The first time I hired someone, I wish I’d known it’s much better to think about the outcomes you’re hiring for. With that in mind, work backwards to the experience and skills required for a person to succeed in this role.

I. Not in chronological order

The first time I went through the process of hiring someone, I thought it through from the first step to the last step. Write a listing for a role. Get resumes, interview people. Hire someone, hand them a laptop. Rinse and repeat.

At the end of the process, I learned that was suboptimal. At no point had I thought about how hiring this actual person (not an abstract role) at this actual company (one with peculiarities and specific needs) would create the outcomes we need to succeed. I wasn’t thinking about how to help this kind-of-person swim instead of sink. That was my mistake!

I should have thought about what it looks like for someone to succeed on our team and solve the problems we’re facing, then shape the hiring milestones around that.

II. Succeed despite yourself

In my defense, it’s really easy to naively approach hiring in chronological order. We need to fill a $language developer role, so write a job listing for a $language developer. Post it to the job sites, review the resumes and cover letters. Talk to people on the phone about that kind of role, in general. Have them do a code exercise to demonstrate how they perform in that role. Schedule face-to-face interviews to make sure they’re the real deal. Extend an offer and set a start date. Greet them when they walk in the door, make them do paperwork, hand them a laptop. Rinse and repeat.

We’ve all been through it, so it seems natural to approach it that way. Yet, the process is so miserable and the outcomes so mediocre. Somehow we stick with it. (There’s more to unpack there, someday.)

Spoiler alert: a great candidate found us, it all worked out, and that person was wildly successful. Everyone lived happily.

The lesson for first time managers is: some of your early successes are because you inherited an excellent team, not because you’re a natural gift to the craft of management.

Luckily, after the offer was out, I put together a 90-day plan for the new hire so they knew what was expected of them, what they would be doing, and how to succeed on this team. Besides being prepared enough to take advantage of our luck, this was my best move.

III. Work backwards from outcomes

What I should have done is thought about the outcomes from the future, backwards.

Suppose it’s three months after a new team member has joined the team and they are wildly successful.

  • What are they doing that makes them so effective?
  • What goals did I give them for the first day, week, month and quarter that led them down that path?
  • What are the outcomes this organization is looking for from this role?
  • What are the learning curves they’ll have to climb to make those outcomes happen?

By thinking through and answering questions about what success looks like at this point at this company I’ll know what would make a successful hire and what I should look for in candidates.