Six Ways to Know If It’s Time to Leave

Tim Wolfred, a leader in the field of nonprofit executive transitions, on how to weigh both the organization’s needs, and your own heart.

Six Ways to Know If It’s Time to Leave
11 mins read

A wise leader regularly checks for signs it’s time to transition to something new.

Are you tired, a bit listless? Maybe the demands of the job seem ever more burdensome, or the board seems increasingly dissatisfied, or your retirement clock is ticking. Do you need more than a megavitamin? Even better is this advice from Tim Wolfred, a pioneer and leader in the field of nonprofit executive transitions, on how executives can weigh both the organization’s needs, and the needs of their own heart.

Executive directors don’t have term limits. Although some executives are fired or forced out by boards, most executives make the determination themselves of when and how to leave. Like other life decisions, it takes awhile to come to the decision to leave, or to come to the decision to stay.

So how can you tell if it’s time to leave? Based on research and consulting with hundreds of nonprofit executives struggling with this question, we’ve developed six indicators — each with some follow-up steps — to help you with your thinking process.

Do one or more of these statements resonate with you?

1. I keep returning to this thought: the organization needs to go in a new direction (or to a new level) and I’m not the right person for it.

This is the most common reason given by executive directors who have decided to leave their positions. As just one example, a very successful executive had led a large mental health agency for 25 years. The organization’s quality and success had led to both external and internal pressures to grow even larger, but the executive just knew he wasn’t the person to do it. His working style depended on having his finger on everything, and simply put, he didn’t have any more fingers. When he thought about trying to control and lead a larger organization, he just couldn’t see himself in the picture.

In another instance, an organization knew that its next phase would require instituting a fundraising program that would go beyond the government contracts and foundation grants on which the organization had been built. The executive director, highly talented in multiple ways, just couldn’t get herself behind the idea of major gifts and individual fundraising. She knew it was the right step for the organization, but she wasn’t up to taking that step herself.

If this sounds like you: Start preparing yourself and your organization for your departure. For yourself, have coffee with executives who have left their jobs: you’ll learn how it felt and get ideas about what to do next. For the organization, have a talk with the board leaders about an intentional process of transition. Take pride in the fact that you are leading the organization in a crucial way through a thoughtful and planned departure.

2. I’m burned out and I know it.

Some executive directors fantasize about a fire destroying their office. More than one executive director has even confessed to a secret desire to get cancer because “it would be a way out.”  In the mornings, the thought of going to work seems like a horrible drag. One minute you hate the funders, the next minute the board, the next minute the staff. Especially that *****ing idiot!

You may be wishing you could leave, but your financial situation means you can’t quit without having another income in place. Test yourself with this question: “If someone offered me a job that looked less stressful but paid the same, would I jump at it?”

If this sounds like you: If you can, take a sabbatical of at least two months. Get outside the situation to allow yourself a different perspective. Use the time to talk with a career counselor about what else you might do.

Find the right person to talk with: perhaps a thoughtful friend, perhaps a therapist, perhaps a nonprofit consultant or coach.

It’s also possible that you may just have to leave. By now, you’ve probably tried many ways to reduce the stress, but none of them have worked well enough or long enough. Your physical and mental health and your personal relationships may be suffering from the stress you are experiencing. Your organization will find its way.

3. I don’t think I’m burned out, but other people think I am.

Many executive directors are often so committed and so busy that they may not realize that they are losing energy and freshness, and that not only are they suffering personally, but that the organization is experiencing the diminishment of their talents. Do you find that you’re not as present at meetings? Less available to others? Are you frequently impatient, or crankier than usual? Do your co-workers ask you if you’re tired, ill, distracted?

If this sounds like you: Reach out to the people in your life who can help you reflect on your situation and who will push you to think it through (not just sympathize). Consider getting an executive coach to help you figure out how to renew yourself, and/or what else you can do. But don’t just try to power through it. This is an organizational matter as well as a personal one: give it the attention it deserves.

Reach out to executives you know who have left their jobs, and ask them how they knew it was time to leave. Ask them what they regret about leaving, and what they don’t regret. Find out what they’re doing now. Their answers will spark new ideas you haven’t thought of.

4. I can’t stand my board anymore… and/or, I can’t seem to please the board no matter what I do.

I’m sick of them. Nothing I try works. I feel alienated from them. Why do we have to have boards anyway? Feelings like this often emerge after a couple of years of a slow deterioration of the executive-board relationship. Executives often blame the board for the poor relationship, and it’s hard to know which side is right.

If this sounds like you: Consider this… maybe it doesn’t matter who’s right. By now you’ve tried many things that haven’t worked. Maybe both you and the organization will be better off if you go off and start fresh somewhere else with new people.

Alternatively, you can decide just to live with it. Perhaps you have little influence over board recruitment, and you don’t see much hope for the future. Just as some people accept working for a bad boss because they love the work, maybe a bad board is simply the price of having a job you love and work you find important.

