Episode 335: Steve Legler on 100 1-minute conversations
Oct 6, 2026
Host Steve Legler is joined by Jessica McGawley, founder of Dallington, a boutique London firm supporting families with the developmental and relational sides of significant wealth. For the past decade, Jessica and her team have worked exclusively with teens and 20-somethings in enterprising families, a generation often left out of conversations that will shape their futures.
Drawing on her recent Financial Times article, Jessica explores why well-meaning wealth managers, lawyers and trustees can sometimes cross professional boundaries with younger family members, and why an advisor who has served the parents for decades may not be a neutral presence in a child’s life.
Jessica and Steve also discuss confidentiality and cultural expectations, preparing young people for public attitudes toward wealth, and how her Rising Gen program helps siblings and cousins explore the different paths their family enterprise might take and what each could mean for their relationships and responsibilities.
Jessica closes with a reading recommendation for parents and advisors, and a reminder that exceptional business leaders and wealth creators may need more support as parents than we sometimes assume.
Recommendation: Atlantic publication, Russell Shaw https://www.theatlantic.com/newsletters/2026/08/how-raise-resilient-children/688449/
All views, information, and opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of Family Enterprise Canada.
Guest bio
Jessica McGawley founded Dallington in 2016 after many years working with families and family offices around the globe. She trained in Psychodynamic and Systemic Consulting at the Tavistock and Portman NHS Foundation Trust and is also an accredited mediator. Her work applies systems-psychodynamic and systemic thinking to the specific challenges faced by the rising generation of families of wealth and family enterprises.
Jessica works with rising-generation members from UHNW families to step into adulthood with confidence, purpose, and healthier family dynamics. She works alongside private client advisors, wealth managers, trustees, and family office teams to deepen conversations around family dynamics, communication, and rising-generation readiness through consulting, co-facilitation, training, and bespoke advisory offsites.
You can learn more about Jessica McGawley on her website, Dallington’s website, and on LinkedIn.
Key Takeaways
Key Takeaways
[:22] Steve Legler welcomes Jessica McGawley, founder and Principal Consultant at Dallington, and asks her to explain what her work with rising generations primarily focuses on.
[1:54] Defining rising generations can mean a wide bracket of ages, and Jessica chooses to focus on late adolescence and early adulthood.
[2:39] Jessica shares the moment in her career that led to her interest in that specific subset of enterprising families.
[3:42] Including teens and young adults in conversations that will directly affect them in the near future is exposing them to learning and growth opportunities.
[4:38] Jessica touches on the intellectual malleability of those formative years and how important they are in terms of building skills and knowledge.
[5:40] How receptive are UHNW parents to including their kids?
[6:49] Collaboration and proximity are increasingly popular, but they come with pitfalls; Jessica details potential problems, especially for teens and young adults.
[9:47] Jessica touches on whose responsibility it is to maintain professional boundaries and how to measure the proper level of personal relationship that is appropriate as an advisor.
[11:16] While collaboration is important, Jessica underscores the critical importance of staying within one’s specialty when it comes to advising.
[13:05] Why neutrality can save relationships.
[14:41] Establishing parameters with the rising generation around confidentiality can save you from some complex situations in the future.
[15:42] Some cultures view confidentiality differently; Jessica shares an experience and the life moments where cultural clashes are more likely to arise.
[18:25] Jessica shares how she prepares the rising generation to face the demonizing. She also touches on a personal negative experience with the media.
[23:00] There is a fine line between letting knowledge of a family system inform your decision-making as an advisor and letting it lead your advisory work.
[24:28] Jessica shares moments when her advisory work surprised her clients.
[27:25] The inheriting of relationships is an important step to manage.
[29:01] Jessica shares her book recommendation as well as her advice for advisors.
[30:58] Steve thanks Jessica McGawley for sharing so much of her expertise and invites listeners to subscribe.
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