Let's Talk Family Enterprise

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 [: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. If you enjoyed today's episode, you can subscribe to Let's Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues. Share your thoughts with us at [email protected]. Mentioned in this episode Raising Resilient Children — The Atlantic, Newsletter by Russel Shaw I teach children of the super-rich how to discover their purpose, by Jessica McGawley More about Family Enterprise Canada Family Enterprise Canada FEC on Facebook FEC on Twitter FEC on LinkedIn

Host Aileen Miziolek speaks with Andrew Keyt, founder of Generation6 and a business strategist and succession planning expert with more than 25 years of experience working with family enterprises. Andrew previously led the Loyola University Chicago Family Business Center and the Family Business Network – United States, and is the author of Myths and Mortals: Family Business Leadership and Succession Planning. The conversation explores why families often reach for more governance and structure when conflict resurfaces, even when the underlying issue may be an unaddressed mental health challenge such as depression, anxiety, or substance use. Andrew explains how individual struggles can ripple through the entire family system, why privacy and stigma can leave families feeling isolated, and how to balance compassion with accountability when someone needs help. He also shares practical starting points: leading with curiosity rather than diagnosis, building a "protection team" of trusted truth-tellers, and treating emotional openness as a skill families can practice rather than a one-time fix. This episode offers a candid, research-grounded look at why emotional health belongs at the centre of family enterprise resilience, and how families can begin talking about what is often the hardest topic to raise. Hear more from Andrew on this topic at the Families Summit of Minds (FSOM) 2026, November 20–22 in Banff, Alberta. 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 Andrew Keyt, MFT, MBA, is an internationally known business strategist and succession planning expert for family-owned businesses. He has established a global reputation for advising large family enterprises, resolving family conflict, and restoring communication. His family business insights were featured in The Wall Street Journal, Chicago Tribune, Los Angeles Times, Fortune Magazine, The Economist, and Family Business Magazine. Before founding Generation6, Andrew was President and Founder of Keyt Consulting, assisting family enterprises with succession and strategic planning, dealing with family conflict and communication, and executing emergency management transitions. He has worked extensively with some of the largest enterprising families in the United States. You can learn more about Andrew Keyt on LinkedIn, the Generation6 website, and on AndrewKeyt.com. Key Takeaways [:22] Aileen Miziolek welcomes Andrew Keyt and launches this episode by asking him how he came to focus his work on the intersection of mental health and family enterprise. [4:13] How the COVID pandemic underscored the importance of mental health challenges in family enterprise dynamics. [5:42] Leaning on structure can be misleading when tackling emotional problems; Andrew explains the pathways to building a safer environment. [7:56] Andrew offers some tips on how to open the door to a safer environment and healthier patterns for family systems. He also highlights early pitfalls to watch for. [10:09] A family impacts each other every day; making sure we care for the well-being of every member of the family is critical in ensuring the system remains healthy. [12:40] Andrew explains that there are many paths to holding people accountable for their behavior and touches on the importance of boundaries while leading with love and compassion. [14:20] Coping with all the change starts with understanding the situation and building the proper support structure for the situation. [15:57] Andrew explains where privacy concerns stem from and how to counter them. All breakthroughs come from some measure of vulnerability. [19:58] The skills to create safer environments begin with emotional regulation and consistency. Andrew explains how this practice is honed and why this practice is critical. [22:33] Unity and cohesion are what sustain families across generations. Andrew breaks down the paradox between individual and collective. [26:01] Mental health issues that stay unaddressed generally get worse, and when it comes to enterprising families, the health of the system can directly affect the health of the business. [28:13] Looking out for changes in behavior can help speed up the identification of possible problems, [30:07] Where can families start? [32:16] Andrew touches on the nature of the process when multiple support resources are available. [34:04] Andrew offers the one thing he believes every advisor should add to their practice. [35:05] The couples that stay together have common characteristics that can be cultivated by families. [38:12] Andrew shares some resources. [40:06] Aileen thanks Andrew Keyt for sharing so much of his expertise and invites listeners to subscribe. If you enjoyed today's episode, you can subscribe to Let's Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues. Share your thoughts with us at [email protected]. Mentioned in this episode FAMILIES SUMMIT OF MINDS 2026, November 20-22, 2026 in Banff, Alberta From Stigma to Strength: Cultivating Mental Health for a Thriving Family Business, by Andrew Keyt "FROM SILENCE TO STRENGTH: Mental Health in Family Business" More about Family Enterprise Canada Family Enterprise Canada FEC on Facebook FEC on Twitter FEC on LinkedIn

