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 financia