Should Startups Hire from Corporates?

It’s tempting to think that someone from a big successful company will gallop in and give your little startup hockey-stick growth. That’s a common expensive misconception.

Trust me, I spent 10 years climbing the marketing ladder in a big company! My secrets to success: Present great decks, build political alliances, spend millions on agencies and manage up. Will any of those skills help your startup be successful?

The Fundamental Difference

Big companies already have a playbook, so they hire people to come in and execute. (That’s easy!) Startups need to figure out their playbook, and that’s hard. So look for people who can do two things:

1. Reason Well - Bright & curious, able to think from first principles, identify your riskiest assumptions and test them, and make good decisions about which work to do.

2. Get Stuff Done - Scrappy and resourceful, will roll up sleeves and do whatever, wear lots of hats and draw the owl.*

Interview Questions

I would not categorically rule out “big company” types. But make sure they have the intellectual honesty and mental flexibility to embrace drastic change. Here’s how I figure out whether a candidate can write the playbook or just follow it:

• "What do you see as the key unknowns in our business right now? And how can we bottom them out quickly?"

• "What did it take to succeed in your last job, honestly?” (and a followup) "What do you think it will it take to succeed in this new job, how is it different?"

• "What’s something you learned from a customer recently in your current job that surprised you?”

• “If you needed to test some messages on your first day at the office, how would you do it? Literally what would you do?" (roll up the sleeves?)

When you hire someone, do not expect them to have all the answers! Expect them to make good decisions about which work they do, execute fast, and learn how your company can grow. (Here's my object lesson on growth mindset leadership.)

* Draw the Owl is one of Twilio's company values, it means “there’s no instruction book, go figure it out.” But it’s much more hilarious than it sounds.