OKRs & Texas Hold

September 22, 20205 min read

Tim Whitmire is the founder of CXN Advisory , where he coaches executives on strategy, goal setting, alignment, and execution. He is the co-founder of F3 Nation and co-author, with David Redding, of Freed to Lead: F3 and the Unshackling of the Modern-day Warrior . In this Voices of OKR feature Tim identifies the similarities between poker and the OKR-driven goal setting. 

After 10 weeks of having everyone housebound during the first stages of the pandemic this spring, my three kids — ages 20, 18 and 14 — wanted to add variety to our board game rotation. They found a set of poker chips I bought 20 years ago (and hadn’t used in maybe 18 years) and told me they wanted to learn to play.

Given my minimal experience, it was less about me “teaching” than all of us learning together. We spent the summer playing small-stakes Texas Hold ‘Em — usually a $5 buy-in and ante of a dime or blinds of a dime and a quarter.

Everyone learned to shuffle properly, we worked out a system for keeping two decks of cards in rotation and we fell into a routine of playing quickly and efficiently. Once you find that rhythm, logistics fall away and the core of the game — and our individual approaches to it — starts to reveal itself.

My 14-year-old youngest son plays recklessly and unpredictably, as one might expect of a teenage boy. His 20-year-old older brother, our rule-following first-born, plays an opportunistic grinder’s game. My 18-year-old daughter, a competitive swimmer, plays fiercely, like she’s attacking a tough set in the pool.

In her new book, The Biggest Bluff , the psychologist and writer Maria Konnikova notes that Texas Hold ‘Em — particularly in its No Limit variation — is thought to be the version of poker that best simulates real-world decision making (and possibly the single best game of any kind in that regard). Players receive two “hole cards” that only they can see and use those cards to make their strongest five-card hand from the five “community” cards that are dealt face-up on the table.

“Because the only other cards (beside the community cards) you know for sure are your own, you’re in a game of incomplete information,” Konnikova writes. “You must make the best decision you can, given the little you know.”

The amount of incomplete information in Texas Hold ‘Em creates a particularly useful balance between skill and chance. Two hole cards is just about as practical a ratio as you can have — enough unknown to make the game a good simulation of life, but not so much that it becomes a total crapshoot. … 

In No Limit, you can bet everything you have at any point. And that’s what makes this game a particularly strong metaphor for our daily decision making. Because in life, there’s never a limit. 

Maria Konnikova 

Hearing Konnikova interviewed by Stephen Dubner in a recent Freakonomics podcast made me realize the similarity between poker and the OKR-driven goal setting on which I advise clients.


Unknown factors

First, there’s the role that unknown factors play in planning. I often coach OKR clients to build objectives that account for what I refer to as “contingency” — the reality that unforeseen and unknowable outside forces will often upset what the 18 th century Scottish poet Robert Burns described as “the best laid schemes of mice and men.”

In poker, you can be dealt a strong hand, calculate odds accurately, benefit from a great set of community cards, bet your hand in the most rational manner possible — and still lose to another player holding an even better hand. This is the proverbial “bad beat.” In business, I can set a clear and compelling objective, identify and track clear, measurable Key Results that advance the organization toward the objective, hit all of my marks — and fail to reach it because of unforeseen outside forces.

Both situations are shocking, confusing and breed uncertainty about how to go forward. Which makes it critical in poker and OKRs to conduct an after-action review. Review the reasons why you played the hand or pursued the objective the way you did, make any necessary adjustments and — most important — drive on with confidence.

You might conclude: I picked the wrong Key Results to track and will adjust my approach next quarter. Or, you might decide: I did everything right; it was just a bad beat. Either way, that clear-eyed review is essential to being able to continue in the game as a rational actor, and not a guppy at a table of sharks.

Measuring What Matters

There’s a second critical way in which Texas Hold ‘Em parallels OKRs (and business goal setting in general).

At their foundational level, OKRs are grounded in metric- and data-driven Key Results that you monitor to track whether you are on your way to your Objective. It’s all about numbers, outputs and what John Doerr memorably terms “measuring what matters.”

Similarly, the foundation of effective Texas Hold ‘Em play is the ability to internalize data and metrics — to track the development of the set of five community cards (which are played in three stages), realistically assessing the odds – not only that you will be able to build a strong hand but also the chances of another player holding a strong hand. You play (or fold) your hand accordingly.

But in poker and OKRs, numbers aren’t enough.

The OKR Art

In recent years, tournament poker famously has been overrun by high-level, data-driven math savants — the same “quants” who have had such a huge impact in fields like finance and professional sports. Their approach is not dissimilar to that of an organizational leader who wants to build a numbers- and data-driven business and dreams that OKRs can be a “set it and forget it” solution for organizational execution against goals.

In her book, Konnikova makes a convincing argument that math skills aren’t enough in poker, that the very best players must combine science with art — the ability to read other players, make reasonable assessments about whether they’re bluffing, and play their own hand accordingly.

My experience with OKRs parallels this. The “science” is in drilling down to Key Results, understanding your organization’s processes and tying outcomes to the right metrics. But that’s not enough.

The OKR “art” is in moving from that foundation to team-driven Objectives that inspire collaboration and align to organizational mission and shared purpose.

The art is in the right balance of “business as usual” objectives and team-driven “change” objectives; in allowing individuals the space to build Key Results and metrics that they can truly own; in developing a native OKRs language that organizational leaders can use to achieve elite-level execution.

A team aligned around goals and committed to working all-out to achieve them? That’s a truly unbeatable hand.

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