If I were to grade the five boxes across every Strategy Choice Cascade that I have ever seen, the How-to-Win (HTW) box would get the lowest grade—even lower than Enabling Management Systems, which is the least understood box. To remedy the weakness, I am dedicating this Playing to Win/Practitioner Insights (PTW/PI) to Why the How-to-Win Strategy Choice is So Hard: How to Overcome the Challenge. And as always, you can find all the previous PTW/PI here.

Key feature of weak HTW choices

I have talked extensively about the key weakness of HTW choices both in a previous piece in this series, From Laudable List to How to Really Win, and in my viral video, A Plan is Not a Strategy. The weakness is that the so-called HTW is in fact a list of initiatives, one that doesn’t pass the key test of stra

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