Legacy Builders: Strategies for Building Successful Family Enterprises

Cultivating Resilience: From Resistance to Openness


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In this episode, Judi Cunningham shares insights on building resilience when faced with adversity during strategic planning for family enterprises. We explore the importance of facilitating open and curious dialogue to understand differing perspectives, giving family members agency in conversations, and assessing what's truly important to make clearer decisions.

Hear Judi's perspective on transforming unproductive communication into a constructive discussion over time, establishing clear family versus business roles to reduce confusion, and implementing information-sharing protocols as more households take ownership. She offers examples of leaning on wider communities or specialists like her Trella Advisory Group when alignment remains elusive internally.

Throughout our discussion, Judi offers insightful takeaways to put into action - make room for open dialogue even when uncomfortable, clearly delineate family versus business roles, implement structures around information flow and decisions as ownership broadens, and don't hesitate to access outside help when stuck.

About Judi Cunningham

Judi Cunningham is the founder of 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.

Resources discussed in this episode:

  • https://purposefulplanninginstitute.com/

Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.

  • Website: BeaconFamilyOffice.com
  • LinkedIn: Cory Gagnon
  • LinkedIn: Beacon Family Office
  • Email: [email protected]

Contact Judi Cunningham | Family Enterprise Consultant and Educator: 

  • Website: trella.ca
  • Twitter: @TrellaGroup
  • LinkedIn: Judi Cunningham
  • Phone: (604) 360-1516
  • Email: [email protected]

We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises.

Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.

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Legacy Builders: Strategies for Building Successful Family EnterprisesBy Cory Gagnon