Beyond the Founder’s Shadow: Empowering Rising Generations to Reimagine Legacy

In this episode, Tim Yeung shares his insights on navigating family businesses. As a family enterprise advisor, he emphasizes the importance of finding one’s path, maintaining a growth mindset, and effectively communicating with others. Tim discusses the challenges of differentiation and creating an identity separate from the family business. He highlights the psychological barriers that next-generation family members often face when joining the business, such as the pressure to live up to the founder’s legacy and the need to establish credibility.

Furthermore, Tim emphasizes the significance of a shared vision, core values and focuses on human capital for the long-term success and legacy of family enterprises. He stresses the importance of the older generation believing in and supporting the younger generation’s choices. Tim also discusses the concept of a family bank as a mechanism to encourage entrepreneurship and support family members’ endeavours. Finally, he underscores the value of co-creation and involving all family members in shaping the family’s vision and legacy for future generations.

About Tim Yeung

Tim Yeung brings valuable knowledge from his ten years of experience working in his family’s successful multi-generational commercial real estate business. His transition to a Family Enterprise Advisor role reflects his strong background in business and a deep understanding of family enterprise dynamics and governance structures. Tim is a Mechanical Engineer from the University of British Columbia who graduated with distinction. He is also a certified Family Enterprise Advisor (FEA) and a trained Certified Professional Co-Active Coach, preparing him to guide families toward prosperity.

Born and raised in Vancouver, Tim is a life-long learner. He is deeply devoted to his love of sports analytics, powerlifting, and personal development. His interest in fostering a growth mindset extends to competitive gaming. Tim is married and has two beautiful girls, and in their family’s spare time, they love to go for picnics and ice cream.

Resources discussed in this episode:

  •  Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett (Author), Dave Evans (Author)
  • The Courage to Be Disliked: How to Free Yourself, Change Your Life, and Achieve Real Happiness by Ichiro Kishimi, Fumitake Koga, et al.

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

Contact Tim Yeung | Family Business Advisor (LGA): 

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 Tim Yeung, Family Enterprise Advisor for Lansberg Gersick, and Associates (LGA). from his ten years of experience working in his family’s successful multi-generational commercial real estate business. His transition to the role of a Family Enterprise Advisor reflects his strong background in business and a deep understanding of family enterprise dynamics and governance structures. As a certified Family Enterprise Advisor and trained Certified Professional Co-Active Coach, Tim is well-prepared to guide families on their journey toward alignment and prosperity. 

My goal is to be the most curious person in today’s conversation with Tim Yeung, where we explore the journey of an engineer developing into a skilled advisor guiding families toward alignment and prosperity. Tim will share insights on supporting the next generations as they shape their own identities and differentiate amidst internal pressures to conform to the family enterprise. We’ll explore how advisors can gently encourage the quiet voices while calming those eroding unity to help families commit to difficult conversations today to set their enterprises up for resilience tomorrow. 

Now let’s dive in!

Cory: Great.  Welcome, Tim! We’re excited to have you here today to share your wealth of knowledge and experiences. Let’s dive in, shall we?

Tim: Sounds good.

Cory: Tim, imagine you’re delivering a commencement speech to the graduating class of 2024, and you have the chance to fire them with your story.

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

Tim: That’s a great question. I was putting my thought to this, it really struck me that a book I’ve been reading called “Designing Your Life” is aligned with a lot of my life experience and unsurprisingly, put more succinctly and more eloquently than I did myself, which is that, I think there’s this feeling, and maybe it’s because I come from an engineering background.

Wanting to do the optimal thing, wanting to get it right and I think there’s no wire cutter art goal for how to live your best life. We want a GPS. I want a GPS for what it looks like to live my best and most fulfilled life.

But you can’t have a GPS when nobody’s lived your life before. I think the way they put it and then the way I’ve enjoyed reading about it is that we don’t need GPS. We just need a direction and a compass.  From there, we can choose our adventure, kind of like those old choose-your-own-adventure books where you flip to this page and then follow the thread where it goes. I think in our lives, it behooves us to think about our lives that way too. The problem with being obsessed with optimal is we spend more time analyzing than actually living.

