In this piece, accountant Cat Santini outlines the essentials of family-business succession planning using a real-life example of a business she supported.
For many small-business owners or family-owned businesses, succession planning is the monster under the bed. They know it’s lurking, but they’d really rather not look. Especially in family-run businesses, where emotions, money, and legacy are all mixed up in ways that make even the simplest conversations feel hard or downright impossible.
It doesn’t have to be that way.
I worked with a multi-generational farming family who are living proof that, with the right plan (and a bit of patience), succession can actually strengthen both the business and the family.
The starting point: total gridlock
When we first met, they couldn’t see a way forward. The plan was to split the farm up – a painful decision, but one that seemed inevitable. Everyone had different ideas, different priorities, and frankly, different levels of trust in each other.
If we’d left it there, they would have spent hundreds of thousands of dollars buying duplicate equipment, lost the efficiencies of scale, and probably damaged family relationships beyond repair.
But I asked them to give me 12 months. They agreed. One structured plan. Regular meetings. Clear financial modelling. Accountability to each other. No “we’ll see what happens” vibes.
The plan: one step at a time
We treated succession planning like a living, breathing project, not a one-off document you stick in a drawer.
Each month, we met as a group and individually. We adjusted the plan as real life happened. No one was allowed to hide behind excuses or bail when things got hard.
Financially, we mapped out a structure that made sense for sustainability. Emotionally, we created a space where everyone had a say, including some hard conversations.
It was a balancing act: giving the next generation real authority while still valuing the experience of the parents.
The result: a stronger business – and stronger relationships
Fast forward a few years, and not only is the farm still intact – it’s thriving.
More importantly, so is the family.
The parents got to see their kids step up while they were still around to support them. The kids got real experience without feeling abandoned or set up to fail. And family gatherings are filled with laughter, not tension.
The family structure stayed whole. The business stayed efficient. The relationships stayed strong.
It’s an extraordinary outcome when so many succession stories, especially in farming, end in disaster.
What small-business owners can learn (even if you don’t own a farm business)
Here’s what made all the difference for this business, and what can make all the difference for you:
- Start early. Succession isn’t something you sort out a year before you want to retire. The earlier you start, the more options you have – financially, operationally, and emotionally.
- Structure matters. Good financial planning isn’t just about saving tax. It’s about setting up a structure that makes it easy (and desirable) for the next owner to step in.
- Make it a process, not a one-off event. Businesses, people, and life circumstances change. Your plan needs to be flexible and updated regularly, not set in stone once and forgotten.
- Communication is everything. Regular meetings, individual check-ins, and clear accountability are what keep everyone on the same page (and avoid the “he said, she said” dramas).
- Bring in someone neutral. Emotions run high when you’re dealing with family or long-standing employees. Having an independent advisor can help keep conversations constructive and stop old wounds from derailing the future.
Succession planning is one of the biggest gifts you can give to the people who will carry on your business after you. Do it right, and you’re not just handing over a balance sheet; you’re handing over a legacy. And trust me, it’s a much better story than the horror stories we’ve all heard.
