When Doing It Right Means Letting Go

True leadership ends with stepping aside.

Several weeks ago, I sat down with George (as in Zimmer, for those new to Curmudg). We text and email often, but when we’re both in Hawaii, we make it a point to catch up in person.

In some respects, it feels like two old friends sitting on a park bench—not a bad park bench, I know—comparing the good old days. And most times, I leave pondering something I hadn’t thought of either before or sometimes at all.

On this occasion, George blindsided me:

“Why did you retire when you did?”

It was a long time ago—2002—and at the time I told myself that it was because I had many other things I wanted to do with my life. Which was true, and I have kept myself from gathering dust since.

But as I thought more about the question—now, so many years later—something else came to mind. There was another reason:

I retired early because I had done my job too well. In the last decade of my time at MW, we went through explosive growth (something I talked about in an earlier column, Wall Street Loves Shiny Objects). And as part of that growth, one principle we lived by was “train your replacement.”

It was baked into our culture—store managers became regional managers; some went on to corporate roles. And the same held true in senior leadership. It happened at every level.

When the company went public, my dual role overseeing both merchandising and marketing became unsustainable. That’s when we recruited Jayme Maxwell, who built an entire marketing department that was strong enough to seamlessly absorb two acquisitions within the span of a few short years.

Around the same time, I saw that Jim Zimmer (yeah, George’s sibling) had a better eye for fabric swatches than I did, so I stepped aside and let him use his talents. Later, Eric Lane structured what became a large merchandising organization in a way I never could have.

By the late 90s, I was mostly hands-off with merchandise and marketing and moved over to searching out companies for MW to buy and Wall Street communications (from a non-financial perspective). After buying two companies in quick succession, the company wasn’t in the market anymore. And Wall Street, ever on the lookout for the next shiny object, was content with less frequent updates.

With less day-to-day urgency came a new kind of clarity:

I could finally see how strong the team around me had become—and how little they needed me to keep things moving.

In each case, I recognized that others had talents beyond my own—and gave them room to use them. Over time, I made my job expendable. Kinda.

Was I then, or even now, complaining? Not at all.

Allowing others to reach their full potential with barely an occasional nudge from me was always a source of great pride.

If you lead well, you won’t be needed forever. That’s not failure—that’s success.

Yes, sometimes we had to bring in outside talent—there’s nothing wrong with that. But the core remained: identify talent, empower it, and get out of the way.

Two lessons in servant leadership come into play here. They’re equally important and help to cement lasting leadership in any organization, regardless of size and industry.

1. Promote from within. At Men’s Wearhouse, we meant it. The only time we went outside was when the job required an expertise we simply didn’t have in the stores—accounting, marketing, or the occasional technical niche. Otherwise, we built leaders from the ground up. And that made all the difference.

2. Back off and let people shine. Those talents might not be the same as yours. In fact, especially then. The goal isn’t to build clones; it’s to build confidence.

So, let me ask you what George asked me: Why do you do what you do?

Is it to stay indispensable, or to leave behind a team that thrives without you?

If it’s the latter, don’t be afraid to work yourself out of a job.

That’s how you build a legacy—and a great company.

TL;DR: Leadership isn’t about staying essential—it’s about building others up until you’re not.