Host Steve Legler speaks with father-son duo Grant and Owen Cockshott, President/CEO and Product & Marketing Manager of Innovair, a third-generation, Winnipeg-based supplier of industrial gases and equipment, and the most recent winner of FEC's Family Enterprise of the Year Award. Grant and Owen open up about accepting the award on stage together, and what the experience of Symposium looked like from a first-timer's perspective versus someone who attended peer advisory groups decades earlier. The conversation traces the business's evolution across four generations, from Grant's entrepreneurial grandfather to his engineer father to the sibling partnership that shaped Grant's own leadership style, and now to Owen's arrival with a marketing background and fresh instincts for social media and e-commerce. They speak candidly about working with family enterprise advisors on both governance and structure, the value and limits of requiring outside work experience before joining the business, and how Owen built a standalone e-commerce venture from a Harvard case study, turning it into a genuine business within a business. The episode closes with father and son each offering advice to the next generation stepping into family enterprise. This episode offers a grounded, multigenerational perspective for family businesses navigating succession, new ideas, and the balance between honoring legacy and continuing to reinvent. 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 Grant Cockshott is President and owner of the Innovair Group, a third-generation family business with its head office located in Winnipeg. The family business was started in 1946 by Grant's grandfather and has just over 100 employees between Ontario and Saskatchewan. Grant is a graduate of the University of Manitoba (BCom, Hons.), and has attended Harvard Business School's annual Executive Education program through YPO (Young Presidents' Organization) for the last 8 years. Grant has a background in the Balanced Scorecard strategic planning process, Innovation Engineering, and Continuous Improvement. You can learn more about Grant Cockshott on Innovair Group's website and on LinkedIn. Owen Cockshott is Product and Marketing Manager at Innovair Group, a family-owned Canadian supplier of industrial and medical gases, equipment, and related technologies. He holds a Bachelor of Management in Entrepreneurship and Innovation from Dalhousie University and completed an MBA at Queen's University in 2025. As a fourth-generation member of the Cockshott family enterprise, Owen contributes to the continued development of a company whose roots date back to a Winnipeg acetylene distributor founded in 1946. You can learn more about Owen Cockshott on Innovair Group's website and on LinkedIn. Key Takeaways [:22] Steve Legler welcomes two special guests — family enterprise leaders of Innovair Group: Grant Cockshot, CEO, and Owen Cockshot, Product and Marketing Manager, and asks them about their experience winning the Family Enterprise of the Year award at the 2026 Family Enterprise Symposium in Vancouver. [2:53] Owen shares his first experience at Symposium and offers a few key takeaways for young family leaders. [4:40] Attending Symposium requires a bit of preparation; Grant shares how he and Owen chose to tackle the event to maximize their visit. [5:59] Grant shares how he and his brother joined peer advisory groups in the early 90s and found those experiences extremely formative. [7:19] Owen shares his own experience joining a PAG in what seems to be a rebirth of that kind of offering. [8:26] Owen and Grant take turns talking about the work they have been doing with their own family advisors. [12:13] Grant offers that while structure may be one of the more important aspects of working with an FEA, governance is far more critical in maintaining an enterprise over time. [14:43] From generation 1 to 3 and beyond, Grant shares his experience. [18:09] Working outside the business doesn't need to be a hard rule, but it does have some serious benefits. Owen shares his own recent experience. [21:04] Working outside the business offers you an opportunity to see what you want to add to your own enterprise, but also what you don't. [23:45] Becoming an intrapreneurial organization requires listening to the youth! Grant shares how he likes watching Owen launch businesses within businesses. [26:17] Owen shares his advice on making your own path as a young family enterprise leader. [28:44] Grant shares his piece of advice for an enterprising parent! [29:57] Owen shares his piece of advice for young family enterprise members about to join. [30:47] Steve thanks Grant and Owen Cockshott for sharing their experience and invites listeners to subscribe. If you enjoyed today's episode, you can subscribe to Let's Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues. Share your thoughts with us at [email protected]. Mentioned in this episode Innovair Group Dear Younger Me: Wisdom for Family Enterprise Successors, by David Bentall FEC podcast episode: "Dear Younger Me with David Bentall", August 17, 2021 More about Family Enterprise Canada Family Enterprise Canada FEC on Facebook FEC on Twitter FEC on LinkedIn

