Roots, Wings, and Responsibility: Developing the Judgment to Carry Family Decisions Forward

In this episode, Cory Gagnon is joined by Judi Cunningham and Tom McCullough for a timely conversation on how families can make better decisions together. From estate plans to ownership transitions, it’s rarely the decisions themselves that hold families back; it’s the buildup around them. Roles are unclear. Assumptions go unspoken. And sometimes, one voice dominates when collaboration is what’s really needed. Judi and Tom share what gets in the way, and more importantly, how families can start moving forward with clarity, confidence, and trust. Pulling from years of experience in family systems, governance, and family office strategy, they offer practical tools for navigating complexity without losing momentum. Whether it’s building development plans for the next generation, turning good intentions into written agreements, or understanding who actually gets to decide what, this session is packed with insight. If your family is working through a transition or trying to avoid the next standstill, this conversation will help you create more alignment without overcomplicating the process. About Tom McCullough  Tom McCullough is Partner at Corient and Managing Director at The Ultra High Net-worth Institute, the leading Canadian multi-family office. He has spent over 35 years in the wealth management/family office field. Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask and Family Wealth Management: 7 Imperatives for Successful Investing in the New World Order. He is an Adjunct Professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management MBA program. He is an Entrepreneur-in-Residence at Western University’s Ivey School of Business and a member of the Editorial Board of the Journal of Wealth Management. He was recently awarded ‘Best Individual Contribution to Thought Leadership in the Wealth Management Industry’ by the 2020 Family Wealth Report Awards. Contact Tom McCullough | Corient Website: corient.com LinkedIn: Tom McCullough Email: [email protected] About Judi Cunningham Judi Cunningham is the Founder and Senior Consultant at Trella Advisory Group, a consulting firm that works with family enterprises and families of wealth. With a Master’s in Family Systems Counseling and over 25 years of experience, she excels in navigating complex family dynamics and business challenges. Judi’s strategic insight and facilitation skills help families find alignment and address tough decisions. Judi is known for her innovative educational initiatives. She pioneered the Family Enterprise Advisor Program, establishing global standards for professional advisors. In addition to her for-profit work, Judi volunteers her time to support multi-generational family success. She serves as the Chair of the Board for the Purposeful Planning Institute, which helps advisors serve families of wealth and families in business. Contact Judi Cunningham | Trella Advisory Group Website: trella.ca LinkedIn: Judi Cunningham Twitter: TrellaAdvisoryGroup Email: [email protected] Phone: (604) 360-1516 Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd. Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: [email protected] Resources discussed in this episode Innerwealth RACI Model Wealth of Wisdom Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.