Legacy Builders: Strategies for Building Successful Family Enterprises

In this special panel episode of Legacy Builders, Cory Gagnon is joined by Barb Schimnowsky and James Grieve for a focused conversation on how family enterprises can prepare for next-generation leadership. Drawing from their work in executive search, governance, succession planning, strategy, and family enterprise advising, Barb and James examine what leadership readiness looks like beyond age, title, or family position. They discuss how governance can clarify roles and decision-making, why succession conversations are often delayed, and what families can do before the transition becomes urgent.

In this episode, we’re joined by Keita Demming, Partner at The Covenant Group, award-winning author of Strategy to Action, and trusted advisor in strategy, design, and innovation. We explore how strategy becomes a lived practice through intentional behavior, personal development, and the quality of our conversations. Keita shares his approach to coaching leaders through conflict avoidance, curating effective inner circles, and aligning day-to-day actions with long-term vision. He introduces a powerful shift in thinking from chasing outcomes to asking better questions and what it means to lead with clarity and courage.

In this episode, we’re joined by Andrea Lekushoff, founder and CEO of CONTEXT Studios, where personal stories become powerful tools for connection, continuity, and leadership. We talk about the invisible value of lived experience, how one person’s reflections can clarify identity, honor legacy, and even shape culture across generations. What does it mean to “be seen” by the people who come after you? How do stories become more than memories, and why is capturing them now, not later, a strategic decision?

In this episode, Dr. Dennis T. Jaffe, Senior Research Fellow at BanyanGlobal Family Business Advisors, joins us to explore how family enterprises can evolve with intention across generations. A globally recognised adviser, educator, and author of Wealth 3.0 and Borrowed from Your Grandchildren, Dennis brings decades of insight into how families build shared purpose, navigate complexity, and sustain legacies that matter.

In this episode, Shauna Trainor, Principal at A&O Partners, invites us into the often overlooked spaces where clarity, courage, and connection shape the future of enterprising families. Drawing from her background in business, psychology, and systems thinking, Shauna helps us reframe how family conversations become the foundation for shared decision-making across generations.

In this episode of Legacy Builders, we welcome Krista Rabidoux, Partner at Andersen in Canada, for a thoughtful conversation on leadership transition, generational readiness, and the emotional complexity of family enterprise. With over two decades of experience in U.S.-Canada cross-border tax planning and deep involvement in the family enterprise space, Krista shares how clarity, adaptability, and inclusive governance can help families move forward, especially when navigating uncertainty or change.

In this episode, we welcome Kristen Heaney, Founder & Coach of In Three Generations, LLC, a trusted coach to financially successful families, and an authentic voice in the wealth management space. Known for her unique perspective as an "unprepared inheritor in recovery," Kristen brings a deep understanding of family wealth challenges, bridging the gap between gratitude and burden while helping families navigate the complexities of wealth preservation and transition. Together, we explore what it takes to honour legacy while fostering individual expression, touching on unconscious behaviors, stewardship responsibilities, and what it means to redefine success across generations in wealth, family, and life.