I’m guilty of this, that you want to get the perfect system. You want to get the perfect schedule. You want to get the perfect framework for things. You spend more time doing that than actually doing the thing. I think we do that with our lives as well. That’s what I would tell people, which is to have a place where you want to go and start to figure out how you want to get there and be okay knowing that there are going to be multiple ways of getting there. That it’s okay to figure that out on your own.

Cory: I love that. Tell me a little bit about the engineer, that mindset of analyzing how have you kind of navigated that within your life? Because I’m sure there have been challenges as you’ve found yourself looking for that GPS?

Tim: I think, there’s a feeling of wanting to get it right. I think it’s because you want to like, at least for me, it’s like, I want to get as good as possible as quickly as possible. That’s where on the one hand, there’s a humility in that and just admitting, I don’t know best.

I just want to figure out someone else needs to tell me, “how to do this the best way”. But I also think part of it is realizing that they’re not necessarily, and no one will know it better than I do myself.

I think where the engineering, I want to say it’s been helpful, is the way off and maybe this is my engineering background. I don’t know. It’s hard to separate.

I haven’t lived a separate life where I didn’t go to engineering to see what it was like, but I think engineering has given me the desire to understand everything I learn in anything I’m interested in 1st principles.

At a base level, how does this all work? Do I understand it? All the tactics and things like that. Those are just applications of those principles. I think that’s where the engineering has helped me.

I want to think of a place where it hasn’t helped me. I think it hasn’t helped me where sometimes you can be stubborn around data? I’m sure you’ve all experienced in your practice where there are lawyers who are good at talking to other lawyers.

There are engineers who are good at talking to other engineers, and accountants, the same thing. It’s the engineers and the lawyers and the accountants that are good at talking to lay people who are the best at what they do.

I think similarly, sometimes I can get too caught up on what the data says thinking I’m talking to other engineers thinking I’m talking to people with the exact same kind of mindset values, or ways of thinking as I do and it isn’t very helpful.

Because, you have to be able to meet people where they are and I think especially that’s in my work now, working with families, you can’t expect them to meet you or who you are.

Cory: I appreciate that so much Tim, in that there are these experts in their field that work with as you say, people, and the work that they do can be tremendous, but without the ability to communicate that with the people and have them buy-in, the plan, the design, whatever it might be, that they’re delivering can be sabotaged so easily.

And in your experience as an adviser and as you’ve formed how you approach things, how have you found that holds in your practice?

Tim: I love geeking out on things and I have to realize for myself that just because I like geeking out on things doesn’t mean other people do. I’m guilty of this and I want to bring everyone along on my geeky ride of the things I’ve been learning.

I think really where it comes down to is instead of what I’ve actually been going through, like a YouTube course recently. One of the things they talk about in this YouTube course is that the viewer doesn’t want you to show them how smart you are. They want to feel smart. And so I think similarly in conversations with people, it’s not about making this person feel smart necessarily.

But it’s really about instead of impressing people’s knowledge, it’s really actually about being curious and being able to help them actually articulate where they want to go whether I’m already working with him or not.

There’s a guy named Chris Do. He runs the future as a creative company. He talks about how when you’re working with a potential client, it’s really just about helping them articulate where they want to go because We assume people already understand where they want to go, but most people don’t. And that’s for a variety of reasons, sometimes people are stuck.

Where sometimes people don’t yet have the courage to even put into words where their dreams are and where they want to go. That’s when you work with people that’s actually, the gift that we have to give, which is we get to help them articulate that and get them excited about that future and where they want to go. Then if it aligns with your expertise, then you can support them.

And if it doesn’t align with your expertise, then you can direct them to people from whom they can receive that support. And in so doing, you’ve made a gift. You’ve given them, a service either way.

