Every Executive’s Departure Has a Style. What Will Be Yours?

Updated June 4, 2022

Get my replacement here at least six months before I leave so I can train him. That was how Alice⁠[*] responded to my question about how she saw the upcoming CEO transition going.

Alice’s organization had just hired me to find her successor and advise them on the transition between Alice and the new CEO. My response to her statement could have been, “no cause for alarm.” Alice was retiring as the CEO, and transitions and retirement always create an element of anxiety. Also, departing execs often overestimate how much overlap their successors will need.

But, the way she said it — staccato, jabbing her index finger into her palm to emphasize each word — THAT was more than a little concerning. I thought, “Oh boy, I may be dealing with a “general” here.

In his book The Hero’s Farewell, professor Jeffrey Sonnenfeld looked at how America’s corporate CEOs left their jobs.[i] He found four common departure styles. He called them “monarchs,” “generals,” “ambassadors,” and “governors” to describe how they leave.

  • Monarchs seem to stick around forever, and most don’t leave voluntarily; instead, they are forced out by the board, poor health, or death.
  • Generals often leave reluctantly, having been forced to relinquish command. And, when they leave office, they cause havoc for their successor.
  • Ambassadors leave gracefully and maintain a close relationship with their former organization, often through a formal role.
  • Governors move to other top leadership positions or high-level roles with little drama.

When nonprofit leaders change jobs, there seems to be a fifth pattern from what I’ve seen. I call this one “stewards.”

Stewards leave with grace, but unlike ambassadors, they don’t stay involved with the organization in a formal way. Most of them do what I call “hand off and ride off.”

Some move to another leadership position, like governors, while many are ready to leave those responsibilities behind. For some, that could mean retiring full-time. Others put their current skills to use in a less demanding position elsewhere. And still others might pursue an encore career in an entirely new field, using skills they already have, rekindling dormant talents, or developing new ones.

Stewards move on and maintain friendly but unofficial ties with their former employer.

Leadership style doesn’t predict departure style

Sonnenfeld says that the way an executive leads doesn’t affect how they leave their job. A hard-charging CEO’s exit, for example, could involve any of the departure styles. But one thing is sure: the way a leader leaves has a big impact on the succession process.

Let’s look at how.

The problem with monarchs

Not every long-term executive is a potential monarch. Monarchs aren’t a problem because they hang around too long. Instead, it’s when their leadership loses relevance because they become complacent or aloof in the role. Their relevance starts to erode, but they don’t recognize it, or worse, ignore it.

More than a few of the 100+ CEO transitions I’ve consulted on and the hundreds more our firm has handled involved monarchs who were being eased out. There was a growing gap between what the organization needed from its leaders and what the executive was giving in these situations. As these executives lost relevance, so did their organizations.

For example, in one transition assessment interview, a senior staffer said about the departing CEO, “Several years ago Sue went on sabbatical, but part of her never returned. She’s here physically, but part of her never returned in spirit. All this time, we’ve been drifting along. We are doing okay, but just okay.”

As the assessment progressed, I learned that while Sue’s organization was “drifting along,” a competing group started up. And the competitor peeled off a large part of my client’s most influential members. At the same time, some important funders in the community lost interest and quietly left.

Because the CEO had lost focus, the organization didn’t keep pace with the changing needs of a large group of its most valuable stakeholders. Sue was complacent and lost situational awareness. And her leadership was no longer relevant. Worse yet, she was utterly clueless about it.

As a result, the gap between her approach and the organization’s leadership needs widened.

Regular performance evaluations are the best way to avoid these situations. But most executives aren’t receiving consistent, beneficial reviews and feedback from their boards. And the longer an executive has been in place, the less likely the board will review them.

In one survey, nearly half (47 percent) of responding CEOs said they had not received a performance evaluation in the previous year.[ii] In another study, more than half (53%) of executives who had received a review said the board’s assessment was “only a little useful,” and another 15% said it was “not useful at all.”[iii]

But what if Sue’s board defied these odds and the board had evaluated her performance regularly? She might have been able to shift, and the organization might have avoided or stemmed the member and funder exodus sooner.

Monarch-led nonprofits, like Sue’s, often drift along until they reach some breaking point. A mounting crisis spotlights the underlying problems, or board leadership (often new leadership) declares the situation intolerable and compels the board to take action. Drifting toward a breaking point is costly and painful for everyone involved.

Dealing with a general is the board’s problem

“Generals” is Sonnenfeld’s term for ex-CEOs who become disruptive to their former organizations. That’s one of the challenges with generals – they’re typically not recognized as generals until they’re out of office and causing trouble.

Here are two cases that demonstrate that dealing with a misbehaving general is the board’s job, not the new CEO’s.

These ex-CEOs had not mentally moved on from their previous roles despite handing the job over to new executives. Both were overly vigilant about their successors and interfered openly. They continued “checking in” with their former employees despite our coaching. And they were all too happy to tell staff and the board about what they saw as their successor’s flaws and make them seem even worse.

In one case, the former CEO, in effect, ousted the new executive because the board caved in. Despite being advised to remain objective, judge the successor on her own merits, and tell the former executive to stop interfering, the board did nothing and allowed the situation to worsen.

