Finding Your Fit: Designing Custom Roles Across Generations

In our latest episode, Bill Brushett, Advisor, Director, and TEC Canada Chair, shares his insights on intentional leadership development and succession planning in family enterprises. With over 40 years of experience spanning roles from President & CEO of Family Enterprise Canada to National Clients & Services Partner at Grant Thornton LLP, Bill brings a powerful combination of financial acumen and executive wisdom to help families navigate generational transitions and strategic growth.

Throughout the conversation, Bill illuminates the interplay between emotional connection and strategic foresight in family business success. He explores compelling perspectives on mentorship and peer learning while offering practical guidance for developing next-generation leaders. His framework for creating meaningful transitions emphasizes the importance of intentional design and external influence, providing valuable insights for families seeking to build lasting legacies that honor both individual aspirations and collective purpose.

About Bill Brushett

Bill Brushett is a highly accomplished leader, advisor, and mentor with over 40 years of experience in financial management, executive leadership, and governance. Currently working closely with family enterprise boards, he offers strategic guidance on governance, leadership transitions, and sustainable growth. As a TEC Canada Chair, he mentors emerging executives and business leaders, creating transformative growth opportunities. His previous role as President & CEO of Family Enterprise Canada saw him championing family-owned businesses, helping them navigate succession planning, governance, and wealth stewardship. During his distinguished career at Grant Thornton LLP, he rose to become National Clients & Services Partner, providing oversight for multiple service lines and steering client strategies.

A Chartered Professional Accountant with ICD.D and FEA certifications, Bill’s credentials reflect his commitment to excellence and diverse expertise. He holds a Bachelor of Commerce from Memorial University and is a Fellow of the Institute of Chartered Accountants of Newfoundland & Labrador. His community engagement includes contributions to the Arthritis Society, St. John’s Board of Trade, and Memorial University’s School of Business Advisory Board. Beyond his professional life, Bill is a dedicated family man who values time with his wife, children, and grandchildren, and continues to empower leaders, strengthen businesses, and foster meaningful legacies through his various roles and initiatives.

Resources discussed in this episode:

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

Contact Bill Brushett | TEC Canada Chair: 

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at Assante Financial Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. And on this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.

Today, we welcome Bill Brushett, a distinguished Advisor, Director, and TEC Canada Chair who brings over 40 years of expertise in financial management and executive leadership. Previously serving as President & CEO of Family Enterprise Canada and National Clients & Services Partner at Grant Thornton LLP, Bill now guides family enterprise boards while mentoring emerging executives as a TEC Canada Chair. His expertise as a CPA, ICD.D, and Family Enterprise Advisor specializes in governance, succession planning, and wealth stewardship, empowering leaders to build lasting legacies across generations.

My goal is to be the most curious person in today’s conversation with Bill Brushett, as we explore how intentional design, emotional connection, and external influence shape the success of family enterprises. We’ll delve into his rich insights as a TEC Canada Chair and trusted advisor on the intersections of mentorship, peer learning, and purposeful succession planning. Together, we’ll uncover Bill’s perspectives on developing next-generation leaders, creating meaningful transitions beyond retirement, and building the right chemistry in peer advisory groups.

Now, let’s dive in! 

Cory:  Well, welcome, Bill. We’re excited to have you here today to share your wealth of knowledge and experiences with us! Let’s dive in, shall we?

Bill: Yes. I’m ready to go. Thank you for having me. I’m looking forward to this!

Cory: Now, Bill, imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story.

 How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Bill: That’s a really good way to start. It certainly makes you reflect a lot yourself, Cory. And and so really there’s key messages, maybe two or three key messages that sort of inform my whole career. It’s not just one event, and maybe I’ll just share that.