I think that for me has been really helpful trying to just meet people where they are, not assuming that they know as much as I do because they probably don’t spend their time. They spend their free time reading about family enterprise advising books. Right? And that’s totally good and fine.

 I need to meet them where they are, understand where their problems are, and try to help them articulate where they want to

Cory: Right. And Tim, going back to the fact that you trained as an engineer and now doing this work, I feel as though there’s somebody in your past who’s helped you articulate, where you are going, maybe helped with the map and the compass is as you talked about. How did you make that change and be on the path that you’re on today?

Tim: I think for me, personally, I think we all need these people in our lives who have dropped in at different points. Sometimes directly, sometimes very indirectly, have really pointed me to “this is what you’re good at”. This is who you can become. For me personally, I worked in my family business in real estate development for 10 years. I like to think that I am good at my job. I think I had a fairly good understanding of the industry. But it was the gift of working with one of my employees, and I had a super difficult conversation.

And it was that conversation where I saw that employee’s career just completely turned around. It was in that moment that I reflected on this, years later, I realized, hey, “of all the things I’ve done in this real estate career of mine, that was by far the most satisfying.”

I got the most excited about seeing that person realize all of their potential. I think it was that realization that was that compass. There’s a lot of different vocations and jobs I could have done that would lean into this people development, compass, this clue that I was given, and I decided to try out this family advising.

I didn’t know if I would be any good at it. I didn’t know if it was going to be a viable career. I’m happy to say that I think I’m okay at it, and I think it is a viable career.

And the result has been good. But it was really that clue of exploring and trying and testing this out. It was because of my reflection on what I really enjoy, what I really found satisfying, and what gave me a ton of energy in my work that directed me directed me in this way.

Cory: That’s going back to your comment about people spending more time analyzing than living. It sounds like that was that turning point of living at that discovery point.

Tim: For sure. And I think there was the additional kind of speed bump of I care about my family business. I worked for a year in my family business in Hong Kong. I grew up in Canada, so I couldn’t speak Cantonese by the time I was in my teens, and so part of my going back and living in Hong Kong was I wanted to learn the language.

What I didn’t realize in learning a second language in my twenties, was that I finally kind of experienced firsthand the plight of not knowing how to speak the native language.

People think you’re stupid because you can’t communicate realizing that you can’t be funny if you don’t have the vocabulary or the timing to nail your jokes, you’re certainly not smart if you can’t even ask for water properly. Right?

I realized how much was given up for me to come to Canada. And because of that, I had this deep affection a deep abiding affection in my family business and what it meant and what it gave to me.

For a long time, it was kind of my dream to be able to support and lead the family business. It took me a long time, I think, to realize that my affection for the business actually didn’t mean I had deleted it, especially if that wasn’t really where my skill set was. That was the other kind of hurdle that I needed to kind of understand for myself and decide for myself.

Cory: That realization Tim, where you were on your journey within that family of business where the aspirations of leadership were there to that realization that maybe you didn’t need to do that. How did the pressure from within or external pressures play into some of your decisions?

Tim: I’m fortunate in the sense that in my family, there were no external pressures. My family was really supportive of me entering the business, and they were really supportive of me pursuing this new job as well or this new vocation as well.

The pressure really resided with me. I think it resided with me and being a little too caught up in what I thought other people were thinking. There’s a fantastic book. It’s called “The Courage to be Disliked”. It talks about how it walks you through, this thought experiment of you can’t please everyone. And if you do try to please everyone, you will become kind of nothing in that process. That’s the short version of it.

Part of actually living a good life is the courage to be disliked. The courage to just do things and not be beholden to what you think other people think. That was a big turning point for me is, If people are going to think whatever they think about my decision, I need to be okay with that. I need to be able to expect myself for the decisions I make, and I need to be not beholden to what I think other people need.

Cory: Now as you mentioned Tim, the external pressures weren’t felt in your work with family enterprises and the families that you’ve met either as an advisor or within your community. Is that common?

