The outgoing leader should never pick their successor. Leadership succession is too critical to be left to one person’s preferences or legacy goals.

The successor lasted less than a year. A federal fraud investigation followed. Within another year, the entire organization shut down.

I wish this story was unique. It’s not. The details are more dramatic than usual, but the dynamics are common.

I was asked to work with a board for both strategic and succession planning. That’s an important combination, and I was glad to see it. Leadership succession is the single most important strategic decision a board is likely to make. But most boards don’t sufficiently prepare for it.

The planning retreat was difficult. The board wasn’t accustomed to providing leadership. They were used to affirming the direction provided by a strong executive. That’s risky, but especially when the topic is succession.

After the retreat, the CEO pulled me aside. He introduced me to a member of his team—someone not involved in the retreat.

“He’s going to be my successor,” he said. “I’ll let the board know soon.”

I was surprised. The board didn’t know. I had just spent most of the retreat preparing them to lead this process.

I chatted briefly with the heir apparent. He seemed nice. Probably effective in his current role. But nothing suggested experience or aptitude for executive leadership.

The process moved forward as the outgoing leader intended. The board accepted it. The outgoing CEO retired.

You already know the rest of the story.

But it’s easier to let the outgoing leader choose.

Many boards want this. Many outgoing executives push for it.

For the outgoing leader, it’s often about legacy. A desire to preserve their vision or protect their work. Sometimes they don’t trust the board’s timing or decision-making. And often for good reason. Most boards are unaccustomed to providing governance-level leadership. They’re more comfortable being consulted than offering direction.

But the executive is their single employee. Selecting that person is their highest strategic responsibility. Failing to do so is a failure of governance. It’s negligent.

Letting the outgoing leader choose feels easier. Especially because they usually pick someone familiar. Loyal. A strong lieutenant.

It feels stable.

And on the surface, it often is. These “handpicked” successors typically stay in their role longer than most CEOs. On average, they hold the position almost twice as long. They know the culture. They know the players.

That’s good, right?

Not always. Here’s why.

Three common issues with this leadership succession approach:

1. Reinforces weak governance
   When the outgoing leader drives succession, it prevents the board from stepping into its proper role. This translates to a board that doesn’t set vision, oversee strategy, or evaluate performance. That’s another way of saying – the board doesn’t learn to do its job.

2. Cloning bias
   Outgoing leaders often try to clone themselves. They choose someone they believe is like them. This is in contrast to choosing someone who is able to lead and build the vision of the organization. Instead, they choose someone who will not challenge the status quo.

3. Weak lieutenant syndrome
   Successors are often loyal ‘doers’—people who executed the leader’s vision. But they aren’t used to providing direction. They’re used to following it.

Combine a weak board with a weak leader and problems will emerge.

The Consequences

1. Strategy stagnation
   No one leads. Nothing changes. It feels stable—for a while. But this is often a mask for decline.
2. Building a museum
   Successors may try to preserve what was. Especially if the former leader was charismatic or well-loved. But museums preserve the past. They don’t build the future.
3. Turnover
   Leadership change triggers transition. Even in well-executed succession. But when the process feels ‘fixed’ or like a ‘backroom deal,’ staff start reconsidering their roles. Especially if they felt overlooked or passed over by the succession process. Or if they don’t believe the successor can lead. Regardless, when an outgoing leader chooses their successor – expect that the next year or so will be followed by the loss of key players.

What works better

• A board-led process, guided by vision and strategy.
• The outgoing leader informs the selection criteria—not the selection.
• The board chooses.
• The outgoing leader mentors and onboards the new executive.

Leadership succession is a board’s duty and a leader’s legacy. When done well, it protects both the organization and the people within it.

I’ve built a free resource to help you walk through this. The Succession360™ Toolkit.

If you’re a board member, this is your responsibility.
If you’re the outgoing executive, this is a better way to secure your legacy.

Either way, don’t leave it to chance.

Download the toolkit. Or contact me. I’ll help you walk through it.

Take good care,

Christian