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One of the most difficult things a leader ever has to do is walk away.

Whether it’s by choice, by retirement, or by termination, too few leaders show their best selves on the way out. This pattern holds true across industries and the costs of it are deeply damaging.

Sadly; a generation of long term charity leaders have provided far too many examples of what not to do. There are numerous well known stories of leaders who hang on too long, become self-serving in their final seasons, meddle in the organization after their departure, or are found to have betrayed their integrity.

There are many other similar stories that are known only to a small number of affected people.

Why is it so hard for leaders to leave?

1. They have too little identity outside of their role. We want leaders who exemplify the cause and values of the organization, but when that becomes the centre of their sense of self the thought of leaving it behind is devastating. It drives a dark insecurity that pushes good leaders to do things they would never have done in their better moments. 

2. They haven’t invested properly in developing successors. Many of today’s senior leaders never experienced being mentored by their predecessors. They rose to the top of their field somewhat independently and, while they may believe in the idea of preparing for succession, they simply don’t really understand how to help younger leaders prepare for senior roles. This leaves them with a sense that no one is ready for the responsibility and that they have to maintain control themselves.

3. They have no outlet. Decades of holding authority in primarily top-down leadership structures does not prepare the leader for stepping aside and finding influence in other ways. They are aware of all the accumulated knowledge and wisdom they hold and don’t know what to do with it if not in the first chair. The very real sense that what they offer is important is undermined by an inability to conceive of a way to contribute differently.

4. They thrive in power. Weaving through all the previous challenges is the truth that many leaders have become so accustomed to having, using, and managing power that the prospects of living without it are demoralizing. 

So what can we do better?

1. Normalize transition. Succession planning needs to be a constant, not something we reluctantly engage in when the current leader appears near departure. I’m an advocate for long term leadership but it’s unwise to not be always preparing for the possibility of change. Boards can take initiative on this with lead staff.

2. Mentor them in mentoring. Create the expectation that senior leaders are actively developing the leadership ability and technical skills of all their direct reports. Building understanding of generational tendencies with a resource like Sticking Points may be useful. Provide mentors with training, active feedback from their mentees, and accountability to deliver on this as a non-negotiable aspect of their role. 

3. Form exemplary peer groups. Senior executives need to move beyond the “lonely at the top” idea by actively connecting with current peers (and successfully retired examples). Seek out leaders who have departed well in a variety of ways and make it part of your dialogue. Share stories of transitions that went well and dig behind the scenes to find out what it took to make that happen.

4. Actively dismantle the damaging myths of leadership. Beyond the previously mentioned myth of isolation, there are expectations that leaders need to hold authority, control the organization, dominate meetings, and retain their influence. None of this makes for healthy transitions. More collaborative models of leadership and approaches that emphasize the leader’s role as developer rather than controller of the organization set a better tone. More than that; leaders seeing their identity beyond their work needs to become typical and affirmed.

5. Promote healthy versions of retirement. The idea that the only options are 60+ hour weeks or complete leisure is outdated and unhelpful. Look into creative options of part time consulting, board work, voluntary mentoring, resource development, and exploring new interests. The phrase “choice to work” helps me reframe the idea of a stage of life beyond full time employment.

It seems every relevant expert agrees there is a coming wave of leadership transitions and a shortage of qualified leaders to take over. The best way to manage this challenge is ensuring that succession is prepared for well and handled in ways that allow departing veterans to continue sharing their hard won wisdom even after they move on. Accomplishing this requires intentionality from boards, senior leaders, and successors. As leaders, we know the importance of handing this well. We can’t afford to continue seeing sloppiness, selfishness, stubbornness or insecurity making things more difficult. 

Photo by Anete Lusina from Pexels 

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