The not-for-profit sector finds itself uniquely challenged as the baby boomer generation ages. The social change and movement-building culture of the 1960’s and 70’s resulted in the creation of a large number of social service non-profit organizations. The pioneers who began working at those agencies and later grew into executive director leadership positions are now reaching retirement age. One estimate has 75% of not-for-profit leaders retiring over the next few years. Individually, these people face personal challenges to stay financially viable and socially relevant and their organizations face a potentially greater challenge of leadership that they may not have had to deal with in their history.

Some organizations are keeping their senior leadership long after the traditional age-65 retirement date. This is an easy route for the board and, in many cases, welcomed by the leader who may not have prepared for the day he or she might stop working.

Leadership change is always a challenge but it can be more difficult for the many long-term leaders at the head of many organizations today. The organizations may completely identify with these long-term personalities and usually, change at the top may spur changes at other senior management positions at a time when the new leader needs that senior management experience the most.

Of course, the leadership position at an organization is ultimately the responsibility of the board. Recognizing when it is time for a long-term leader to leave can be the most difficult decision they have faced during their term of membership. Board members may have little or no experience with business succession. Questions of how to enable the organization to survive and thrive when a long-term leader leaves are sometimes new to the board. Questions of board strength, staff strength as well as finances arise and must be addressed.

Ideally, when a leader is ready to leave, the organization is well prepared for the leader’s departure. Both are ready for their new futures. In reality, a leader and the organization are rarely aligned perfectly. In all too many instances the long-term leader wants to leave but is reluctant because of uncertainty about what to do next. The board should challenge the long-term leader to continually assess their level of interest, energy and motivation for staying and whether the organization is at a point that it can successfully go through a transition. The long-term plans of the leader are as important as the condition of the organization and the board should probe both topics as it eyes the timing for future succession.

Hopefully this post exposed some of the complex dynamics that challenge succession planning and its execution at many not-for-profits today. The transition after this one will certainly be easier. The next layer of not-for-profit CEO’s are not likely to have been in their job for 20+ years. While they may build the organization larger or better or both, they are distant from its founding and their attachment is more that of a caretaker than that of a parent. Starting the conversation about the future – the future of both the CEO and the organization, is the place to begin.