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Field notes · Family business · 2026

Succession is a conversation.

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When a business owner calls about succession, they usually expect a technical answer. A freeze, a trust, a buy-sell agreement, a tax structure. Those tools matter, and we use them. But the structure is the easy part. The hard part is the conversation that has usually been put off for years.

Who actually wants to run this? Who is being lined up because they share a last name, not because they want the job? What is fair between the child who stayed on the farm and the two who moved to the city? Has anyone said any of it out loud? I have watched solid plans fail because the family never had that talk, and simpler plans hold up because they did. A succession plan written without the conversation is just a document. A plan built on the conversation is a transition people can actually live with.

There are real mechanics to get right, and they are worth doing well. Capital gains and the lifetime capital gains exemption. Shareholder agreements. Keeping the farm or the company eligible for the rollover rules. Life insurance to equalize between the children who are in the business and those who are not, or to fund a buy-out. Coordinating with your accountant and your lawyer so the tax plan and the legal documents say the same thing. We handle all of that. We just start with the people, because the structure has to serve a decision the family has actually made.

Questions worth asking before the structure
  • Does the next generation actually want the business? Have you asked them, plainly?
  • Who will lead, and who will own? They are not always the same people.
  • How do you treat children who are in the business and children who are not, fairly?
  • What does the founder need to retire comfortably, and where does that income come from?
  • What happens if you are gone, or unable to work, before the plan is finished?
  • Are your accountant and lawyer working from the same plan, or three different ones?

None of these need to be answered in one sitting. They need to be opened. Often my job is to be the neutral person in the room who makes it safe to start, and to keep the tax and legal pieces moving once the family knows what it wants.

Your Next Step · the workshop

A guided half-day to start the work.

If the conversation has been waiting for the right moment, the workshop is a good place to begin. Your Next Step is a half-day, in-person session where we work through a planning workbook together and map out the decisions a succession needs, with the tax and legal pieces flagged for your accountant and lawyer.

You leave with a written set of next steps and a follow-up call with me on the calendar. $1,500 per family or business.

See the workshop →

If the conversation in your family has been waiting for the right moment, the right moment is usually a quiet one, before it is forced. We can start there.

Want to talk it through?

If any of this raises a question about your own situation, the next step is a short conversation. No charge, no pressure. Just pick a time that works.

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