Operations · 2026-02-18

When to hire (and when not to)

Hiring too early kills early companies. Hiring too late kills growing ones. The in-between is narrow and hard to find.

The most common mistake I see founders make is hiring too early. The second-most-common is hiring too late. The window between the two is narrow.

The "hire too early" symptoms

When you hire under these conditions, you get someone who spends their first 3-6 months figuring out what their job is. Those are months you're paying for with no clarity about what you're paying for.

The "hire too late" symptoms

Here the damage isn't direct cost, it's opportunity cost. Everything downstream of the bottleneck stalls.

The threshold

The right time to hire is when: you've done the role yourself, you can articulate what success looks like, the work is predictable enough to explain, and the hire would obviously ship more per month than the cost.

If any of those is missing, the hire will probably disappoint.

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