You have to get my successor in here at least six months before I leave so I can train him! That was how Alice Hendrix[1] responded to my question about how she saw the upcoming CEO transition going.

I had just been engaged by Alice’s board to help them recruit and hire her successor and to help the board manage the transition process. My initial response to her comment could have been, “no cause for alarm”; Alice was the departing CEO and an upcoming transition always produces some level of anxiety. Plus, many departing executives overestimate the amount of overlap necessary with their successor. But, it was how she said it — staccato while jabbing her index finger into her opposing palm to emphasize every word. Now, THAT was a little disconcerting. My thought was, “Is she a ‘general’ or a ‘monarch’ who’s being eased out by her board?” But what does that mean? “General”? “Monarch”?

Jeffrey Sonnenfeld, now at the Yale School of Management, studied the departure styles of America’s corporate leaders when they leave the CEO role. He chronicled his findings in the book, The Hero’s Farewell.[2] Sonnenfeld found that corporate CEO departures seemed to follow one of four patterns, which he summed up using the metaphors “monarchs,” “generals,” ” ambassadors,” and “governors.”

  • Monarchs stick around forever and usually don’t leave voluntarily; instead, they are forced out of office either through board action, ill health, or death.
  • Generals leave reluctantly, often forced to give up the reins. Frequently their retirement time is spent plotting a return to power.
  • Ambassadors leave gracefully, but quite often maintain a close relationship with their former organization, sometimes through a formal role.
  • Governors, like ambassadors, usually leave the role with little drama but quickly shift their attention to another top leadership post or high-status position elsewhere.

Based on my work with nonprofit executives, I believe there is a missing category — a pattern I call “stewards.” Like ambassadors and governors, stewards leave gracefully. But unlike ambassadors, they don’t retain a role with the organization. And, unlike governors, they don’t head off to another CEO role. Instead, they slip rather easily into a new role or life situation in the community.

When they leave the role, Stewards “hand off and ride off.” They don’t stick around, overshadowing the new leader at their former organization. Nor are they antagonistic toward their former employer. Rather, they move forward, finding a new path and passion in their post-career life. For some that might be full-time retirement. For others, it’s parlaying their skills into a new employment role or even an encore career. They maintain friendly and fond relations with their former employer without formal ties to it.

For many stewards, their new life involves an ensemble of activities melding lifelong passions with new discoveries. For example, one former executive director I know has had a lifelong passion for painting, and he was a masterful fundraiser throughout his career. Now his post-career life involves working as a contract fundraiser for various nonprofits, but balancing that with time in his painting studio. Another former CEO discovered a new-found interest in capacity building that she now pursues with gusto, but that’s coupled with a lifelong interest in travel. What these executives have in common is that they are clearly stewards. They are happily fashioning their post-career lives.

For the stewards I’ve observed, post-career life involves a bit of bricolage[3] — the opportunity to build their new lifestyle by creatively combining past experiences, resurfacing diverted interests and capitalizing on present skills. One executive told me, “I’m making it up as I go along.” But to me, her lifestyle looks akin to the creative improvisations of a good jazz musician who’s turning a lifetime of practice and interests into a whole new approach to self-expression.

The problem with monarchs

Sonnenfeld found that leadership style doesn’t predict departure style. In other words, a hard-charging CEO could turn out to be a governor or an ambassador (or a steward) when it comes time for their departure. One thing is for sure: departure style deeply influences the success of the succession, especially if the leader loses relevance and the organization begins to drift or if the organization’s leadership needs outpace the leader’s abilities.

Certainly, an organization’s leadership needs can change because of growth of the organization or situations where the increasing complexity of the organization outstrips the executive’s capacity to lead it. But I believe a bigger source of disconnect is executive complacency. Of the well over 100 CEO transitions I’ve been involved in, more than a few involved monarchs who were being “eased out.” These situations almost always involved a complacency-driven disconnect between the organization’s leadership needs and the leadership style and attention the executive was willing or able to provide. These executives had lost relevance and their organizations began to lose relevance as well.

