The Day My Best Employee Quit

In December 2013 the company was in its 22nd year, revenues and profits climbing steadily, and I was living under the pleasant illusion that everything was fine.

Then Jake resigned.

Jake was one of my leading people, and he was leaving to join one of our competitors, which stung twice. I asked him why. And because he was honest, and because he had nothing left to lose by telling me, he actually answered.

The business lacked direction, he said. Things were always somewhat chaotic. He wanted more training and development than we were giving him. He wanted to work somewhere that knew where it was going.

My first reaction was that he was crazy and didn't know what he was talking about. We were growing. The numbers were good. What direction did he need beyond up?

That reaction lasted about two weeks. Then the denial wore off, and I started actually thinking about what he had said, and the thinking got uncomfortable.

The Ceiling Was Me

You've heard the expression: people don't leave jobs, they leave managers. Until Jake left, it never once occurred to me that I might be one of those managers.

But look at what he had actually described. We were thirty-five people by then, and I was still running the company exactly the way I had run it at three people: flat structure, everyone essentially reporting to me, decisions flowing through my office, no articulated vision beyond this year's revenue. My management style hadn't changed since 1991. The company had grown; I hadn't. I had always run things with an authoritative style, my way, everyone along for the ride, and it had worked, in the sense that the numbers went up. But nobody, including me, could have told you where we were going. We were a bus with a driver and no destination.

Around the same time I read Onward, Howard Schultz's book about returning to Starbucks, and something in it landed hard: the difference between running a company and leading one. I had spent twenty-two years running. Every business eventually hits a glass ceiling. Mine had a name and a face, and he had just handed in his notice.

Jake was right.

The Rebuild

I committed to fixing it, and for once I mean actually fixing it, not announcing it.

I read everything on leadership and business transformation I could find, looking for my own mistakes in other people's chapters. I hired a Director of Operations, a polished senior executive, and I still remember our first meeting: him on one side of the table with the resume, me on the other, an entrepreneur getting ready to hand the reins of an entire department to an unknown entity. When I hired him I remember thinking, "I'm hiring someone to do work I've always believed only I could do." That thought turned out to be the problem I was solving. He became one of the best hires of my 27 years. We promoted one of our salespeople into management, and for the first time, the company had a leadership layer that wasn't just me. I hired a branding company and a consultant, and we did the work I had skipped for two decades: an actual vision, an actual mission, actual corporate values. We surveyed the staff anonymously and got answers that were flattering in places and stung in others, and we acted on the ones that stung.

Then, on April 10th, 2014, we held our first State of the Union. Thirty-five of us squeezed into the boardroom, a fairly large room that felt small that morning. I was nervous, which is not something I normally am before a presentation. We were about to take the covers off a new and revisioned company, and I remember looking around before I began and wondering: would people believe me? Would they come along for the ride? Was it even possible to revision the company? I had spent twenty-two years asking people to trust my instincts. This was the first time I was asking them to believe in a destination. I announced the new vision, the new goals, the new structure, and one big commitment: we were going to double the company in the next few years, and nobody was going to lose their job doing it.

The staff didn't roll their eyes. They leaned in. It turns out people want to be led somewhere specific. Jake had been telling me that on his way out the door.

What It Bought

Over the following three years we didn't just hit the goal, we doubled revenue and better than tripled profits. But the number matters less than what changed underneath it: the company stopped being an extension of me and became a thing that could run without me. Managers managed. The vision did work I used to do by force of personality.

I want to be careful with the word "I" in this book, because entrepreneurs have a way of saying "I built this" when what we really mean is: I steered the ship that built this. I worked tirelessly, but it was not done alone, and it was not done in a vacuum. In the later years we hired some of the brightest people I have ever worked with. We had people who would challenge me, challenge themselves, challenge each other, and who never accepted mediocrity. They were empowered to fix problems without running to me first, and when someone did come to me with something I thought they could solve themselves, I pushed back, gently. Some of the proudest work I did was helping people become the best version of themselves.

Nine years after the sale, the staff still get together for a yearly dinner. I'm included. People say it was the best place they ever worked.

I steered the ship. They built the company.

And one more thing, which I noticed and then chose not to examine. The morning after we crossed the doubled-revenue line, the number we had chased for three years, I felt proud for about a day. The chase for it had lit me up for a thousand days. The having of it lasted one. I remember thinking that was strange, and then I remember setting a new goal.

I didn't fully understand what that was worth until a few years later, when I decided to sell. A company that collapses without its founder is not a company, it's a job with staff, and buyers price it accordingly. The transformation that started with Jake's resignation is a large part of why there was something to sell at all.

So here is the uncomfortable arithmetic I carry from December 2013: my best employee had to quit, and be honest with me on the way out, before I could see that the ceiling on my company was me. I got the lesson at 22 years in. I know founders who never get it.

If your business has been stuck at the same level for years, I won't tell you the problem is you. But I'll tell you it was me.

And I would be lying if I told you the company was the only place I ran on outdated settings. Everyone has moments when they catch themselves operating on yesterday's patterns, applied to today's people. Mine is the fixer's reflex. Someone I love brings me a problem, and the machinery that ran a company for 27 years starts up before they've finished the sentence: diagnose, advise, solve. Most people don't want a solution. Most people want to be heard. I know this. I have known it for years. I've learned to ask, do you want feedback, or do you want me to listen, and I ask it sincerely, and then, more often than I'd like to admit, I can't help myself anyway. I try to read the room, to hear the tone under my wife's tone, my kids' tone, and I am regularly disappointed in myself for the unrequested advice that gets out before the reading is done.

The company had Jake. Businesses hand you resignation letters; the honest ones even tell you why on the way out. Families and friendships almost never do. The people who love you mostly stay, and stay quiet, which means the same flaw that a company will beat out of you in 22 years can run at your dinner table for a lifetime, unreported. I got my letter at work. At home, I have to be my own Jake, and I am not always a very good one. Improved, since 2013. Clearly not mastered. Working on it.