“I think we might be focusing on the wrong metric!”

For the past hour I had been in conversation with two brothers mapping out their plan to take over the family business – strategic timelines, exit dates, backwards planning from June 2026.  Everything appeared on track except I felt something was missing.  So, I threw this statement into the conversation as a curve ball.

The brothers looked at me bewildered.

I continued:

“The true measure of the success of this plan is not whether you end up owning the business. It’s whether you can all sit down as a family for Christmas dinner and enjoy each other’s company.”

The room went quiet.

“That’s the true measure of success here. Not the June deadline. Not the perfect exit strategy. A succession that leaves you owning the business but damages your relationships with each other, or with your Mum and Dad? That’s a failure. If different outcomes happen but the family stays close – that’s the win.”

One brother leaned back in his chair. The other looked at his hands.

Up till that point they had been asking themselves: “How do we get Mum and Dad out of the business by 30 June 2026?”

Whereas the REAL question should be: “How do we explore this honestly, protect our family relationships, and make the best decision for everyone – whatever that decision turns out to be?”

The difference? The first creates pressure and potential resentment. The second creates space for truth.

I suggested the conversation with Mum & Dad should be something like this:

“Mum & Dad – we love what you’ve built. We’d be honoured to take it over someday. But we love you more than we love the business. So let’s spend the next 6-12 months genuinely exploring whether succession makes sense for everyone. But here’s the key: if at any point you’re not ready, or this doesn’t feel right, we need you to tell us honestly. The business is negotiable. Being your sons isn’t.”

Here’s the hard truth: There’s nothing the brothers can say or do to convince their Mum & Dad to be ready to exit the business. That readiness is their choice alone. Any pressure might force them to pretend to be ready while they end up resenting their sons for making them feel that way.

In succession planning, everyone pretends it’s 70% financial and 30% emotional. The reality? It is the other way around.  Because there will be other business opportunities in life.  You will only ever have one family.