The first thing I’d start out with, which, to me, is so important. It’s really whatever you decide to do. You know, you’ve got your future ahead of you. It’s yours to design and to sort of live. And so whatever you decide, whatever path you decide to choose, it’s really important that you be intentional. Be purposeful about what you’re doing. You know, lots of younger people in particular will start out on a career and they’ll be happy in a job and they’ll wait for the next promotion or something. But you can’t be like that. Don’t leave it to chance or to fate. That’s not going to work out in your favor in the long term. And luck, some people say, I was lucky. And, yeah, you might have been in the right place at the right time for certain things. And luck may be a part of your journey. But what you have control of is what you do. And so be intentional, be purposeful. and think a little bit longer term.

In my own case, I started out, very young professional, and I decided I wanted to be a partner by the time I was 30. It’s a pretty linear path in a professional services firm, but of course, it’s all about performance. I was really focused on hitting that goal. So that was really important to me, and I was successful at that. So that was really about being intentional about where you want to get to.

The thing you got to remember is, hope is not a strategy. You can’t hope for your future. You have to really plan for it. But I’d also caution about overplanning. Don’t be so specific. It’s like, where do I want to go? What does this journey look like? To me, that was the most important from early in my career to even now with the things I’m doing now, just being intentional and purposeful about what I’m doing, why I’m doing it. Find your “why.”

The second thing that I have learned, which was tough for me in a way because I was trained as a professional CPA. And, you know, it’s very technical and so on. But I would say first and foremost, focus on people. I don’t care who you are in life, how successful you are. You’re a successful business owner, successful CEO, and so on. Strategy and the technical side of things are only going to take you so far. You need good people. You also don’t know everything there is to know. And you don’t know what you don’t know. So you need to have great people around you in order for you to be successful.

Just think of any great successful business owner or CEO today. They didn’t do it alone. They had a great team. They had other people maybe outside the organization that were helping them, mentoring them. It’s really important to really find great people.

It reminds me of something I learned a long time ago. It’s a bit of a quirky maybe, sort of way to define leadership. And leadership to me is about making yourself redundant. First you find great people. Hopefully they share your values and so on. You instill some sense of vision and purpose, create that shared vision for the future of your organization, provide them with all the support they need. You need to be their champion. And then just get out of their way. Find great people and get out of their way. That’s a recipe for success, I find. Have I got time for one more?

Cory: Absolutely.

Bill: One more thing which was really beneficial to me over my whole career. And it’s not just in your career. This will serve you well in all your relationships. And it’s a little bit specific. But to me, it’s really important. And it’s about sort of our behavior, and particularly how we interact with others, and how we respond to others and to events and so on. And I learned this about 15, 20 years ago.

I was at a conference, and there’s a little formula. It’s ‘E’ times ‘R’ equals ‘O’. E stands for events, things that happen to you. R is your reaction or your response. And O is the outcome.

So, imagine you’re in a situation, put it in the context of a family business, you know, you’re challenged by a sibling about your vision for the future or something and so on can be really emotionally charged. And how you react to that is going to determine the outcome. Are you going to react negatively to that person who just said something negatively to you about your vision? And what’s the outcome of that likely to be? The thing to do in a situation like this is to reframe that R.

So, the difference between reaction and response. Don’t react to events and things and issues, respond to them. And the differences in not being, just spur the moment, what’s on the top of your head, our brains are all wired to do that. Take time to reflect, and think of it in the context of what outcome I want from this relationship, from this event, from this opportunity I have in front of me. And so my response needs to be, reflect, exactly the outcome I want.

So those are the things that I’ve learned that have really been, as I reflect, have been important in my career. So I’d like to pass that along to the graduating class.

Cory: Amazing! And, as you talk about intentionality, being purposeful in the work that you do now, how are you seeing people designing their life and ensuring that they’re not leaving it to chance?

Bill: This plays out in a big way in family business, Cory. When we talk about transition, generational transfers, succession, and all of that, it’s a difference between success and failure. When you leave that, what’s the future like, when are my children going to get involved in the business or the next gen, looking at their parents, what’s my future? Should I get involved with my parents or not?

If we’re not intentional and purposeful about thinking that through planning for that, then you’re going to get completely different outcomes. And so intentionality is critical. It’s critical in life.

