Lessons from the Workshop

    Hire for the problem you have, not the company you describe.

    Most bad hires are made against an imagined future org chart rather than the actual bottleneck in front of you.

    By Michael O'Callaghan ·

    Founders write job specs for the company they intend to become. Scale experience, big-name background, someone who has run a team of forty. Then they hire that person into a company of nine with no team to run.

    The mismatch isn't ability. It's that the person was bought for a problem that hasn't arrived yet, and the problem that has arrived — nobody has named the customer clearly — goes unowned for another year.

    The useful exercise is to write down the single bottleneck that, if removed, would unblock the most. Then hire against that sentence and nothing else.

    You can hire again. That's the part founders forget under the weight of a hiring decision — it is reversible, and treating it as permanent is what makes it expensive.

    If the next hire feels like a guess, it's usually a clarity problem before it's a hiring one.

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