A couple of years ago, I was attending a Small Business Association (SBA) class that was specifically designed to prepare the CEOs of government services companies to graduate from being a small business and enter “no man’s land,” as described by Doug Tatum. As the conga of CEOs who had successfully navigated the “too big to be small, too small to be big” waters talked to us, one made a comment that was not, as I saw it, directly related to main topic of the class. But it struck me square in the forehead. He said, “if you wait until you’re already tired to transition out of your CEO role, you’ve waited too long.” It wasn’t long until I realized that the comment was, in fact, quite directly related to the topic at hand.

When I started AVIAN in 2006, I was my own first employee. I worked eight-hour days in support of a government customer, and spent my nights and weekends working on the company trying to make it grow. I worked non-stop. It took five years to reclaim my evenings, seven years to get my weekends back, and a decade to find some semblance of work-life balance. By year 12, the company was running smoothly, allowing me to spend more time with my family. It felt like I had “broken through,” we had made it, and the company was secure. Then came year 17, and the realization that small business graduation was fast approaching.

We found ourselves thrust back into start-up mode. I was working 16-hour days, nights and weekends, only I was 20-years older. When people asked how things were going, my answer was ‘sporty.’ I thought back to the SBA class and I realized I was already tired.

Approaching the end of your tenure as CEO is always difficult, but I think founders have an extra challenge, having worked so long and hard to raise their company up from nothing. But when you run a business, hard work is the norm, so how can you tell when the time has come for real organizational change? When grit and perseverance are no longer the keys to finding your way out of a tough spell? It’s not easy, but here’s what it looked like at AVIAN.

We had hit what Les McKeown calls the “whitewater” stage in Predictable Success. Operations within the company became increasingly complicated as we were preparing ourselves to start competing with billion-dollar giants versus other small businesses. The fun part of scaling was over; I was back to the grind of working nights and weekends, but this time with far less energy and enthusiasm.

I thought back to the SBA class again and realized the time had come. I was CEO and president and there was too much ground to cover. Between running AVIAN, integrating a recent acquisition, and launching a startup, I couldn’t focus. I couldn’t concentrate on strategic growth while still managing daily operations. I needed help. It was time to bring in a president to handle the day-to-day, so I could refocus on vision and long-term strategy.

Once I decided it was time to promote my Chief Operating Officer (COO) to president, I took the idea to my board. My COO, a retired U.S. Navy Commander, had been with AVIAN for over a decade, proving himself a very capable business leader, so he was the natural choice for the president role. The board agreed, but they wanted a detailed plan for how it would work in practice, a concept of operations.

Together with my COO, soon to be COO/President, we mapped out the new organizational structure.

As two retired Navy Officers, we were meticulous in our planning—clarifying reporting relationships, defining responsibilities, and even considering the cultural shifts this change would bring. I was to fully transition into the CEO role, focused on growth and strategy, while my COO would fully manage the operational side as president.

In the CONOPS design, we agreed to one critical element; if my COO was to be president, I must fully allow him to be president. He re-designed the company’s organizational structure the way he wanted it to operate, and put in place a whole new leadership team, hiring one new key position, and promoting four people into leadership roles. He had a few asks of me: refrain from making any decision on his behalf, not attend his leadership team meetings, and let him be in charge. I had one ask in return: to shield me from issues that don’t really require my attention by creating some sort of screen or filter and not distract me from my new role. Symbolically, I even moved my COO into my large president’s office and myself into a small corner office on the other side of building to make it clear to everyone who was now in charge.

I was immediately ecstatic. So many items from my habitual to-do list vanished, as they shifted over to the new president. After the shift, we established a drumbeat of meeting fortnightly to make sure the transition was going smoothly and the CONOPS was working as designed. We called it the Same-Page meeting. And then slowly we began to witness cracks in the new construct; as with any major change, it turns out it wasn’t quite so easy.

Despite our careful planning, one of the biggest surprises was the innocuous cultural resistance to this shift. I’d underestimated how deeply my presence was embedded in the company’s culture. Even as I tried to step back, employees kept looking for me to be a part of things and comments like, “you’re missed when you’re not here” started to creep up. Don’t get me wrong, the new president was doing an amazing job setting his own strong, caring culture, but letting go of the old takes time. More time than you think.

Another issue was the overlap in roles. Our new president retained his COO title while stepping into the president position, which created confusion about responsibilities, especially among his fellow C-Suite. This blurred the lines in our leadership structure—a mistake I now realize needed to be addressed.

The last was my own understanding of my new role. As the CEO, I am a visionary who never met an idea I didn’t like, but that comes with consequences when I break the new organizational structure lines and start sending opportunities directly to the business development team who feel compelled to act. It’s not a pleasant feeling to hear your senior leadership team talking about ‘reeling in Kevin,’ but it’s to be expected and properly managed.

We are a year into this transition and AVIAN is in a decidedly better place, but we’re still experiencing some growing pains. My president runs the company effectively, giving me the space to focus on strategic initiatives like partnerships and long-term growth. We meet every other week to stay aligned, and I’ve managed to step back from the operational details.

I expect that once we better settle into this structural shift, life is going to improve. I feel closer to reconnecting with the passion and excitement that characterized the periods where we burst through a growth period and felt successful. The company IS in great shape, and we are most of the way across no man’s land; now I just have to finish the work of making sure it stays that way long after I am no longer the CEO.

Are there any universal lessons here for CEOs, and especially founders, contemplating a similar move? Here’s what I’ve learned. Know when it’s time; don’t wait until burnout forces your hand. Plan meticulously, but stay flexible; you need a clear CONOPS, but be ready for the unexpected—especially when it comes to company culture. Clearly define roles; avoid overlapping titles or responsibilities. Respect the cultural shift; transitioning leadership isn’t just a structural change, it’s an identity shift. Employees need time to adjust, and the new leader needs space to grow into the role. Finally, don’t underestimate symbolism; small gestures can significantly impact how the transition is perceived.

Transitioning from a hands-on President & CEO to being a strategic leader isn’t easy, but it’s necessary for sustainable, long-term growth. As with all phases of company growth, the rewards are preceded by challenges, and nothing is as easy or smooth as you would hope. But if you have reached this point, and especially if you are an Evergreen® leader, you have been doing this long enough to know that the best outcomes are worth the hard work and the struggle.