That question came from a nonprofit leader I coached last year. She wasn't planning to leave tomorrow. But she was thinking about the future, and the uncertainty around it was weighing on her.

I've heard this thought more and more over the last few years in my coaching conversations. I've noticed that many leaders are afraid to speak about it in their organization. And that fear of speaking about it is causing challenges in organizations.

We need to talk about succession planning, not as a formal HR process or a massive document but as a necessary leadership conversation. A conversation that builds hope creates sustainability and helps our sector thrive.

In a recent episode of CharityVillage Connects, I had the opportunity to speak with Mary Barroll from CharityVillage about the very real succession crisis facing nonprofit organizations.

I'm grateful for the conversation because we need to have conversations more often and more openly.

Here's some of what Mary and I discussed and a bit more to help you, whether you're the current leader thinking of stepping away or someone wondering what the future holds for your organization.
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Too often, no one knows what comes next.

• Boards aren't initiating the conversation.
• Leaders feel unsure of how to bring it up.
• Staff are left in the dark.

The result? A lack of true leadership on the team and in the organization, lost momentum, and talented individuals walked away from roles they might have otherwise stepped into if the path had been clearer and they had felt supported to grow and step into the role.

Succession planning isn't just about choosing a replacement. It's about growing the next leader, helping them build their confidence and capacity. At the same time building confidence in that upcoming leader across the organization. Without it, we risk confusion, instability, and a big mess when something initiates the leader moving on.

• Avoidance from the board – Many boards don't want to "poke the bear," especially if the current leader is also the founder. They aren't sure they can legally ask those questions. Or they wonder if it will give the wrong message to the leader that they aren't wanted anymore.
• Survival mode culture – When we're all trying to keep up with reporting deadlines, funder demands, and program pressures, planning for something five years down the road feels impossible.

And yet, that's exactly why we need to start now.

​Another major gap? We're not developing the right skills.
When someone is promoted from the front line into a leadership role, they're often handed policies, reporting forms, and a few HR documents—and expected to figure the rest out.

But technical tasks are only part of the job.
What new leaders really need to learn are:

• How to motivate and inspire others
• How to manage your emotions (and your team's)
• How to build hope during change and uncertainty
• How to have tough conversations and deal with prickly personalities
• How do you set boundaries when you are a people pleaser, perfectionist, or performer so you don't burn out?

We call them "soft skills," but they're foundational to effective leadership. And in most nonprofits, they're rarely taught.

That lack of preparation leaves new leaders overwhelmed and uncertain, and it reinforces the cycle of burnout and leadership avoidance.
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Did you know there was a time when I didn't know if I could keep leading?

I felt lost, overwhelmed, and completely out of my comfort zone. Maybe you know that feeling too!

I had just stepped into a senior leadership role. I was managing everything relatively confidently. With things going well, I worked my butt off applying for expanded funding. My team and I were so excited when we got it.

However....

When that large new contract arrived, the increased responsibility, staffing demands, travel, and budget oversight felt hugely overwhelming. I was scrambling to hold things together, feeling like I was on a conveyor belt that just kept speeding up.

Things started to slip. I didn't always keep my word. I pushed my own agenda without truly listening to my team. I was no longer the leader they had once trusted. That year's performance appraisal was like a slap in the face: My staff clearly said, "Kathy lacks integrity." That comment hit hard.
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Engagement plummeted, and tension rose. There was whispering behind my back, and even a grievance was filed against me. I felt isolated and afraid I might lose my job.

You may feel this way, too. Maybe you've been in a meeting, putting on a brave face, all the while wondering if everyone else can tell that you feel completely lost, ready to fall apart and wondering why you are doing this job anymore but also very stuck!
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I knew I had a choice: I could quit, or I could do the hard work of rebuilding my leadership from the ground up. I chose the latter.

I started by doing the inner work. I took a step back, paused, and reflected on who I wanted to be as a leader. I got support from a coach who helped me see my blind spots and guided me through the process of realigning my actions with my values.

I used THE INFINITE LEADERSHIP LOOP, the same process I teach in Character Driven Leadership for Women, to help me navigate my way forward. I learned to PAUSE, PONDER, and PIVOT with intention. 

Slowly but surely, as I had the courage to PROCEED into conversations with my PEOPLE, I started to rebuild trust with my team and restore my own confidence.
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If you've felt like you don't know what you're doing, if you've struggled with imposter syndrome, lack of support, or fear of failing, you're not alone.

We all face moments where we feel off-balance, unsure, or overwhelmed.
But those moments are also choice points. They are opportunities to decide how you want to show up as a leader.

In Character Driven Leadership for Women, I share not just my own story but practical tools to help you:

• PAUSE and recognize when you're in survival mode.
• PONDER your options and choose your response with intention.
• PIVOT from reaction to grounded, values-driven action.
• PROCEED with clarity and confidence, knowing you've aligned your actions with who you want to be as a leader.
• Reconnect with your PEOPLE by listening, showing up with integrity, and creating a culture of trust and open communication.

This is what THE INFINITE LEADERSHIP LOOP is all about. It teaches you to take those difficult moments and use them to build your character, confidence, and leadership impact.
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