I Built an Organization with Great Success, Then I Failed at Leaving It

Lessons on Moving on From an Organization You Built

A lot is made of the triumphs and tribulations of building an organization. Every entrepreneur chases the feeling of pride, success, and accomplishment that comes with realizing organizational success. The glamorized feeling of creating a great company is what fuels our entrepreneurial spirits. Yet what is seldom talked about are the challenges that come after you’ve built your organization and achieved success; when you leave the organization you started.

This is something I’ve experienced first-hand over the past several months as I prepare to graduate college and leave a college organization that I helped found, built up over two years, and served as the first President of. As I have handed off the role of President, CEO, and COO (effectively the roles I was performing) over the past several months, I have learned more about being a good leader than I did when I was the one running the show. The transition away from an organization that I built has been harder than I could have anticipated, and I’ve made mistakes along the way. In fact, while I’ve always considered myself a strong leader and enjoyed success as President, my departure is best classified as a failure, yet one that has taught me a great deal.

What I have learned is that how you leave an organization is just as important as how you run it. And while there are countless books, TED talks, and MBA courses on how to start an organization, there are few on how to leave one. While there is no rulebook, and each organization is different, the following are some lessons I learned from my own experience handing over control of an organization:

The Worthiest Successor is Not Always the Perfect One — And That’s Okay

One of the biggest challenges founders face when they leave their organization is the challenge of choosing a successor. As the founder and the leader of your organization, you’re naturally going to have a high interest in the selection process. Being involved in the process is a good thing — you want to find someone who matches your ideals and has a strong appreciation and understanding of what you’ve built. Even if you’re not the sole decision maker on the matter, the board will likely value your input. Given all of this, it is very important that your selection process is rigorous and you find the worthiest successor possible.

That being said, no matter who you choose, how great their appreciation for the organization, or how great of a leader they really are, chances are they won’t be perfect. Only if you clone yourself and then continue to run your company will your successor always do things the way you would do them. Watching your successor do things you would not, interpret your mission and values in a different way than you did, or take existing projects in new directions can be the hardest part of leaving your organization. Yet trust your choice — you played a large role in choosing who your successor would be and trained them the very best you could, now it’s time to let them take what they’ve learned and execute their vision. Part of the reason you started your own organization in the first place was because you wanted to do things your own way and didn’t want someone else telling you how your vision should be executed. You owe your successor the same freedom.

It’s also important to note that you are naturally going to view everything your successor does through the lens of how you would go about solving the same problem. You have a bias towards your own leadership style. It’s important to be aware of these biases as you may end up seeing the benefits of another leadership style or see how other tactics can be equally or even more effective in accomplishing certain goals.

Set Up a Trust-Based Communication System

Regardless of how hard you try; it is going be difficult to let your successor do their own thing and stay silent on the sidelines. You’ve likely built some kind of mentor/advisory relationship with your successor, and it’s natural to want that relationship to continue at least during the first several months after they take over. They probably would appreciate the relationship continuing as well, given that they will likely face challenges they did not anticipate and be looking for someone to turn to for advice. Yet it doesn’t hurt to discuss what you both would like this relationship to look like ahead of time.

This was my biggest mistake transitioning out of my organization. While both my successor and I had said casually that we would like to remain in touch after I had left, we never expressed our impressions of what that would look like. I knew better than to constantly offer my input on the job he was doing or each decision he faced, knowing I would hate if someone did that to me. But I quietly hoped he would come to me and ask my opinion on how to approach a problem, or which direction to pursue. But that never happened; and so I stayed silent, though increasingly disappointed and feeling shut out, and increasingly frustrated at the decisions that my successor was making that he didn’t bother to ask my opinions on. As I remained in the organization, other members began to pick up on my frustration, and a silent war began between my successor and me, which proved to be a dismal example of leadership to the group, especially those new members who had recently joined. The emotions eventually boiled over into a heated exchange between my successor and me.

It was only after this exchange that the two of us were able to sit down and assess the sources of our frustrations. We shared our mismatched expectations of how we envisioned our relationship. Realizing the trust we had established working together in the organization previously, as well as how much we did appreciate each other’s leadership and insights, we agreed to go back to a habit we had practiced during the transition process and meet for weekly coffee. It was then that we could catch up on matters facing the organization, a carved-out time for him to ask for my input and advice if he chose to, and further cultivate a trust-based relationship that put me at greater peace with eventually leaving the organization.

