A common theme in speaking with founders is their struggle to know when it’s time to step aside. And there’s a common misconception: when you hire your replacement, you’re hoping they’ll do as good a job as you did—or maybe 80-90% as good. But here’s the truth: no one can ever be you, but they don’t need to be. In fact, they might be better.
Here’s my story…
One day, a board member, sensing my frustration with running a scaling business, rocked my world when he said, “You know you can hire someone to help you with the CEO role, right? Let them take on the stuff you don’t like, and you can focus on what you do enjoy.”
I had always known you could hire people to assist in areas like engineering, finance, or admin. But it had never crossed my mind that you could bring someone in to assist with CEO responsibilities. I’m not talking about an assistant—I already had one—I mean a true right-hand person. Someone I could trust to execute even the most sensitive and important tasks a CEO handles.
Excited at the prospect of offloading some of those spinning plates, I was ready to open the door and bring in this mythical creature. But before I could, I realized how much “cleaning” I needed to do first. It was like tidying up before the cleaner arrives—you don’t want them to see the mess! I felt I had to fix everything before bringing someone in.
I had to resolve our revenue recognition issue, because only I understood the numbers. I needed to fix our broken pricing model. Our technology was a constant mess, and the sales funnel needed improvement. Plus, I had to prepare for the next board meeting. Oh, there were also a few dozen other of other fires that I needed to put out. The list of problems felt endless. With so many plates in the air, I slumped back into the captain’s chair and prepared myself for another decade of steering the ship alone.
That is, until my board member called to say he had found the perfect candidate—a talented individual he had worked with before. He had arranged a Zoom meeting for us to see if there was a fit. If it weren’t for that push, I might still be “cleaning up” the company, preparing for the new CEO to join—even three years later.
The call went perfectly, and despite being burnt out and overwhelmed, I hired him. Worst case, I figured, if it didn’t work out, I’d be back to where I started. So, I took the leap.
We hired a Chief Revenue Officer (CRO), and I began transitioning the CEO tasks I no longer enjoyed to him. In hindsight, he was my Sheryl Sandberg to my Mark Zuckerberg.
I hesitantly opened the door to my house, messy with all the tasks I hadn’t had time or the skills to clean up. I braced myself for his horror and immediate resignation. But to my surprise—and delight—he looked around at the mess and just started cleaning. With his experience and knowledge, tasks that seemed like Mount Everest to me were projects he knocked out before lunch.
Over the next year, I handed off most of the responsibilities I no longer wanted, allowing me to focus on product development and strategy. Eventually, I realized the CRO was even better suited for these tasks than I was. After 15 years of running the company, I was completely burned out, and it was time to step aside.
A year later, at dinner in Florida with my family and the CRO, my father asked him about his strategy for growth. As I listened to him outline his plan, it became clear to my wife and me that he should be the CEO—not me. It wasn’t just better for me personally, it was better for the company, its employees, and shareholders.
So, I stepped down as CEO and let the CRO transition into the role. He took my CEO salary, and I became solely an owner, earning my compensation from my ownership stake.
Takeaways from my experience:
1. Hire someone 200% better than you. Don’t settle for someone who’s 90% as good. Find someone who can truly elevate the business.
2. Don’t clean the house before you bring someone on. If those messes have been there for years and you haven’t cleaned them up yet, you won’t suddenly do it now. Let the new person tackle the problems—they’ll probably be better at it than you.
3. Replacing yourself is doable—and highly recommended if you’re ready. It’s one of the best decisions you can make when the time comes.