For example, during one memorable transition-assessment interview with a senior staff member, she commented, “Several years ago, Sue (their departing executive director) went on sabbatical, but she really never came back. She’s here physically, but she never came back mentally. So, we have been drifting along all that time. We are doing okay, but just okay.” In the assessment, I discovered that during the years that the organization was “drifting along,” a competing organization emerged and peeled off a large part of my client’s highest dues-paying and most influential members. During the drift, the CEO had lost focus, and the organization had not kept pace with the changing needs of a large group of its primary customers. The organization had lost its edge because the departing CEO was managing like it was yesteryear. She was basking in past glories. She was complacent and lost situational awareness.

There isn’t any problem with working as long as you want. The problem is when there’s a disconnect between the leadership needs of the organization and your ability to shift to meet those needs. To be clear, it’s not an issue of age. It’s an issue of complacency.

That’s where monarchs are most prone to run into trouble. Over time, their leadership approach can lose relevance. Why? Ok, this is anecdotal, but in my experience, monarchs often become increasingly self-referential. Over time, they begin to see themselves as the star of the story and the organization as their stage, and, in their myopic state, they begin to lose awareness of the changes around them. At their worst, they begin to act like the organization is there to serve them. Thus, the gap between their leadership approach and drive and the leadership demands of the organization begins to widen.

The only way around this is feedback, but most executives aren’t receiving regular, useful feedback from their boards. Generally, nonprofit boards do a pretty lousy job of evaluating their CEOs, and the longer an executive has been in place, the less likely the board is to provide vigorous and useful feedback. One study reported that nearly half (45%) of nonprofit executives hadn’t had performance evaluation in the past year. And of those who had a recent evaluation, two-thirds said the board’s review was “only a little useful” (53%) or “not useful at all” (15%).[4]

If the executive in the example above had been receiving regular evaluations, she might have been able to shift, or the board might have been able to stem the exodus of members sooner.

Consequently, some nonprofits drift along until they reach some breaking point: either the organization confronts a crisis that brings the underlying issues into focus, or board leadership (typically new leadership) declares the situation intolerable and compels the board to act. Drifting toward a breaking point is costly — and painful — for everyone involved.

Dealing with a general is the board’s problem

One challenge with generals is that their tendencies usually don’t show up until after the transition to their successor has taken place.

Two contrasting cases come to mind that underscore the fact that it’s the board’s responsibility to deal with an interfering departed general, not the new executive.

In both cases, the departing executive hadn’t really mentally moved on from the role. Both were hyper-vigilant about their successor, and overtly meddlesome, feeling no qualms about “checking in” with their former staff members. And unfortunately, all too ready to magnify the perceived flaws of their successor while the successor was trying to find her sea legs.

In one case, the general was successful in her campaign to oust new executive because the board caved in. Despite counsel to stop the former executive’s meddling, remain objective and evaluate the successor on her own merits, the board refused to demand that the former executive stop interfering. They let the situation fester, and ultimately they let political pressure outweigh their fiduciary responsibility.

In the other case, the board stood strong, buffering the departed executive and fairly assessing the successor based on the board’s own criteria. The successor went on to have an outstanding tenure and the organization prospered under her leadership. But the process of getting there was not without challenges, requiring the board to step up and put the interests of the organization first. In this case, the “general” ultimately had to be ejected from the organization.

These two cases underscore the fact that, as the departing executive, once you leave the organization, it’s the board’s and your successor’s organization, not yours. And there’s one surefire consequence of meddling, you’re going to look like a schmuck. Moving on is the only high road.

These cases also highlight the importance of an engaged board with strong leadership, especially during a CEO transition. If the leadership of the first board had been as courageous as the second, the entire trajectory of the transition, and potentially the future of the organization, might have been different. The board’s job is to manage the transition. And, managing a CEO transition is a bit like flying an airliner. Anybody can sit at the controls when it’s on autopilot, but when stormy weather hits, you need astute and potentially unflinching leadership guiding the transition.

