Why The Best Leaders Play Poker, Not Chess
Imagine I offer you a deal right now.
Option A: I hand you a suitcase with $10,000 cash. It covers your mortgage for a few months. It’s safe. No strings attached.
Option B: We flip a coin. Heads, you win $100,000. That’s a down payment. That’s seed capital. Tails, you get nothing.
Which one do you take?
If you calculate the “Expected Value“ Option B is worth $50,000. It is mathematically 5x better than Option A.
But if you are “managing risk” in the traditional corporate sense, you take the suitcase (Option A). It’s safe. It’s certain. You won’t look foolish for going home with zero.
But the best leaders I know? The ones actually moving the needle?
They take the flip. And if it lands on Tails... they just find another coin.
They do this because they understand the single most important truth about high-stakes decision-making: You are not playing Chess. You are playing Poker.
The reason so many brilliant leaders are currently frozen in analysis paralysis is that they are trying to play Chess on a Poker table.
The Certainty Trap - The Decay Rate of Information
In Chess, you have perfect information. You can see every piece on the board. There is a theoretically “correct” move for every configuration. If you stare at the board long enough, you can solve it.
In Business (and Poker), you have imperfect information. You can’t see the market’s hand. You can’t see the competitor’s hidden cards. You don’t know if the regulator is bluffing.
The anxiety you feel - that knot in your stomach when you look at your Q4 roadmap - isn’t because you aren’t smart enough. It’s because you are waiting for the fog to clear. You are waiting for 100% certainty.
But here is the uncomfortable reality I tell my teams: If you wait for 100% of the information, you are no longer making a decision. You are making a calculation.
And there is a hidden tax to this calculation: The Decay Rate of Information.
Every day you wait for perfect data, the data you do have becomes 1% less true. The competitor launches. The candidate takes another offer. The customer sentiment shifts.
By the time you finally feel “safe,” you arrive at a decision that is factually correct for a reality that no longer exists.
A imperfect decision made with speed often beats a perfect decision made with latency.
Bet Sizing - The Amazon Door Strategy
So, if we accept that we can’t wait for perfect info, how do we bet without going broke?
We need a system for Bet Sizing.
This is where Jeff Bezos’s “One-Way vs. Two-Way Door“ concept stops being a cliché and starts being a risk management tool.
Most leaders suffer from paralysis because they treat every decision like an “All-In” moment. They treat a $5,000 marketing experiment with the same gravity as a $50M acquisition. They fold winning hands because they are scared to bet blind.
To fix this, you have to label your bets properly:
The Two-Way Door - These are your low-stakes, reversible bets. If you walk through and don’t like the room, you simply turn around and walk out. The strategy here isn’t perfection; it’s speed. The value of the bet isn’t just the outcome, but the information you gain from the flop. Launching a feature flag to 5% of users isn’t a marriage; it’s a date. If it goes bad, you pay the check and leave. In this zone, the “Undo” button is your single best risk management tool.
The One-Way Door - These are the irreversible decisions where you can’t go back without paying a massive tuition. Selling the company, firing a co-founder, or migrating your entire data stack to a new cloud provider - these are the moments that require deep diligence. Here, you slow down. You gather more information. You deliberate. This is where you actually spend your precious “governance tokens” ensuring you have the conviction to push all your chips into the middle of the table.
The mistake isn’t making the wrong bet. The mistake is treating a Two-Way Door like a One-Way Door. Speed is a quality of the decision.
Playing for Position Not a Single Hand
Now, let’s look one step further. This is where the amateurs get separated from the pros.
Amateur players play the cards in their hand. Pro players play for Position.
In leadership, we tend to look at decisions in silos. “Is this a good deal?” “Is this a good job offer?” “Is this a profitable client?”
But real strategic leverage comes from Second-Order Thinking. You have to ask: “Does this decision buy me the asset I need for the next move?”
An agency leader take on a client that was a nightmare on paper. The margins were razor-thin. The demands were high. The P&L looked terrible. A novice leader would have folded instantly to “protect the bottom line.”
But this leader wasn’t playing the P&L of that specific deal. He was playing for position. He knew that having that specific logo on the website validated the agency for the Enterprise tier. He was willing to “lose” $50k on the hand to buy a seat at the table where $1M deals were happening. And he was right - that case study generated $2M in new pipeline within six months.
Now - here’s another example. This logic also applies perfectly to your own career trajectory. I often see leaders agonizing over the choice between “Golden Handcuffs” - a safe, high-paying role at a tech giant - and a chaotic, lower-paying role at a high-growth startup.
Let’s be honest: walking away from RSU grants feels like setting money on fire.
To the siloed thinker, the startup looks like a bad bet. “Why take a 30% pay cut to work harder with less stability? That’s folding a winning hand.”
But the strategic thinker isn’t looking at the salary; they are looking at the Asset Accumulation. They realize that the “safe” job is actually a plateau. They choose the messy startup role because it is the only place they can buy the specific asset they are missing: the ability to build from zero to one.
They are consciously trading short-term liquidity for long-term Career Capital. They know that the “loss” they take on their paycheck today is the tuition they pay to become a Founder or CTO three years from now. They aren’t folding; they are buying in.
Does this bet give you the chips you need to sit at the high-stakes table next year?
The Poker Mindset vs Resulting
I’ll leave you with this concept from Annie Duke‘s Resulting. It is the dangerous tendency to judge the quality of a decision solely by its outcome.
In poker, you can play a hand perfectly - calculate the odds, read the table, make the right bet - and still lose to a lucky river card. That doesn’t mean you made a mistake. It just means the 10% chance event happened.
If you judge your leadership solely on outcomes, you will drive yourself insane. You will become risk-averse. You will pick Option A every single time because you are terrified of the 50% chance of zero.
But if you judge your leadership on the quality of your process - on your ability to distinguish a One-Way Door from a Two-Way Door, and your ability to play for the next hand - you build something resilient.
The goal isn’t to be right every time. The goal is to keep playing until the odds tip in your favor.
So, here is my question to you:
Look at the biggest decision stalling your team right now. Are you waiting for 100% certainty on a Two-Way Door?
Stop waiting for the chessboard to clear. The coin is in the air. Call it.
I’d love to hear your thoughts.
#Leadership #DecisionMaking #Strategy #Management #CareerGrowth #RiskManagement #PokerVsChess