Boy this can be a tough one.
Your best managers are often working for you already. Promoting from within is often the least risky and most expedient way to get a manager or a VP. You already know what she is capable of. She knows the product and the customers. And you know the gaps and where to backfill.
And it works pretty well when you are growing slowly, and just making 1 management hire at a time.
What gets hard is when you are growing quickly.
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Jason Lemkin, Khareem Sudlow