What accounts for the differences in departure styles?

The differences in departure styles boil down to one thing: the mindset of the departing leader. Sonnenfeld suggests that the leader’s departure mindset is shaped by two factors: first, the leader’s sense of the trappings of the position and how strongly they identify with the role, and second, the leader’s sense of heroic or transcendent personal mission and their sense of completion about that mission. Together these two factors provide a potent psychological glue that bonds the leader to the role.

To further explain the psychological factors at work, Sonnenfeld draws on the writings of Otto Rank, a psychologist who proposed that leaders and artists share similar traits. They both derive a sense of creativity and freedom from their work. Sonnenfeld explains, “[like] actors, authors, and other ‘work-intensive’ professionals, they are different from many other types of workers in that they have enormous discretion over their work conditions, a nearly insatiable drive to create, and a reluctance to concede that their crusade is complete.”

The sense of freedom coupled with the creative urge results in both artists and leaders becoming what Sonnenfeld refers to as “work intensives,” people for whom work is less about work and more about self-expression. More recent research would refer to these folks as ”work engaged.” Work engagement is “a positive, fulfilling, work-related state of mind that is characterized by vigor, dedication, and absorption.”[5] Vigor is the experience of mental resilience and a high level of energy while at work. Dedication means you’re enthusiastically involved in your work and you feel a sense of “significance, enthusiasm, and challenge.” Absorption means “being fully concentrated and happily engrossed in work, such that time passes quickly.”[6] Together, these are robust, gripping psychological forces that bond the leader to the role because the work itself is intrinsically rewarding. Couple intrinsically rewarding work with a nonprofit’s heroic mission, and it is no wonder why some leaders appear superglued to their jobs. This is especially true for those leaders who lack outside interests, where work is the central focus of their lives.

There is a difference between work engaged and workaholics. This topic is too broad to cover here. But in sum, while both work engaged and workaholics tend to work long hours, the work engaged do so voluntarily because they find the work intrinsically rewarding. On the other hand, workaholics feel compelled to work and are consumed by their work, thinking about it on the job and off.

Is there a preferred departure style?

When it comes to preferred departure styles, I think it boils down to two questions. First, do your departure intentions align with the leadership needs of the organization? In other words, is your leadership style still relevant, with the outlook and drive necessary to continue to guide the organization forward? Second, have you prepared for (or even thought about) what a successful post-career life might look like for you? (For more on that, see my article on post-career success factors.)

Based on my observations, anecdotal though they may be, the stewards and governors I’ve worked with seem to be the happiest in their post-career lives. They were able to move on, for the most part gracefully, and find freedom, satisfaction, and enjoyment after they left their organizations. My experience with happy monarchs is somewhat limited because of the nature of my work. Often our work with monarchs involved organizations that were heading for a difficult transition, which obviously skews my experience to the negative. Yet, I am certain that there are monarchs out there who continue to enjoy their work and whose boards are happy with their performance.

Ambassadors — those who maintain a formal role with the organization — can be a mixed bag in the nonprofit world because of the possibility of overshadowing the successor. Due to differences in board dynamics, nonprofit CEOs SHOULD NOT follow the corporate model and join the board of directors. Likewise, assuming a formal staff role within the organization can be similarly problematic. Externally officed “emeritus” or advisory roles seem to work slightly better. But, these are rules of thumb based on experience, and individual results may vary. There are very few absolutes when it comes to leadership succession. The real test of any kind of ongoing relationship is that for it to work at all, it has to work for your successor first. If you do have an ongoing role, make sure there are plenty of check-in points, and if it’s not working out for your successor, then you, the departing leader, MUST take responsibility. Depart gracefully.

Can we shift departure styles?

Can we shift styles? My honest answer is, “I don’t know for sure.” There’s not enough research out there on departure styles to be helpful. But I would like to think that by engaging in some honest questions, leaders can at least become aware of their departure style tendencies, and, through diligent effort, design a departure path that satisfies them and protects the interests of their organization. Here are a few questions you might ask.

