Let’s talk about one of the most important conversations many mission-driven organizations aren’t having: succession planning. Leadership changes are inevitable, with most CEOs leaving their roles after about six years. Yet, research from BoardSource found that only 29% of nonprofits reported having a formal succession plan. Without a plan, organizations risk losing hard-earned momentum and mission impact.
While some transitions unfold with little disruption to operations and relationships, many reveal gaps that should have been addressed months or even years earlier. So why do we put off planning until a departure is looming?
We asked Pyper Davis, former CEO of Educare DC and current Founder & President of Just Impacts, to share her practical and people-focused philosophy on leadership succession. Whether you’re a CEO thinking about your organization’s future or a senior leader developing your team, her advice can help you build more change-ready and sustainable organizations.
A longtime client and friend of Staffing Advisors, Pyper has over 30 years of C-level experience across the media and education sectors. Now a consultant, she helps executives, boards, and funders navigate strategic changes and growth through CEO succession planning and coaching. What follows are a few highlights from our conversation.
Why Succession Planning Stays on the Back Burner
Pyper ties the lack of attention to succession planning to our basic human tendency to avoid discomfort, “A lot of organizations don’t plan for it because it’s uncomfortable to have difficult conversations.”
Boards worry that raising the topic might signal dissatisfaction with their CEO, while CEOs fear that initiating the discussion could suggest they’re ready to leave. And down the chain it goes. Senior leaders may hesitate to discuss their career aspirations with supervisors, fearing it could be misinterpreted. And without an institutional model to follow, they don’t plan for someone to fill their role when they leave.
Pyper shared that overcoming the discomfort begins with making these conversations routine. You can’t always control the timing of a leadership change. There are times when an organization or leader is in crisis. But if you embed this work into regular operations, you build an organizational structure that can weather the unexpected without missing a beat.
“The best way to do this work is to make it part of your annual processes, just like performance reviews and professional development. It’s really about investing in people’s growth, placing value on continuous learning, and building a culture of looking ahead.“
Creating a Succession-Ready Culture
In a succession-ready culture, talking about career growth and staff changes is a normal part of the organization’s evolution, not cause for alarm. Transparency and consistency are the keys to making it work.
For CEOs, succession planning should be a standing item in board discussions and annual reviews. CEOs should self-advocate for performance reviews if they aren’t getting them and make sure this topic remains on the board’s agenda.
- Reframe the conversation from “Who will replace me?” to “How can we secure the organization’s long-term success?”
- Be open about what you think about your tenure, how you want to grow, and your plans.
- Talk about whether those align with the organization’s strategic direction.
- Revisit the conversation periodically.
Senior leaders should ask direct reports to reflect on their current work and share their career goals. These conversations can help to identify team members who have the potential and desire to grow into a more senior position when the time comes. Managers should be encouraged to do the same.
“At the end of the day, almost everything comes back to relationships. You need a healthy way to talk about what you do well and what you’re struggling with at whatever career level. You need to build that trust.”
What Will the Future Hold?
Throughout our conversation, Pyper emphasized that CEO succession planning is highly context-specific, depending on the current and future state of the organization, in addition to individual professional goals. It’s an ongoing balancing act between what the organization needs, the leadership capabilities currently in place, and training, professional development, or advancement opportunities.
Succession is deeply intertwined with strategic planning. Pyper suggests thinking about your organization’s strategy and potential challenges 3-5 years out. “If your organization has climbed a big hill over the last ten years with one leader, what will the CEO’s job responsibilities be 5 years from now? What leadership skills and experience will be needed then?”
“Your organization isn’t the same as it was when you hired the last leader. The scale and impact are different, and there will be new skill gaps. What you needed then may not be what you need tomorrow.“
Using a similar succession-ready mindset, senior leaders should also regularly assess how roles have changed, what their teams need now, and what’s coming next. Everyone in a people-management position should be doing this forward-looking assessment of their teams.
Drawing a Roadmap for Growth
Now for the good part: identifying and developing internal talent. Pyper shared that while you can’t promise anyone a promotion, having explicit conversations with potential successors about their interests and readiness is the first step.
“Would you ever be interested in doing a job like this? It’s not my call, and I don’t know when it will be available, but if you want, I can help prepare you.” Be upfront about what is involved, how you can support them, and the work they’ll need to do on their own.
