Business strategy is often compared to chess – a game of perfect information where the best players can think many moves ahead. While this might work for some aspects of business, product management is actually much more like backgammon. Let me explain why this matters for how we approach product strategy.
The Illusion of Perfect Strategy
Chess masters succeed through deep calculation and precise prediction. They can plan multiple moves ahead because they see all the pieces and know all possible moves. But product management operates in a world of incomplete information and constant change. Customer needs evolve, technology shifts, competitors make unexpected moves, and market conditions change unpredictably.
This fundamental uncertainty means that trying to plan your product strategy like a chess game – plotting many moves ahead with precision – is likely to fail. We need a different model.
Embracing Randomness
In backgammon, the dice introduce an element of randomness that players must work with, not against. Similarly, successful product managers embrace market uncertainty rather than trying to eliminate it. Just as a backgammon player can’t control the dice but can position their pieces optimally for different possibilities, product leaders can’t control market changes but can build adaptable strategies.
Like in backgammon, even the perfect move doesn’t guarantee success. You might make the optimal choice for a particular market situation, but external factors beyond your control can still lead to unexpected outcomes. The key is understanding that success comes through consistently making good decisions over time, not through perfect prediction.
Calculated Risks in Uncertainty
Backgammon teaches us about taking calculated risks under uncertainty. Sometimes you must leave a “blot” exposed for strategic advantage – just as in product management you might need to take calculated risks like entering a new market segment or deprecating a legacy feature.
Playing too safely in backgammon often leads to losing – the same is true in product management. You need to take strategic risks, but timing and position matter. Having strong market position or customer loyalty can make certain risks more manageable, just as having well-positioned pieces in backgammon makes aggressive moves less dangerous.
Adapting After Every Move
Perhaps the most important parallel is the need to reassess and adapt after every move. In backgammon, each dice roll creates a new board situation requiring fresh analysis. Similarly, in product management, each market change, customer insight, or competitor move requires reassessing your position and strategy.
This constant adaptation is why rigid long-term product plans often fail. Instead, successful product leaders build flexible frameworks that can adapt to new information while maintaining strategic direction.
Mastery Through Probability
In both backgammon and product management, true mastery shows not in individual moves but in consistently better outcomes over time. A master backgammon player will win more often than a novice, not because they never lose, but because they make better probabilistic decisions consistently.
Similarly, great product leaders aren’t those who never fail, but those who:
- Make consistently good decisions based on available information
- Understand and manage risk effectively
- Learn and adapt quickly from both successes and failures
- Build positions of strength that increase odds of success
What This Means for Product Leaders
This backgammon mindset leads to several practical implications:
- Build adaptable strategies that can respond to different “dice rolls” rather than rigid plans
- Take calculated risks when position and timing are right, rather than always playing it safe
- Focus on developing good decision-making processes rather than seeking perfect predictions
- Measure success through consistent results over time, not individual outcomes
- Invest in understanding probabilities and patterns rather than trying to eliminate uncertainty
The next time someone suggests you should be thinking five moves ahead like a chess master, remember: product management is more like backgammon. Embrace the uncertainty, take calculated risks, and focus on making consistently good decisions over time.
What’s your experience with managing product uncertainty? How do you balance planning with adaptation in your product strategy? I’d love to hear your thoughts in the comments below.
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