The job of the nonprofit executive is one of the most rewarding I know. It is also among the most challenging, requiring a deep passion for the work and the ability to juggle competing demands, sustain multiple relationships, and manage a very possibly under-resourced infrastructure.

So it is not surprising that the point of transition is full of tension. Anyone who has replaced a leader knows the sense of excitement and trepidation you bring to the first day. What will you find and will you be able to handle it? On the other side, any departing executive who has made a difference knows the worry-filled nights just before leaving. Are you leaving any messes that will trip up your successor, tarnish your legacy, or in any way cause harm to this program about which you care so deeply?

This article provides practical guidance to exiting and entering leaders, with a particular focus on founders and executive directors of long tenure. What follows is derived from my executive transition work with more than a hundred organizations, the research that flowed from some of this work, most recently with the Annie E. Casey Foundation, and my own experience as the first executive director of a neighborhood development organization.

Seizing a Pivotal Moment

During the last decade, field research by the Neighborhood Reinvestment Corporation highlighted the risks of failed transitions to boards and organizations. They found that most transitions (as many as 70 percent) are “non-routine” and occur due to an organizational crisis or the departure of a founder or visionary leader. This research also demonstrated that poorly managed executive transitions incur high costs to organizations and communities.

Failed transitions often cause repeated executive turnover, loss of organizational focus and momentum, and extended periods of under-performance. In extreme circumstances, organizations enter a downward spiral, eventually going out of business and leaving in their wake a host of broken commitments and financial entanglements.

Unfortunate as this individual organizational failure might be, it’s not the worst outcome. The costs of these very public failures do not accrue just to the organization in question; they ripple out and can cause a loss of confidence in an entire field or in nonprofits in general.

Executive transitions generally work best when we approach them intentionally, when we consider the significant personal and professional challenges present, and when we understand that they represent what I like to call a “pivotal moment.” Think of the tension as a source of energy. When approached from this perspective, transitions present a unique and rare opportunity for significant shifts in organizational focus and major leaps in organizational capacity.

Preparing to Leave

Three clusters of issues shape (and sometimes shake) all executive transitions, particularly as a founder or long-term executive decides to move on.

Making a Decision

Founders are generally conflicted about whether and when to leave. In the Casey Foundation’s research on this issue, every founder or long-term executive studied experienced personal ambivalence and a period of indecision. If you are feeling a little wobbly in making this decision, you are not alone.

In one organization, where the executive/founder is at least as recognizable as the excellent community organization he runs, close friends report that he has “been talking about leaving in five to seven years for more than ten years.” This public exploration is fairly common but, in most cases, probably something to avoid. It is, however, indicative of how difficult it is for highly competent—and highly invested—executives to make that final decision to leave.

There are two dimensions associated with making the decision to leave–the personal and the organizational. The personal decision usually needs to come first. This involves confronting tough questions, including:

* Do you want to keep doing this job?

* How well are you currently doing it? Have you consciously or unconsciously begun to disengage?

* Are you staying because you are not sure what else you might do, or because it is right for the organization and you?

* Are you financially ready to move on?

It may be too difficult to answer these questions without help from a relatively objective and wise friend. Choosing someone, or a few people, to help you through these decisions can be invaluable to you and those around you. Remember that, as a leader, your actions or lack thereof affect individuals, the organizational culture, and the organization’s position as a whole.

The second aspect of the decision is what is right for the organization; it is a difficult question for any executive, especially for founders, to consider objectively on their own. The key question is: how ready is the organization for this transition?

Here are two sub-sets of concerns: first, what strengthening actions are needed before making a public announcement of a departure date? And then, can you identify the actions that need to happen and make sure they occur, or do you need help? Key areas to look at in determining organizational readiness are staff shortages in administrative support, systems, infrastructure (including technology), and board and staff development.

But there may be times when a leader—for whatever reason—cannot stick around to strengthen the organization because it’s just time to go. Such cases may call for an interim executive. (See below.)

Your personality, way of handling tough and/or emotional issues, and departure timetable often determine how the ending takes place. To be fair to others, try to limit the effects of your own personal style of decision-making by reflecting privately, and then talking with some trusted allies, or an organizational consultant. Choose a consultant who can assist you and eventually the organization as a whole in reaching as clear a picture as possible of the health of the organization, how the transition process can add strength and capacity, and what role the executive should play during the transition and hiring.

Grooming Your Successor? Think Again

A founder or long-term leader’s passion for the cause often feeds a strong drive to pick or groom the successor. Unfortunately, I have seen few cases of the successful grooming of an internal successor. Some of the reasons for this may be:

* It’s the board’s decision. No matter whom you pick or how well you prepare them, even if the board is aware of your plan, it has a right and a responsibility to hire the executive.

