Six Nonprofit CEO Succession Readiness Questions

In preparing for nonprofit CEO succession, too often timing gets confused with readiness. A prior post (“Three Phases of the CEO Succession Timeline”) makes a distinction between timing and readiness, pointing out that they are different but related things. For succession purposes, timing has to do with the sequencing of events while readiness has to do with the willingness to change and the preparation to navigate change. If you are a nonprofit CEO planning to retire, succession readiness involves preparing yourself and your organization for the transition process leading up to your departure as well as preparing for what’s on the other side of the departure threshold — for both you and your organization.

That earlier post also pointed out that, in planning for CEO succession, more time gives you more options. Beginning the groundwork several years ahead of your departure date, if possible, dramatically increases the possible range and depth of the preparations.

These two states of readiness — organizational and executive — are interrelated, as illustrated in the Readiness Grid (below). The ideal scenario is a high state of readiness on the part of both prime actors in CEO succession — the organization and the executive.

The Readiness Grid

Let’s take a look at the factors that contribute to succession readiness.

Organizational readiness

As the departing executive, there are three overarching questions you should ask yourself about your organization’s readiness: first, is my organization sustainable (or, at least, stable)? Second, could a successor do my job? Third, are our people ready for the transition?

Readiness Question #1 – Is my organization sustainable?

For succession purposes, sustainability means that your organization has the factors in place to endure as a high-value community or societal asset over time.[1] Six factors underpin sustainability —business model, organizational strategy, board and board leadership, executive leadership, resources (strengths, not just finances), and culture/operating climate — which we will explore in future posts.

As the CEO, you are in the best position to initiate and guide the sustainability planning and building activities. You are also in the best position to drive the process — engaging your management team and board in assessing the organization and strengthening the factors that are questionable.

If your departure timeline does not allow for this deeper dive, at a minimum, ask yourself, are there aspects of the organization that are a bit shaky? Are there areas that represent a vulnerability? Are there things you would want to shore up before you would feel comfortable handing the organization off to your successor? Is the organization at least stable?

Readiness Question #2 – Could a successor do my job?

Has the organization and CEO position evolved in ways that would make it difficult for a successor to step into the role? Is the organization overly dependent on your particular approach to the job? In short, is the current construct of the job doable by a successor?

The longer an executive has been in place, the more likely it is that the organization and the job have grown up around that individual. And the position may be an idiosyncratic reflection of your particular interests, skills, and talents. Without some serious rethinking of the position, it may be difficult for a successor to be effective in the role.

A related question to ask is, should a successor do my job? Should the role going forward be different than it is today? In other words, is the organization of the future calling for a different style of leadership, different skill sets, or a different outlook than what you possess? (I know that’s an incredibly difficult question to ask, but it’s a vital one. It’s a question your board really needs to engage.)

Unpacking, refitting, and recalibrating the job to the future is an important readiness prep task.

Readiness Question #3 – Are our people ready?

How prepared are your teams to be a part of the organization of the future and to play their role in the transition? Your board? Your senior executive team? Your staff? Are they ready to help the organization and your successor flourish?

Does your board fit the current and future governance needs of the organization? Do you have strong leadership in place that’s able to devote sufficient time to the transition? Do they or will they “get it” that a CEO transition is a pivotal event and that selecting a new CEO isn’t an everyday hiring decision? Will they be willing to invest time in some honest assessment and reflection about the organization’s future before jumping into search mode? Does the board have a strong sense of itself and its role, or does it overly rely on the executive (you) to function? At the other end of the spectrum, does the board micromanage? The board should see its relationship with your successor as a partnership and be prepared to create a strong alliance with the new executive.

Does your senior management team fit the organization’s current and future leadership needs (especially if you are no longer in the CEO role)? What’s your honest assessment of your bench depth? Are there individuals on the team who you are propping up? Are there individuals who are likely to leave when you do? Is the team working together effectively? To what degree is the team prepared for the transition and what will it take for you to get them ready?

