Round Trip Employees: When It Works & Maybe When It Doesn’t

My second boss came from a very big, very old tech company.  He inherited one of their firm rules:  “When you leave, if you leave … you can’t ever come back!”

I didn’t get that rule.  If someone great left, wouldn’t you want them back later?  Things change.  Life changes.

In fact, right after that we hired a roundtrip employee as our CTO in my first start-up and it was amazing.  He already had years of domain knowledge and expertise, knew exactly what to do on Day 1 … and yet left all the drama of the past behind.  It was magical to have an A+ team member also be almost 100% scaled up his first day.  We did amazing things.

Still, as time has gone on, I’ve tried the trick again and again, and it hasn’t always worked.  The lessons may be obvious, but I thought I’d summarize them here.  Especially in tougher times, folks may be knocking on your door again.  Should you take them back?

First, what doesn’t work, or at least hasn’t for me, in re-hiring:

  • Folks that left for a company that was a better fit.  This is a very logical reason to leave.  And yet, there’s always another start-up out there.  I don’t think most people leave a product that isn’t a fit.  They leave a manager and a situation that isn’t.
  • Folks that left because of their manager.  Yes, maybe that manager wasn’t you.  Maybe you think it can be fixed, with a new manager or even just reporting to you now.  But I’ve usually found there is just too much to get over.  Even if their manager is gone.
  • Folks that left over accountability.  Sometimes, folks leave because you push them too hard.  That’s common in a start-up.  And you’ll look back and think, he/she was great except for … getting certain things done.  They were a great engineer, a great designer, a great salesperson … except they never got certain things done on time that mattered, or never owned certain projects they said they would own.  I’ve never seen time solve this issue.
  • Folks that left because they got burnt out.  You’d think you could fix this the second time, if they come back.  Maybe you can.  But I’ve never found a way to, never seen it really work.  Maybe because you’ll end up creating a similar environment again.
  • Folks that left for a much better job.  This should work, coming back here from greener grass that didn’t end up being quite so green.  But the thing is, couldn’t they and you find a way to do it at your company?
  • Folks that left on bad terms.  No matter why they left, I’ve found leaving on bad terms is always a flag for a rehire.  If they quit without notice. If they wrote a toxic note on the way out.  We all make mistakes.  We’ve all been young and done dumb things.  You gotta forgive.  I’ve just never seen a roundtrip hire that left on bad terms work out the second time.

What has worked in re-hiring, at least that I’ve seen:

  • Folks that left for a promotion you couldn’t make.  These folks left for the best of reasons.  A great sales rep that you didn’t have room to promote to manager.  A great engineer that wanted to be a team lead, but there wasn’t enough of a team to carve out.  A customer success superstar that wanted more responsibility than you had room to give her.  If these folks left with plenty of notice, and if they left things better off than when they started, they are often great to re-hire.
  • Folks that left because you topped them. If they left slowly.  If you brought in a CRO or CMO over them, and they gave it a shot for 90 days, but it didn’t work … they often can work out again.  Often in a somewhat different role, but topping top achievers is always tough and complicated.  If folks leave after being topped on good terms, you almost always want them back later if there is a fit.
  • Folks that left to start their own company.  Actually, this often doesn’t work. Sometimes, they just have to be the boss after this.  But sometimes it can.
  • Folks that realize you were the best boss they ever had.  This sometimes is enough.  Good bosses are often taken for granted, and probably they should be.  Sometimes folks just don’t realize this until later.  If the loyalty is still there, sometimes coming back can work well.  You might need to reach out to these people and make sure they know they can come back.
  • Family reasons, moving away, etc.  Hopefully these are obvious.  Folks that have to leave for non-work reasons are often great re-hires.  Sometimes, the best of all.  Oftentimes, they are OK coming back in “utility infielder” roles where they help wherever help is needed.  But don’t let them leave in the first place 🙂  Keep them on in some fashion if you can.  But if they do, keep the door wide open.

So I think my old boss was wrong. Roundtrip hires can work.  But maybe only about 50% of the time.

Make sure it’s for the right reasons.  You may find different scenarios work for you.  But these are the ones that have worked for me, and the ones that haven’t.

Published on April 28, 2020

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