Via Sequoia Capital

The number one thing that I’ve learned from a hiring perspective: the main thing that I ask C-suite [candidates] now if I’m going to hire them is, “Can you draw out what your org would look like in 3 months, 6 months, and a year?” It is insane how many people can’t do that. It is wild to me that it is really hard for people to do.

There are different levels of ability [here]. There’s, “Can you describe [the profiles you need]?” There’s, “Can you map out every single one of those hires, what they [will] do, and can you think of who would be a good person or who would be a good fit for it right?”

— Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months, at 11:37

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Winston Weinberg, CEO of AI legal platform Harvey, has a go-to screening question for C-suite and VP candidates: Can you map out what your org looks like in 3 months, 6 months, and a year?

Most people can’t, not because they don’t know how to plan, but because they don’t know how to scale an organization.

• Leaders who don’t scale keep doing what they did as individual contributors. They stay in the weeds and don’t build leverage around themselves.
• Leaders who do scale know who their key hires need to be, what those people will own, and how to remove themselves from the “glue work” that keeps them from doing the core of their job.

Founders are often suspicious of executives who immediately want to hire, assuming they’re empire building. Weinberg flips that instinct: if a leader does not focus on creating leverage for themselves, they won’t succeed at scaling their organization.

His current focus as CEO reflects this belief. He spends time with his leadership team identifying who their lieutenants should be, then helps hire those people.

The org-drawing question is a quick, effective test: can this person think ahead about leverage?