Finally, consider making one last big effort to change your relationship with the board. Push for a serious conversation with the board leaders, acknowledging that both you and they feel uncomfortable with the relationship. “Maybe I should be leaving, but I need to hear directly from you what you’re thinking.” Take responsibility for changing the situation; ask yourself, “What can I do differently to change this situation for the better?”

5. My clock is ticking.

For executives who have been on the job 20 years or more, the question naturally arises: is it time for the organization to have me leave, and/or is it time for me to have me leave? Executives with tenures of 10 or more years who are in their early 50’s or older also start to hear a ticking clock. It isn’t always a good idea to leave just because of your age or tenure. There are effective, always-fresh executives who are in their 70’s or even 80’s, or who have been on their jobs 30 or 40 years. But for most people, tenure or age raises the question of a timeline for departure.

If this sounds like you: Ask yourself: Would I contribute more to the cause in another job or role? Is there something else I want to do before I retire or become less vigorous? What can I be doing on the job within the next year to prepare myself for the next phase of my life… whether in one year or ten years?

6. Family roles are calling me.

Many executives want to stay on their jobs, but they have family responsibilities that pull at them. Maybe one of your grown children needs you to watch the grandchildren so that she can focus on her own career. Maybe you have a child who needs more attention and time than you’ve been able to give, or a family member who is ill. Perhaps you have an aging parent who needs you to move nearby.

If this sounds like you: Remember that leaving your job or even leaving the workforce isn’t necessarily a permanent decision. Maybe you can leave the workforce for a few years, or move to another state for a few years. One executive returned to her childhood home to be with her mother for the last two years of her mother’s life. She then returned to the city where she had been living, found a new job, and is grateful she made the decision to spend the time with her mother.

Lastly, taking on the executive position in a nonprofit takes a lot of courage and requires a wide range of skills. It also takes courage and smarts to know when to give the reins back to the board as they direct the organization’s next phase. For the good of the cause and the constituents, the wise leader regularly checks for the signs that it’s time to transition to something new.

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About the Author

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Tim Wolfred, Psy.D., inaugurated the Executive Transitions program at CompassPoint Nonprofit Services and authored Managing Executive Transitions: A Guide for Nonprofits (Fieldstone). He has consulted to dozens of nonprofits in CEO change, and has served as a nonprofit interim executive director 16 times. He’s seen a lot.

Articles on Blue Avocado do not provide legal representation or legal advice and should not be used as a substitute for advice or legal counsel. Blue Avocado provides space for the nonprofit sector to express new ideas. Views represented in Blue Avocado do not necessarily express the opinion of the publication or its publisher.

28 thoughts on “Six Ways to Know If It’s Time to Leave

  1. Today in Lexington, Kentucky, I passed out this article to a room of executive directors before a workshop got started. One of them burst out laughing when she read the part about someone wishing she had cancer . . . she said that SHE had had the exact same thought many times! Other people in the room agreed. One young ED said she has been wishing she would get swine flu so she wouldn’t have to go to work for a few weeks. It’s so telling that the pressures get so great that this is what people start to think. Thanks for a great article, Tim. Jan

    1. Thank You! Thank You! Thank You!
      This article reassured my very hard decision of saying good-bye.

      1. This article also reinforced my decision to resign from my current role. It is extremely important for me to begin a new job search before I am completely burned out. This is truly the best choice for my organization.

  2. I’m sure everyone identifies with at least one of these scenarios, or has experienced before leaving their last job! In my example, in my last job, I felt a combination of "the Board won’t do what we need them to do" and "the job needs to move on, but I’m not the one to do it" and I approached my Chairman to say that I thought it was time I moved on. As such, I informally handed in my notice whilst I started my job search, which allowed the Board time to consult on what they really expected from the Executive Director, draw up a more ambitious person specification and recruit someone who I will readily admit was of a higher calibre than myself and ready to move the organistion to the next level. Serendipity meant that, in the 6 months between my conversation with the Chairman that I was looking for a new job and actually starting the new job, we were able to recruit my replacement and have a 2 week handover period. I didn’t want to abandon our very small charity/non-profit/ (UK expression) third-sector organisation with no-one at the tiller and, by talking this through with the Board, I am happy that the whole process of leaving was done gracefully and comfortably to the extent that I still regularly see my former Chairman as a friend!

    1. What a great example of how to leave with grace! Congrtulations on having had the kind of candid relationship with your board of directors in which it was safe for you to say it was time to leave. I suspect you had a good history of tackling tough topics with your board. Building the habit of candid communications is so important.Tim Wolfred

  3. Today is the last day for the executive director at our non-profit organization. I’m the board president and she confided in me that she has never felt appreciated by the board nor has she felt that the board works as a team. I know she works hard and the board may not live up to her expectations, but I feel we do our best given our very small numbers (6). I would just like to make her transition as positive as possible, but I’m afraid it’s too late.
    Any suggestions?

