Succession Planning Process: How to Build a System that Survives

Video Timestamps

00:00 – 05:27: Greg’s Background and Why He Wrote His Book
05:28 – 15:05: Why Some Businesses Survive vs. Why Some Don’t
15:06 – 16:08: Governance > Estate Tax Planning
16:09 – 19:13: Four Reasons to Own a Family Business
19:14 – 26:02: The Four Hats of Ownership
26:03 – 28:06: Succession Planning is a Puzzle, Not a Contest
28:07 – 32:28: The Importance of a Shareholders’ Agreement

Welcome to The Trusted Room, a series about the conversations that really matter. So much of the financial industry focuses on the math, portfolios, markets and returns but the conversations clients thank you for are about family, purpose and the things money can’t measure. We created The Trusted Room to bring those conversations out into the open.

In this episode, Greg Monday — a shareholder at Reinhart Boerner Van Deuren and author of The Lawyer's Guide to Family Business Succession Planning — argues that the succession planning process is about far more than tax-efficient wealth transfers. Drawing on decades of experience and two contrasting real-world stories, he makes the case that governance, not just estate documents, is what determines whether a family business survives the transition from one generation to the next.

5 Key Takeaways

1. Governance can matter more than estate tax planning 

Greg's defining insight came from two real cases: A business with an estate plan collapsed after the owner's sudden disability, while a business without a plan survived because it had governance that safeguarded it from being publicly listed. The succession planning process should build a decision-making system that continues past the founder.

2. There are four reasons to own a family business

Income, wealth accumulation, occupation and legacy. Not every next-generation family member values all four equally. Realizing which reasons matter to which family members helps you decide how to allocate ownership, wealth and income across the next generation.

3. Every owner wears four hats (and not everyone needs all four)

Shareholder, board member, executive and directors. A founder often wears all four at once. But in the succession planning process, you can separate them: Voting shares can be split from economic value, board seats can go to non-family members and not every family member needs to run the business day-to-day.

4. Succession planning is a puzzle, not a contest 

Too often, families treat the CEO role as the "family prize" and some attorneys even encourage a dog-eat-dog approach. Greg reframes succession as a jigsaw puzzle where the family collaborates to put the pieces together and nobody is trying to "win" the puzzle. Understanding the pieces — governance, ownership and roles — lets you educate the family on what's actually possible.

5. The shareholders’ agreement is the most overlooked part of the estate plan 

When families end up in court over a business, the most common reason is that there was no shareholders' agreement in place. A single owner may wonder why they need one if they're leaving stock to multiple children. Greg's advice? Treat the shareholders' agreement, operating agreement and governance documents as part of your estate plan and do that work now.

The succession planning process is a system you build. Estate tax planning matters but it's the governance structure underneath that determines whether your business survives the transition from one decisionmaker to many, so do the governance work now with your attorney and your advisor.