Host Aileen Miziolek speaks with Managing Director of The McQuaig Institute, Venessa Vasilakeris. Together, they talk about how using assessments in leadership development can be transformative inside a family business. In family systems where trust, perceived favouritism, and emotional history can distort even the most straightforward decisions, objectivity is not a luxury — it's a leadership necessity. Aileen and Venessa unpack how assessments create a shared, neutral reference point that depersonalizes tension and reframes differences as strengths rather than flaws. The conversation moves from personality and competency tools to 360 feedback, benchmarking, and leadership development, exploring not just what assessments measure, but what conditions need to be in place for them to actually work. They're candid about where assessments go wrong: the fear of being pigeonholed, the danger of running a 360 process before a team has the psychological safety to hold it, and the all-too-common pattern of a great debrief followed by nothing. What emerges is a clear argument that implementation matters more than the tool itself, and that the families who get the most value are the ones who keep the conversation alive long after the results come in. For business-owning families and the advisors who work with them, this episode is a practical and thought-provoking look at how awareness becomes the lever for lasting leadership growth. 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 Venessa Vasilakeris is a dynamic leader with over a decade of experience helping hiring managers and HR professionals build, grow, and develop individuals and teams. As Managing Director at McQuaig, she combines deep expertise in recruitment and talent management with a passion for innovation. Venessa has led the development of tools that empower organizations to make better people decisions, enhance productivity, and foster stronger human connections. Venessa holds a BA from McMaster University and is certified in The McQuaig System. Outside of work, she's an avid learner, passionate traveler, and devoted dog mom to Douglas. You can learn more about Venessa Vasilakeris on LinkedIn. Key Takeaways [:22] Aileen Miziolek opens the episode with an observation about leadership in family enterprise and introduces Venessa Vasilakeris, Managing Director at the McQuaig Institute. [1:08] Venessa shares what services McQuaig offers in the context of leadership within family business. [2:55] The core differences between corporate and family enterprise when it comes to talent management. [4:57] Venessa explains how the vast array of assessments can make it difficult to choose the right tool. She shares some tips to ensure you use the one tailored to your needs. [6:15] The power of personality. [7:47] Unlike personality, competency can be developed and nurtured. Vanessa speaks to the synergies that can arise between personality and the great 8 leadership competencies and shares the functioning of the Competency 360 assessment. [11:36] Venessa weighs in on the importance of transparency when it comes to assessment. In order to avoid conflict, some conditions must be met to remain outside of personal dynamics. [14:35] Correcting the fear of pigeon-holing with assessments. [18:39] When it comes to succession, keep in mind the number one thing successful leaders have in common, regardless of style! [20:00] Venessa shares prime examples of the opposing siblings phenomenon. [22:22] From relative pet peeve to super power. [24:06] What does it look like when the assessment results are embedded into how the company functions? [26:34] Venessa explains benchmarking through the lens of recruitment and development. [29:53] How can families get started with assessments, what should they look at, and what do they need to prepare for? [33:49] Aileen thanks Venessa for sharing so much of her expertise and invites listeners to subscribe. If you enjoyed today's episode, you can subscribe to Let's Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues. Share your thoughts with us at [email protected]. Mentioned in this episode For more resources on assessments, visit McQuaig.com — A proud family-owned Canadian business. More about Family Enterprise Canada Family Enterprise Canada FEC on Facebook FEC on Twitter FEC on LinkedIn

Host Steve Legler speaks with Susan St. Amand, President and CEO of the James A. Burton and Family Foundation, about the upcoming release of the 'Burton Report' on Canadian Family Business. Their conversation explores the vital role family enterprises play in Canada's economy and communities, the challenges surrounding succession and public policy, and the importance of stronger collaboration between enterprising families and government. 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 Susan St. Amand is President and CEO of the James A. Burton & Family Foundation and Founder of The Sirius Group Inc., based in Ottawa. With more than 30 years of experience advising enterprising families, she is a trusted authority on family enterprise governance, continuity planning, and strategic philanthropy. She is the immediate Past Chair of Family Enterprise Canada (FEC). She has chaired more than six boards while serving on over two dozen others, including the Ottawa Community Foundation, the Ottawa International Airport Authority, the Royal Ottawa Foundation for Mental Health, CALU, the Institute of Corporate Directors Ottawa Chapter, and a privately held steel company. Susan is also a founding member of the Women for Mental Health campaign at the Royal Ottawa Centre for Mental Health. You can learn more about Susan St. Amand on LinkedIn and on the James A. Burton Foundation website. Key Takeaways [1:20] Steve Legler introduces Susan St. Amand, President and CEO of the James A. Burton and Family Foundation. He launches the episode by introducing the Burton Report on Canadian Family Business to the audience. [2:53] The Burton Report was a long time in the making, Susan explains its genesis, construction, and purpose to support and maintain Canadian enterprises. [5:28] Family enterprises seed, water, nourish, and grow more entrepreneurs, a necessity in today's economically shifting world. [6:56] Susan touches on the importance of family enterprise in the changing demographic structure of Canada. [8:11] Proper data and information are needed for the government to support family businesses effectively. [10:02] Susan discusses the current information gaps and how to palliate them both on the business and the government sides. [14:14] Transitions can be scary, but family enterprises think multi-generationally, and as such, provide stability through time. Advisors are critical in creating that long-term vision. [19:00] Susan shares her thoughts on the role advisors may have in the sale of family enterprises outside of the family or even internationally. [23:06] Succession planning currently marries poorly with the Canadian Income Tax Act. Susan offers a perspective on overcoming this. [26:00] Susan shares a vision for family enterprises and their relationship with the government of Canada. [28:21] Susan explains how the James A. Burton Family Foundation plans to support family enterprises for the economic future of Canada. [29:47] Susan offers some of the results that enterprising families would be looking for in an amelioration of their relationship with the government. [32:05] The importance of family enterprises in our very own communities. [32:48] Susan shares her reading recommendation and a piece of advice for advisors. [34:36] Steve thanks Susan for sharing some preliminary information on the Burton Report and invites listeners to sign up for Symposium, which will be held May 25‒27 in Vancouver, BC. If you enjoyed today's episode, you can subscribe to Let's Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues. Share your thoughts with us at [email protected]. Mentioned in this episode www.ppi.ca James A. Burton Family Foundation Symposium 2026 The History of Money: A Story of Humanity, by David McWilliams More about Family Enterprise Canada Family Enterprise Canada FEC on Facebook FEC on Twitter FEC on LinkedIn