Fundraising Strategy • Campaign Planning • Board Engagement


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Hello Friend,


As we come to the end of another season in Southwest Florida, I’m already starting to hear rumblings from board members and executive directors about the leadership transitions we often see this time of year.


I’m delighted to feature an article by my colleague Barbra Kavanaugh, Partner with Interim Executive Solutions, a national firm that places experienced interim CEOs and nonprofit executives during leadership transitions. Barbra works with nonprofit boards and organizations across the country on interim leadership and succession planning and is based in South Florida.


Barbra will be in Naples this June—if you’re interested in meeting with her to learn more, I would be happy to make an introduction.


As always, I’m here to support your fundraising, strategic planning, and board leadership success.


Warm regards,

Tracy Connelly, CFRE


Managing Leadership Transitions

by Barbra Kavanaugh


“I just sat down with my coffee to review my emails—and there it was… the message from the Executive Director giving notice.”

—said every Board Chair, at least once.


Whether anticipated or unexpected, leadership transitions are among the most challenging moments for any nonprofit organization.


  • A long-tenured founder preparing for retirement.
  • A newer executive who isn’t the right fit.
  • Or a sudden departure during a time of uncertainty.


Regardless of the situation, the impact is immediate—and widespread.


  • Staff look for reassurance
  • Board members take on unfamiliar responsibilities
  • Funders and community partners watch closely


A Growing Reality Across the Sector


Leadership transition is not rare—it’s increasing.


  • Fewer than 1 in 3 nonprofits have a written succession plan
  • A majority of nonprofit leaders expect to leave their roles in the coming years


In short, many organizations are not fully prepared for a moment that is increasingly inevitable.


The Space Between One Leader and the Next


Executive searches take time—often several months.


In the meantime:


  • Programs must continue
  • Staff need direction
  • Donors expect confidence
  • Critical decisions can’t wait


This “in-between” period is not just a gap—it’s a critical phase to manage well.


The Role of Interim Leadership


More organizations are turning to professional interim executives.


An experienced interim leader can:


  1. Provide steady leadership during uncertainty
  2. Support staff and board dynamics
  3. Assess organizational strengths and risks
  4. Clarify priorities for the next CEO
  5. Maintain momentum with donors and partners


Many boards find this period becomes an opportunity to strengthen the organization for its next chapter.


The Right Question


Instead of asking:

“Who should our next CEO be?”


Consider asking:

“What does our organization need right now to ensure the next leader succeeds?”


A Resource for Our Community


Author and interim executive leader Barbra Kavanaugh will be in Southwest Florida this June.


If your organization is navigating a leadership transition—or wants to be better prepared—I’d be happy to connect you.


Schedule a Conversation with Barbra now


Final Thought


Leadership change is inevitable.


With thoughtful planning and the right support, it can become a defining moment—one that strengthens your organization for the future.

Professional Credentials in Fundraising & Philanthropy Workshop - April 28


I am delighted to be co-presenting a workshop with Gina Dengler, CAP, CFRE, and Dolly Farrell, MPA.


April 28

8:30am-10:30am

The Collaboratory in Fort Myers


Hosted by the Association of Fundraising Professionals Collier-Lee Chapter, this free workshop qualifies for 1 CFRE Education Point (Category 1.B).


The session is ideal for anyone interested in professional development. Earning a recognized credential can open doors, strengthen your expertise, and enhance career opportunities.


Please register and plan to join us.

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