Tim: I would say in most families, I work with the internal pressures are quite strong. There is an expectation around being in the business or being a certain way, acting the way we did. I think that  there are positives in terms of the transmission of tradition and legacy, but there are also negatives in terms of a stifling environment.

That’s a recipe for a very unfulfilled life a life where you feel like you have made none of your own decisions and that someone else has made all of them for you and while that may feel very dutiful and obedient, it’s a matter of time before that feels like a straitjacket.

There’s a model of couples and it helps people understand whether you’re in the healthy spectrum or unhealthy spectrum. And it doesn’t matter. There are 2 axes. 1 axis is cohesion, like how close you are and the other axis is flexibility. You can’t have a family that is so flexible, that’s chaos. You can’t have a family that’s so inflexible that it can’t move. You don’t want a family that’s so fully fused that it has no identity, what’s ever outside of one another. You also don’t want a family that’s so alienated or distant from one another. You’re basically not family. You just don’t want to be on those extremes. Right.

In families where the internal pressures are too strong, you tend to land on that flexibility spectrum. That is a very unhealthy place for families to be because almost by definition, families’ businesses, and lives change. If we operate within a super inflexible system, it will be incapable of managing those changes in the future.

Imagine driving a car, I’m not sure how bad Calgary roads are with potholes and stuff. Imagine having a car with 0 suspension, that would be terribly uncomfortable. In fact, the car would probably break at some point. Right? And that’s what families do.

When families are so inflexible, they don’t build the resilience, and the capacity to change. They’re basically betting on glass roads. They need a glass road or else their car will break, and that’s not a good bet.

Cory: Let’s go back to the word identity. Being in that position of next-gen, identity can be difficult to shape. There’s oftentimes a large shadow cast by the generation, either the founding generation or the generations before, how do you find that shaping identity has its challenges, being that next-gen?

Tim: I think you’ve hit it on the head Cory. Identity. I think it’s Peter Weeks that talks about this. Peter Weeks or “The Conflict Equation”. I forget which one. The chief psychological barrier for family businesses is differentiation. For each new generation to actually create their own identity and believe in their own capability and self-worth.

That’s a process that happens fairly naturally outside of family businesses. You grow up, you go away from university, you get a job, you have you’re gainfully employed. Therefore, you’ve set up a household life outside of your parents. In family businesses, that doesn’t often or often doesn’t occur.

You come home for internships. You come home right after you finish university, and you’ve got your first job. You’ve never created an identity outside of the family. When you don’t overcome that. It’s something that kind of weighs on you when someone asks you, are you just here? Because of your last name well, you may kind of feel like that’s kind of a jerk question to ask, but you may also not have the confidence to rebut or to feel okay about yourself after.

I think it is a tremendous issue. I think some people don’t have that issue, but for a lot of people, they do. That’s the chief psychological issue for family members entering the business. And how do you get around that?

I would say that’s where generally a lot of advisors would work with their clients and say it’s probably a good idea for any family member before they join the business to work somewhere else. Not just for their credibility within the business but for their charitability, and how they view themselves.

When you’ve worked 3 to 5 years at an external company where they didn’t have to employ you because your last name didn’t mean anything there. That goes a long way in terms of you feeling confident in who you are, what your capabilities are, and what your skills are.

When you’ve only done that in your own family business, that tends to be a question mark that hangs around.

Cory: Right. Now going back to the advisor family and how they’re developing that as they’re developing this human capital, this next generation, what sort of considerations do you suggest as you’re working with families on that?

I think a big part of it so J Hughes talks about this idea that the founder has been usually wildly successful. Has a dream for what the business will be, what the family’s legacy will be, and we often get caught up in that gravity.

In some ways, differentiation creating your own identity is being able to not run away from that gravity, to not go to another solar system and pretend your family doesn’t exist, but it’s also not to get sucked in and be completely and, captured by it. It’s to create a boundary around that gravity and decide what it means to you.

