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I’m absolutely sure this skill exists, that people with more experience/expertise in a particular business eventually learn it, but I’m not sure how to teach it or even learn it for myself (for a particular business) It seems most people just trial and error their way to it.
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And, yes, ‘stupid iteration’ and ‘trashing wildly’ are real failure modes, and common in earlier stage companies, mostly because ‘doing the grindy work makes us feel good about ourselves, and helps us avoid the difficult questions about our product.’
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To be clearer: the skill lies in deciding WHICH hypotheses are worth testing. In nearly every business/product, some hypotheses are so dumb they shouldn’t be tested. The problem is having the judgment to make that call consistently.
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What this looks like in practice: saying “well you wouldn’t know until you try, right?” to everything. This is true, but bets have costs. Also it probably implies that no judgment or intuition for the space exists.
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A pretty good consolation skill is finding out which leaders definitely don't have the ability to differentiate but think they do, then keeping them from wreaking havoc
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Once I built a hacky mobile web prototype of a prospective native mobile experience as a POC to see if the idea was worthwhile. 1-2 days vs weeks. Is that the kind of scenario that you’re talking about?