Courageous Conversations: Saying What Needs to Be Said in Family Business
Some of the hardest parts of leadership aren’t about strategy or business knowledge—they’re about people. Whether you’re a family member or a non-family member working in a family business, navigating relationships can make courageous conversations complicated. How do you say no without feeling guilty? Address the “elephant in the room” without damaging a relationship? Advocate for yourself while maintaining important relationships? Ask for help? Set boundaries and still be seen as committed and capable?
And with Thanksgiving just around the corner, those family dynamics may soon follow us from the conference room to the dinner table!
We’ll explore Radical Candor, a simple and practical framework for having honest conversations while still showing that you care. We’ll talk about why women, and especially women working alongside family, can sometimes find these conversations particularly complicated, and how greater clarity can strengthen relationships rather than threaten them.
We’ll tackle real-life leadership challenges around boundaries, difficult conversations, self-advocacy, and protecting our time and energy. Bring a situation you’re wrestling with if you have one or simply come ready to learn from the experiences and wisdom of other women who understand the unique dynamics of family business.
Come ready for honest conversation, practical tools, shared wisdom—and perhaps a few strategies you can put to work before Thanksgiving dinner!
This roundtable is facilitated by Donna Musilli of DM360. With more than 35 years of leadership and coaching experience, Donna brings a rich background in partnering with family-owned businesses to strengthen leaders, support next-generation transitions, and build healthy workplace cultures.
All women from Conway Center member companies - family, non-family, and service provider members - are welcome and encouraged to attend these quarterly roundtables.

