The #1 Startup Hiring Mistake

Reading through my Medium posts, you could conclude that I’m obsessed with mistakes. It’s probably true — as a product manager I’m obsessed with having a thesis about how the world works, and then understanding why it did or didn’t go as I expected. It’s especially fun when the problem is complex, like hiring. There are so many things that could go wrong (or right). It’s hard to say which levers are most important in generating the result.

In the last 7 years, I grew with a growth-stage company from ~100 to ~1000 employees. And then helped build out the first team of ~30 at another as employee #3. I have interviewed hundreds of people across functions and watched our hiring decisions play out for 5+ years in front of us. And I’ve come to the conclusion that the worst-fit hires shared one big trait in common: they’re the wrong fit for the stage of the company.

Bringing big company tools, politics, and processes blindly to an early-stage startup is a great way to slow things down, and eliminate one of your big competitive advantages (speed) as an up-and-comer. It seems obvious. So why does this mis-hire still happen so often? A few trends I’ve noticed off the top of my head:

1. We like credentials
   Early-stage hiring is hard, because you have to sell your brand, mission, vision from scratch. We’re flattered that people with credentials are interested in us, and we’re excited to capitalize on their know-how. It can be easy to make assumptions about what someone is good at or the depth of their experience based on a resume or brand name.
2. We’re overselling
   To get great people in the door, you have to sell a vision and believe in something beyond what you have. Unfortunately, you can easily cross the line into selling that your company is more mature than it actually is, and misleading people about the nature of the day-to-day job.
3. People really believe they can do it
   The hardest part about this fit-for-stage problem is that it is often genuine — people really believe that they will adapt to the stage. They don’t realize that they don’t enjoy the type of work they’re being asked to do until they’re already in it.

The good news is that these issues can be mitigated:

• For early-stage startups, experience with other early-stage startups is its own kind of credential.
• When selling, try to give candidates enough of a concrete foothold to really understand the maturity of your business (# employees, # customers, next big unlock you’re pursuing and their role in it).
• In your interview process, try to give people an opportunity to pressure test the belief that they want to move to early-stage. Give them a challenge or a discussion question that’s really representative of the day-to-day work.

Your recruiting is as good as the clarity you have about what you need.