Lessons for Nonprofits Facing a Leadership Transition

Written by Duncan McDougall:

If you’ve ever served as a nonprofit board or staff member, you know that even in the best of times it’s a considerable challenge to meet client needs, keep programs running smoothly, staff happy, and books balanced. That level of difficulty increases substantially when you’re also changing leaders at the same time. It can feel like trying to swap engines while you’re still flying the plane. Tales abound of nonprofits that faltered, or even failed, following a mishandled transition.

In 1998, I founded the Children’s Literacy Foundation (CLiF), a nonprofit that inspires a love of reading and writing among under-resourced children throughout Vermont and New Hampshire. Since then, the Waterbury Center-based organization has supported and inspired more than 400,000 young readers and writers in more than 90% of towns in the Twin States.

A few years ago I decided that in 2023, after serving as CLiF’s Executive Director for 25 years, it would be a good time for me to retire and pass the reins to a new leader.  To increase the chances of a successful transition, I decided to interview those who had gone through the experience so we could benefit from their hard-earned lessons: What worked? What didn’t?  What is essential to do? What should we avoid at all costs?

I eventually interviewed outgoing executive directors, incoming executive directors, and/or board chairs from 17 nonprofit organizations that had recently experienced leadership transitions. Most were based in Vermont or New Hampshire.  Some lessons seemed obvious. Others were surprising. The following are the most useful insights I gathered from those interviews:


Capture the Organization’s DNA and Executive Director’s Vision

Every organization is different. The outgoing Executive Director (ED), Board, and staff should take time to capture what makes their nonprofit unique and successful. The ED – especially founding EDs – should download their vision for the organization and what makes it work.  You don’t need to follow that vision in coming years, but it usually includes a lot of hard-earned wisdom you don’t want to lose.

Have a Strong Strategic Plan in Place

Create a strong and clear strategic plan that extends at least 6-12 months into the transition. It helps maintain stability and continuity during the transition, and provides a road map for the new ED while they get their feet under them.  It’s vital that all Board members understand and embrace the plan. The new ED can start to make their mark through shaping the next plan.

Don’t Forget Fundraising

Communicate with all donors – especially your key supporters – in advance of the transition.  Make sure they feel informed, and that the transition is viewed in a positive light.  Many nonprofits use a transition, especially one involving a founding ED, as a fundraising opportunity.  Consider creating a campaign to honor the outgoing ED.

Know What You’re seeking in a New ED

Nonprofits need their EDs to possess different skills at various points in their evolution.  You often don’t want a carbon copy of the outgoing ED. The Board needs to think deeply about what skills they are seeking in a new ED.  A search firm can help with that process.

Choice of Search Firm is Key

If you decide to use a search firm, its main value is not just providing access to candidates, but also its experience with dozens of similar transitions, knowing what questions to ask, and having an effective process.  And it’s key to have a good chemistry between the Board and the firm’s representative. The best firms will challenge your assumptions, and will conduct a strong background search with final candidates. You don’t want any surprises.


Limit Time When Both EDs Are Onsite

Having the two EDs onsite for too long is a major risk to transition success.  Any overlap should likely last no longer than 2-3 weeks – enough for the incoming ED to learn the ropes, but not so long that staff and supporters start to wonder who’sin charge.  If more time is required, the new ED can consult with the outgoing ED offsite or by Zoom for a set amount of time (say, up to 40 hours over the first 2 months). It’s up to the new ED to initiate the contact when needed.

Public Event to Mark Transition

There should be some sort of public event to celebrate the transition. This gives you the opportunity to make clear the transition has taken place, to welcome the new leader, and to recognize the contributions of the former leader.  Some organizations chose to have two events so the former leader doesn’t overshadow the new ED. 

Transition Relationships with Major Donors

This is another potential cause of transition failure. It’s essential for the outgoing ED to successfully transition relationships with major donors to the new ED.  These supporters must feel comfortable with the new leadership. This process can be through in-person meetings, or via Zoom, and may occur before or after the actual transition, but it’s critical that it take place.

Staff Input Is Key

The staff should provide their thoughts on the type of person they hope to see in a new ED, and have a chance to meet final candidates and offer their impressions.  But they should not be asked to rank the final candidates. Ultimately, it’s the Board’s decision, and it may not pick the same person as the staff.

Long-Term Commitment

Try to get a sense from the candidates if this job is a long-term commitment, or a stepping-stone to something else.  You ideally want someone who wants to be here for many years.

Do They Know Vermont?

Be careful hiring someone from a warm climate who has never lived or gone to school in a northern, rural state like Vermont.  Sometimes, after a year or two, the ED or their partner suddenly realize it wasn’t what they expected, and decide to leave. Then you’re back to square one.


Outgoing ED Should Not Serve on the Board

The outgoing ED has so much experience, wouldn’t you want to have them on the board? No, you don’t. It creates a situation where the new ED now reports to the old ED.  That’s a recipe for disaster.

Keep Financial Goals Steady for the First Year

It’s helpful not to swing for the fences in the first year.  Keep financial goals steady as the new ED gets used to the position and develops relationships with major donors.

Support the New ED

Every new ED would benefit from the support of the board. In at least the first year the board should increase their efforts regarding fundraising. The Board chair could meet informally with the new ED every month or so in the first year to offer any assistance, and to make sure any challenges are addressed early. The board can also arrange mentoring or coaching for the new ED if necessary. The board should also maintain communication with the staff  to make sure their concerns are heard.

Recent research suggested that almost half of nonprofit executive directors are considering departing from their jobs or are actively taking steps to leave.  Since many transitions occur unexpectedly, boards should consider developing a succession plan in advance so they are not scrambling when the time comes.  If your nonprofit is facing an upcoming leadership transition, I hope the above suggestions prove useful to you.

Duncan McDougall ([email protected]) founded the Children’s Literacy Foundation (CLiF) in 1998 and served as its Executive Director for 25 years. Duncan has an MBA from the Tuck School of Business at Dartmouth College.  He worked as a management consultant for 7 years. He has also been a freelance writer, teacher, and public radio commentator, and is active in local environmental and political campaigns.  He and his wife live in Waterbury Center, Vermont.