I think developing your human capital at some level means you have to support the next generation in finding their own identity, giving them the space to reconcile who they are, who they want to choose to be with what the family legacy is.

Coming to a healthy balance of what that means, does that mean you have to work in the family business? That’s a very hard imposition to make. I think the healthy one would always be to welcome you into family governance. You don’t have to work here, that kind of stuff. He also talks about the idea that families are fundamentally in the business of having every member. That could land in a variety of applications, but it’s a heart stance. Does the family believe they want every member to thrive?

Therefore, they can create their own identity and who they are, and the family’s going to support that.

Or does the family at some level believe unless you work in the business, you are kind of nothing?  Or unless you surpass dad, you’re not measuring up. That would be a really unhealthy way to pursue this or to, stand in relation to the rest of the family.

Cory: Right. And so that culture of thriving as individuals to be able to have the family as a collective thrive. A lot of balance within that. How have you seen it, do you have any examples of families that have done that well?

Tim: I think the families that have done that well have, and it’s scary, but have believed in their kids to make good choices. A lot of families that I’ve seen believe that the way to protect the future is by limiting the opportunities for the kids to screw it up, whether it’s through a trust structure or through various mechanisms to prevent, share ownership. That is one way of going into the future, that’s kind of like growing your bottom line by cutting expenses only.

it’ll work until it doesn’t because, at a certain point, there will be no expenses left to cut. For certain family members, if you only believe that they’re going to screw it up, eventually at some point, they will screw it up.

 I think the families that I’ve seen be successful at this, the older generation believes in the younger generation.

If the older generation is just waiting for the shoe to drop, it’s just waiting for the younger generation to disappoint them. To show them their true colors, don’t measure up, that’s going to be hard, and that’s going to come through in everything that the family does.

The one family I’m thinking of, the parents believe in their kids, and it shows. It’s purely because of that the kids have succeeded.

Cory: Right. As you mentioned, the idea of increasing that bottom line and great metaphor Tim, of cutting expenses, is the equivalent of having very tight structures in place. From the revenue side of things, what would you say would be some examples of behaviors and practices from that perspective?

Tim: I think it changes in every family. I think one really positive practice is, the practice of a family bank, a part of the capital that’s specifically allocated to support the endeavors of the family. I think the beauty in my opinion of that structure is that if a bank lends you money at best. They care about you as a customer, but really in terms of business, what they care about is that you make your interest payments and then you pay back the loan, the bank didn’t lose money. If you do all that, they’re happy.

If a family bank makes a successful loan to an entrepreneur in the family and they pay back the interest and they pay back the principal, Well, then now that business is thriving.

Well, the family bank is twice. The first win was the normal bank win, which was that they got their money back. The second win was they accomplished their purpose of supporting entrepreneurship. They accomplished their purpose of seeing that member thrive.

That’s like one mechanism, and it doesn’t have to be the only one, but I think it’s a fairly elegant one for one encouraging family members to start new businesses and 2, submitting to the rigor of some type of family process to show that they’re going to put all of their hard and effort into it.

Cory: I love that. And talking about purpose, there’s much purpose within different families and the way that they define that is different. Family banks are a great tool and they know.

I think there are some best practices there that we could dive further into but within that purpose, a lot of families have constitutions and have things to find and some are on that journey of defining them. What have you seemed to help really get down to that core of what’s the family’s purpose and how are they going to continue on that journey to accomplish that?

Tim: I would say, Cory, I think purpose is important, but I would put a shared vision above the purpose. Shared vision and shared core values are the things that I would put above the purpose because the shared vision is why you’re staying together and excited about where you’re going to go.

I think you have you’ve decided to come together, to go on this journey and the shared vision is that compelling picture of the future. That the family wants to get to is willing to even do the hard work to get to. Doing those extra family meetings, working on the constitution, and considering how to evolve policies as the family changes takes a lot of work. A lot of it, it’s not like you’re getting paid for it. You’re going to get some benefits from the family in the future, but you’re not doing it purely on a time basis for money.

