Practice Makes Stewards: How Families Develop Decision-Makers Across Generations

In this session, Cory Gagnon is joined by Doug Gray and Torri Hawley for a thoughtful conversation on how families develop stronger decision-makers across generations. While many families assume readiness will emerge over time, this discussion makes the case for something more intentional. Exposure alone is not the same as preparation. Real development takes practice, feedback, and the kind of learning environment that allows rising generation leaders to build confidence before pressure arrives. Together, they explore what often gets mistaken for readiness, why fear shows up on all sides of the transition process, and how families can create more space for growth before responsibility becomes urgent.

Drawing from experience in executive coaching, adult learning, succession, and family enterprise development, the conversation offers practical insight into how capability is built over time. Doug and Torri unpack the importance of structured practice, safe failure, feedback, and intentional learning design in preparing future leaders for real responsibility. They also explore how families can move beyond assumptions, create more productive communication, and recognize that readiness is not only about the next generation, but about the whole system being prepared to support transition well. 

About Doug Gray

Doug Gray is the founder and CEO of Action Learning Associates LLC and co-founder of AssessNextGen LLC. He is a leadership consultant and executive coach who specializes in succession and next-generation development with family enterprises. Through his 360 assessment work and peer development groups, Doug helps rising leaders strengthen communication, decision-making, and feedback skills before transition pressure escalates.

Contact Doug Gray | Action Learning Associates, LLC

Website: Action-Learning.com | AssessNextGen.com | AI4Advisors.co
LinkedIn: Doug Gray
Email: doug@action-learning.com

About Torri Hawley

Torri Hawley is the chief learning officer at Tamron Learning, where she leads learning strategy and designs wealth education experiences for enterprising families and their advisors. She focuses on building confidence and stewardship capacity through intentional, adult-centered learning design, helping families approach learning as a long-term succession strategy. Throughout this conversation, Tori brings a practical perspective on how structured learning, safe practice, and clear purpose can help the rising generation of family members prepare for meaningful responsibility over time.

Contact Torri Hawley | Tamarind Learning

Website: tamarindlearning.com
LinkedIn: Torri Hawley
Email: thawley@windway.com

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

Website: BeaconFamilyOffice.com

LinkedIn: Cory Gagnon

LinkedIn: Beacon Family Office

Email: beaconfamilyoffice@assante.com

Resources discussed in this episode

AssessNextGen
RACI Structure

DISCLAIMER

This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor at Beacon Family Office at CI Assante Wealth Management Ltd. This is not an official program of CI Assante Wealth Management Ltd., and the statements and opinions expressed during this webcast do not necessarily those of CI Assante Wealth Management Ltd. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact me at (403) 232 – 8378 or visit beaconfamilyoffice.com to discuss your particular circumstances prior to acting on the information presented.