The nonprofit workforce is changing at every stage of the career journey. Younger professionals bring different expectations to work, experienced talent is harder to retain, and many organizations are approaching leadership transitions without a clear succession path. This three-part series explores these shifts and what they could mean for the people, organizations, and communities that depend on a strong nonprofit sector.

 The Leadership Cliff: Nonprofit Succession in an Era of Instability

What happens when a longtime nonprofit executive announces plans to retire, the board begins looking for a successor, and everyone realizes no one is ready to step in?

For some organizations, the departure has been anticipated for years. For others, it comes unexpectedly, prompted by burnout, a change in personal circumstances, or simply the realization that the demands of the job have become unsustainable. Either way, the announcement sets off a familiar series of questions. Who will lead? How quickly can someone be found? Will donors remain committed? What happens to the relationships, institutional knowledge, and organizational momentum built over decades?

But perhaps the most important question is one that should have been asked long before the executive announced a departure: Who has been preparing to lead next?

Across the nonprofit sector, leadership succession is becoming more complicated at precisely the moment organizations can least afford disruption. Funding uncertainty, rising service demands, increasingly complex operations, and changing workforce expectations are reshaping what it means to lead a nonprofit. At the same time, the experienced professionals who might once have formed the next generation of executive leadership are not always there to take the reins.

The result is a leadership challenge that goes well beyond replacing a retiring executive. It raises questions about the long-term strength and sustainability of nonprofit organizations themselves.

A Leadership Pipeline Under Pressure

In the first two articles of The Nonprofit Workforce Reset, we examined changes occurring at different stages of the nonprofit career journey.

Younger professionals are reconsidering what they expect from nonprofit employment. They still value mission and purpose, but increasingly want the compensation, professional development, stability, and work-life balance that make a career sustainable.

Meanwhile, experienced mid-career professionals – the managers, program directors, development specialists, and operational leaders who keep organizations functioning – are confronting their own difficult choices. Limited advancement opportunities, compensation pressures, expanding responsibilities, and organizational instability can make remaining in the sector less attractive.

These developments are connected, and their consequences become especially visible when an organization needs its next executive leader.

Traditionally, many nonprofits have relied on an informal leadership pipeline. Talented employees gain experience, take on greater responsibility, build relationships with funders and community partners, and eventually become candidates for senior leadership. This progression depends on people staying long enough to develop the knowledge, confidence, and experience required to lead.

But what happens when that progression breaks down?

When promising younger professionals leave before establishing long-term careers, and experienced mid-career employees move on because advancement feels out of reach, organizations lose more than individual contributors. They lose future leaders.

The leadership cliff, in other words, does not begin when an executive announces a departure. It begins years earlier, when the organization stops building the people who could eventually take that executive’s place.

The Job Has Changed. Has the Leadership Model?

The executive director role has never been easy. But today’s nonprofit leaders navigate an increasingly demanding mix of financial, operational, workforce, and community responsibilities.

They are expected to secure funding in an uncertain environment, maintain strong relationships with donors and boards, respond to growing community needs, recruit and retain talented employees, manage compliance and financial accountability, and demonstrate measurable impact. They must also guide organizations through technological change, shifting workforce expectations, and, in some cases, increasingly complicated public policy environments.

In smaller organizations, many of these responsibilities fall on one person, often with limited administrative support.

The toll is becoming increasingly visible. The Center for Effective Philanthropy’s State of Nonprofits 2026 report found that 46% of nonprofit CEOs said their own burnout was a major concern, up from just under 30% in 2025. This is more than a workplace wellness issue. It raises serious questions about the sustainability of nonprofit executive leadership.

For leaders who have spent decades building an organization, the commitment to its mission can make it difficult to step away. For those considering moving into executive leadership, however, the responsibilities can raise a different question: Is this a job I actually want?

That question deserves more attention.

Nonprofits often assume that capable managers and senior staff naturally aspire to become executive directors. Yet success in program management, development, finance, or operations does not automatically mean someone wants the financial pressure, fundraising expectations, public accountability, and personal demands of the top position.

Some may be interested but feel unprepared. Others may look at the executive’s workload and conclude that the additional responsibility is not worth the tradeoff.

This creates a challenge that succession planning alone cannot solve. Organizations must consider not only whether they have qualified people who could become leaders, but whether they are creating leadership roles that talented people want to pursue.

When the Organization Becomes the Leader

Another vulnerability can remain hidden until a longtime executive prepares to leave: the degree to which an organization’s identity, relationships, and operations have become concentrated in one individual.

This is particularly common in founder-led organizations and nonprofits where an executive has served for many years. The leader may be the primary relationship holder with major donors, the organization’s most visible community representative, its institutional historian, and the person employees turn to when difficult decisions arise.

These relationships are often among the organization’s greatest strengths. They can also become a source of risk when too much depends on one person.

Consider what happens when a departing executive holds decades of knowledge about why certain programs were created, how key partnerships developed, which funding relationships require special attention, and what informal agreements shape the organization’s work.

A new leader can inherit the title, but not necessarily the trust, context, and relationships that made the previous leader effective.

For boards, this can create an uncomfortable realization. What appeared to be a strong, stable organization may have depended more heavily on one individual than anyone recognized.

The financial environment makes these vulnerabilities even more consequential. The Nonprofit Finance Fund’s 2025 State of the Nonprofit Sector Survey found that 85% of respondents expected demand for services to increase, while 36% had ended 2024 with an operating deficit. Leadership transitions taking place under these conditions leave little room for extended uncertainty or disruption.

