I’ve Helped Navigate 7 CEO and Executive Director Transitions in 2 Years. Here’s What I’ve Noticed.
Seven.
In just the last two years, I’ve helped organizations navigate seven CEO and Executive Director transitions.
Some retired.
Some were terminated.
Some chose to move on.
And in many cases, I helped the organization navigate the transition, stabilize the team and eventually welcome a new leader.
Seven transitions is enough to start noticing patterns.
And there’s one in particular I can’t ignore.
The leaders who came in and were successful did something remarkably simple:
They listened.
The best new leaders don’t come in trying to prove they’re the leader
The strongest incoming CEOs and Executive Directors I’ve worked with spent their first few months learning.
They met with employees.
They asked questions.
They wanted to understand the history of the organization—not just what was written in the Board materials.
They asked:
What’s working?
What’s not working?
What have you tried before?
What are you worried about?
What do you think I need to know?
And most importantly, they made employees feel heard.
They didn’t come in on Day 1 announcing a reorganization.
They didn’t immediately start replacing people.
They didn’t spend their first month trying to prove why the Board hired them.
In fact, unless something truly urgent needed to be addressed, they generally didn’t make major changes during their first 60–90 days.
They observed.
They listened.
They learned.
Then they led.
The leaders who struggled did almost the opposite
I’ve seen the other side too.
The leaders who struggled tended to come in believing they already knew what needed to be fixed.
Before they understood the organization.
Before they understood the employees.
Before they understood why certain decisions had been made in the first place.
And there were a few behaviors I’ve seen repeatedly.
They talked badly about their predecessor.
Maybe the previous CEO made mistakes. Maybe that’s exactly why the organization needed a transition.
But criticizing the person who came before you rarely builds confidence with employees.
Because here’s the thing:
Some of those employees may have loved that leader.
Some worked alongside them for 10 or 15 years.
Some helped build the very systems you’re now criticizing.
When you disrespect the previous leader before understanding the history, employees may hear something very different:
You don’t respect what we built either.
They treated employees as replaceable
This is another big one.
A new leader walks into an organization, identifies people they don’t immediately connect with and assumes:
“We’ll just replace them.”
Sometimes, yes, changes need to happen.
Leadership transitions can uncover performance issues, skill gaps and positions that no longer make sense for where the organization is going.
But institutional knowledge is incredibly valuable during a transition.
The employee who has been there for eight years may know why a process exists.
They know the clients.
They know the donors.
They know the Board.
They know the history behind that strange policy nobody can explain.
They know what was tried three years ago and why it failed.
You can hire someone new.
You can’t instantly replace institutional knowledge.
And they thought they knew everything
This might be the biggest difference I’ve seen.
The successful leaders entered with curiosity.
The struggling leaders entered with certainty.
There’s an enormous difference between:
“Here’s what I think we should do.”
and
“Help me understand why we do it this way.”
One assumes the answer.
The other creates the opportunity to discover it.
And that distinction matters enormously when you’re walking into an organization that has just experienced a major leadership transition.
The first 90 days aren’t about proving yourself
There’s enormous pressure on a new CEO or Executive Director.
The Board hired you for a reason.
You probably walked in with a mandate.
You have ideas.
You can immediately see things you’d do differently.
But unless there’s a compliance issue, financial emergency, serious employee relations concern or another urgent business need, you don’t have to fix everything immediately.
Your first job is to understand what you’re inheriting.
Talk to employees.
Meet with managers.
Understand the informal influencers—not just the people with senior titles.
Learn what’s working before deciding what’s broken.
Figure out which parts of the culture are worth protecting.
And understand why people stayed through the previous transition.
Because those first few months aren’t just your opportunity to evaluate the organization.
The organization is evaluating you, too.
Employees are watching how you speak about their former leader.
They’re watching how you treat the people who have been there the longest.
They’re watching whether you ask questions or make assumptions.
They’re deciding whether it’s safe to tell you the truth.
And they’re deciding whether they want to follow you.
Seven transitions later, my advice is surprisingly simple
If you’re stepping into a CEO or Executive Director role:
Spend your first 60–90 days listening more than changing.
Respect the history before you rewrite it.
Treat institutional knowledge like an asset.
Don’t confuse a new perspective with knowing everything.
And remember that the employees you’re inheriting aren’t obstacles standing between you and your vision.
They’re the people who may ultimately help you achieve it.
I’ve now watched seven organizations navigate CEO and Executive Director transitions in two years.
Different organizations.
Different circumstances.
Different leaders.
But the pattern keeps showing up.
The strongest new leaders don’t walk in saying, “Here’s what we’re going to change.”
They walk in asking:
“What do I need to understand?”
And then they actually listen to the answer.
By: Cara Barnes
