I keep a daily journal. Every now and again I look back and find a gem. I just found one from three years ago, January 4th, 2021, that led with “We had probably our best day skiing ever. The girls were so happy to cut through the piles of fresh snow (4-5 inches of powder)…The day was memorable because it was just plain fun…it was close to perfect.”
But that wasn’t the most noteworthy part. My younger daughter, then age six, asked me a ton of questions as we ascended the chairlift. She asked:
“What would happen if a sea turtle ate a pine needle?”
“Do snakes pee?”
“How long is a snake’s throat?”
“How do they make rubber?”
Now, none of these are terribly revelatory. They’re not going straight into a Questions Asked Hall of Fame. But they do represent the practice of asking questions, being generally curious, that’s so very important to the strategic art.
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Strategic performance is a competition. Against some adversary. Just like a duel (as Clausewitz might’ve put it). In a duel, as John Boyd’s OODA loop advises, our ability to sense the adversary is critical. (While I have misgivings about the utility of the OODA loop, I do think the concept is useful in this particular case.) Question-asking is a key part of a strategist’s sensing system.
Intelligence assets, like data and hi-res cameras, mean nothing if you don’t ask the right questions that point those powerful assets in the right direction.
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Questions are a practice like many others. You have to ask a lot to get down to the right ones. Start with wondering about the urinating habits of snakes might just lead to the one that unlocks your next strategic challenge.