Hiring 10x Execs

Jonathan Swanson
3 min readMay 13, 2020

Hiring execs is one of the highest leverage things you will do as a founder. It’s also the thing that founders most consistently mess up.

If you do it right, it will transform your trajectory. If you mess it up, it will set you back months or years — or worse.

Here’s how to get it right:

1. Forget about traditional interviews. Execs are polished, so it’s hard to uncover their weaknesses in a few hours of interviews. But there’s a place where both their strengths and weaknesses are intimately detailed: 360 reviews. If I’m serious about an exec after a few conversations, I ask them to share their most recent 360 review. I also offer to share mine. I say something like:

I want you to intimately know my strengths and weaknesses, and I want to know yours as well. I will share my last 360 review with you so we can discuss it on our next chat, and I’d like you to share yours with me. I know it won’t be perfect and some parts may be unfair. I’m just looking for you to walk me through it so we can discuss.

No exec has ever turned down this request. If they did, it would be an instant red flag.

2. Scale outbound 10x. Top execs are hard to find. You need to widen your search far beyond what you do for ICs. When I was searching for a new board member for Thumbtack, I sent 83 queries like this to high-value contacts by following this method: 1) Draft an email template. 2) Dictate a voice note with a personalized message (just one sentence) for each recipient, to be included in the email. 3) Task your EA with adding the notes to emails and sending them out for you. Using this method, you can send 100 personalized emails in an hour, instead of 10 hours.

3. Calibrate to the top 1%. Because most execs present well, it’s nearly impossible to extract signal from them unless you’ve calibrated your search against top talent. You need to know what A+ looks like. To do this, ask your investors to name the top one or two execs they’ve ever worked with for the position you’re hiring for (e.g. CFOs, if you’re looking for a CFO). The goal isn’t to meet people to hire, but rather to calibrate your search against top 1% talent.

Here are questions you should ask the top 1% execs:

How do you define your mission as an exec?

Can you walk me through each component of your job in detail?

What qualities should I be looking for in this role?

How should I interview for this role?

Are you open to interviewing a candidate or two so I can calibrate with you?

I struggled for months to find a 10x candidate when we searched for a VP of People at Thumbtack. So I hit pause and calibrated our search by getting to know the best: Laszlo Bock. We leveraged Laszlo for sourcing, interviewing and closing until we found our 10x exec.

Searches for execs last anywhere from 3 months to an entire year. Start early, set your bar against the top 1%, and grind away until you find your 10x exec.

Even if you run a perfect search process, you will still make mistakes. I don’t know a single founder who hasn’t mis-hired an exec. What separates stellar founders from the rest is they recognize these mistakes within the first few months, quickly ask the exec to leave before lasting damage is done, and re-start the process better calibrated the second time around.

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Jonathan Swanson

Co-founder & Executive Chairman at Thumbtack, former White House staffer, lover of life