 You’re doing it because it’s important to you. I think a shared vision is super important.

I think values are equally important because you can’t get to a shared vision if you don’t have shared core values to some level, you can get there if you have different values, but it doesn’t work if you have incompatible core values. I could think of if there’s an oil and gas family, and one family member is just staunchly against anything that creates greenhouse gases.

I mean, that’s going to be very hard for those siblings, let’s say, to stay in business together, it would, in some ways, be a much healthier decision for those siblings to buy one out and for them to remain family that still talks to each other, but not in business together. Right?

I think in my mind, the core values of your foundation, and you need that to get to have a shared vision. And the shared vision is the galvanizing cry or rallying cry for where the family wants to go.

That will make all the family meetings and the extra work worth it.

Cory: Right. Going back to the cohesion and flexibility, as you speak of those values and how is that alignment able to work within the family and knowing when it will work and maybe when it won’t. What’s the definition of success? As you say, the vision. How vivid is this within families that you’ve seen be successful at this?

Tim: I think it’s pretty vivid. I think I’ve had a lot of people do this where I try to have them think about where they want to see their family, and the legacy of what they’ve built in 50 years. They’ve long gone. They’re not around anymore, and their family is thriving and flourishing. And what do you see? And I would be very surprised to hear anyone say I see a portfolio that has grown at 20% annualized.  I doubt that that’s the picture that they see.

I think what they see are grandchildren or great-grandchildren that they don’t know that still know each other and care about each other because of what the family has done to get them there. I think it’s some variation on that picture. Maybe there’s a business in there. Maybe there isn’t, maybe there’s a special family vacation house. Maybe there isn’t. I think it’s that realization that that picture of the future is in some shape or form thriving human capital.

I don’t think you will find a family where that picture in the future is thriving financially. And so, I think that’s the common thread. Is that it’s coming back? I know it sounds really bad, but it’s coming back to the people because all of this has meaning only because of the family to do with it.  Otherwise, you’re just an investment club with the same last name.

We just happen to or slightly familiar last names because maybe there are a few different last names in there. But that’s the problem is unless you just focus on the human capital, that family capital, then you could just be a hedge fund, and I think that’s where the smart families focus on the human capital knowing that if you do that, the financial capital take care of itself.

If you don’t focus on the human capital, the human capital decay will eventually decay the financial capital as well.

Cory: Yes. And well, let’s go back to that vision and the family creating that. The legacy is 50 years from now and who in the family do you typically see initiating that?

Tim: Often that’s a little bit of the trap, I think everyone will just invariably look to the matriarch or the patriarch. And while that’s important and every family is different, I don’t think that’s wrong. The stickiest reason I could get my work done with families extremely quickly.

We could do everything in a few hours because I could just give them the best practices. I could tell the patriarch, the matriarch. Is this good? And they would say, yeah. And then we’re done, right? But the problem with that approach is that when you just look to the matriarch patriarch to sign off on everything and no one else is involved, it’s not that sticky.

People aren’t fully invested. They may even feel even though it’s status quo, they may not feel heard.  That’s really where, ideally, maybe the vision is ceded by the Patriot Matrix, but the rest of the family needs to be able to engage and have a voice and some level of authorship of that vision or where the family wants to go for it to stick.

For the family to coalesce around it. That’s where people use the word like co-creation. it’s created together in an organic process. That’s not, predestined or preordained. That’s where you and I know this sounds a bit like a used car salesman selling myself thing, but it’s not just me.

I think people can work with anyone, but this is where it’s really useful to work with external facilitators and advisors who aren’t part of your system that can see and bring in different voices that can call out or not call out, encourage the quiet ones to join in, to quiet the loud ones that talk too much, and to try to bring the family to a collective understanding of where they want to go. Instead of the loud majority or let’s say the loud minority dictating the outcome.

Cory: And Tim, as you mentioned, the matriarch and patriarch could sign off and say, good, “let’s move on”. But then there’s who’s carrying the baton to make that legacy come to fruition.

