hiring to fix a problem you don't understand
Handing a problem you can't define to someone you just met, and calling it delegation.
You can’t outsource a problem you haven’t framed. Handing a function you can’t define to someone you met last week only looks like delegation. It’s how founders lose their companies without noticing.
Watch the chain form. The raise depends on traction. Traction is the cofounder’s job. The cofounder hired a contractor. The contractor has the numbers. You’ve made yourself responsible for holding a chain together while everyone on it is quietly incentivised to let it slip. Someone hands you a sheet that says forty-four thousand users and you accept it. The moment you take your hands off the wheel, the car keeps the same speed for a while — then drifts.
The fix is to do the hard thing badly, yourself, first. Not forever — just long enough to know what good looks like. That means the founder makes the first fifty cold calls and hears no from forty-five of them before anyone is hired to “own sales.” A founder who tells me his cofounder will handle sales and he’ll just do the tech has usually never sat in the discomfort long enough to know what he’s hiring for. Anyone who can talk can sell; the gap is never skill, it’s whether you’ll do the uncomfortable thing long enough to understand it.
Understanding the problem means you can ask two questions deeper than the person you hire. Forty-four thousand — does that count people who signed up and never verified? Which three of last week’s bug fixes actually mattered? Why is this on the roadmap and not that? You stop being a philosopher and become a ticket checker, and that’s the job. Holistic thinkers make great artists and terrible operators.
So the order is: frame it, do it badly, learn where it’s hard, then hire someone better than you at the thing you now understand. Hiring before that step isn’t buying a solution. It’s buying a layer between you and a problem you still can’t see.