Possibility Portraits
Martin’s method for generating strategic options worth considering: fully imagined possibilities, adjudicated by logic, never by advocacy strength.
The arc has four steps: get psyched up, define the problem, paint possibility portraits, then make the choice, enforce it, adjust it. The distinctive move is the third. A possibility portrait is a fully imagined strategic option, a coherent mini-cascade with its own where, how and required capabilities, not a bullet point on an options slide. Bullet points cannot be tested; portraits can.
Three generative engines
Analogy. What structurally similar situation, in any industry, was solved well? Import the logic, not the surface: the discipline that makes analogy useful rather than decorative, and the reason judgement built across contexts compounds, Strategy as Craft. Trade-off. Take a constraint everyone in the industry accepts and imagine refusing it, or accept one everyone refuses. Most category-defining strategies are one of these two refusals grown up. Anomaly. Find the data point that does not fit, the customer who behaves "wrongly", and imagine a strategy for a world where the anomaly is the rule. Anomalies are the future arriving in sample sizes analysis is trained to discard.
Adjudication
Portraits are judged with What Would Have to Be True, never by advocacy strength: map each portrait's conditions, find the pivotal doubtful ones, test those. The method operationalises Strategy as Logic Not Analysis, imagination first, logical discipline second, analysis in service of testing conditions rather than generating conclusions. The room's most senior voice gets no extra weight, which is half the method's value in practice.
How this connects to OKRs
Portraits feed the goal system from above: they generate the options a discovery track tests, and the validated portrait becomes the quarter's bet, with its pivotal conditions carried into Key Result narratives. Teams that skip the portrait stage tend to write OKRs for the first idea that survived a meeting, which is how a quarter's focus gets spent on an option nobody compared to anything.
One line to keep: Generate more than one possibility before you spend a quarter on the first idea that survived a meeting.
Our synthesis of Roger Martin’s published work, sources credited. Read the originals: they’re excellent.
What are possibility portraits? +
Rival, internally coherent stories of how the company could win, generated deliberately by analogy, trade-off and anomaly, then judged by what would have to be true rather than by who argues hardest for them.
How do portraits connect to OKRs? +
The validated portrait becomes the quarter's bet, its pivotal conditions carried into Key Result narratives. Teams that skip the portrait stage write OKRs for the first idea that survived a meeting, spending focus on an option nobody compared to anything.
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