Pass the Hero’s Cape

Having built your company and being the only leader your employees have known, the transition of leadership can be as weird for them as it is for you. They already have a strong working relationship with you, they trust you, and they know that you know how to solve the issues they’re facing. They don’t have that kind of relationship with your successor yet, even if the new leader is making an attempt to get to know the employees on a personal level. Passing off that hero’s cape to your successor and allowing them to handle issues that come up is imperative for them to lead effectively.

After stepping away from the role of President, various members of the organization would continue to text me about issues they were facing, ask my opinion on things they were working on, or complain about the way the new leadership was operating. If I’m being honest, I enjoyed the attention a little bit. It gave me a feeling of importance when internally I was struggling with the feeling that I was no longer significant. I indulged it a little more than I should have. By continuing to solve their problems and reinforcing their concerns regarding the direction leadership was taking, I was sending the message to the members of the organization that I was still in charge, that marching orders should still come from me, and even worse, I was inadvertently creating a divide in the organization.

This only made my successor’s job more difficult and inhibited him from forming the kinds of relationships he needed to lead the organization successfully. Instead of fielding member’s complaints and continuing to solve problems now far outside my job description, I should have pointed them to the new president for guidance and help on their issues and encouraged them to take the initiative to form a relationship with him. Had I done this, my successor would have been able to establish a stronger, trust-based relationship with the members and be able to more effectively carry out his initiatives, not to mention give me a much-needed break from playing the role of Problem-Solver in Chief. Furthermore, by continuing to solve these problems, I was sending the message to my successor that I did not trust him to handle them himself, creating greater division between the two of us.

Give Yourself Some TLC

If you’re an entrepreneur, chances are you enjoy working to some extent. Not too many apathetic people set out to build organizations. If that’s the case, data shows that you are most likely working longer hours each week and taking fewer vacations. If you’re like me, you’re probably fine with that. This relaxing business isn’t for you, right? Well, really it is.

Although you may not feel like you need a full night’s sleep, you’re probably neglecting other things as a result of the time you’re spending leading your organization. What is it — time with family, a social life, eating healthy, exercising, pursuing a hobby (people can still have those at 40?)? I’m willing to bet you don’t have all, or any, of those things in check. You’ve spent years neglecting them in order to lead your organization and achieve success — and it paid off! Now stop neglecting them.

The transition away from working all the time can be a difficult one for a passionate worker (I won’t go so far as using the term workaholic), and was one of the hardest things for me to get used to — I always wanted to still be working and looking for ways to contribute to the organization; after all I was still very passionate about it. Yet as I began to let go and begin to do things I had once only dreamed of — watching a TV show on Netflix, reading from my favorite publications, checking books and movies off my list, and scaling up my exercise schedule, I found these things to be extremely enjoyable, and I gained something from all of them.

Do I still work too much? Maybe. But I have supplemented my work with more of all the things I named above. I have gained a new appreciation for “leisure” and what you can learn from things like movies and books, as well as simple quiet time that may very well inspire you to take your next adventure or launch your next idea. Furthermore, these new interests and ways to spend my times diverted my attention from keeping a laser focus on everything happening in the organization, which was good for both me and the organization.

Trust What You’ve Built

After I began taking care of myself, getting some rest, and moving away from the day to day of running the organization, I was talking to a friend of mine about my nervousness regarding the organization’s future. Looking perplexed, he said to me “Why don’t you trust what you’ve created?” Not knowing the ins and outs of the organization, the personalities of the new leadership, or even much about the industry we operated in, it seemed obvious to him that if I had spent all this time building an organization that I was so proud of, if I had built a truly great organization, then it would be strong enough to continue without me. He was right.

Although operational decisions may not be the ones I would have made, or the direction the organization pursues may not be the exact one that I would have followed; what I was most proud of during my time as President was values-based culture I created and held every member of the organization to. Our organizational values could be recited by every member of the organization and were central in our decision making. The basic tenants of our culture were strong and informed the programming we put on and the way our people treated each other. Looking back on my time leading the organization, those were the things that I was most proud of, much more than any tactical thing that I accomplished. And those were the things that no one was looking to change. To use Simon Sinek’s “Golden Circle” Theory, our “What’s” may change, maybe some of our “How’s,” but our “Why” was strong enough to remain intact. And if the core of the organization was intact, it would always be a successful one and one I could be proud of being a part of.

Entrepreneurs talk so much about the challenges of starting an organization, but little of the equal challenge of leaving one. The way you leave the organization you started sends a message to your employees, your customers, and your stakeholders, and can determine your organization’s long-term success. To be a good leader, be a good leaver.

Organizational psych guru interested in values based organizations, Gen Z, and the Future of Work. Working to create a happier, more productive workforce.

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