It’s critical in any career you might want to pursue. But if I put it in the context of family owned business, I think it’s the difference between success and failure, and transition and succession. Intentionality, purposeful planning around.

It came out actually quite clearly in the research at Family Enterprise Foundation when we did the series next gen and, Ready, Willing, or Interested was one of the titles, and the last piece was a bit more of a qualitative sort of study around preparing the next-gen. And it’s really about what’s that recipe for success, and what are the things that need to be in play to create the environment for success. And it comes right in there as one of those four.

There’s emotional connection, getting alignment and some coherence of vision around across generations. But then intentionality over what journey you’re going to embark on. And there’s no one journey. There’s no one recipe there, but being intentional about it and aligned on it. That’s where intentionality comes in.

Cory: Right. I like what you said about emotional connection, Bill, because sometimes the family business is, can be the loved member of the family, or it can be the black sheep sibling that the parents spent more energy on the business than they did on the kids. And it could even be from a spouse perspective. When you’d say emotional connection, how does that come to be in from a success criteria?

Bill: So it’s like anything in life. You can’t really connect properly with whatever is going on in your life or event and so on unless you have some emotion in play in the game, in my mind. So, for someone, a family patriarch, matriarch, to think they’re going to be able to bring their children into the business and have them be successful and so on without getting them emotionally connected to that business.

Now, I say “that business,” but in most respects, it’s probably just business in general, generating a bit of an entrepreneurial sort of spirit and mindset in the children, and then having them connect to that and what you’re doing. What happens with next-gen, sometimes they just might not be interested in the manufacturing, the machine shop, or something like that. But they can still be connected to the concept of business ownership and that entrepreneurial sort of mindset, and instill that in the next generation. And you have to start early with that. We all have a tendency to be really protective over our children and so on.

And I think how parents get into trouble in the whole succession game is they’re too protective, and they isolate the children from all the toughness that goes on in running a business and being successful and so on. And they give them probably a little bit of a silver spoon treatment and so on. You need to be able to involve them early. Get them to understand how business works. What is it we do? Why do we do it? How do we run our business? How do we treat our employees? How do we get them connected? That’s what I mean by an emotional connection, emotional connectedness to the business. You have to instill that. The earlier you start, the better. I mean, it’s not like it’s a lost cause if you haven’t done it at a very early age. But I think that sets a foundation for everything else that comes in terms of transition and succession and all of that.

Cory: And now, Bill, you made a comment about focusing on people. And I love how you said, involving that next-gen early and getting them to understand how we treat our people. And that next-gen, they’ll learn by the actions of the people around them. And if we’re giving them that silver spoon and they’re being treated differently than what we’re treating others, that can probably cause a bit of damage. So in that leadership transition and teaching them, how do you think that it would be best to strategize that and really be intentional there?

Bill: That’s a really good question, Cory, because that brings up another point, which to me is problematic probably in some family businesses. When the development of the next-gen and so on is sort of internally focused.

They watch their parents, they watch other leaders in the business. And that’s the only thing they know. If things are going well and their parents are amazing leaders, that will be great. If they’re not, that can be a problem, which is what I think you’re basically saying. What to me is important is that, when you’re thinking about preparation and next-gen, think about some external influence. That may mean working outside the family business for a while. Observe and gain from that experiential learning, working in another environment and so on. You’ll pick up a lot of things that you can bring back with you, skills you’ll learn and so on.

The other thing that’s really, and even today, which is where I’m really focused now, the whole notion of mentorship and coaching even, and they are different. We could talk about that too. Mentorship for that next-gen and having someone outside the organization.

So if you’re being mentored by your parents to take on a leadership role, I think there’s a big gap. You’re missing something there. First of all, where do you cross the line from being the parent and the mentor of your adult children? And it gets really fuzzy. And so, I think there is significant value in outside experiences, and outside influence, and outside third party mentorship, coaching, and so on. To me, that’s going to really accelerate the growth and development of the next-gen in terms of being ready to take over a family business.

