Any leadership transition can be fraught with uncertainty and difficult decisions, but founder transitions can be particularly wrenching. Contributions by a founder over the lifetime of an organization can span organizational culture, funder and partner relationships, and vision for the future. Staff, board, external stakeholders, and leader, alike, often find the transition more difficult than expected, even with the best-laid plans.

Laurel Dukehart

This was the case for Laurel Dukehart, the former CEO of Gateway to College National Network, when she began planning for retirement in 2014. Since 2003, she had led the national replication of Gateway, a program of Portland Community College and Portland Public Schools. In 2008, with the help of a spin-off grant from the Bill & Melinda Gates Foundation, she was directed to create a successful and independent national nonprofit, a position from which she retired in March 2015.

Here she reflects on how she managed her transition, highlighting the challenges she faced and lessons learned along the way.

When did you decide to leave Gateway, and how did you arrive at the decision?

I made my decision early in 2014. I wanted to give at least a year's notice, which was a driving factor for me, so I told the board that I planned to leave in spring of 2015.

My timing was influenced by where we were in our business plan. We were in the middle of our third business plan, and I wanted the transition to happen when there were still a couple of years left on it. I felt it would be best for the board and for the organization if the new leader had a bit of a roadmap in the beginning.

Another factor was that when I looked at the skills and activities needed during the last two years of the plan—such as being a comfortable spokesperson, having strong national marketing experience, wanting to be out on the road a lot, developing new kinds of funders—the role didn't seem to align with my areas of strength.

In the first phase of the organization, I was the right person. I'm very entrepreneurial, so for the design and implementation of national replication and rapid growth, and developing the new organization, staffing up, and building a national board, I felt very comfortable.

A third factor was more personal. I had been working 60-hour weeks for years. I traveled constantly. I was of an age and in a financial place where I could retire and step back from that lifestyle. I wanted the organization to find somebody who was as energized and as committed as I had been through my 12 years with Gateway to College.

When did you first raise your retirement with the board, and what steps did you take to help them embark on the organization's next phase?

I discussed it informally with a few board members in February or March of 2014. We already had a strong succession plan, so one of the steps I took was to re-familiarize them with it. I had done a lot of research on how other organizations had gone through transitions. I gave them a good how-to book, Tom Adams' The Nonprofit Leadership Transition and Development Guide, which had templates on exactly what to do. I also shared sample communication strategies and press releases from other organizations, and was able to offer an analysis I'd done on several search firms I'd researched a year or two previously, during an aborted search for a different position.

What was the board's biggest concern?

Its biggest concern was our funders and the fact that they all had strong personal relationships with me. This was something that we had to think about, especially because we were funded by just a handful of large foundations.

The board also wanted a lot of time to plan before we went public with the news. One challenge was that we held quarterly meetings. Being a national board, we had to fly people in from all over, so meeting every three months during this time was difficult. I made the formal announcement at our April 2014 meeting, then we took the July and November meetings to dig in and plan, with the expectation that they'd interview final candidates at the February 2015 board meeting.

The board also wanted to wait to communicate with the staff. And, I was a little bit less comfortable with that, but followed their request so they had time to plan.

How did that work for you, still being the acting CEO?

I will be honest that it was a strain for me to know my plans and not be able to share them with my executive team. A number of them had been with me for 10 or 11 years. With the board's approval, I shared my news with the executive team just before the July board meeting. We told the rest of the staff and started implementing our external communications plan in September of 2014, with the target transition date of April or May of 2015.

How did the staff react?

There was some sadness. Staff members saw me as the face of Gateway to College, but I always believed that everybody played a role in being the face of Gateway. Staff also were concerned about whether we would see the business plan through. They and the board were very committed to the plan, so I was able to tell them that the board, like me, wanted to make sure that it was implemented fully.

Another concern was the role staff would play in the search process. We needed to build trust that the transition would work well and that their interests would be considered. To do this, the board created a plan that called for a transition committee and a search committee, and we agreed a key staff member would sit on each to act as a liaison back to the staff.

How did you communicate the retirement to funders and partners?

We decided that all of our funders would get a personal phone call from me and an offer that, if they had questions, they could speak with the board. The board was very open to making sure the funders were comfortable. Then, when we did the big communications roll out in September, we used email. There were three pieces: a letter from me, a letter from the board chair, and a press release.

For the Gateway to College partner programs, we had a separate process, where they received the same thing, but the letter was more tailored to my relationship with them. We also held several webinars for any Gateway program staff nationally who wanted to ask questions.

What concerns did partners and funders raise?

Our communications went a long way to alleviating concerns. It took a lot of time, but it was time well spent and was one of the reasons we wanted to give the transition such a long runway.

With the funders, something happened that I didn't expect, though. They were all, I think, comfortable with the plan and with the board. They knew we were trying to be thoughtful and strategic about my transition. But despite their confidence in our process, most of our funders put their future fundraising decisions with us on hold, waiting to see who the new president would be. A number of big programs and grants that I had been hoping to finalize before I left were put into limbo. This was a big lesson learned. A critical part of my transition plan was that I would be shepherding these fundraising projects during my last months with the organization. We ended up losing around eight months of productive fundraising time.

What role did you end up playing in those last months?

The task for me became to encourage business as usual, to reassure staff that the business plan was moving forward, and to make sure the two committee liaisons kept staff informed of the transition process.

I also implemented a new performance management system, which I had begun before I announced my departure. I worked with the senior team on their plans and goals, and helped roll the process down to their staff. My intention was that when the new CEO arrived, I could give her a packet with reports from each of the executive team members, along with a four- or five-page memo from me. These would serve as my hand off to say, 'Here's where we are. These are the quarterly goals we set for the last year, here's how we did on those goals, and here are the goals for the next quarter.' This also served to make sure that the executive team was ready for their new boss. I wanted to help them put their best foot forward with a new person.

But, to be candid, in the last two to three months I didn't feel as productive as I would have liked, largely because of the stall in the fundraising work I had expected to be busy finishing up.

Did you participate in the onboarding of the new CEO?

No, the board felt that a clean break was needed to give the new CEO the opportunity to come in as a leader. During the board's interview process for the two finalists, I did meet with each of them privately to answer their questions. But to be clear, I didn't interview them. I was very careful to respect the board's role there.

What advice would you offer leaders planning their own transitions?

I strongly recommend a succession plan. We had a detailed one, so it wasn't an abstract concept when I announced my retirement. Our succession plan was up to date—we reviewed it on a yearly basis along with an emergency business continuity plan. We also had a detailed multipage communication strategy delineated by audience, also updated yearly.

Also, it's important to help the board understand that it takes a significant amount of time to do this right. It also is easier if your board meets monthly. Our organization has quarterly meetings, so, in my case, the transition largely hijacked the work of the board for three quarterly meetings in a row. But having a current business plan in process for staff to routinely report goals against made it easier for the board to change its focus for a period of time and lead a successful transition.