Succession Planning Roundtable

Talking Across the Generations: Having the Difficult Conversations That Keep a Family Business Moving

In a family business, the hardest conversations aren't usually about the business at all. They're about what's left unsaid - between a founder who isn't ready to let go and a next gen that's afraid to ask. They are about retirement, roles, in-laws, siblings who work in the business and siblings who don't. When those conversations are avoided year after year, they don't disappear. They come back as tension, confusion, and decisions made by default instead of by design.

Bea Wolper of EWJJ Law and Meredith Sugar of Taft/ will lead a practical, honest discussion about why talking across generations is so hard, what each generation is really trying to say (and often isn't), and how families can create conditions for conversations that strengthen the business and the relationships behind it.

We'll dig into topics such as:

Why some conversations never happen
Why topics like stepping back, mortality, and control feel so loaded in family business, and why silence feels safer in the moment but costs far more over time.

What each generation actually hears
Why the same words land differently coming from your dad or daughter, how old patterns shape today's conversations, and how to listen to the message instead of reacting to the person delivering it.

Setting the stage for a productive conversation
How timing, location, and preparation change the outcome, why talking isn't the same as deciding, and when it helps to bring in a neutral facilitator.

Building a rhythm for family communication
Moving from one-off, reactive conversations to regular family meetings where expectations get aired before they become problems, including how to include family members who don't work in the business.

Whether you're the current generation trying to start the conversation or the next gen trying to be heard, this roundtable is built for honest exchange. Come listen, share if you'd like, and take home ideas from other families you can use in your own conversations.