How do you replace a popular, effective, outgoing leader?

I worked with the board for months on succession planning. The process was painful. Boards are rarely asked to make decisions that are this visible and consequential. They are more accustomed to vetting the suggestions of the executive. The sense of “It’s all on us” was creating analysis paralysis.

I was asked the typical questions:

• “Can we just ask the outgoing CEO to pick their replacement?”
• “Is there someone on the team that we can just promote?”
• “Do you know someone we can hire?”

These questions are understandable. But they can be a form of avoidance. These kinds of questions are intended to find an easy solution. Not the kinds of questions that are able to produce a quality answer.

The real questions – there are two – that should be asked. But they can feel challenging to answer:

1. “What are you trying to build with this organization? What do you want to build or accomplish in the next five or ten years?”
2. “What are the characteristics of someone who can lead that organization?”

The first question is usually easy to answer if the board is accustomed to actively providing governance-level leadership, especially through strategic planning and follow-through. It is very difficult to answer if they never participate in strategic planning or have always relied on their CEO to produce the vision and strategy.

Unfortunately, most boards discover: “We don’t have any idea.”

These boards are usually made up of smart, educated, committed people who are used to knowing things and being good at things. All of a sudden, they feel insufficiently prepared for the task and nervous about making the wrong decision. Call it anxiety. Or fear.

Whatever it is, it doesn’t feel good. And that triggers interesting (to me) behaviors.

If you think this song is about you…

It’s not. At least not specifically. But if it feels familiar, that’s because statistically, only about 50% of boards feel confident about their succession planning.

But this is a false assurance: Only about 25% of boards of privately owned companies actually have a succession plan in place. This is mirrored in non-profits as well.

The results of this approach? Widespread failure.

Depending on the research you look at, roughly 50% of CEOs will not last 18 months. Other research shows that two-thirds of boards believe that their choice of successor has ended in failure.

Why don’t we hear about this?

1. Boards and CEOs view this as a ‘family issue,’ keeping it quiet and using euphemisms to soften the perception of failure.
2. The time gap between the succession decision and the clear signs of failure is long enough that people fail to connect the dots.

Boards Default to Safety

Boards don’t want to fail. They want to make a good choice. But they confuse choices that feel safe with choices that are safe.

Why? Psychology.

Boards tend to be both risk-averse and conflict-avoidant. Additionally, most people struggle with cognitive discomfort around unresolved decisions—it’s physically uncomfortable.

Choosing a successor has great risk. It can easily go sideways. Robust conversations around succession, vision, and strategy can have friction, and friction can feel like conflict.

There is a sense of urgency to resolve the problem, so deliberation and thoughtful search processes feel like stalling.

The tendency is to default to the easiest, fastest decision:

• Ask the CEO to choose their successor.
• Go with a known quantity who will likely maintain the status quo.
• Accept whoever landed in the interim position.

In my experience, which is mirrored by national statistics, four out of five boards will choose the ‘safe’ option.

That is: They’ll promote an employee to the role of CEO. In almost all instances, this person was not initially on their radar and hadn’t been groomed for the role. They are usually a loyal employee, were productive in their current role, but most importantly, they are a known quantity. An easy decision.

A safe decision.

But is it actually safe?

The Reality: Succession Failure Is Common

Statistically, 40% – 70% of these successions will fail within 18 months. Nearly half of these will include the departure of the executive. But the path to failure is rarely immediate and obvious. Usually, it is a slow diminishing of performance, strategy, and the departure of key employees.

The length of time between the leadership transition and the acknowledgment that “this didn’t work the way we hoped” can take even longer. Because of this time gap, the association between poor succession planning and the triggering event that causes the board to acknowledge failure isn’t well recognized.

And because both the board and outgoing CEO want to save face, they both develop euphemisms to explain why they are parting ways, so it isn’t visible.

How “Safe” Choices Lead to Slow Failure

“Better the devil you know than the devil you don’t,” a leader recently told me.
“I prefer to work with angels,” was my response.

Familiar, known quantities are attractive. The board doesn’t know where to look for a successor, doesn’t feel like it has time to look, and just wants:

• Resolution to the question
• A resolution that feels like it is as close to the status quo as you could hope for

They want to feel safe or at least safer. However, feelings are deceptive. Reaching for internal candidates who were never prepared, assessed, or truly considered until the last minute is not, in fact, a safe decision. These are panic picks.

They make sense at the time – but, as described above, they rarely work.

What Strong Looks Like—and Why Boards Avoid It

A strong, effective leader is one who makes decisions and acts in ways that are aligned with your organizational values, and is able to confidently move towards accomplishing your vision.

The Seven Steps for Planned Succession

Here is the structured approach I’ve used successfully with boards that want real results.

1. Clarify organizational values and vision.
2. Identify who is responsible for the succession process.
3. Prepare the leader, the board, and the organization.
4. Identify the ideal successor profile.
5. Build and assess a candidate pool.
6. Conduct the search and selection process.
7. Develop an onboarding and transition plan.

Stop Choosing Safety—Start Building Strength

Boards that want to do this right must step beyond the known and comfortable. The good news is that this helps you build a more robust and effective organization. Good succession planning is a part of good strategic thinking. It’s really no more difficult than that.

The Succession360 Toolkit provides that structured, step-by-step framework that moves you from analysis paralysis to decisive action. It’s written as a DIY guide. But if you’d like help, contact me.

Don’t resign yourself to choosing the best devil you know. Angels are out there. Learn to see them.

Take good care,
Christian