What’s your biggest product mistake — and what did it teach you?

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I let a legacy product stay live for 2+ years to placate a few key customers instead of making them migrate (with hand holding) to our newer, better solution. The cost to maintain both systems was probably the same as losing those customers, which in retrospect I realize was not going to happen anyway. I failed to stand up to leadership.

Now I always sunset legacy products with a published deprecation schedule and block all new features and most bug fixes, positioning it as inevitable fact. It’s like telling kids, “Sorry, but bedtime is at 8pm. My hands are tied.”

I once pushed to launch a feature based on internal excitement rather than clear user demand. Adoption was low, and it created unnecessary complexity in the product that we later had to undo. It taught me the importance of validating assumptions early and often. Just cause something sounds valuable internally doesn’t mean it solves a real user problem.

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