Over the past decade-plus I’ve hired many dozens of people. Many of these hires went spectacularly well, and I still feel immense gratitude to have had the chance to collaborate with those people. Others went less well, and created some of the most agonizing personal experiences of my life.

What unites both of these paths is that I was the primary decision maker in these situations. Many of the standout successes and painful failures are still with me today.

Informed by the past joys and pains in hiring, with Metalabel I’ve taken a more intentional approach to hiring that’s proven to be helpful so far.

Collaborate before commit

The first new piece of how I hire is to always collaborate with someone on a real project before making a final decision.

That collaboration should be bite-size — something that would only take a day or two or a couple of weeks at most — and the person should be compensated for it. Ideally it’s not a project where they’re handing over a finished project, but something where you get to simulate the act of working together: commenting on each other’s work, problem-solving together, sending emails and DMs back and forth. You want to get a sense of what it’s actually like to collaborate, not just the window shopping of an interview process.

Using the collaborate before you commit approach empowers both the candidate and the person hiring, because they both have the agency to decide whether the situation feels right to them. Was there chemistry? Was there magic? Was it more awkward than you might have liked? All of this is pertinent information. Actually doing something together is how to get a true sense of that.

Reference checks

The other component that I’ve learned to put a lot more emphasis on are reference checks.

Reference checks are something I’ve almost always done, but in the past more something that was more half-hearted rather than a step to really learn from.

This year, however, I’ve adopted a standardized set of questions for reference checks that have proven to be quite helpful. They are:

  • How would you describe the candidate to someone who doesn’t know them?
  • What is the context in which you know the candidate?
  • How many people have you worked with in a similar context? How would you compare the candidate to those other people?
  • If this person’s name comes up in your inbox, DMs, or they’re calling you, what do you feel? What do you expect they’re reaching out about?
  • If you were coaching this person to up their game in a new role, what would you tell them?

These questions have helped reveal some of the individual strengths, weaknesses, and opportunities for growth in someone we’re considering working with, and gives us a fuller picture of who they are through the eyes of the people who have really worked with them before.

Nothing is more important

As is obvious to anyone who’s had the responsibility and opportunity of hiring, there’s nothing more important than doing this well. A great hire will unlock dramatically new outcomes and possibilities. A poor hire will mire a project in mud until a tough resolution is created.

When I speak with other CEOs and founders about their own organizations, a constant refrain I hear is they wish they’d hired more slowly. Every time they ignored the voice in their head that raised a doubt, every time they said to themselves “well we need somebody to do this,” every time they’d settled for anyone that didn’t elicit an immediate “hell yes,” they came to regret it. And these are very, very hard things to undo.

I’ve come a long way on my own journey hiring people, and know there’s much farther to go. But from this point forward, I’ll never pull the trigger without first taking these steps.