The answer is not to diminish the contributions of longtime leaders. It is to ensure that their experience and relationships become part of the organization’s enduring strength rather than leaving with them.

That means developing other leaders who can represent the organization, expanding relationships beyond the executive office, documenting critical knowledge, and giving staff opportunities to participate in decisions that shape the organization’s future. Leadership continuity should be built into everyday operations, not addressed only when someone announces a retirement date.

The Replacement Trap

When a respected executive leaves, boards understandably want someone who can preserve what has been built. The search often begins with a description of the departing leader’s experience, strengths, relationships, and accomplishments. The temptation is to find another version of that person.

But the qualities that made an executive successful over the past 10 or 20 years may not be the same qualities an organization needs for the next decade.

Perhaps the departing leader excelled at building programs and community relationships, while the organization’s next phase requires stronger financial systems, organizational restructuring, or new approaches to revenue generation. Perhaps the organization has grown beyond the leadership structure that supported its early years. Or perhaps the greatest need is someone who can develop a stronger management team and reduce dependence on the executive office.

This is where succession becomes a strategic decision, not a hiring exercise.

Before launching a search, boards need to look beyond the person who is leaving and examine the organization that remains. What has changed? Where are the vulnerabilities? What capabilities will be essential in the years ahead? And equally important, what support will the next leader need to succeed?

Replacing a highly respected executive with someone who inherits the same overwhelming responsibilities, insufficient resources, and unrealistic expectations does little to strengthen the organization. It may simply begin the next cycle of leadership instability.

The goal should not be to find someone who can fill the previous leader’s shoes. It should be to prepare the organization for the leadership it needs next.

Succession Is a Board Responsibility, Not an Executive’s Exit Plan

Most nonprofit boards recognize the importance of succession planning. Yet recognizing the need and being prepared for an actual transition are two very different things.

Research suggests that the gap remains substantial. In its 2023 Nonprofit Talent and Leadership Survey, DRG found that 71% of responding nonprofit executives had not communicated a succession plan for their position to their board. Only 22% reported having a formal plan shared with their board.

The implications are significant. An organization may have an emergency succession document that identifies who will assume temporary authority if the executive director becomes unavailable. That is an important safeguard, but it is not the same as having a long-term leadership strategy.

A meaningful approach to succession requires boards to understand the organization’s leadership capacity, identify potential internal successors, recognize gaps in experience and skills, and anticipate how future organizational needs may change the executive role.

It also requires candid conversations with the current executive. These conversations can be difficult, particularly when a leader has devoted much of a career to the organization. Discussions about retirement, future leadership, and organizational dependence may feel personal. But avoiding them does not protect the leader or the organization. It simply postpones decisions until the choices may be fewer and the pressure greater.

Boards must also recognize that succession is not solely about the executive director. The departure of a chief financial officer, development director, program leader, or other senior professional can create significant disruption, especially in organizations with small leadership teams.

The same workforce pressures affecting executive recruitment are also influencing these positions.

An organization that has not invested in developing and retaining experienced staff may discover that its succession challenge extends across multiple levels of leadership.

Preparing for the Next Chapter

No single solution exists for the nonprofit leadership cliff. Organizations vary widely in size, resources, mission, and leadership structure. A small nonprofit faces different succession realities than a large, established institution with multiple senior executives.

But the underlying principle is the same: leadership continuity must become an ongoing organizational priority.

For some nonprofits, that may mean investing more intentionally in mid-career employees’ professional development, providing opportunities to manage budgets, lead cross-functional initiatives, or build relationships with board members and funders. For others, it may require rethinking executive responsibilities, strengthening senior management positions, or exploring shared leadership models that distribute responsibility more sustainably.

Boards may need to revisit compensation, leadership expectations, and the resources available to support an incoming executive. They may also need to recognize that an external search, while sometimes necessary, cannot substitute for years of internal leadership development.

Perhaps most importantly, organizations must create an environment in which talented professionals can imagine a future for themselves.

That brings us back to the larger workforce reset. If younger professionals cannot see a sustainable career path, they may leave. If mid-career employees cannot find opportunities to grow, they may leave. And if experienced professionals look at executive leadership and see an unsustainable job, they may decide not to pursue it.

By the time an executive departure occurs, those decisions have already shaped the available leadership pool.

The Future of Nonprofit Leadership Starts Long Before the Search

Throughout this series, we have examined three challenges that are often discussed separately: changing expectations among younger professionals, the loss of experienced mid-career talent, and the growing complexity of executive succession. Together, they tell a larger story.

The nonprofit workforce is changing, but many of the structures organizations use to attract, develop, retain, and promote talent have not kept pace.

For a sector built on long-term community relationships and enduring missions, that disconnect carries significant consequences. Organizations cannot fulfill their missions without people who are willing and able to sustain the work, develop the next generation, and eventually assume leadership.

The challenge is not simply finding the next executive director. It is ensuring capable, committed professionals are ready to lead, and organizations are strong enough to support them.

For nonprofit boards and executives, the most valuable succession conversation may not begin with: Who will replace our leader? It may begin with a more fundamental question: Are we building an organization that the next generation of leaders will want, and be prepared, to lead?

That is where the nonprofit workforce reset becomes a leadership imperative.

The Leadership Cliff: Nonprofit Succession in an Era of Instability is part three of a series examining the structural workforce changes shaping the future of nonprofit organizations, from emerging professionals to executive leadership. The full Nonprofit Workforce Reset Sector Brief will be published in December 2026.