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A Leader’s Digest Blog

By Tess Escay Reynolds, Leadership Advisor and Founder of On-Hand Leadership Partners


Twenty years ago, I made the radical decision to leave my business-sector job to run a small nonprofit in San Francisco, focusing on employment social enterprises.  It was not an easy or quick decision. It came down to a distinct sense of “call” that I couldn’t shake, a quickening of my heart towards a cause that held both meaning and purpose, and a conviction to do this ‘now or never.’  I had a lot to offer, and a lot to learn too.  The promise of meaningfulness did materialize, and I can now say it was worth it.

Act I. Early Thoughts About Leaving

Five years into the job, I seriously wondered whether it was time to go.  I had achieved a financial and strategic turn-around, and the organization was in much better shape than when I started.  But the work was so much more back-breaking and heart-breaking than I had imagined.

The backbreaking part?  Yup, fundraising.  One is never done raising money.  The more you raise this year, the more you have to raise next year.  That means more grant applications to write, more donor and solicitation meetings, more fundraising events, more thank you notes and reports…  The sad statistics are that about half of first-time donors don’t give again.  So fundraising is essentially a leaky bucket to begin with, yikes!

Backbreaker #2? Hiring and retaining top talent. I was able to hire MBAs and MSWs and have them work well together, for less than half what they might make in the private sector.  Becoming a more successful organization meant that we had to hire more, train more, work harder at staff development and retention, and constantly rebuild our culture and teamwork.

Far worse than the backbreaking work was the heartbreak.  I particularly remember September 2008.  The mortgage-triggered financial crisis reduced donations while also cutting the value of my retirement plan by 40% — and I barely paid attention, because that month, three of my youth got shot.  Not the children that I birthed, but three youth in our programs.  One died, one survived, and another was paralyzed for life. All my hard work on strategy, fundraising, talent development and operations didn’t seem to matter.  I wanted to quit.  

I ended up staying 11 more years. What turned me around? It was not money or people.  It was air.  I needed to put the oxygen mask on myself before I could help others.  By grace, a friend invited me to join a ‘Soulcare’ program, and for a year I filled my soul with light, goodness and spaciousness. I took retreats, I learned to invite silence and solitude, and I learned all over again how to love and receive love.  

A year after Soulcare, I had the capacity within me to lead my organization through its first capital campaign – yes, in the middle of a recession.  We set out to raise $10 million in three years; we ended up raising nearly $15 million in four years. We grew threefold thanks to that campaign, and expanded across the Bay.  Lesson One: Only when my own fuel tank is full can I generate more fuel for my organization. 

Act II.  The Board Fears My Leaving so I Must Imagine Leaving

As the organization grew in scale and impact, my Board decided that my departure, whether planned or unplanned, would pose great risk to the organization.  A Board member led the effort to create an Emergency Succession Plan and a regular Succession Plan.  He found some good templates, and worked with me to define how the organization would keep running without me.  At first it felt like another “To-Do” but when it was done, we all felt good that we knew what to do if I was ever hit by a bus or something.  All the critical information was in one Board-approved document that we could pull up in the event of an emergency.  

More than the content, the process got my Board talking about important issues like, “Is there, or should there be, an internal successor?”  The answer is different for every organization, but in our case, we decided that a truly great internal successor wouldn’t be happy to remain #2 very long, so we should just focus on building a strong leadership team and worry about a CEO replacement when I was truly ready to step down.  The Board made me promise that when that time came, I would give them adequate notice.  “A year or so” is what I heard at the time.  

Having a Succession Plan in place is like having a Strategic Plan. Or maybe it’s more like having a Crisis Response Plan, like what to do in the event of an earthquake or a fire, which we in San Francisco take very seriously. You don’t like preparing one but you’re very glad to have one in place.  Lesson Two: Having a Succession Plan is quite freeing! 

Act III.  Thoughts About Leaving, For Real

The third time I thought about leaving was different. I was feeling tired again, this time in my body rather than my soul.  Sixteen years of driving 2-3 hours a day was wreaking havoc on my back, and my 10-to-12-hour workdays didn’t leave much room for exercise.  My blood pressure, cholesterol and blood sugar were rising steadily – not dangerously, but enough to prompt me to re-examine my lifestyle. Besides the health-related warning bells, something fun was also emerging in my life: a grandchild was on the way!  I had been a working mom from the day my kids were born.  I thought, wouldn’t it be fun to be involved with little ones before I got too old to pick them up?