    1. I love this article and have to reply to this post. Too often I see this guilt-blame dynamic between board and EDs. You sound like a thoughtful and compassionate board chair. If this is the current EDs last day, probably the best you can do is tell her what you posted here: you work hard and are passionate, and we deeply appreciate everything you’ve done for us. I’m sorry that we may not have lived up to your expectations, and that it made your job harder. I wish you the best. Then plan to give her a nice reference…and move on.The more important question is, how do you create a better dynamic with the next person? If the relationship is still positive, do an exit interview with the ED. Ask her what, specifically, she wished you had done differently. If possible, ask the staff the same thing – better yet, have a neutral third party interview them to protect them from fears of retaliation. Ask the people you interview – and your fellow board members – the same questions – what do you want from a board? How would you measure our success? My personal view is that six people is probably too small for a board, but it depends on the org. and what you’re doing. In any case you should start by asking, what kind of board (size, membership, diversity, etc) does this organization need to meet its mission? What does this organization need that board to be doing? Best of luck to you…as they say, the first step is admitting you have a problem, and it’s great that you have taken that step!-Jeff in Oregon, 12 year repeat offender ED 🙂

    2. It is never too late for someone to feel appreciated for all the hard work they have done! Sending her a handwritten note expressing your appreciation for her years of service will let her know that her contributions did not go unnoticed. We all like to be thanked in a personal way.

  4. Great article. Thanks Tim for your clear articulation of the six statements. As a 2 time ED (14 years total) and an organizational development consultant and coach I have seen and experienced these dynamics again and again and it is hugely helpful to have them laid out where it’s easy to see them like this. I wish I’d had this article when I was struggling to decide whether to leave my last ED position, and I will certainly use it with organizations in the future.
    Another powerful clarification tool for executive directors (or anyone else) in any of these scenarios is the question "What do I want?" It seems simple, but it is amazing how infrequently we really ask this question and pay attention to the answer. If you are having any of the experiences Tim describes, I invite you to put the question on post-its in places where you’ll see it often — the bathroom mirror, the steering wheel, the top of your computer monitor — and letting yourself notice what comes up each time you read it.
    Tasha Harmon, coach and facilitator,

  5. I love my organisation and its work, but after seven years feel I am becoming stale and unmotivated. The article is well timed and I find myelf nodding over all but point four, and even some of that applies. Time to let the board know I’m ready to move on.

  6. I love my organisation and its work, but after seven years feel I am becoming stale and unmotivated. The article is well timed and I find myelf nodding over all but point four, and even some of that applies. Time to let the board know I’m ready to move on.

  7. Great article Tim! When I was coaching a long term ED last year, her goal came down to “leaving and finding a new job” and when this was articulated back to her, she started to cry because now it was real. Through coaching, we discussed her individual goals, likes, dislikes, hold-backs, and limiting assumptions. We detailed her “perfect next job” and set her to explore career options. During this time we also worked on redesigning her job and relationships at the agency to make it more attractive to the next ED. Well, the ED ended up redesigning her own job so much that now she loves it and is re-energized, enthusiastic and passionate about her job, agency and life. Both ED and agency are thriving. Leaving can be one way of change but there may be other options for change too.

  8. I am curious about the author’s contention that EDs who have been in the same job for 30 or 40 years can continue to do a great job. I believe the author’s observation, but my 30 years of NPO experience certainly disagrees with this. I have seen the opposite occur in many situations: after about 12-15 years most leaders become empire builders, authoritarian, entrenched and clinging to the position, less innovative, defenisve about criticism or new direction, not supportive of new mid-level leadership, etc.

    Generally, I think ED’s need to move on at the height of their game, seek the next challenge where they can advance an organization, and be remembered with fondness rather than bitterness by the organization they leave behind. This is especially true in small organizations. In large organizations sometimes the ED can gracefully move from hands-on leadership to some type of emeritus status, or hand over more of the operational control to a COO person.

    These questions are quite similar to the enreprenuer who builds a successful organization, but then stays in control to long and eventually harms the baby to whom she gave birth.

  9. Such a delicate yet relevant topic as reflected by the anonymity of comments. Recently I resigned from a position due to the lack of opportunity for personnel and professional growth, leadership as well as low wages, growing stress and impact on relationships. Although I was not in an Executive position, my struggles were similar to those mentioned. After a brief tenure, my dissatisfaction grew rather than diminished no matter my intent for starting each week with a fresh outlook and plans for success. I realized that the environment could not satisfy my vision for mission fulfillment, passion and leadership in a field of my expertise. During my short tenure, I created a “bucket” list for reasons it was time for me to “buy my ticket” out of the organization and step onto the escalator to unknown adventures. I spoke (repeatedly) with friends of my struggles and questions with resigning. Perhaps my struggle stemmed from being underemployed but I do feel that most anyone can have similar issues and questions when struggling in an unfulfilling position.

  10. Our ED needs to move on but refuses to do so. I am afraid she will drive our organization into the ground just to maintain authority and a paycheck. How can we encourage her departure?

    1. Your ED probably can't be "encouraged" to depart. If she likes the authority and needs the paycheck, she probably won't leave on her own. If several staff feel strongly that she is running the organization into the ground, it may be worthwhile to ask the board chair for a meeting. But you'll need some evidence to make your point. Good luck. Jan

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