Tim: And 100%.

Cory: And in that transition of, call it hour or the dominance within that family system. How do you see the evolution of some of those visions? Because it could be 2 generations, 3 generations ago that had this vision. And now the world’s a different place.

Tim: I 100% agree that the baton needs to be carried on. The torch needs to be not just passed on. It needs to be grabbed and they should want this. That’s the ideal. They 100% need to be latitude and some flexibility and understanding of what these values mean to the next generation.

They 100% need to be Latitude and understanding of what this vision means to us now. You can imagine when we were growing up, what was being super forward thinking around caring for the environment. We were just talking about recycling.

And I think if you were just to talk to kids nowadays about recycling, they would kind of be, like, are you a little behind? We’re well, that’s kind of like you are that is the lowest common denominator in caring for the environment. It’s a complete given that you would recycle. Not a big deal.

The big thing now is the electrification of our transportation system. It’s thinking about where we buy our products. We’ve moved so far behind. But if a family was environmentally inclined, and they were still just stuck on recycling. Well, that’s kind of ridiculous. Right?

We need to have a belief in the next generation that they have the care for the legacy and the understanding of the context to be able to reinterpret that for what it needs to mean today. And more importantly, if they’re going to come together, they need to come together around something. Unless they have some ability to affect what that thing is, is we’re going to be hard for them to commit to one another.

They can commit when they have some ability to affect that decision. They will commit when they have some ability to affect where they’re going.

Cory: Right. I love that. And as you said, ensuring everyone has that voice in that process is so important that they’ve bought in and are willing to participate.

Tim: Well, and I think just an important point around that too is that there’s a difference between a voice and a vote, a family might decide that certain people in their family have a voice, and some people have a vote, and the voice. And as long as people understand how that’ll work, as long as people feel heard, people can go along and be happy with a choice that they wouldn’t have themselves made. As long as they feel good about the process.

Cory: Yes. Feeling good about the process rather than the result is great. Tim, as we near the end of our conversation today, there are a few questions that I ask each guest. Are you ready for the tough ones?

Tim: Sure.

Cory: Alright. Now what is one key strategy that you believe is most essential to building a successful family enterprise?

Tim: I think this is maybe another thread that is run along a lot of our discussion today that we haven’t talked about yet, which is inter-generational teamwork.

For those dreams to be passed on, for that expertise in that particular business to be passed on. For that trust to be built, you have to have teamwork between generations. And I love the word teamwork because it’s a gradient.

When that top draft pick comes up on the flames, even if he’s an amazing player, he’s not the captain the first day he joins the team. And he might not even be on the 1st unit power play, but he will eventually earn that.

Eventually, the team will understand what that guy is capable of, and they will give him responsibility commensurate with his capability. But more importantly, they will always be aligned with where they’re all going. They’re all trying to win the game.

And I think that’s what family businesses need, whether it’s within the business structure or outside the business structure, you need to have that intergenerational teamwork.

Cory: I love it.

Tim: The rookie coming in doesn’t need to have a vote, but they need to have a voice, and they need to at some level have growing responsibility. Because unless they learn alongside, then they’ll just never learn. And when you are no longer there to pass this along, they’ll just be kind of left to fend for themselves with the experience that they’ve never garnered.

Cory: Fantastic. That does go so well with our conversation, Tim. Now next question would be, what is the most common challenge that you see family enterprises encountering when it comes to wealth transition that and generational continuity?

Tim: I think it’s a difficult conversation. I gave myself a birthday present over the family day long weekend, which was when my family was up in Whistler skiing, and then that’s the busiest weekend, the year up in Whistler. And so I gave myself a ski class, and it’s called the Extremely Canadian Steeps Program.

They’d take you on all of the gnarliest scary parts of the mountain. Also, because you get to bypass lift lines. Anyways, they’re taking us to these scary parts of the mountain and these are consequential steeps. There’s a couple of times they said, we’re coming in here and someone had died here, died here this year.

