Lessons from the Workshop

    Founders don't need more information. They need permission.

    By the time a founder asks me what to do, they usually already know. What's missing is someone to say it out loud with them.

    By Michael O'Callaghan ·

    A surprising share of clarity work isn't analysis. Two hours in, the founder says the thing they already suspected — kill the second product, let that person go, stop chasing enterprise — and looks up to see whether it's allowed.

    It isn't cowardice. Founders sit alone with decisions that have consequences for people they know personally, and the isolation makes obvious things feel reckless.

    So I'm careful not to perform insight I don't have. Often the most valuable sentence in the session is: yes, you're right, and you've been right for a while.

    More data would not have helped. The dashboard was never the obstacle. A second serious person in the room was.

    If you already know what to do and haven't done it, two hours with someone outside it tends to help.

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