Do you have monarch tendencies?

Does your notion about exiting your organization involve some version of “carrying you out boots first?” If so, honestly, what’s the likely impact of that scenario on your organization’s long-term vitality? In the near term, do you have a board-adopted succession policy and a backup plan for your position that includes someone who is cross-trained to step into your role in an emergency? Also, keep in touch with the board about organizational performance and direction. As a possible monarch, you’re probably a long-tenured executive. The longer an executive has been in place, the more deference the board gives to that executive — up to a breaking point. Use your authority in your leadership to open a discussion about performance and relevance questions; otherwise, you might be in for a rude awakening on the day that the board has a different idea about your leadership relevance. Finally, have you considered that moving on might be a growth opportunity – a gateway to a new way of life presently not visible to you? Might hanging onto the role be cutting you off from greater richness in life to be had elsewhere?

Are you a possible general?

Do you have a hard time imagining your organization not just thriving, but surviving with anyone else but you in the CEO position? How do you imagine that scenario playing out? You should also be prepared for a rude awakening by the board. My suggestion is to get a succession plan in place, pronto. Find the joy in cultivating the next generation of leaders, and develop some life-compelling interests outside the organization.

Might you be a governor?

Do you see retirement or post-career life as a pathway to service in some other organization or another capacity in the community or your profession? Do you feel like your personal sense of mission continues, but you need a change of venue? Are you actively preparing potential internal successors? As part of your exit strategy, you may want to begin exploring what that change in venue might involve and what next leadership challenge might make your heart sing.

Do you think you’re an ambassador?

Do you easily imagine leaders on your team or in your community being able to step into the role? Are you actively developing the leadership talents of members of your team? Do you see retirement or your move into post-career life as an opportunity to continue to serve your organization in another capacity? Do you think it’s in your constitution to step out of the limelight and into an emeritus or other “ex-CEO” role? Also recognize that your ongoing involvement in the organization has to be at the behest of your successor, and the relationship must be under his/her control. Be prepared to have a “Plan B.”

Finally, are you a potential steward?

Similar to ambassadors, can you see the possibility of leaders on your team or in your community being able to step into your role? Are you cultivating the leadership talents of team members? Do you have a post-career project in mind that is drawing you forward and that has you excited about your next chapter of life? Do you have a social support circle — friends and outside colleagues — who matter to you and to whom you matter? Are you aligned with your spouse or significant other about the timing of your departure, and do you have similar notions about the composition of post-career life together?

I hope this article has given you a glimpse into the impact that your departure style could have on your organization, your board and staff, and yourself. Hopefully, these ideas will enable you to choose a departure style rather than having fate thrust one upon you. I encourage you to take a moment (or many moments) to create a vision for how you want to leave your role and step into life’s next chapter. My hope is that you depart on a high note, being fondly thought of, respected for your leadership legacy, and admired for the grace that you demonstrated in your departure.

Related Articles

Six Nonprofit CEO Succession Readiness Questions

Every Nonprofit CEO Needs an Exit Strategy



[1] Name was changed to protect identity.

[2] Sonnenfeld, Jeffrey A. The Hero’s Farewell: What Happens When CEO Retire. Oxford University Press, 1991. Available on Amazon.

[3] “Constructed or created from a range of available things.”

[4] Cornelius, Maria, Richard Moyers, and Jeanne Bell. Daring to Lead 2011: A National Study of Nonprofit Executive Leadership. San Francisco, CA & Washington, DC: CompassPoint/Meyer Foundation, 2011.

[5] González-Romá, Vicente, Wilmar B. Schaufeli, Arnold B. Bakker, and Susana Lloret. “Burnout and Work Engagement: Independent Factors or Opposite Poles?”. Journal of Vocational Behavior 68, no. 1 (2// 2006): 165-74.

[6] Bakker, Arnold B. “An Evidence-Based Model of Work Engagement.” Current Directions in Psychological Science 20, no. 4 (2011): 265-69.