Lessons from Keith Rabois: How to Interview an Executive

Great insights into hiring executives at early stage startups from @zebulgar & @rabois 🔥 As a founder, what should you look for? As an executive, what do you need to bring to the table? Esp. Interesting for folks early in their careers http://delian.io/lessons-2

Key takeaways

  • Is the role creating or protecting value?
  • Do they have an ownership mentality?
  • Can they think strategically?
  • Do they fill the critical gaps of your leadership team?
  • Does their working style fit your org?
  • Are they a magnet for talent?

Creating vs. protecting value

“First identify whether the open role is value creating or value protecting. If it’s value creating, focus on ideas they’ve taken from start to finish even if they aren’t related to the role.”

“If it’s value protecting, focus on whether they have lots of prior domain expertise related to the value you expect this role to protect.”

Loved this distinction. All startups begin without value. In the early days you need executives that can take risks to increase value. In the later stages, (once the company is worth something) hire people to protect the value that’s been created.

Re: value creation roles (e.g. product, engineering, marketing, sales, etc). Look for ambitious risk takers. They don’t need to have had this exact role previously in their career. Focus more on understanding if they’ve implemented important initiatives at prior roles.

Re: value protection roles (e.g. finance, general counsel, operations). Look for the opposite. The person you hire should have deep experience doing exactly what you’re asking them to do for you.

Ownership mentality

“Effective executives need to be able to take things off your plate, not add to it. They solve problems before you even know about them... completely own everything within their scope and not constantly be looking to you for direction.”

“Our favorite question which reveals whether a candidate has this mentality is to ask them ‘What would you have done differently at your last company if you had been CEO?’”

Such a key question. The folks you want to hire have agonized over this. Even if they weren’t in an executive role. They’re the kind of person who’s kept up at night worrying about whether the company they work at is as great as it could possibly be.

Good indicators for this question: 

  • Answers are substantive and thought-out strategies
  • Quite different from what their prior company was taking
  • Owns mistakes, using “we” and “I” more often than “they”
  • Can talk about this for hours, from different angles

Strategic thinking

“This one is amongst the most difficult to assess. You are trying to figure out whether this candidate can keep a business equation in their head and understand how to pull all of the various levers that affect that business equation.”

How do you assess this? Ask if they have any questions about your business. If they posses this skill, they will:

  • Want to understand your business equation and which levers you have discovered so far
  • Zero in on key risks and structural advantages
  • Understand each step of your funnel
  • Ask the same questions that keep you up at night about the long-term viability of the business

Filling in the gaps

“...write down all of the existential risks to the business, and all of the strengths of the current leadership team. Wherever there is the biggest gap amongst the biggest risks is where you should focus on for hiring.”

Hire people who complement your team’s skillset and round out the missing pieces that are critical to your business / where you’re most vulnerable. E.g. if you have a great product org, bring someone in who can own distribution

Working styles

“You also want to assess how this person works and how that would fit into your organization… Assessing someone’s workstyle requires doing real work with them. You want to spend at least 15-20 hours with an executive before hiring them.”

We used to do this for years at Buffer 💯 When we made an offer (for any role), we started with a 6 week “bootcamp” period that allowed both parties to get a sense of what it was like to work with each other on real projects.

Leadership and a magnet for talent

”...what you are looking for here is whether the candidate has built teams before… someone who is a magnet for talent. When you hire them, they have a list of 5 people who they will immediately be able to recruit in.”

This is an especially interesting point for those of us early in own careers. Who’s on your list? Would they come with you?

These relationships are built over years, and likely with the people you’re already working with. How can you become the kind of person who, when you get that executive role, they’d gladly join? Build the well before you’re thirsty.

Originally published as a Twitter thread,

Made with ⚡️ in California