Cory: Absolutely! And so, Bill, you know, we’re talking about that internal focus, really getting that emotional connection to the enterprise, which can be transferred from the parents, from the family. But now we’re talking about external influence. Let’s talk a little bit about intentionality, bringing back that word around that external influence. You mentioned working outside, and many people do mention what it is that we can gain by being that experience outside of the family enterprise. How would you recommend designing that?

Bill: Well, I think you need to customize that to the individual, the business, what’s the industry. And so, I think it’s a pretty wide range of factors that you need to take into consideration. If you have the opportunity, for example, to work in the same industry with a competitor even, it’s probably great. You learn the business and the industry as well as having exposure to other people.

Working in a completely different industry is probably beneficial in some ways because you might be in a more service oriented, people focused business if you’re in, like, I think you got to do it. It’s customized to the individual and to the situation. So that’s the approach I would take. I would look at what are the gaps in terms of the learning or knowledge that exists today. Where can you pick up some of that? What external organizations-people would be influential and helping? And then try and create a little roadmap for that individual. So that’s how I would approach it. And I think that’s the only way you can really do it. There’s no one set way to design outside influence.

I mean, some families had these, to me, two rigid policies around, you know, you got to work outside the family business for a minimum five years before we can open up the opportunity for you and so on. And I actually, I won’t mention names, but I had this conversation five years ago with someone, one very well known Canadian family who did that had significant, they were like in 5th gen or whatever. And they had this significant sort of next-gen and they had that policy in place. And they found that they lost control.

These people say, this is a great career. I’ve spent five years here. I’ve invested five years in this role. I don’t want to just come back to the family business, right? So you’ve got to be careful. You’ve got to customize it to what works best. I mean, if you don’t need someone to take over the family business for five years, that might work. Or if you don’t need them to come into other leadership roles.

Cory: Now what about mentorship? Where does mentorship fit into that puzzle?

Bill: To me, mentorship is, and maybe I’d wrap it all together, Cory, if I could. Mentorship, coaching, and I think a hybrid there depending on, again, on the circumstances and the individual, can be beneficial. And what I’ll also throw into the mix on this is connecting with peers. So, peer groups and so on. I see them all sort of playing a role in that development of the individual. So, mentorship, particularly, I think it’s great to have someone who’s your champion, who’s going to help you identify that plan.

I talked about being intentional and purposeful. What’s that plan? How is it going to unfold? What happens if, those sorts of discussions and scenarios, and saying, okay, you know, what’s the gaps? What are my weaknesses? I’m sure most people would agree you are your own worst enemy when it comes to, okay, what are my weaknesses? What are the gaps, and how do I fill them? That’s the role of a mentor, I think, can help you identify the gaps, develop your strengths, and be that sounding voice, a real champion for you to guide you through your journey.

Coaching is a little bit more specific. Coaching is about those specific challenges I have, either in the work I’m doing today or my career and so on, how do I sort of work through those and find options and solutions that are going to work. That’s where coaching comes into play, and that there might be a role for that. You have to juggle that a little bit, mentor, coach, and so on. Where do you get specific in terms of how you’re working with someone?

And then the peer group experience. To me, I’m a firm believer in peer groups. I think there is significant benefit value that comes out of being connected in a very more formal way. And I’m not a big fan of formality, but in a more formal way. At Family Enterprise Canada, they have the personal advisory groups, the peer group experience for people working in family business. And I’ve heard so many testimonials out of that. People say, I wouldn’t be here today if it wasn’t for my peer group.

And it’s similar, which is another thing I’m involved with now, the CEO Peer Group Experience. I think you can gain a lot from being connected in with peers who are facing similar issues, challenges, maybe similar opportunities that can help you really think through, make better decisions, smarter decisions, and accelerate that growth and development of you personally or your business and so on. It’s a really powerful model, I’ll call it, that I think will serve next-gen and family business really well to be connected in.

