Sometimes the roots go just a bit too deep.

Many of us have lived it in one way or another: a passionate individual forms an organization, builds it from scratch, and eventually it’s time to pass the torch. Sometimes it goes beautifully, where the founder has created a solid organization and is simply ready to let go and let the organization start a new chapter. Or perhaps the founder successfully turns over leadership and is invited to stick around as a thought partner. Sometimes, however, a leadership transition is fraught with unexpected challenges as the leader struggles with letting go. When the founder’s roots run a bit too deep, the entire organization struggles.

A Founder’s Successful Transition

Several years ago, I became the founder of a local nonprofit that started a public charter school. Having no interest in actually running the school, I became the board president and gladly looked for qualified staff to take the reins and carry out the vision of the founding board. Even with this mindset, it was still very hard to let go. We struggled with our first executive director and eventually separated with that individual after the first year. The separation was stressful for everyone, even though it was clear that our very first hire was not a good fit. After their departure, I took some time to reflect on the role I played in the challenges faced by our first leader. There was a lot to learn.

After hiring our second executive, I resigned from the board and offered to be available if the new executive needed to talk. A fresh board took over and I took a year to relax. The new director was able to establish themselves as the leader and experienced some incredible success over their first year. I developed a good relationship with the executive director and offered support whenever it was needed. After a year, I was asked to rejoin the board to help address some upcoming challenges, but only did so after a deep heart-to-heart with the executive director, where I affirmed my support for their efforts and clarified roles and responsibilities. Today, the executive director and I have a great relationship, where we value candor and transparency and we both fulfill our roles with enthusiasm and in the spirit of collaboration. It is such an incredible gift to be working with the organization.

When the Roots Run Too Deep

Prior to starting the charter school and nonprofit, I was the founder of a large family recreation organization. Some of my best memories are of the outings I led with that organization. After growing the membership to over 1,000 families over the course of just two years, I made the difficult choice to move 1,500 miles away and try a new adventure. The group was not yet incorporated and I left it in the capable hands of two friends who took over management. I stayed involved on the periphery, mostly sharing thoughts about my original vision for the group when asked. I was confident that my friends would manage it as they felt was best.

Ten years later, one of the group’s managers (and also a personal friend) decided it was finally time to move forward with incorporating as a nonprofit. They asked me to join the founding board. Having spent the past decade as a nonprofit manager and coming off the high of a successful leadership transition at the charter school, I eagerly agreed. Even though I was technically the founder, my friend had been running it for a decade and I was there to help them start the next chapter. It was exciting work and I was thrilled to serve as a source of support.

However, even though I did not feel like the founder, I was still perceived as the founder. My efforts to set up internal operating systems – something I do for a living – were interpreted as undermining the board president, who was also a close friend. Tension mounted. I kept chipping away at the myriad of tasks that are part of nonprofit startups, but my friend resisted my help and admonished me for stepping over boundaries. I used as many tools in my toolkit as I could to clarify roles and responsibilities (and also demonstrate that I was there to help, not hinder), including implementing project management protocols, suggesting a catalytic leadership approach, and even making just a basic roles and responsibilities spreadsheet. None of it helped. To me, it began to feel as though my roots as the founder ran too deep.

Even though my involvement ceased a decade ago, my friend was trying to give me a role in the next chapter of the organization as a gesture of kindness. As a nonprofit manager, I jumped in and did my nonprofit management thing. This was a normal role for me, but I moved too quickly for the comfort level of the rest of the board, who was still trying to find their way. I felt the board president wasn’t following through on their role and they thought I was overstepping. Resentment increased and feelings were hurt. Eventually I resigned from the board, acknowledging that my friend perceived my help as interference and needed the freedom to find their own way. Had I not been the founder, I think we could have moved towards a direction of thought partnership, but with our unusual past, it was simply too much to navigate.

