Why Wait Until the Seat is Empty?
It usually starts with a call.
A CHRO or board member is on the line.
“Our CXO resigned today. Can you help?”
I’ve been on the receiving end of that call more times than I can count. And I am always glad to get it.
But I’ll tell you something that might sound strange coming from someone who has spent more than 30 years in executive search:
It’s the call I would rather help you never have to make.
Why do we wait for the empty seat?
Executive search has earned a reputation for being transactional.
A seat opens. A search starts. Candidates are identified. A leader is hired. Everyone moves on.
But I don’t think the transactional nature of our business exists only on the search firm side.
Organizations often wait until there is an empty chair before seriously thinking about who should sit in it next.
And I understand why.
Succession conversations can be uncomfortable.
Budgets are easier to approve when there is an immediate vacancy.
There are always more urgent priorities competing for a leadership team’s attention.
And when the person currently sitting in the role is doing a great job, planning for that person’s departure can feel unnecessary or even disloyal.
Until Thursday afternoon when the resignation arrives.
Then everything becomes urgent.
The research tells us we aren’t as ready as we think.
This is not simply something I have observed during my career.
Current research suggests there is a meaningful gap between confidence in today’s leaders and confidence in what happens next.
Heidrick & Struggles’ 2026 CEO & Board Confidence Monitor found that 70% of respondents expressed confidence in their executive leadership team, yet only about 4 in 10 were confident their CEO succession planning positioned the organization well for the future.
Think about that for a moment.
We can have tremendous confidence in the people leading our organizations today while being far less prepared for the day one of those people is no longer there.
And that day eventually comes.
Sometimes it comes through retirement.
Sometimes through another opportunity.
Sometimes through an unexpected life circumstance.
Sometimes because the organization itself has changed and needs something different from the role.
Whatever the reason, succession is not evidence that something went wrong.
Leadership changes.
The question is whether we have prepared for it.
Urgency changes the conversation
Urgency is good for the executive search business.
I can admit that.
A critical leader leaves and suddenly an organization needs help finding someone exceptional.
But urgency being good for my business does not mean urgency is good for yours.
When the clock starts making decisions for us, the conversation changes.
We begin asking:
Who can we find quickly?
Who is available?
Who can step in?
Instead of having the time to ask:
Where is this organization going?
What will this role require three or five years from now?
Do we have someone internally who could grow into it?
What capabilities are missing from our current leadership team?
Who exists in the external market that we should already know?
Those are very different questions.
And in my experience, the second set leads to much better conversations.
Succession should begin before search
I would love to see organizations think about executive talent less as a vacancy problem and more as an ongoing leadership responsibility.
That starts with three things.
1. Know your internal bench
For every role that would materially affect your strategy, revenue, operations or reputation if it suddenly became vacant, ask:
Who could step in tomorrow?
Then ask a different question:
Who could genuinely be ready to earn this role in the next 18 months to three years?
Those are not necessarily the same person.
One is emergency coverage.
The other is succession.
Knowing the difference matters.
2. Know the external market
One of the misconceptions about executive search is that you engage someone like me only when you need a list of candidates.
There is tremendous value in understanding the market before you need the list.
Who is leading well in your industry?
Who is emerging?
Who has the capabilities your organization may need next?
What are exceptional leaders expecting from organizations like yours?
How does your internal talent compare with what exists externally?
That is market intelligence.
And it is much more useful when you have time to learn from it.
3. Build relationships before you need them
Some of the best executive relationships are built over years, not weeks.
That has been true throughout my career.
People remember who called when they did not need something.
They remember conversations that were genuinely curious rather than transactional.
They remember people who took an interest in where their career was going rather than simply trying to place them somewhere.
Relationships create options.
And options are extraordinarily valuable when an organization eventually faces a consequential leadership decision.
Start with your most critical roles
This does not need to become an enormous succession initiative tomorrow.
Start with one conversation.
Gather your leadership team and identify the roles whose unexpected vacancy would create the greatest risk to your strategy, revenue, customers, operations or reputation.
Then place each role into one of three categories:
Successor identified.
Successor developing.
No successor.
That simple exercise may tell you more about your leadership risk than a hundred pages of workforce planning.
Then ask another question:
What do we know about the external market for the roles where we are least prepared?
Now you are no longer waiting for a search.
You are building readiness.
Succession is also a form of generosity
I think about generosity differently than I did earlier in my career.
It is one of the reasons I wrote Living a Generous Life.
Generosity is not simply about money.
Sometimes it is about what we leave ready for the person who comes after us.
A leader who develops people, creates opportunities, shares knowledge and prepares others to step into greater responsibility is doing something incredibly generous.
Succession may be one of the most practical expressions of legacy in business.
It says:
This organization should be stronger after I leave it.
The people coming behind me should be more prepared because I was here.
That is not planning for your irrelevance.
That is leadership.
The question I would ask:
If one of your most critical leadership roles opened tomorrow, would you be ready?
Not:
Could you launch a search?
Of course you could.
Would you know what you actually need?
Would you understand your internal options?
Would you understand the external market?
Would you have relationships with people worth knowing?
Would you have enough time to make a thoughtful decision rather than simply an urgent one?
If the answer is no, that is useful information.
Because today you still have something you will not have after the resignation call.
Time.
And that is exactly when the best talent conversations should begin.
Up Next Month:
AI Can Find More Candidates. Can It Recognize the Right Leader?
Next month, I want to talk about something I’m seeing more and more in executive search: AI.
There is no question that AI is changing our industry. It can help us find more people, process more information and move faster.
But faster doesn’t always mean better.
Because at the end of the day, we aren’t just looking for candidates. We’re trying to understand people.
Can this person lead? Can they build trust? Can they navigate the culture? Do they have the judgment this particular organization needs? And can they lead where the business is going, not just where it has been?
AI can give us more information. But there are some things I don’t think we can afford to lose sight of as we use it.