In the end, this board let political pressure win out over their duty as trustees.

In the other case, the board did what a board should do in these circumstances. The board stepped up – they rebuked the former CEO (who had a one-year contract as an “advisor”) and objectively assessed the successor’s progress based on the board’s criteria.

The successor had a stellar tenure, and the organization thrived under her direction. But getting there wasn’t easy. The board had to step up and courageously put the organization’s needs ahead of their comfort. In the end, the general wouldn’t change his ways, so he was asked to leave the organization.

These examples demonstrate the importance of having an engaged board with solid leadership, particularly during a CEO transition. Imagine if the first board’s leaders had been as courageous as the second – the entire transition process and possibly the organization’s future could have been different.

The board leads the transition. But leading a CEO transition is similar to piloting an airplane. Anyone can sit at the controls when the weather’s good and things are running on autopilot. But when storms come, you need strong, unflappable leadership at the transition helm.

What accounts for the differences in departure styles?

What separates departure styles is the mindset of the departing leader.

Sonnenfeld says several factors shape an executive’s departure mindset: first, how strongly they identify with the role. Second, is their sense of a heroic or transcendent mission. Third, their sense of completion about their mission. In other words, they “are” their role and have a lot of unfinished business and unresolved feelings regarding their life’s mission. Together, these factors create an emotional bond that binds the leader to the role.

Sonnenfeld bases his reasoning on the work of Otto Rank, a psychologist who argued that leaders and artists have similar traits. Their work provides both leaders and artists with a sense of creativity and freedom.

Like actors, authors, and other ‘work-intensive’ professionals, they differ from many other “workers in that they have enormous discretion over their working conditions, an almost insatiable drive to create, and a reluctance to admit that their crusade is complete,” Sonnenfeld explains.

This sense of freedom, urge to create, and unfinished mission leads them to become what Sonnenfeld calls “work-intensives.” Recent research refers to these people as “work engaged.”

Work engagement is defined as “a positive, fulfilling, work-related state of mind marked by vigor, dedication, and absorption.”[iv]

Vigor is the experience of mental resilience and high energy levels at work. Dedication means that you feel engaged in your work and feel a sense of “significance, enthusiasm, and challenge.” And absorption is “being fully concentrated and happily engrossed in work, such that time passes quickly⁠.”[v]

Because the work is so rewarding, these psychological forces keep leaders deeply connected to their roles. With fulfilling work and the heroic missions of nonprofits, it’s no wonder some leaders seem super-glued to their jobs. This is especially true for leaders with few outside interests.

Work-engaged people are sometimes mistakenly labeled as workaholics because, like workaholics, they put in long hours. But the work-engaged do so voluntarily because they find the work itself rewarding. Conversely, workaholics not only feel compelled to work, but they are also consumed by their work, thinking about it on the job, at home, and in their free time. Workaholics are at the mercy of their work.

Which departure style is best?

Among the transitions I’ve consulted on and the hundreds of alumni of retreats for long-term and founder executives, I’ve noticed that stewards and governors seem to be the happiest in post-career life. In most cases, they move on gracefully and find freedom, joy, and contentment after leaving the CEO role.

Ambassadors, those who maintain a formal role in the organization, can be hit or miss. It’s an approach that requires some careful thought and preparation. The success of a post-CEO role within the organization boils down to psychology, chemistry, and structure.

  • Psychology – can the departing executive step away from the spotlight and remain in the background while the new executive takes the lead?
  • Chemistry – can the new and former executives get along?
  • Structure – arrange it to avoid creating situations where the old might overshadow the new. For example, the ex-CEO takes a long break so the staff, board, and new executive can “gel” as teams. They don’t have an office at the organization, at least for a while. And they don’t take a seat on the board (as some boards want the former exec to do) for at least a year. Again, to give the teams time to gel.

For years, practitioners have advised “hand off and ride off” as the best approach. It’s advice based on the collective wisdom of a network of practitioners with direct experience in hundreds of CEO transitions.

Recently, some articles have profiled nonprofits that have made the ambassador approach work. To the extent these articles outline what factors made their particular ambassador arrangement successful, they’re helpful. But a few exceptions don’t negate the fundamental soundness of the “ride off” advice, at least as the starting point.

I’m not saying “never take the ambassador approach,” but if you do, proceed with caution.

The test of an ongoing role for the former CEO is that it must work for the successor for it to work at all. If you go this route, make sure there are a lot of checkpoints where you can ask, “How’s it going?” And if the situation doesn’t work for the new executive, the former CEO needs to take responsibility and leave with grace. You don’t want to end up with a general-inside-the-house problem.

Some questions to ask before entering into an “ambassador” arrangement:

  • Is there a compelling case for an ongoing role?
  • Can the people involved make it work?
  • Have you structured the relationship and arranged the engagement to ensure success?

Can executives shift departure styles?

There isn’t enough research on departure styles to say for sure. Still, based on my experience, I believe many executives can – but they must be open, flexible, and self-aware. Through careful work (and some coaching), they can approach their exit in a way that satisfies them and protects the interests of their organization.

