Letting Go

Roy Rapoport
3 min readMar 1, 2023

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This is the story of one of the three most important leadership lessons I learned.

Back in 1996 or thereabouts, while I was working in IT at Macromedia, my boss sent me to the Center for Creative Leadership’s Leadership Development Program (LDP). LDP was a 5-day program; I was doing it in San Diego while home was San Francisco (it’s an amazing program, BTW; the second important leadership lesson was also one I learned during this week).

I had a relatively junior engineer working for me, Mike. Mike was prone to sometimes getting in trouble for not being particularly thoughtful. These things happen.

On Tuesday, I got a page from my senior engineer. I excused myself from the class and called her back. “We have a problem,” she said. “We had a conference call with engineering and Mike really made an ass of himself, and now engineering’s out for Mike’s head.” I thanked her for letting me know and told her I’d take care of it. I called Mike back and asked him what happened, and then said “OK, I can’t quite deal with all of that right now, but don’t worry about it, it’s going to be fine. I’ll deal with it when I come back on Monday. Meanwhile, I want to give this situation room to breathe and space to relax, so don’t go to work for the rest of the week, take it off. Don’t worry about your PTO balance, I’ve got it covered, just don’t go to work, I’ll let the team know, and I’ll see you in person on Monday.” He acceded, we hung up, and I let my senior engineer know Mike wasn’t going to be around for the rest of the week. I then went back to class, knowing that situation was handled.

Thinking that situation was handled.

The day after that, mid-day, I get a page from my senior engineer again. I call her back. “Didn’t you say Mike was going to take the rest of the week off?” she asks, and — with a heavy heart — I tell her I did. “Well,” she responds, “we had another call with engineering, and Mike got on it, and it just got much, much worse.” I was flabbergasted. So I called Mike and asked him what happened there, given my understanding he was going to take the rest of the week off. “Well,” he responded, “you told me not to go to work. I didn’t, I stayed home — and dialed into that call.”

That evening, before dinner, I found one of my classmates at the hotel bar, having a drink, and joined him. I was upset, and outraged, and confused, and a whole lot of other feelings, and I shared with him what was going on at work, because I was at my wits’ end to figure out how to deal with it.

He shrugged phlegmatically and said “Let me tell you the most important leadership tenet I’ve managed to learn in my life.”

You can’t make people do good work. You can’t stop them from doing bad work. All you can do is share context and enforce consequences.

That’s it.

At the time, he was talking about how we deal with direct reports, of course, but I’ve found that this approach is critical to working with reports, bosses, peers, and … everyone we deal with at work. I can give you information. When it’s up to me, I can enforce consequences. Everything else — Everything Else — is up to you.

I was reminded of that yesterday as I was talking with a coworker who was flummoxed by the behavior of one of our shared peers and was utterly committed to trying to get our shared peer to change their path while ignoring the very obvious indications that change would not happen. You can’t make people do anything. Share context. Enforce consequences. That’s it. The rest? The rest is up to them.

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Roy Rapoport

I have goats. I work in technology. You know most of the rest.