The Hardest Part Of Succession No One Talks About

Almost every family business owner I meet agrees that succession is important. They say it with conviction. The next breath is usually something like, “We will get to it when things are a bit quieter.” Or “We all know roughly what the plan is.” Or simply, “Not yet.”

It is not that families do not care. They care deeply. It is that succession touches something far more personal than most other decisions a business has to make. It raises questions about identity, ageing, purpose, fairness, relationships and what happens when long-standing roles begin to change.

No strategy document can remove that. Succession is emotional before it becomes practical. And unless that is acknowledged, even the most sensible plan can stall.

What follows is a grounded look at the human realities that sit beneath every succession discussion in a mid-market family business. These are the patterns I see every week.

1. Stepping Back Is Harder Than It Sounds

People often think of succession as a simple handover. In reality, stepping aside as a founder or long-serving leader is rarely straightforward.

If the business has been part of your life for thirty or forty years, it is not just a job. It is the rhythm of your week. It is where your relationships sit. It is where your reputation was built. Stepping back means redefining who you are and where you put your energy.

Leaders often say they are not worried about letting go of power. What they are really unsure about is what comes next. Purpose is hard to replace.

A founder once said to me, “I am happy to step back, I just do not know how to have a good Monday without this place.” That is not resistance. It is honesty. And it is very common.

2. When Plans Are Unclear, People Fill The Silence

If succession is delayed or talked about vaguely, uncertainty begins to seep into the organisation. It is rarely dramatic, but you can feel it.

• Senior staff start reading signals

• The rising generation wonder whether to wait, push or step back

• Non-family executives quietly ask themselves if they have a future

• Good people hesitate to commit to long-term plans

All of this happens behind closed doors. No one wants to be the one to raise it. But silence becomes a story, and stories quickly become assumptions.

A short, honest conversation can steady a business. Without it, energy drifts, confidence softens and people begin to guess instead of knowing.

3. The Rising Generation Carry A Weight They Rarely Show

From the outside, it often looks as if the rising generation are eager to take over. On the inside, it is usually more complicated.

We hear things like:

• “I want more responsibility, but I do not want to look like I am pushing Mum or Dad out.”

• “I want to modernise the business, but I do not want people to think I am criticising the past.”

• “I feel I have to prove myself twice, once to the team and once to the family.”

• “If I say I am not ready, will they think I am not committed?”

Most of this is never said out loud, but it shapes confidence, behaviour and relationships. A healthy succession process recognises this pressure and gives the rising generation room to develop without fear of judgement.

4. Non-Family Executives Become The Quiet Casualties Of Unclear Plans

Family businesses depend heavily on strong non-family leaders. Many have been with the business for years and are trusted deeply.

But when succession is uncertain, these leaders often feel the most exposed. They wonder whether the next generation will trust them, whether their role will change and whether the balance of decisions will shift.

They rarely say any of this. They simply start to consider other options. Often quietly.

The irony is that these individuals are usually essential to a stable transition. Keeping them engaged requires clarity, respect and early communication. Not knowing is what unsettles them.

5. Choosing Between Family Members Is More Delicate Than Most Admit

When more than one family member is involved, succession becomes even more emotionally charged.

Parents want fairness. They want harmony. They want to avoid hurting anyone. They want the family to stay together long after the business passes to the next generation.

So decisions are often softened, delayed or left open. Everyone remains “in the running” which feels polite but ultimately leaves no one prepared.

The families who handle this well put time into understanding each person’s strengths, motivations and suitability long before a decision is needed. Clarity protects relationships better than avoidance ever can.

6. Shadow Leadership Can Quietly Derail The Successor

Even after the handover, some leaders stay involved in ways that confuse the organisation. They do it out of care, not control. They want to protect the business. They want to make sure decisions are thought through.

But if the outgoing leader continues to influence key decisions, people naturally defer to them. The successor’s authority softens. The organisation receives mixed messages. Confidence weakens.

Stepping back does not mean disappearing. But it does require agreement about boundaries, roles and when involvement is helpful rather than unhelpful. The most successful transitions define this early and revisit it often.

7. Legacy Matters, But It Can Become Restrictive

Leaders care deeply about what the business stands for after they leave. They want continuity, loyalty to the past and respect for what has been built. This is their legacy.

This commitment is positive, but it can slip into overprotection.

• Some leaders delay succession because they fear their work will be undone

• Others choose a successor who thinks and acts exactly as they do

• Some hold onto day-to-day involvement longer than is helpful

The strongest transitions separate the values that must endure from the habits that may no longer serve the future. Values stay. Ways of working evolve. That distinction matters.

8. Why Families Avoid Succession Even When They Know It Is Time

These are the five most common reasons families hesitate to begin the real succession conversation:

1. There is still plenty of time.”

2. “I do not want to create tension in the family.”

3. “We are too busy to think about this properly.”

4. “We should wait until things settle.”

5. “I do not want people to think I am stepping aside.”

All understandable. All human. But all carry consequences.

The longer succession is postponed, the more emotional the decision becomes.

9. The Families Who Manage Succession Well Share Three Traits

Across the businesses I work with, the most effective transitions have three things in common.

Trait 1 - They start the conversation early

Succession is not an announcement. It is a journey. Beginning early removes pressure and creates space for development and clarity.

Trait 2 - They communicate openly

Even partial clarity is better than silence. When people know the direction of travel, they stop guessing.

Trait 3 - They involve the right people

Succession is not one person’s burden. Boards, non-family executives and advisers all play a role. Shared responsibility makes the transition steadier.

A Final Thought

Succession is not only about the next leader. It is about the future of the business and the future of the family. When handled early and openly, it strengthens both.

The true measure of leadership is not how long someone stays at the top. It is what continues to thrive after they step back. And for many family business owners, that is the legacy that matters most.

About the Author - David Twiddle, Managing Partner at TWYD & Co., works closely with founders, family businesses and family offices on leadership appointments, succession and alignment. He has spent more than twenty years advising on people and leadership, with a particular focus on the moments where families face key decisions about the future.