Reading path · 3 pieces · About 23 min
What would make you change a strategy you believe in?
Start by separating strategy from a feature plan. Then try to disprove your strongest assumption. Finish by judging how the strategy learns and changes, not just how persuasive it sounds.
Who this is for: Product managers, founders and engineering leaders with a strategic bet to defend—or reconsider.
Take away: A testable assumption, a disconfirming check and a review point.
Start reading ↓Estimates use 250 words per minute, rounded up for each piece. Allow extra time for the reflection at the end. Open a piece for its selection note and available summary, then continue to the original.
01 / Replace the feature plan
Melissa Perri separates desired outcomes from a predetermined list of things to build. Use the distinction to expose where your strategy assumes the answer before the team has learned enough.
Pause here: Could two different solutions serve the outcome you have named?
02 / Look for disconfirming evidence
Mike Fisher turns skepticism into assigned checks: examine a critical assumption, separate advocacy from validation and agree on stopping criteria. Reserve the strongest checks for consequential, hard-to-reverse bets.
Pause here: What would prove your most confident assumption wrong?
03 / Judge the strategy in phases
Will Larson evaluates the speed and cost of refinement alongside impact. A strategy that once worked can enter a new phase; abandoning it need not invalidate the original decision.
Pause here: Has the diagnosis changed, or are you merely defending the original plan?
Perri’s 2016 essay makes room for discovery inside strategy; its Uber example is explicitly hypothetical, not an account of Uber’s planning. Fisher adds checks against premature certainty. Larson then complicates the idea of a single verdict: a strategy can work in one phase and become costly in the next. Together they suggest a cycle of direction, challenge and revision. Neither a tidy plan nor a failed prediction settles the question of quality on its own.
Digna Legi synthesis of the linked readings, not a claim that the authors endorse this combined approach.
Put five minutes aside
Use paper or your own notes app. These prompts are Digna Legi’s exercise, drawn from the readings.
Before you leave: Which assumption will you try to disprove, and when will you review whether the strategy should change?
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