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Felipe Bovolon's avatar

Roger, one additional turn of the screw on why planning keeps winning.

Planning is *organizationally compatible* in a way that strategy never can be. It produces shared documents, aligns calendars, generates the feeling of progress, and never requires anyone to confront the possibility that the firm's theory of winning is wrong or nonexistent. Strategy demands the opposite: uncomfortable truths about competitive reality, genuine uncertainty held open rather than collapsed into false confidence, and consequential choices that create visible losers before they create system-level winners. Organizations are coordination machines, and coordination selects for agreement, predictability, and the suppression of disruptive ambiguity. Those are the exact conditions under which strategy suffocates.

This is also why the AI problem is worse than benchmarking on steroids. AI gives organizations an extraordinarily efficient way to scale the *appearance* of strategic thinking (the polished frameworks, the well-structured scenarios, the articulate slide decks) without any of the painful judgment underneath. If firms were already substituting planning theater for strategic judgment, they can now produce that theater at industrial scale and with greater plausibility.

Strategy is not a lost art because we forgot the techniques. It is a lost art because the institutions we built are allergic to the conditions it requires. Your restoration project matters because what has to be restored is not knowledge of frameworks but organizational tolerance for the discomfort that real strategy produces.

Juan Miguel Robles's avatar

Hi Roger!

The Lost Art of Strategy is one of the most fascinating topics in the field of strategy. Thank you for writing about it! An entire book could be written on it alone with so many examples that are seen everyday.

I thoroughly enjoyed all of your insights, especially the sections on the history of strategy and what happened with the key players who shaped it. It was really great.

What concerns me most is humanity’s growing habit of rushing everything—eating fast, reading fast, watching videos at double speed, and now even thinking fast.

I’m not against speed when it makes sense, but not everything should be rushed.

This raises some important questions (please don't answer them for me!, I just wrote them to reflect about what is happening).

How can a business leader truly understand what’s happening across all business dimensions if they demand answers desperately and urgently right now?

How will their mind form accurate hypotheses about the situation?

What happens when decisions are made so quickly that the choices were flawed from the very beginning?

Will those hasty decisions end up wasting significant time, money, and resources?

My final reflection on this is:

Are we entering an era in which deep thinking and reflection themselves are becoming also another lost art?

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