From there, you’ll need to help that person (or people) get hands-on exposure to different aspects of the role they might grow into. The idea is to build on their strengths and invite them to the table. At the CEO level, a few examples include:
- Shadowing key processes like budgeting or strategic planning
- Presenting to the board in their areas of expertise
- Leading organization-wide strategic initiatives with your guidance available as needed
- Participating actively in funder or high-level stakeholder meetings
For senior leadership roles, the roadmap to getting exposure and building skills will be less complex than the CEO level, but the same transparency rule applies. Be clear about what the opportunities are and the time and effort required to get there.
“Some of this is self-interest. If you want to take the next promotion, you have to think about who can take your place. But at its core, succession planning is really about investing in human capital and building a growth mindset, with everyone at every level having these conversations.“
As you create a development plan, think about the relational dynamics in the rooms you are inviting these individuals into. Have frank conversations about the challenges of breaking into what can be well-established hierarchies of power and if or how that might impact their experience.
Women and people of color are traditionally underrepresented in top leadership roles across many industries. And there are many ways people are treated as “other” at the highest career levels. It’s your responsibility to make sure anyone you are mentoring has the right support and awareness going in.
Whether it’s an internal or external candidate who ultimately steps into a CEO or senior leadership role, this kind of reflective career development strengthens your entire organization. Team members gain valuable skills, you develop a stronger leadership bench internally, and if an external search is conducted, you’ve done the hard thinking to attract and evaluate candidates who can make a lasting impact.
Building Without Burnout
As you identify and nurture potential successors, it’s important to balance growth with realistic workloads. Career development shouldn’t come at the cost of burnout. “We don’t all have 200% to give. You have to actively plan to make all jobs sustainable,” Pyper shared.
Consider a scenario where you’re developing two or three strong internal candidates. The extra responsibilities could become overwhelming without enough support. You might need to get creative in shifting responsibilities, offer an extra stipend, hire a consultant to handle roving tasks, allocate other team resources, or adjust timelines. In the long run, it’s worth it. You’re helping these individuals advance in their careers while evaluating their leadership potential in action.
Some leaders worry about investing too heavily in development only to have people leave for other opportunities. Pyper addresses this concern head-on: “People worry, ‘What if we develop our people and they quit?’ Well, what if you don’t develop them, and they stay?”
Just Enough, Not Too Much
The way a leader enters an organization can have a significant impact on their future success. Figuring out the right level of support during onboarding is another balancing act.
“There’s merit to having a short overlap between the old and new leader—like maybe a week or two,” Pyper advises. “But after that, the former CEO should step out of the role completely. Ideally, the new CEO will have access to that person, but they need the space and time to learn the business.”
This clean break gives the new leader space to establish their own approach while ensuring they have access to institutional knowledge when needed. It also helps staff or team members adapt to new leadership without confusion about decision-making authority.
Pyper also warns against being overly critical of someone new to a leadership position. If you conducted a thorough hiring process, whether through internal leadership development or an outside search, trust in your decision. You don’t want to ask questions or make comments that might undermine the new leader’s confidence in their ability to succeed.
“In those first several months, the job of the board chair or supervisor is to support and encourage the new CEO or promoted person and help them build trusting relationships. It’s not to pick at them or monitor or make them feel insecure.“
Honor, Celebrate, and Document
Founder or long-tenured CEO departures mark profound organizational shifts that affect everyone, from staff to stakeholders. “These exits are really important to think about,” Pyper notes. “Organizations need to grieve the process and celebrate and honor the person in a way that’s appropriate.”
These leaders have often shaped the organization’s identity, culture, and key relationships through years of service. Their departure can naturally trigger anxiety among staff and stakeholders about the organization’s future direction and stability.
Beyond celebration, these transitions require careful attention to preserving institutional knowledge. Long-tenured leaders typically hold deep insights into stakeholder relationships and organizational history that should be discussed and documented in detail.
“A public show of gratitude goes a long way. It’s not just for the person leaving but also for the people who stay, so they know that everyone’s contributions are valued even during a time of transition.“
Plan Today for Impact Tomorrow
At its core, succession planning is about creating organizations resilient enough to carry their missions forward through whatever the future holds. When we normalize conversations about growth and future leadership, we do more than prepare for inevitable changes. We create environments where people can openly discuss their aspirations, where career development becomes a shared endeavor, and where change becomes an opportunity rather than a crisis.
Pyper’s approach to leadership builds something far more valuable than a talent pipeline. It builds trust. Trust that the organization values its people, trust that everyone’s contributions matter, and trust that the mission everyone has worked so hard to advance will continue to thrive through future generations.
“The best legacy you can leave is placing the organization in good hands and in a high-performing condition. If an organization fails after a leader leaves, it isn’t because they were indispensable. It’s because they didn’t plan well.“
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