Before the Sale: Building Trust Around Family, Money, and the Next Generation

Hi, and welcome back to ValuationPodcast.com — the podcast and video series where we talk about business, valuation, and the real-life issues that come with both. I’m Melissa Gragg, a financial mediator and business valuation expert in St. Louis.

Today I’m joined by Emily Bouchard — family transition specialist, author, and speaker — and we’re going beyond the numbers. Our topic is: Before the Sale: Building Trust Around Family, Money, and the Next Generation.

Because when a founder-led or multi-generational company is heading toward a transition — whether it’s a sale, gifting, or passing leadership — it’s never just a transaction. It’s identity, legacy, fairness, transparency, and trust… all at once.

If your family business is thinking about “what’s next,” this conversation is for you.

5 Key Takeaways

1. A business sale is an identity event, not just a financial event. Founders often need emotional preparation for “who am I after this?”
2. Role clarity prevents resentment. Ownership, leadership, employment, and “perks” must be defined before trust fractures.
3. Transparency needs structure. Families need governance (owners council, board, family assembly) to decide who knows what, when, and why.
4. Fair isn’t always equal — but it must feel fair. Especially when some heirs work in the business and others don’t.
5. Capture the legacy before the doors close. After a clean sale, access ends — archive stories, artifacts, lessons, and values before you exit.

Q&As from this episode

Q1: What should a family business do before selling a company?
A: Before selling, families should align on legacy goals, clarify roles and ownership expectations, and set a communication plan so trust doesn’t break during the transaction.

Q2: Why do business owners regret selling their company after a sale?
A: Many owners regret selling because they weren’t emotionally prepared for the identity shift and loss of purpose that can happen within 6–12 months post-sale.

Q3: How do you build trust between siblings in a family-owned business?
A: Trust grows through transparency, clear governance, role definition, and shared agreements on distributions, perks, and decision-making—so assumptions don’t turn into resentment.

Q4: What’s the difference between fair vs equal in family business inheritance?
A: Equal means everyone gets the same. Fair means the structure reflects contributions, roles, and needs—especially when some heirs work in the business and others are passive owners.

Q5: When should you tell family members you’re planning to sell the business?
A: Families should start with shared values and legacy conversations early, then disclose sale discussions in a structured setting (like a family assembly) so everyone hears it at the same time.

Emily Bouchard:

https://emilybouchard.com/

As a fractional Chief Learning Officer and Family Dynamics Advisor for Family Offices and Financial Advisory Firms, I bring over 20 years of experience working with multigenerational families of wealth. My role is to empower clients and their advisors with knowledge and skills to maximize the benefits, while minimizing the pitfalls, associated with financial wealth. 

With a background in social work and marital and family therapy, I focus on the human, social, intellectual and spiritual capitals to make sure the financial capital is a force for good for families and the communities they love."

Melissa Gragg

https://www.valuationmediation.com/