Solid exit planning — both organizational and personal — is the best preventive medicine to avoid issues during and after the transition.

A case for coaching

We think of executive coaching to help an executive do their job better, not to help them leave their job. But experience suggests that boards would be well advised to support coaching for their departing executive.

For most executives, moving out of this role is the most emotionally challenging life transition they will face in their careers. And, no matter how hard we try to keep emotions out of the workplace, emotions always win. Coaching can smooth out what is nearly always a bumpy psychological path. Given that the entire succession and transition process can take up to a year or more, investing in coaching can benefit both the executive and the organization.

Advice for the would-be monarch or general

As pointed out earlier, monarchs and generals are the two most risk- and messiness-prone departure styles. Consider the following to avoid becoming a monarch, an executive who loses leadership relevance, or a general who causes mischief after leaving.

Is “going out boots first” your idea of leaving your organization? Do you find it hard to imagine your organization surviving and thriving with someone new in the CEO position? If so, how is this going to affect your organization?

You may also be a long-tenured executive. The longer an executive has been in office, the more deference the board will grant that executive – up to a certain point. Consider that the board may be thinking about succession, even talking about it, but unwilling to bring it up with you yet.

Take the first step. Put your authority and political capital to work; start a discussion about performance and relevance. Be open to discussing succession options.

On a personal level, have you considered that moving on might be an opportunity for growth – a gateway to an exciting new chapter that you can’t currently see? Holding on to the role may prevent you from living a more fulfilling life after your career.

Take stock of your outside interests and what functions in your community or other organizations interest you. Be open to what’s next beyond your current job and “flirt with possibilities,” as transition expert Herminia Ibarra[vi] says. Then create or identify a “magnetic” post-career project. One that will draw you toward a new future so you can put your leave-taking into a better context.

Advice for the would-be governor

Is your life’s mission yet to be fulfilled, but do you need a change of venue? Do you feel called to a new mission or one outside your current organization’s scope? If so, you might be a governor. Someone who moves into another role at another organization or creates a new role for themselves, maybe starting a business or another nonprofit.

Consider creating an exit plan (even if you haven’t set a specific departure date). Two to three years (at least 18 months) ahead of the transition is the best time to start this sort of planning. See this article: What to do when you’re ready to leave the executive director role.

Advice for the would-be ambassador

When you think about your life after you step down as CEO, do you see yourself still working for your organization but in a different role? Are you sure you’ll have no problem stepping out of the spotlight and taking on an emeritus or other “ex-CEO” role? If you answered “yes” to both questions, you might be ready to be an ambassador.

If you go this route, proceed with caution, as discussed earlier in this article. Recognize that your successor must direct your continued involvement, and they must manage the relationship. (Don’t let the board dictate your continued involvement.) If you’re asked to serve on the board, decline – at least for a year. And don’t agree to a “spare-tire” role because the board wants a backup plan for if the new executive doesn’t work out.

Make sure your post-CEO intentions are discussed openly with potential successor candidates. Finally, if you take a role, have plenty of check-ins and a “Plan B” to leave if things aren’t working out.

Advice for the would-be steward

If you’re ready to turn over the role and move on into a completely new chapter of life, you might be a steward.

Make sure that the personal side of your exit plan covers these post-career success factors:

  • A magnetic post-career project that is drawing you forward and has you excited about the next stage of your life.
  • A strong (not necessarily vast) social support circle — friends and outside colleagues who matter to you and to whom you matter.
  • Alignment with your spouse or significant other about when you want to leave your job and plans for your life after work.
  • A financial plan that supports your goals.


My objectives for this article were (1) to provide insight into how an executive’s departure style affects the organization, board, staff, and themselves. And (2) to help executives consciously choose their departure style rather than letting fate decide.

If you’re a CEO planning to leave the role, take a moment (or many moments) to outline how you want the next chapter of your life to look.

Create an exit strategy that will prepare you personally and professionally for your departure from the position. Leaving will be easier if you have a plan for the future that’s pulling you forward.

My hope for departing executives is that you leave the organization not only on a high note and respected for what you’ve accomplished but also admired for the grace you displayed in departing.

Do you have questions about putting these ideas into action?

Book a free, no-obligation Zoom meeting with me. Here’s a link to my calendar:

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[*] Pseudonyms have been used throughout to preserve anonymity.

[i] Sonnenfeld, Jeffrey A. The Hero’s Farewell: What Happens When CEOs Retire. Oxford University Press, 1991.

[ii] BoardSource. Leading with Intent: BoardSource Index of Nonprofit Practices. Washington, DC: BoardSource, June 2021.

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

[iv] 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 (2006): 165-74.

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

[vi] Ibarra, Herminia. Working Identity: Unconventional Strategies for Reinventing Your Career. Boston, Mass.: Harvard Business School Press, 2003.

For more on planning your succession journey and leaving your organization well, check out The Nonprofit CEO Succession Roadmap: Your Guide for the Journey to Life’s Chapter or click here to learn more about Don’s executive succession and transition planning and support services.