I took the time to clarify my personal goals.  c

I signed up (secretly) for an executive transition workshop.  I worked on my personal readiness, and what I call a pre-departure plan.  I privately formed a ‘kitchen cabinet’ of three trusted friends who had gone through their own transitions and lent me loads of wisdom, as well as practical tools, along my journey.

During my annual evaluations with my Board, I began giving transition signals, saying that I saw myself remaining in my CEO role for “no longer than five years.” Then it became “two to five years” …and then “about two years.”  Until one day, I said to my Board Chair and Vice-Chair, “I would like to leave in a year.”

My transition did take a year.  I came prepared to that meeting with a draft Transition Plan and a high-level Communication Plan – but my Chair and Vice-Chair asked me to set aside my prepared slides, so they could simply process my decision and let it sink in.  

A few days later, we discussed how to communicate my news to the rest of the Board.  I had great Board relationships, so I insisted on talking with each one over the next few days.  I asked everyone I spoke with to keep it confidential until I emailed them that all Board members had been communicated with.  It is a testament to my Board that there were no communication leaks that week. Everyone honored my request to have one-on-one communications with every Board member.  I think that went a long way towards 100% Board retention and 100% Board engagement throughout my transition. 

Within weeks of my telling the Board, we had a Board Retreat scheduled. My Board Chair and I reset the Agenda to focus on my transition. That confused my executive staff a bit, since several were used to attending the annual Board Retreat, but thankfully they trusted me and went with the flow. (When it came time to share my news with staff, I took a similar approach of progressive disclosure, and again, there were no leaks prior to the all-staff meeting when I made the official announcement.)

My estimate of a one-year transition period assumed that a nationwide search would take six to eight months; it took seven-plus.   Prior to the Search period, the Board needed four to six weeks to organize themselves, interview search firms, and prioritize the essential characteristics they wanted in the next CEO.  After the search ended and my replacement had accepted the offer, he needed a graceful exit from his current job, so that added another six to eight weeks to the timeline. We also had an overlap period when I worked part-time to help with fundraising and complete a national initiative.  Had I been leaving for another job, a one-year transition would not have been possible, and the Emergency Succession Plan would have triggered scenarios of Interim CEO roles.  Fortunately, I had planned for a one-year transition, and that is what it took.  (The public view of the transition looked closer to eight months.)

My advice to all ED/CEOs: Have an Emergency Succession Plan, at a minimum.   To those who are starting to imagine a transition, start with an Organizational Sustainability Assessment, which helps you see what needs shoring up whether you leave tomorrow or ten years later.  To all, I pass on these key lessons I learned from my mentors and my own experience:

  • Plan early, plan thoughtfully, and plan with the organization’s interests in mind (and not your own).  You are allowed your part of the plan, but it must be subordinate to the organization’s.
  • Invite others to share the transition workload, such as the Board and other senior staff.
  • Build a personal “kitchen cabinet” for support.  Leaving a CEO post can surface all sorts of emotions and personal concerns that you can’t air at the office.
  • Allow time, lots of it.
  • Communicate inside and outside, often and honestly.
  • Exit for real.  Don’t hang around like the ghost of Christmas past, as a friend once told me.  If you’re putting on a new hat such as an Advisory role, take off the old CEO hat and set it aside.  There’s no such thing as hat-switching when it comes to successful executive transitions.

More on how to do succession planning well are in my two articles on this topic in REDF Workshops.  


I am happily “pretired.”  I work four days a week doing meaningful, rewarding work that leverages my strengths and experience.  Much of it is paid work as a Leadership Advisor and Coach to nonprofit ED/CEOs and their Boards, and sometimes their executive staff too.  I also do unpaid but rewarding work, serving on two nonprofit Boards (a family foundation and a nonprofit) and on the Advisory Council of REDF.  On Fridays when I don’t have Board meetings, I hang out with my two granddaughters, ages four and two, who keep me nimble and youthful in spirit.  Best of all, I get to live out one of my favorite quotes, credited to former British Prime Minister Benjamin Disraeli: “The greatest good you can do for others is not just to share your own riches but to reveal to them their own.”

About On-Hand Leadership Partners

On-Hand Leadership Partners was founded by Tess Escay Reynolds, who is a Leadership Advisor, Coach and Consultant for nonprofits and philanthropy.  She brings on-the-ground leadership experience and demonstrated success in program and talent outcomes.  Currently Tess works with ED/CEOs, leadership teams and Boards to achieve sustained impact for the people they serve and lead. Her work includes executive coaching, Board development, succession planning and the design and facilitation of staff and board retreats and leadership workshops. Previously, Tess was CEO of New Door Ventures for 16 ½ years.