* The skills needed in a deputy or associate director are often different from the skills needed in an executive, or are perceived that way by board and staff.

* Healthy boards often want fresh eyes and fresh perspective in a new leader, particularly following a founder or long-term executive.

* Internal successors to a founder have a better chance after someone from outside the organization is hired as an interim executive.

There are, of course, exceptions. Occasionally a board and founder agree, and a successor is identified and prepared. However, most of us are better served by developing an effective management team and infrastructure than by grooming a particular person as successor. This will provide your successor with a wealth of institutional memory and an effective management team. Your investment in consciously and continuously grooming new leadership ensures there is a diverse pool of potential executives ready to serve your community. Concerted action to expand talent development reduces the “no one available” challenge so many communities and organizations face.

Setting Boundaries for Your Role

As private considerations about leaving have personal and organizational components, your leaving strategy generally has a private and public phase. The private phase, described above, can begin two to three years or more before the actual transition. The public phase–after the plan to leave has been announced with a date certain—typically will last from four to twelve months. There are two key areas to pay attention to before departure: organizational strengthening and support to the transition management work. After departure, ideally you aren’t paying attention to anything in the organization! (More on that below.)

(A) Readying the Organization

A useful way to think about the most needed organizational readiness work is to ask: What current conditions are most likely to derail or challenge the next executive? Unrealistic expectations by the board and staff for the next executive, the job being undoable because it is really two or three jobs, and lousy financial systems or technology are among the most common derailers for successors.

Executive directors often built networks of trusted relationships that are a key part of their ability to get things done. They use their charm and these relationships to manage cash flow and balance the budget. Besides doing what you can to lower expectations and address gaping problems, record for your successor the quirky idiosyncrasies of what you do. Perhaps you address every direct mail letter by hand or you’ve learned the hard way the pet peeve of your largest donor’s lawyer. Document what seems important, then trust that your successor will need to make her own mark and won’t want to recreate herself in your image.

(B) Supporting the Transition Itself

Typically, some time four to twelve months before the desired exit date for the founder, the transition process becomes public. In most instances, the role and power of the executive begin to shift, often more quickly than expected.

There are three distinct ways you as an outgoing executive can assist the board with transition management:

Hands-on management: Here, you continue to lead the board in making key decisions. You decide if an interim executive is needed or if outside transition or search assistance makes sense, review resumes, and recommend candidates. This approach may appear efficient, but generally does not leave room for the board to assume its full responsibility or increase its awareness and capacity. More than one departing executive who has tried to hold the transition process too closely has gotten feelings hurt when the board feels honor-bound to wrest away control. This can cause misunderstandings that may linger for years.

On-call resource: You defer to the board the key decisions about how to manage the transition process and the selection of a successor. You walk a fine line here, supporting the board when asked without reinforcing unhealthy dependence or maneuvering for a particular outcome. Usually some strengthening of the board, including increased involvement in details previously left to the executive, is required. Using the transition process to strengthen the board and its ownership is in the organization and founder’s interest.

Hands off: This radical, “cold-turkey” strategy is foreign to most executives, but it is the best approach in some circumstances. Here, you conclude that the board, staff, and organization are best served by your total detachment from the process. You do private planning and improvements, announce your resignation and a date, and let unfold whatever unfolds. This works where there are sufficient board leadership and experience to guide the process or where the overwhelming need of the organization is to end dependency on a long-term executive and boldly reposition the role of the board and, in larger organizations, senior staff.

Any of these approaches can work. The key is intentional choice, and agreement between board and founder on what most strengthens the organization and is supported by the internal and external resources.

As departure becomes imminent, the question of involvement after resignation may be raised. (Sometimes it comes up much earlier.) It’s normal for a founder or the board to want the involvement to continue. In a few instances it may even make sense. The big questions here are your motivation and your action’s impact on your successor. If your involvement is designed to assist the successor and he wants the help, a short overlap period can be useful. Staying on the board, or similar longer-term involvements that delay closure, however, are usually not helpful or advised.

The New Executive’s Priorities

While the body of knowledge on founder successions is still developing, experience indicates that attention to the following three basic tasks is strongly recommended for any new executive:

Getting Connected

Early, inquiry-focused, one-on-one meetings with board and staff are vital in the first month. Unfortunately these meetings are too often neglected or half done. Be aware that this can be your biggest self-imposed risk. In one situation I observed, when the executive committee completed the performance review of the successor to its founder, the executive was disappointed that some of the reviews weren’t very positive and indicated a lack of understanding of what he had done. The executive had felt that being in meetings with the executive committee was enough to build the relationships. It wasn’t.