If you’re just taking on a leadership role, going to step into a CEO role in your family business. Yes, you’ve had the experience and knowledge transfer from your parents and so on. But you’ve got new realities today. You’re facing AI. Being able to sit around a table with a group of people, CEOs, making decisions about this themselves to help think through all of that and process what that means, so you can drive success. That’s really, really powerful.

Cory: Absolutely! Now, Bill, I want to talk about choosing. Making that intentional choice, and designing some of these tools that you talked about, to fit the person. And you mentioned next-gen, but I think that there’s also opportunity in the “now” generation to have those peer groups and mentor. We might transition through our career and have people who have led the way and say, here’s what it’s like to be a CEO. But afterwards, I find that as people exit that role, there’s a bit of time that they need to find themselves in what that is. How can it be used not only by the rising generation, but that “now” generation member looking at my future?

Bill: That’s a really good way to position it, Cory. You’re right. Just to be clear, I’m talking about next gen. But next gen and “now” gen should really need to be merged together. And just maybe if I would reflect on the conversation we just had, the mentorship coaching and so on is probably really relevant for the next gen. And the peer group experience would be really beneficial to “now” gen who are already in leadership roles and so on.

To put that follow-up on your point there. For the founding generation, the generation that is looking at the next phase of their sort of life and career and so on. And I don’t use the word retirement very specifically because, particularly in family business, you don’t retire from the family. So, how do you retire from the family business? It’s really about what you do next, and how you contribute and so on. It’s tough for people. We all know that. It’s really tough for founders in particular to exit from that leadership role, the CEO role of a family business. And so the tools would be equally as beneficial to them to figuring out what their role is, what comes next, how do they do the transition.

So having a coach or a mentor, and there’s a number of really good people out there today in the world who coach and mentor family business owners on exits, and coaching or mentoring, and being part of a peer group and say, okay. How are we making this transition? What does it look like? How can I have some purpose for this phase of my life and my career? I think that’s probably the most critical part. And a peer group could help you think that through.

By sharing their own experiences and so on, you get ideas and you support each other. But finding your reason, purpose, the “why” for you of what comes next, sets you up for success on that phase of your career, which is really taking on maybe a mentoring role for the next-gen in the business, but not a leadership role. You have to give up some of the decision making and so on. And I think to the point of your question really is that those tools can, and probably not employed enough by that founding generation, but they can be really helpful.

Cory: And what about choosing a mentor? I think about mentorship, and there’s lots of guys at the country club who may be a bit older. They seem successful. I might ask them for some mentorship. I think there’s lots of pros and cons there. Let’s talk through a little bit of that, Bill, making that decision and finding the right person.

Bill: That’s tricky because it is about finding the right fit. But what’s the chemistry? What’s the experiences of the individual? How do they relate my situation? I think all of that comes into play. So it’s soft. It’s not like, what’s their coaching certification? Did they do the international one or the, you know, that’s not what it’s about. There’s some great coaches out there, don’t get me wrong, and with all sorts of certifications. But my point is what’s the right fit for that individual in that situation? And I think that’s what you have to think through.

So, to your point about someone at the country club or my colleague who’s running another successful business in town, I think you have to be careful about that because that’s not always the best person to provide you with that objective advice. I see it with family business boards too, if I could use that example, because I’ve seen that a lot.

A lot of people in the natural progression say, okay, I want to set up an advisory board. And they’ll bring on some close colleagues and business people they’ve had a personal relationship with, maybe golf with at or something like that, or socialize with in other settings. Or they’ll bring on some advisors, or lawyer, or accountant, or someone because “you’ve been with me for 10 years, you know my business” and so on. And that may not be the best choice. They may be great people. But be very purposeful about thinking through that as well. What are the gaps that I need to help me be successful?

It might not be the person that you golf with or that you socialize with, your spouse outside of business. It may not be your absolutely stunning legal advisor, because they may have certain experiences that don’t really contribute to what you need. So, I think finding a mentor, there’s an art to it. It’s not a science for sure. Right. It’s who’s got the experiences that are going to be helpful to me, who’s going to be objective and give me honest, genuine advice. And who’s a good fit, knows something about my situation or the industry I’m in. I think that’s the process you need to go through to find a mentor.

