Transition is a journey, not an event. I say that often because I mean it. When it becomes an event, it tends to catch everyone off guard, even when a plan technically exists. And what I see most often is that the plan was built around the business and the wealth, with very little thought given to the people who are supposed to carry it forward.
I’ve seen plenty of transitions that looked complete on paper. The ownership structure was figured out. Someone had thought through the what-ifs. And yet 60% of family business transitions still fail. In most cases the structure wasn’t the problem. The family simply wasn’t prepared for what the structure would actually ask of them.
Two generations, one business, two completely different experiences
I talked about this recently on the Business Transition Roadmap podcast with Franco Lombardo, a family business advisor who has spent more than 20 years working with some of the world’s most successful families. His research confirmed something I’ve watched play out in my own work for a long time. Owners and their successors often aren’t experiencing the same transition at all.
Franco’s team surveyed families about their biggest challenges. When they asked the current generation, the top answers were sibling rivalry and entitlement. When they asked the next generation the same question, the top answers were lack of communication and feeling unheard.
“They spend money on structures and governance and investment policies. That creates wealth, and they haven’t done anything to prepare themselves for the wealth they’ve got. So no wonder there’s conflict.” — Franco Lombardo
What that gap actually represents is two generations inside the same business who aren’t even describing the same problem. The owner sees entitlement and rivalry in the next generation. The next generation feels unheard and left out of conversations about their own future. Both of those experiences are real. They just haven’t been in the same room together.
Franco also shared that roughly 52 to 53% of the families he surveyed had traditional governance structures in place, yet nearly 70% said those structures did nothing to address the family dynamics underneath them. The documents were there. The harder conversations hadn’t been.
No amount of planning on paper addresses that. And the longer it goes unaddressed, the harder it gets to close.
What owners plan for vs. what actually needs to happen
Something Franco said in our conversation has stayed with me. He pointed out that current-generation owners tend to plan for their kids with their advisors rather than with their kids and their advisors together. The structure gets built around assumptions that were never actually tested with the people it affects most.
The successor isn’t in the room when decisions get made about their future. They find out later, sometimes much later, what was decided on their behalf. And then we wonder why they don’t feel ownership of the plan, or why the commitment doesn’t hold when things get hard.
This is one of the quieter fears I hear from business owners, rarely said out loud: the worry that their successor won’t actually be able to carry this forward. That they’ll hand over something they spent a lifetime building, and it won’t hold. That fear is legitimate. But avoiding the conversation doesn’t protect the business. It just delays the moment of reckoning until there’s less time to do something about it.
The owners who move through this well are the ones willing to bring their successors into the planning process while there’s still room to adjust. They treat the successor not as someone to plan for, but as someone to plan with.
The people work has to come before the pressure does
What I’ve seen work is treating transition planning as preparation for the family, not just the business. That means thinking through how the people involved, with their different ages, interests and relationships to what’s being transferred, will actually grow into it together. The structure has to be built around them, not the other way around.
And it has to happen before the pressure is on. When families start early, time works in their favor. There’s room to have hard conversations while options still exist, to work through the dynamics that would otherwise harden into conflict, and to let successors actually help shape the plan they’ll eventually lead.
Franco shared something in our conversation that I’ve seen play out in nearly every family I’ve worked with too. Almost every family he’s been brought into has at least one child who was never held accountable, who was saved from consequences over and over again. By the time the family is trying to navigate a transition, that person might be in their 40s or 50s. The pattern is embedded and the fix is harder and more painful than it would have been decades earlier. As Franco said, it is fixable, but the desire to do the real work has to be there.
“You vote with your calendar. Your calendar tells you what really matters to you.” — Franco Lombardo
Families who say relationships matter but invest nearly all of their transition energy in financial documents are voting with their calendar. Growing the business feels concrete and productive. Sitting down with your adult children and talking honestly about entitlement, accountability and what this transition is going to ask of all of you feels like something that can wait.
Until the window closes and the pressure is already there.
When families wait, the cost is bigger than they expect
When families skip the people work and go straight to the structural plan, advisors end up solving the wrong problems. The documents get built around assumptions nobody ever actually agreed to. Then something happens, a family dinner that reveals how far apart everyone’s thinking actually was, and the structure that was supposed to hold everything together turns out to have been built on a foundation nobody tested.
The transitions that hold share something in common. The structure reflects what both the owner and the successor genuinely needed from it, not just what the documents required. The hard conversations happened before the signing because the people in the room had actually worked through what this transition was supposed to do for everyone.
When families wait, those conversations happen under pressure, if they happen at all. The options are smaller, the dynamics are more entrenched, and the pain of working through it is bigger than it ever needed to be.
What a journey looks like when the people are actually ready
I’ve been doing this work for more than 20 years, and I’ve watched transitions that by every conventional measure should have failed, succeed, because the family was willing to do the harder work alongside the structural work. And I’ve watched transitions that had every document in order unravel because they skipped the conversations that would have made those documents mean something.
My wish for every owner I work with is to take a step, and to do it sooner rather than later. This process can be genuinely positive, even exciting, when the people inside it are prepared for what it’s going to ask of them. That preparation doesn’t happen in a meeting with your attorney. It happens in the work you do before that meeting.
That’s what transition as a journey actually means. Not just a handoff that closes on a date, but a process built carefully, with the right conversations, the right people in the room, and enough time to do it well.
Ready to talk through where you are?
At The Transition Strategists, we help owners do the people-side work that makes the structural work actually land. If you’re figuring out where to start, or wondering whether the plan you already have is built on the right foundation, schedule a Discovery Call at transitionstrategists.com/discovery. We’ll help you get clear on what getting this right looks like for your family.