Cory: Wow.

Tim: But, don’t worry. they were just really stupid. So as long as you listen to me, you’re going to be okay. They guide you. They give you step-by-step guidelines and advice on how to do it well and do it properly. They take something that’s super consequential, super dangerous, and they make it approachable.

That’s what difficult conversations are in the sense that when you don’t approach them well when you don’t know them step-by-step and you don’t have a safe space in which to have them, they’re very consequential.  They can scar permanently. They can even maim.

And that’s where having an advisor who is good at holding that space, who is there to keep everyone safe, that is there to give off ramps or to reframe or to I think what you meant was, that’s helpful. And it takes those consequences and it tames them.

But I think the problem is without that external support, you’ve walked into this dangerous terrain, and you’re just hoping for the best. I think that’s why maybe even wisely sometimes families just don’t have these conversations, which creates its own basket of problems.

Cory: Absolutely.

Tim: And so I think that’s one of the really big things that families struggle with. That’s one of the ones where families just can’t be their own doctor.

Cory: Love it. And as you said, some of these con conversations can feel like life or death. Such a large consequence if it goes wrong. As you say as advisors to be able to to hold that space and allow for that to happen without it being so consequential.

Tim, in your experience, what would you say are the top 3 qualities that successful family enterprise leaders possess?

Tim: I mean, there’s so many, but you said you said 3. I had to limit it to these. I think humility.

You need to be able to admit when you’re wrong to know what and what you don’t know. I think almost by definition, all of these family business leaders, they’re not going to be in the 1st generation, and so you can’t think you’re playing tennis. You’re playing basketball. You’re playing football.

You’re playing a team game at this point, and you have to understand where your, strengths end and your limitations start and where you need to be able to admit that and get support, say sorry, all of those things. I think listening I think part of the ability to move forward into the future for families is the ability to communicate well.

It really fundamentally starts with listening to be able to hear what other people are saying to be able to tease out what they’re really wanting to talk about because I think when people feel heard, they almost don’t always care what you need to what you have to say. Because they’re already kind of aligned with you.

I think the last one is being a learner. We have a tremendous capacity for self-deception. I myself included in It’s really supportive of us to be able to adopt the mindset of a beginner to know that we haven’t figured things out.

We haven’t lived our lives yet. We’re just figuring it out whether it’s living your life, being a parent, or being a partner. We haven’t done this before and so we need to have grace for ourselves.

We also need to, I think, adopt a learning mindset that we can continue to grow that we can continue to lean into these challenges, and become more.

Cory: That’s amazing, Tim. They adopt the mindset of a beginner is absolutely. There’s so much to learn in life and the curious one is definitely a great quality of a leader. It’s that fantastic.

Now before we conclude our discussion, I’d like to highlight where our listeners can engage in more conversations that you’re having. Would you kindly provide us with where our guests can find you?

Tim: So I’m active on LinkedIn. I’m there Monday, Wednesday, Friday. I’m posting somewhere between 3 and 5 times a week, so you can catch my content there. If you’re interested in geeking out on family enterprise stuff. You can reach me on my website,

And I’ve got my email in there. You can book time with me if you want to reach out. And I also work and advise families with LGA, Lansberg Gersick, and Associates. So I’m available on both of those websites. So if you want to reach out, that’s where you can find me.

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

Tim: I don’t think so. I think we covered everything. We covered a wide variety of topics.

I think I said a lot of stuff that I didn’t plan, and I hope was not terribly incorrect. I really enjoyed the conversation. Thank you, Cory.

Cory: Fantastic. Well, thank you Tim for sharing your time and the experiences and expertise that you have. Your insights have been extremely valuable and I’m grateful for the contribution to this episode, and I’m sure our listeners will enjoy the conversation as well.

Tim: Awesome. Thank you, Cory!

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This is not an official program of Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those of 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 to discuss your particular circumstances before acting on the information presented

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