A high state of organizational readiness would include an organization that is sustainable, a CEO job that is doable, a board and staff team that fits the current and future leadership needs of the organization, and teams that are prepared for the transition process.

Executive Readiness

After clearing the first personal readiness hurdle — committing to the idea that it’s time to move on — three questions come to the fore: first, am I prepared to set a firm date or a window for my departure and stick with it? Second, am I ready to move on professionally? Third, am I prepared personally?

Readiness Question #4 – Am I prepared to set a firm date and stick with it?

Picking a departure date, even if it is a date range (e.g., Fall 2018) is a critical step for the planning to begin. Many executives pick milestone events. This might be a certain age (turning 66), a work anniversary (your 30th work anniversary), or a particular organization milestone (your organization’s 40th anniversary) as an anchor date for their departure.

Even if you’ve set a departure date, you may still approach it with a lot of ambivalence, perhaps even committing to a date and then reneging on it if circumstances change. A streak of good news could buoy you and make you think that you might like to stick around another year or two. Conversely, an especially bad board meeting or string of bad luck could be so deflating that you feel like you can’t push the exit button soon enough. Unfortunately, your organization and staff will be whipsawed with your vacillations. It kills morale. Don’t waffle on your departure date. This is one of the few absolutes in exit planning.

For your sake and especially those around you, pick a date and stick with it as much as humanly possible. Part of leading well includes leaving well. This means being firm on your date and being accountable for your exit plan.

Readiness Question #5 – Am I ready, professionally, to move on?

Your sense of professional readiness is certainly a factor as you prepare to move to life’s next chapter. Typically, this involves a sense of completion around your significant vocational and organizational goals, which will often intersect or intertwine. How much unfinished business is on your agenda? How much of that do you really need to do? Every executive always has something on the horizon for themselves and the organization — that’s just how leaders work.

Now is the time to prioritize what’s on your agenda. Which items do you need to tackle before you exit the organization? Which items can you let go of because they’re not that important in the grand scheme of things? Which items would be better left to your successor to do, decide, or shape?

Another aspect of your professional closure work is ensuring your organization is prepared for your successor by addressing the organizational readiness factors we outlined above, and by creating a plan to guide the handoff process.

Readiness Question #6 – Am I ready personally?

While picking a date is a critical anchor for the planning, the real question is how ready are you — financially, socially, emotionally, and otherwise — to move into the next chapter of life?

What sort of planning have you done already? For years, it’s been drummed into us by the financial services industry that retirement planning is synonymous with financial planning. While financial security in your post-career years is essential, research and interviews with retired executives point to five success factors, only one of which has to do with money. The other four factors are: (1) health and well-being, (2) an engaging post-career project, (3) meaningful engagement with a strong social network, and (4) alignment with your spouse/significant other.

We are going to explore each of these points in future posts, but I want to underscore the point about post-career projects. In my experience, the executives who seem to glide through the transition, are those who have a project they are moving toward as opposed to a position they are leaving behind. They feel they are gaining something rather than losing something.

Having or not having what I call a magnetic post-career project is among the biggest of the push/pull factors. For this reason, I recommend putting it at the top of your personal preparation agenda.

A high state of readiness on your part would include clarity about a departure date, minimal unfinished business on your professional agenda, and conditions that are drawing you toward your life’s next chapter.

Obviously, the organizational prep work I’ve outlined should be undertaken in partnership with the board, its succession/transition committee and members of your senior staff. However, the departing CEO bears responsibility for instigating the process and helping the board prepare to play a more effective role in leading the organization through the CEO transition.

More time = more options

Starting early also helps with one of the personal challenges that many CEOs confront — the shift in identities that comes with the transition, particularly a transition into post-career life. The research says that the biggest ingredients in successful identity transitions are time and a sense of completion about the current role. Starting your planning work early will enable you to create a glide path toward your next chapter of life.


[1] This description of organizational sustainability was inspired by the description of a workshop hosted by the Monterey Institute for International Studies led by Alfredo Ortiz.

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