Cory: You made a comment about chemistry. And chemistry, when it comes to a peer group, how do we find that alignment and that chemistry where somebody says, this is a great peer group, and I’m going to achieve something great because I’ve positioned myself around this group of people?

Bill: That’s another really good question because, and I would venture to say just about every peer group that’s around has experienced a bit of the challenge of someone who doesn’t fit, or someone who’s a bit disruptive in the group. So first of all, you need processes around how to deal with that so you can remove those people. And they might not be bad people. They’re just not a good fit for the group. So, I think I look at it more from an attributes perspective.

Chemistry might mean, Cory, you and I get along really well. That’s why we hang out together every weekend. That’s not what I mean by chemistry. It’s about mindset And, particularly in a peer group of CEOs, you need to have people with a similar sort of mindset around things like, and I don’t know if you’ve heard the, you know, I think it’s Carol Dweck, The Growth Mindset?

So, you need to be open to suggestions and criticism. You need to be positive, have an optimistic outlook. You need to have a sense of helping others, a purpose, and helping others, supporting others, and a sense of abundance instead of, you know, the opposite is, “I don’t want you to be successful because that takes away from my success.” You need to have a growth mindset. That’s really important. Empathy is really important. Strong EQ overall, being able to relate to others. Then I think you have the formula for having chemistry in the group.

I mean, I might get along. You and I might be great in the group. But we never socialize or anything because that’s not what we’re here for. I think in a peer group experience, particularly the CEO peer group, having the mindset around what you’re there, why you’re there, and how you contribute and give to the group, and what you take away from the group, and finding balance in that. I think that’s what will make it successful.

Cory: Absolutely! And, Bill, talking about people and EQ, you know, in your commencement speech, you talked about focusing on people and that you can’t do it alone. How have you found that people, successfully, make themselves redundant as you mentioned, and get out of the way?

Bill: I probably had some experience with that. To me, it’s about, first of all, EQ is really important for a successful leader in my mind. So you find great people, go to EQ. They also need to know the business. You obviously need those skills and that knowledge. You find the great people to be on your team that really have that growth mindset, all of that. And the role of the leader then and how you make yourself redundant is by coaching and mentoring them to take on increasingly more responsibility and develop their own leadership skills, and help them to grow as an individual, and to grow in their capabilities and competencies. And when you do it right, you create your successors, whether it’s in a CEO role or in the family business, you’ve created that successor.

And then you need to get out of their way, which is what happens with patriarchs and matriarchs and family business. Well, they don’t get out of the way and then it becomes a bit of a stagnation really. The next-gen or the “now” gen are ready, but they don’t get out of the way. So getting out of the way is really important. And that doesn’t mean, leaving necessarily, might mean taking on another role yourself, just like we talked about with founders. What’s your next chapter? How are you going to contribute? Won’t you give up the role of CEO, for example?

Cory: I like that! And, you know, really, what I’ve heard you say is being coachable and having the skill set to be coachable, but also developing some of those coaching skills is important. And coaching that person who’s coming up behind you, but also being coached. It doesn’t matter where you are in that organization. In those three circles, you really do need to be intentional of where are you today, where do you want to go, and who am I helping to backfill, and who’s helping me to get to where I’m going? I love that.

Bill:  Absolutely! You just made me think of something else, it’s critically important in that sort of journey of family business succession, finding the right role for the individual. So, not everyone should be the CEO, aspires to be the CEO, and so on, and you need to understand that. That comes through in the preparation, the transparency around all of that. But what is the right role for family members in the business?

