In every family enterprise, there comes a moment when a rising-gen leader needs more than advice, they need a place to think. The most powerful mentoring relationships involve thoughtful conversations where a rising leader can think out loud, test ideas, and explore the internal conflicts that shape their decisions. In my experience, what rising-gen leaders want most is a place to strengthen their own judgment. Someone who listens closely, helps them see patterns, and encoura

From a trustee’s vantage point, many succession risks don’t start with documents or structures. They start earlier when beneficiaries haven’t had a protected place to develop judgment, self-regulation, and relational capacity. When that development is delayed, trustees inherit downstream issues that look like leadership or governance problems. Preventive mentoring works upstream. It strengthens decision-making before authority, control, or roles are on the table. Used well, i

I’m grateful to the editors at  FamilyBusiness.Org  for publishing my new article on how leadership readiness develops across generations in enterprising families. In conversations with founders and senior leaders, I often hear a quiet tension: a desire to prepare the next generation for greater responsibility while also protecting the principles and decisions that built the enterprise.  On the other side, rising leaders often want to contribute more, but aren’t always sure h

That was the central question  Doug Baumoel  and I explored at the  The Family Firm Institute - FFI  Global Conference in Boston in October. Entrepreneurs build extraordinary enterprises through clarity, conviction, and individual drive. Yet as family enterprises mature, the developmental task shifts: From one leader to many stewards From singular vision to collective capability From “I know the way” to “we can find the way together” This transition isn’t automatic. It’s a le

I recently joined  Cory Gagnon  on the Legacy Builders Podcast for a rich conversation about how families can build decision-making...