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Asking Great Strategy Questions

I frequently get asked a question about questions: What questions should I ask when I am reviewing a strategy? Because of that consistent interest, I am dedicating my 36th Playing to Win/Practitioner Insights (PTW/PI) piece to Asking Great Strategy Questions. (Links for the rest of the PTW/PI series can be found here.)

Three Categories of Questions

I am often asked to evaluate strategies, whether for clients, students, or friends. Rather than focus primarily on whether the strategy is good or bad, I focus on asking questions with the intention of guiding the authors toward their goal of creating great strategies. To provide that help, I ask strategy questions in three broad categories: logic, fit, and distinctiveness. The questions aren’t entirely distinct from one another. There is overlap. But I think that a bit of overlap isn’t a problem if it ensures I don’t miss anything.

With no further ado, here are questions to help hone and refine any strategy…


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