I remember sitting, having coffee with a fairly successful family business owner, as a national business and a few other businesses on the side. It’s just hobbies, almost. And this individual was sitting down and he was saying he was very insightful. He’s saying his daughter was sort of working through the different aspects of the business, gaining experience in different roles and all of that, and that was going really well. And he was talking about his son who’s successful but very artistic, you know, plays in the band, does all these things. And he says, I don’t think my son will ever work in the operating business. But he says, I better prepare him to be a good owner, because he’s going to be, as part of this family, part of the ownership circle, and I’ve got to teach him how to be a good owner, prepare him to be a good owner.

Cory: I love that! Such a good point, Bill, because it’s not one position that creates that success. There’s so many roles. And sometimes we hold multiple roles, but we need to be prepared for those as they come at us.

Bill:  Absolutely!

Cory: Now, as we wrap up and near the end of our conversation, there are a few questions that I ask each guest. Are you ready for the tough ones?

Bill: I am, let’s go for it!

Cory: What is one key strategy that you believe is the most essential for building a successful family enterprise?

Bill: I like that question because you try and wrap everything together. When we’re talking about building a successful family enterprise, probably need to define success. What is success? We can define success for business, and there’s lots of ways to define that, obviously. Success for a family business, family enterprise. And I think it’s about thriving across generations. So it’s a generational thing. It’s not like how successful is this business 5, 10 years. It’s across generations. Success is about finding balance between the three circles. Success of the business, success of the family, success of the ownership group. I think that’s how I define success in a family enterprise.

And so for me the strategy goes back to what we’ve spent a lot of time talking about here, is planning for that. What does success look like in the family? How do we achieve it? What do we need to do? What does success look like in the business? What does the ownership success look like? When do we transition? How do we transition? Being very purposeful and intentional about planning for all those elements, not just laser focus on the business or laser focus on ownership, but you’ve got to be able to plan and bring them all together, and create a little bit of harmony. There’s no such thing as full harmony probably. There’s always going to be a little bit of conflict and tension, and everything else, but bringing as much balance as you can to all of that. I think that’s the strategy I would employ is like, think holistically, think system wide, and plan accordingly.

Cory: Fantastic! And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Bill: Well, we just talked about preparing the next generation. There’s so much stuff wrapped up in that. And that is an overarching challenge. But if I were to drill down a little bit, one of the biggest challenges, and I’ve used this expression, it’s about communication. And that’s a loaded word too. But, you know, here’s what I say. Communication is the cause of all issues and conflict in family business. However, communication is the solution to all conflict and issues in family business.

There’s two sides to that, and you really need to understand that. The biggest challenge is communication. Whether you’re preparing the next generation, you’re thinking of your exit, you’re making big strategic decisions, being able to communicate effectively with each other, transparency is an outcome of good communications, engagement is an outcome of good communications. Communication is so important. It can be the cause of all the issues, and it can be very easily the solution to all the issues and to pursuing all the opportunities you have before you. And so, how do you get around this challenge of communication?

It’s really about being a little bit more formal than families are sometimes comfortable with in setting up processes and structures and approaches to that. Wrap that all together. Someone would say you’re talking about governance. But I don’t use a governance word because it scares too many families. But getting the right processes and approaches in place to facilitate the communication that needs to happen, the sharing of information that needs to happen. When you do that, you build up the competency, the whole group to be able to communicate effectively, to understand each other better, and so on. Communication is the biggest challenge, but it’s also the way you get things done.

Cory: I love that! And a great way to explain governance without it seeming so, so daunting. Bill, in your experience, what are the top three key qualities that successful family enterprise leaders possess?

Bill: There’s so many things that you could bring into play here. But to me, I can think of three that are really, really important. And to me, for an individual, one of the attributes or qualities is strong EQ. We talked about that before in terms of mentoring and development and so on. Having a strong, high EQ, particularly empathy for others, understanding how what you do and say, and the decisions you make impact others, is really important in a family business. I think it’s important for any leader. But you think of a family business, we’re making decisions in the business. How does that impact my family? What are they going to think? And how is it going to impact our future transition? So, having EQ would be one.