Learning from Experience

After this experience, I tried not to internalize what I perceived as a failure of my leadership and attempted to move past my own wounded feelings. The night I resigned from the board and wished my friend well, I poured myself a cup of tea and tried to remind myself that what I had experienced had played out many times before across countless organizations. Having worked on several leadership transitions, I knew that rough water happened. I also knew that the best founders, the ones who truly had the best interests of the organization in mind, transitioned with grace and humility, full of love for the movement they started and the difference they made. I thought about what I could have done differently and decided to publish this post as a case study that might inform others.

Tip for Transitioning Founders

If you’ve managed to read through that entire litany of successes and failures, perhaps you are seeing echoes of your own experiences in the scenarios I outlined above. If you are struggling with your founder or an entrenched leader, here are a few tips to consider:

Have a Transition Mindset from the Start

Many founders discover that they are so focused on getting things off the ground that they do not think of succession planning or leadership transition until the proverbial ship is ready to sail. Founders will save time and potential heartache later on by having a transition mindset from the start. While a charismatic founder is often the driving force behind new programs and donor relationships, nothing is permanent. Ask yourself what needs to be done to sustain and grow the organization after you have moved on. Remind yourself that you want the organization to thrive because of you, not in spite of you. You are the steward of a wonderful movement and your job is to help it sustain itself.

If you brought your friends in to help you launch your first board, start developing your network and expanding your board. Make sure the founding board has an eventual end to their terms and stagger the end dates so you do not lose multiple founders at once. Six months before the end of their term, begin recruitment for a replacement. And once your founders start terming out, celebrate their achievements and thank them for their help.

Define Clear Roles and Responsibilities

Founders do everything, from running board meetings to fundraising to implementing programs. Sometimes one or two people may take on the majority of the work, leading to burnout. And while some board members slowly burn out, others feel underutilized. Even worse, unclear boundaries may also lead to duplication of work or communication challenges.

A roles and responsibilities document helps to address these challenges. These documents can take many different forms, from a simple list of tasks that includes who is completing each task, to a “MOCHA” approach that outlines who Manages, Owns, Consults, Helps, and Approves tasks.

Check back for a downloadable roles and responsibilities template.

Create a Transition Plan

As you begin the transition process, take time to create a transition plan that lists the steps that need to be taken to ensure a smooth transition. This includes everything from changing names on the bank accounts, to sharing a password and accounts document, to making donor introductions.

A transition plan worksheet will be available for download soon.

Be Honest with Your Feelings

Leadership transitions are a big deal. After I started the charter school, it felt like I was sending my baby off to college. I hoped it would succeed and did everything I could to help ease the transition, but ultimately I needed to step aside and let the new team run with it. I had to learn how to keep many of my opinions to myself and change my mindset from that of a decision-maker to a thought partner.

Bring in a Transition Support Person

Sometimes transitions can get complicated. Some organizations may decide to bring in a transition coach or interim director to help with all of the communications, processes, and basic human feelings that are part of the transition process. The Sitka Group offers transition services alongside with a sliding schedule that works with your budget.

Give the New Leader Space to Settle

The new leader of your organization will need time to settle in. Some transition plans include having the founder stay on as an emeritus board member with specific duties, or even a paid assistant to the new executive. Sometimes this works incredibly well, allowing the new executive time to ask question and understand the background. At other times this scenario can turn into a micromanagement scenario, causing tension throughout the organization. Should you choose to stay on in some capacity, consider giving yourself a timeline for transitioning out completely.

whether you are staying on in some capacity or making a clean break, be honest and transparent about when the organization can contact you should they have questions or need guidance. Remember that you are the keeper of the history and story of the organization; no one will ever be able to tell the story about the founding of your program quite like you. Think about how you can serve as a thought partner or advocate for your organization.

Above all, whether you are the founder or an incoming leader succeeding the founder, remember that we are all human. Own your mistakes and celebrate your accomplishments. Acknowledge the immensity of a leadership transition. You will get though this and be better for it in the end.