Succession planning, from heroic leaders to good ancestors

Succession planning is a human challenge, not a systems one

Succession planning does not usually fail because of broken systems.

It fails because of people.

I have been in multiple conversations recently with organisations of different sizes and across different industries, and the same tension keeps surfacing.

Succession is no longer a “best practice” talking point.
It is a live issue.
And it is messy.

Boards know they should plan.
Investors want stability.
Employees want clarity.

Yet one difficult question continues to hang in the air:

how do you persuade a leader to step aside when they do not want to?

The Financial Times recently captured this tension well in a piece on CEO exits, highlighting examples such as Ben & Jerry’s, Diageo, and HSBC. On paper, the logic of succession planning is sound.

In reality, succession is rarely clean.

Ego becomes tangled with identity.
Timing turns political.
Loyalty clouds judgement.
Potential successors hover.
Boards avoid hard truths.
And leaders who have poured themselves into the role struggle to imagine not being essential.

As one FT source put it, succession “is not just an intellectual exercise”. That feels accurate.

Why succession breaks down

What separates organisations that navigate succession well from those that fracture under it?

Not better frameworks.
Not more policy.

But early, honest normalisation.

Succession works best when it is discussed from day one, not introduced during moments of threat. When it is framed as business as usual rather than betrayal. When it is rooted in trust between chair and CEO, not tension or avoidance.

When succession only enters the conversation during crisis, the damage is often already done.

At that point, every discussion feels loaded. Every option feels like a loss.

Succession is not about replacing a leader.
It is about protecting continuity, culture, and decision quality beyond any one individual.

That is what makes it one of the most human leadership challenges organisations face.

From heroic leaders to good ancestors

Most succession conversations focus on who comes next.

There is a deeper question leaders often avoid:

what are we actually trying to pass on?

Thomas Roulet, professor of organisational sociology and leadership at Cambridge Judge Business School, offers a useful reframing. He suggests we move away from thinking of leaders as heroes, and towards thinking of them as good ancestors. People who leave behind the conditions in which others can succeed.

This idea connects closely to Work with Source by Tom Nixon, drawing on earlier work by Peter Koenig. The premise is simple but demanding. Organisations have a source. A set of values, assumptions, and ways of making decisions. Leadership transitions either preserve that source, or fracture it.

I was reminded of this in a conversation with the founder of a global restaurant business. He described his hardest challenge not as choosing a successor, but passing on the baton without losing the culture and judgement that made the business work.

Strategy could be written down.
Financial targets could be handed over.
But intent, decision-making, and values were far harder to transmit.

This challenge is particularly acute in businesses that have scaled rapidly or taken a strong culture global.

In smaller, family-owned organisations, I hear a similar tension. Succession becomes entangled with identity, family dynamics, and politics, making it harder to separate what is emotionally difficult from what is right for the business.

An FT article I read recently reinforced this pattern. Long-tenured leaders often unintentionally bend organisations around themselves. Cultures begin to calcify. Internal successors struggle to emerge. External hires face impossible comparisons. The longer succession is delayed, the higher the emotional and organisational cost.

Add to this a widening generational gap in expectations, values, and ways of working, and the challenge sharpens further.

What good ancestors do differently

The strongest leaders do something quietly counter-cultural. They:

• Nurture two or three potential successors without turning it into a competition
• Rotate high-potential leaders through real responsibility
• Maintain an external perspective so boards retain genuine options
• Accept that the organisation must be able to exist without them

This takes humility.

Succession done well is not about immortalising a legacy. It is about leaving fewer unresolved problems, clearer decision pathways, and enough trust for the next leader to lead in their own way.

Or, as Roulet puts it, enabling future success rather than protecting past identity.

If leadership is stewardship, succession is where that belief is tested.

At Kholo, we support leaders and boards to slow this conversation down, hold the difficult edges, and think systemically about how purpose, culture, and decision quality survive a handover. Not just who takes the role next.

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