In my previous blog The Founder’s Dilemma, I wrote about a familiar pattern in family enterprises: the title changes, the authority doesn’t. A successor is named, but the system remains loyal to the founder who never truly stepped back. On the surface, it looks like a governance failure. Beneath it, something far more human is at play.

That theme is explored in a different but closely related context in The Hero’s Farewell: What Happens When CEOs Retire, written by Jeffrey A. Sonnenfeld.

The book examines what really happens when top leaders step down, and why some exits stabilize organizations while others quietly (or loudly) trigger chaos. Sonnenfeld’s core argument aligns closely with what I see in family enterprises every day: succession is not an org-chart event. It is a human transition shaped by ego, identity, power, and relationships.

And when that human transition is mishandled, the consequences ripple far beyond the individual stepping down.

Leaving is not the same as letting go

One of Sonnenfeld’s most cited contributions is his framework of four departure styles that leaders tend to fall into when they exit:

• Monarchs
• Generals
• Ambassadors
• Governors

Each style reflects a different relationship to power, relevance, and identity after the formal role ends.

What matters is not the label itself, but the impact. Some exit styles create space for successors to grow. Others suffocate them.

Seen through the lens of Blog 118, Sonnenfeld’s work helps explain why “title transfer” without “authority transfer” is so persistent. It is rarely accidental. It is often the natural outcome of how the outgoing leader relates to their own legacy.

The shadow does not come from nowhere

In the family enterprise I described earlier, the founder was not malicious. He was not trying to undermine his son. Much like Sonnenfeld’s “Monarchs” or “Generals,” he had built his identity around being indispensable. Stepping away did not feel like transition. It felt like erasure.

So he stayed present. He stayed helpful. He stayed involved.

And without realizing it, he stayed in charge.

Sonnenfeld’s research makes something very clear: leaders who cannot imagine a meaningful identity beyond their role almost always struggle to leave cleanly. When that happens, the system adapts. People continue to defer. Decisions quietly flow back to the familiar center of gravity. The successor becomes visible, but not sovereign.

The shadow leader is not imposed.
He is sustained.

The cost to the successor and the system

What Sonnenfeld documents in large corporations, I see magnified in family enterprises.

Successors placed in this position live in a double bind. They are expected to lead, but not to disappoint. To perform, but not to diverge. To carry responsibility, while authority remains conditional.

Over time, this erodes confidence, credibility, and trust. Not because the successor is incapable, but because the system never fully authorizes them to become capable in their own way.

Boards, teams, and families then misread the situation. They conclude the successor is “not ready,” rather than recognizing that the exit was incomplete.

The quiet difference between presence and interference

What The Hero’s Farewell adds to the conversation is nuance. It shows that successful exits are not about disappearance. They are about repositioning.

The most stabilizing leaders, Sonnenfeld shows, become Ambassadors or Governors. They remain connected, but no longer central. Available, but not directive. Supportive, without competing for relevance.

This mirrors what resolved the situation in Blog 118. The founder did not vanish. He transformed. He found a way to remain meaningful without remaining in control.

That shift is not technical. It is emotional.

Succession as a psychological crossing

Taken together, The Founder’s Dilemma and The Hero’s Farewell bring us to the same insight:

Succession fails less often because structures are missing, and more often because separation is unfinished.

Leaving well requires grieving a former identity.
Staying involved well requires restraint.
Letting the next generation lead requires tolerating irrelevance in places that once defined you.

Until that work is done, no announcement is strong enough to override the invisible dynamics at play.

Titles can be handed over.
Authority must be released.
And identity must be re-authored.

That is the real farewell every founder and CEO eventually faces.

Photo by Ayrus Hill on Unsplash