high reward, and it requires the guts to buy when everyone else is selling.
This is the hardest archetype to translate to operations. Doubling down on a failing initiative feels insane. But sometimes the right move is to increase investment in something that’s struggling, not because you’re hoping it improves, but because you have specific evidence that the underlying bet remains sound. The difference between a Rabbit and a Hunter isn’t optimism. It’s conviction based on evidence. About a year ago, we had a product feature nobody wanted to touch, let alone sell to customers. I realized that with targeted improvements and internal repositioning, this feature could generate significant revenue. I faced resistance from my team and stakeholders, but we executed, and it paid off.
When Things Go Right: Two Ways to Win
The Raiders sell at the first sign of profit. Their position is up 15%? They’re out. They make money, but they never capture the full potential of their best ideas. They’re Assassins in a bull market—disciplined, but short-sighted.
In business, Raiders are leaders who kill successful initiatives too early because they’re chasing the next shiny opportunity. Who reorganize teams that are finally hitting their stride. Who declare victory and move on right when momentum is building.
The Connoisseurs hold concentrated positions for years. They own few bets, but they own them deeply. They sell sparingly, only when the fundamental thesis changes. They’re Buffett and Munger—patient, convicted, relentlessly focused on a handful of high-conviction ideas.
Great operators are Connoisseurs. They identify what actually matters, commit resources, and stay committed through the noise. They don’t confuse activity with progress. They don’t diversify their attention into mediocrity.
The Hardest Question
The real challenge isn’t understanding these archetypes. It’s knowing which one to be in any given moment.
Because here’s what makes execution so difficult: Sometimes patience is wisdom, and sometimes it’s cowardice. Sometimes cutting losses is prudent, and sometimes it’s panic. Sometimes doubling down is conviction, and sometimes it’s delusion.
The difference isn’t in the action itself. It’s in the question you ask before you act: Has my thesis changed?
When that sales rep kept missing targets, the problem was simple: I had no thesis. I should have had one—either they needed intensive coaching immediately, or they weren't the right fit. Instead, I was just hoping things would improve.
When I doubled down on that unpopular product feature, I had a specific thesis: the feature itself was sound, but positioning and internal buy-in were fixable problems. The pushback I got wasn’t evidence my thesis was wrong. It was evidence I needed to execute harder on changing perception.
The Connoisseurs that Freeman-Shor studied didn’t succeed because they were patient. They succeeded because they had conviction in a well-reasoned thesis and the discipline to re-evaluate it constantly.
What This Means in Practice
When something’s failing, force yourself to articulate: What would need to be true for this to work? Is it still true?
If yes, you should be a Hunter. Double down with conviction.
If no, you should be an Assassin. Cut losses and redeploy.
The only unacceptable answer is “I don’t know, let’s wait and see.” That’s being a Rabbit.
I’ve started applying this to both my own investing and my organisation. At the start of this year, I killed positions I’d been holding onto out of hope, not conviction. I consolidated into 4-6 companies where I have genuine thesis-driven belief. My new rule: if a position drops and the thesis still holds, I buy more.
The same discipline applies to operations. When a channel underperforms, when a hire struggles, when an initiative stalls, I ask the thesis question. And I act based on the answer, not based on comfort or hope.
Because in the end, inaction isn’t the absence of a decision. It’s a decision to let circumstances decide for you.
And that’s the most dangerous form of action there is.