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The Key to Managing Millenials is to Let Them Fail


I’m a millennial. And I’ve learned that if I want to work with the best people in my generation, I have to let them fall.

That might sound cruel, but it’s exactly what millennials are asking for, and exactly how to succeed as a manager.

Confident and ambitious millennials make great team members. I’ve managed 60 millennials across product, design, analytics, and marketing. But hiring them comes with an implicit agreement that they’ll always be learning and taking on new challenges. They expect to bite off more than they can chew.

As an early manager, I wasn’t comfortable with letting my team members fall. I was worried that their failure would both be bad for them and reflect poorly on me. But when I realized many of my millennial team members were frustrated that they weren’t being pushed, I knew I had to let them fail.

While I’m sometimes confident a team member is asking for more than he or she can handle, I now realize that telling them “no” is counterproductive and demotivating.

And eventually they’ll quit.

Instead, I often give millenials on my team something that’s a real stretch. I put them in charge of a project with a big and ambiguous scope, ask them to build something with a new technology, or even give them the responsibility of managing their first person.

These are usually stretch opportunities where failure is okay. I save the mission-critical for people who are proven.

Only by experiencing scrapes and bruises do we realize we have limits. And even after the temporary soreness of failure fades, we remember, at least for a few months, what we’re not quite ready for. In my experience, this has been the key to managing millenials.

You’ll need to resist the parental instinct to jump in and catch them too soon. If they’re not telling you it’s not going well, they haven’t felt their limits.

There is, of course, another upside to this strategy: I’m sometimes surprised when someone runs straight through an obstacle I thought would drag them to ground. That’s how I find my true stars.

Jake Poses is the CEO and founder of a new startup. He previously led product, design, and analytics at Thumbtack.

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