Heller An Shapiro, executive director of a health-related association, describes a more productive inauguration: “My first board meeting was two weeks after I started, and the previous executive was long gone. There was a lot to do; I made it a priority to talk with every board member and listen to why they were involved, what they wanted to contribute to the organization, and what they expected of me. I used this information to do a report and draft a work plan for the board meeting. The board was really impressed; that positive beginning confirmed that I was headed in the right direction and has served as equity for me over and over again.”

There’s an old saying, “The way things begin is often the way they end.” Getting started well means paying attention to key relationships—with board, staff, funders, and community stakeholders.

Learning the Organization

Taking charge of your beginning means paying attention to the organization’s fundamental realities. Look at key documents and talk to people in the know about the organization before accepting the position. If you haven’t reviewed the budget, the audit, last year’s board minutes, any contracts or grant agreements, the personnel policy, and the by-laws, you don’t have the information you need to lead. Some of these may not exist or not be in very good shape. The goal at the beginning isn’t to fix everything, but to take inventory. This is also true in terms of the organization’s position vis-à-vis its constituency, among its peers, and with funders.

This inventory, combined with relationship-building meetings, will give you a sense of the health of the organization and its vulnerabilities. Fully understanding the finances is the Achilles heel of many executives. If numbers aren’t your “thing,” get help. Charismatic founders often manage a very tight cash flow on the float from one grant or contract to the next. As the new executive, you will not “inherit” this talent or, importantly, these relationships. Taking a hard look at the budget, cash flow, grants, and contracts and fully understanding them are essential. Things are not always as they appear. Be prepared for surprises and take them in stride. But don’t make the mistake of unnecessarily talking negatively about the exiting executive to give yourself more room or standing. This will always come back to haunt you.

Setting Direction and Priorities

Building consensus on direction with a board and staff takes time. For most executives, it’s an incremental process. It can take a year or more to fully understand your job and the organization. In the meantime, you are at risk of not meeting key expectations of the board, staff, or other stakeholders. The obvious yet often neglected solution is a written work plan.

Organizations that work with an executive transition consultant will generally receive a written document, prepared in planning the search, that lays out direction and major goals for the first 12-18 months following a transition. Paul Cypher recently gave up an exciting senior manager job at the Rochester Museum & Science Center to lead the Baltimore Museum of Industry. He’s following a founder and interim executive, and the presence of a written priorities document influenced his decision to accept the position. “I was impressed and relieved in the selection process to see how much the board knew about the organization, and how clear they were on direction. Frankly, that clarity and their organized approach to selecting an executive gave me the confidence to move my wife and family and take this position.”

If there is a written document outlining direction and goals for the organization, review and update it and convert it to a 90-day work plan. If there isn’t one, create the plan with the board and staff. A lack of clarity ultimately puts you at risk of arbitrary and changing expectations, unfair evaluation, and perhaps even dismissal. Developing a written plan and asking for feedback and a formal evaluation at six months and a year are insurance for you and increase the chances of organizational success.

Our Leadership Challenge

Each executive and organization has its own definitions of a successful transition but, in general, a successful transition builds and supports organizational focus by ensuring that the leadership style, skill set, and personality are exactly right for the organization at that point in its development. Leadership transition is a powerful opportunity to improve balance and strengthen the reach and power of an organization. Seize the day and work the situation for all the richness it can provide.

It’s hard to get there without a road map. For many first-time travelers, the road to new leadership looks obvious and the path clear. Research and experience indicate the opposite. Transitions are tough, and many embedded complications are less than immediately obvious. In my opinion, a good map and guide are extremely useful. The cost of getting help with transition planning and management is a lot less than the cost of a failed or flawed process and well worth your consideration. (See Resources for Leadership Transition Planning and Management, p. 31.)

For founders, paying attention to your transition is the best way to protect and nourish the legacy of your years of commitment and service. For other leaders and stakeholders, attending to leadership preparation and transition ensures the work you care about is sustained. Leadership transition can be a disaster or a terrific opportunity for strengthening organizations and the field. It’s your choice.

About the Author

Tom Adams is a national leader in executive transition research, practice, and systems building. He is project manager for the Annie E. Casey Foundation Executive Leadership Transition and Capacity Building Project and for Maryland Association of Nonprofit Organizations Executive Transition Initiative. Tom can be reached at 301-439-6635, ([email protected]), or (