The second, which is really important, again, you can put it in the context is just leadership generally. But for a family business owner, being a holistic thinker, system wide thinking. I can think of several family business leaders today who I’ve interacted with who are really good at this. They, in their mind, understand the impact of the decisions and thinking in the context of three circles, the business, the family, the ownership, getting the big picture, and having that holistic sort of approach. That’s really important.

And then the last one, to me, it’s about passion. You’ve got to be passionate about what you do, passionate for the business, passionate for the family and the success of the family. And passion is, when it exists in an individual, it’s contagious. It spreads to the rest of the family, spreads to the rest of the folks involved in the business or the ownership group and so on. So, being passionate about what you do, your purpose, your “why,” why you exist and as a business, and so on, I think, is critical.

Cory: Fantastic! Absolutely! And before we conclude, I’d like to highlight where our listeners can engage in more of the conversations that you’re having, the things that you’re engaged in, maybe listening to or reading. Could you kindly provide us where our guests can find you and some of those resources?

Bill: One thing that I’m more recently involved with, I just recently became a chair with TEC Canada, so The Executive Committee, and I find they have tremendous resources on peer groups and leadership development and so on.

I still refer a lot to some of the studies and research done by Family Enterprise Foundation. I think some of it is amazing. I was involved in it. And I’m not just saying that because I was involved in some of the topics. I didn’t do the research or write the reports, obviously. But I think it’s so insightful in many ways. It brings out things that every business owner and every next gen should be thinking about. Those are probably two of the areas. I still monitor all, there’s so many great things out there.

Your podcast, and other podcasts, and publications from other people in the field of family business, I try to monitor as much as I can and just absorb as much as I can. I’m seeing more and more discussion out there in the literature and recent articles about ownership, and transition of ownership, and things like that, which I think is great. Because today, everyone knows about the demographic bubble and the great transition of wealth that’s going to happen, and there’s a lot of talk about transitional wealth. And I find that there’s not enough discussion about transition of ownership and transition of leadership. And that’s where all the things I’ve been talking about, the mentorship, the preparation, and so on comes into play. So I just encourage people to seek out new material on those topics because I think they’re going to be really important over the next 5 to 10 years.

Cory: Absolutely! I love that, and we will make sure that we link, specifically those three reports that came out over the last few years that the Family Enterprise Foundation had done, because some great material in there. And you’ve you’ve mentioned it a couple times, Bill, and I think that it’s great stuff that’s been done there.

Bill:  Great, thank you!

Cory: I wanted to make sure that we covered everything. Is there anything else that you’d like to share with our audience that we didn’t get a chance to touch on?

Bill: No. I think we’ve talked about a lot of great stuff, Cory. It was a great conversation. Thank you for having me. I really enjoyed this. Hopefully, your listeners will find some of it at least beneficial or insightful.

Cory: I think that your insights will be incredibly valuable to our listeners. I wanted to thank you, Bill, for taking the time to share your experiences and expertise with us today. And we’re excited for the listeners to hear exactly all the things that you contributed today. So thank you.

Bill: Thank you.

As we wrap up this episode, we invite you to reflect on Bill’s insights about intentionality in family business transitions and the value of external perspectives in leadership development.

Whether you’re guiding the next generation or seeking your next chapter in the family enterprise, Bill’s emphasis on purposeful planning, meaningful mentorship, and creating the right roles reminds us that successful transitions require both emotional connection and strategic foresight.

Throughout our discussion, Bill revealed the vital balance between emotional intelligence and strategic planning in family enterprise transitions. Bill’s formula – E × R = O – reminds us that our responses shape outcomes, while his insights on authentic leadership demonstrate that success stems from aligning individual talents with organizational needs. His practical wisdom shows us that family business continuity thrives when we create space for each member to contribute meaningfully while preserving the enterprise’s core values and vision.

For those seeking guidance on strengthening your family enterprise through intentional transitions and meaningful connections, Bill Brushett is here to assist. We’ve included Bill’s links to his socials and contact information in the show notes to support your family business journey.

Disclaimer: 

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This not an official program how Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those how Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at [email protected] or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.

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