Built to Bend: Creating Family Cultures That Can Change and Stay Connected

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In this episode, we’re joined by Katherine Bright, Family Enterprise Consultant at Trella Advisory Group. For nearly two decades, Kathy has helped family businesses navigate the decisions, relationships, and responsibilities that shape continuity across generations. Her work spans consulting, education, and board service, giving her a grounded understanding of the challenges families, boards, and advisors face when certainty gives way to change. Alongside her client work, she teaches and develops training for family enterprise professionals, focusing on leadership, succession, governance, strategy, risk, and productive family relationships. Our conversation explores the role curiosity can play when answers are not yet clear, including the fine line between anxiety and excitement, how families and boards respond to uncertainty, and what can emerge when failure is treated as part of growth.

Kathy invites us to consider what becomes possible when families loosen their grip on certainty, ask better questions, and keep choosing one another even when the path forward is still taking shape.

 

About Kathy Bright

Katherine Bright is a Family Enterprise Consultant at Trella Advisory Group and has worked in the family enterprise world for nearly twenty years. As a consultant, educator, and board director, she works with family businesses to help them thrive across generations. In addition to supporting family enterprise clients, Kathy also guides advisory professionals, helping them better understand the complex needs of family business clients.

From university teaching to tailored training programs for family enterprise advisors and family enterprises, Kathy’s expertise as an educator combines both technical guidance and strong interpersonal connections. She also brings extensive hands-on experience with strategy and governance through her service on multiple family business, government, and not-for-profit boards. Kathy is passionate about leadership, succession and continuity planning, strategy, risk management, governance structures, fiduciary responsibility, and helping families maintain positive and productive relationships within their enterprises.

 

Resources discussed in this episode:

 

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

 

Contact Kathy Bright | Trella Advisory Group

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Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at CI Assante Wealth 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 Katherine Bright, Family Enterprise Consultant at Telos Group. For nearly two decades, Kathy has helped family businesses navigate the decisions, relationships, and responsibilities that shape long-term continuity. Her work spans consulting, education, and board service, giving her a grounded understanding of the challenges families and their advisors face across generations. Alongside her client work, she teaches and develops training for family enterprise professionals, focusing on leadership, succession, governance, strategy, risk, and productive family relationships.

My goal is to be the most curious person in today’s conversation with Kathy as we explore what can happen when families and boards loosen their grip on certainty. We’ll look at the fine line between anxiety and excitement, the role curiosity plays in better decisions, and what becomes possible when failure is treated as part of growth. The conversation also opens a deeper question about what it means for family enterprises to keep choosing one another while building the trust needed to move forward together.

Now, let’s dive in!

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

Kathy: That’s great. Nice to see you, Cory.

Cory: Kathy, imagine you’re delivering the commencement speech to the graduating class of 2026, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise you’ve gained along your career?

Kathy: Well, to start with, I would have to say I feel very sorry for those graduates that are having to listen to me. Like, how did they draw the short straw? And this question itself cracks me up a bit, because my eldest graduated from university just this spring. And I was in attendance there, and I had the opportunity to listen to his grad speech. And quite honestly, Cory, it was a real disappointment. It was like something about a salad. And that made me reflect. The fact that it wasn’t a really spellbinding speech made me reflect on what are our expectations for these speeches, and why are they so seminal in our lives? And I think that, of course, it’s that recognition of reaching a milestone and achieving a major accomplishment. But graduation itself isn’t the thing that launches you. It doesn’t start some invisible score clock that’s counting down and judging your performance, but it does give us an opportunity to pause and take a breath and reflect a little bit.

So if I were truly making a graduation speech, I probably would avoid any reference to a salad. But I also think that rather than these fancy metaphors, which we can get caught up in, I would be a bit more straightforward. So in life, I may have only learned very few things, but for sure, three big principles for me are to try and approach life with curiosity, not judgment, to try and live with a measure of integrity, and to work every day to invest more in the relationships in my life than in any bank account. And I think that those three things are so important to me, because, for example, with curiosity, and by the way, Walt Whitman did not say approach life with curiosity, not judgment. That is a misappropriation, but that’s not important. You know, the world really likes certainty. But what I’ve observed is that the people who really thrive aren’t the ones who come with what they think are all the answers. Instead, it’s the people who remain curious to ask really, really good questions.

Judgment shuts down questions. It shuts down learning. It shuts down conversation, but curiosity opens doors and it opens minds. And there are a couple of places where that principle comes to life. And one place I see it is actually in the boardroom, as banal as that is. But the curious board challenges management and staff to think differently, to expand their vision of what is possible, and to be less afraid to fail. And the other place where I see the curiosity principle coming into effect is in families and in family meetings, where we can help a family turn off that judgment and lean into curiosity. They inevitably learn something new about their family members. These people that they think they know so well. But we are always growing and learning and changing, and it’s maybe not always as obvious on the outside. So that’s one of my key principles.

Another one, of course, is around integrity. If we can live our lives in such a way that whatever we do can be on the front page of a newspaper and headline news, I think that that allows us to live life fully as ourselves. So if we can be in harmony with our values and our beliefs and compassion for fellow humans, we live a life of integrity. And in so doing, we then are freed from worrying about what other people think, what other people are doing, what other people may think of us, and what we think about them, because we are living fully as ourselves.

One of my early mentors used to say to me, what we are comes out. And it took me such a long time to really wrap my mind around what he was saying with that phrase. But to finally really embrace that, I don’t need to worry about what anybody else is doing, because what they are will come out, and it is visible to everybody else. And I don’t have to talk too much about what I’m doing because what I am comes out, and it becomes visible to others.

And then the third one, I guess, is around relationship. And, of course, our greatest assets don’t ever appear on a balance sheet. It really is the people that we choose to walk alongside in our life. The investment you make in knowing yourself and knowing others, and then doing wonderful, amazing things with that knowledge, provides those endless dividends. And it’s easy to put stuff off until the kids are older, until I have more time, or until my business is booming and growing. But those relationships are really the ones that make our lives worthwhile.

And certainly, I talked a second ago about the value of a mentor, and that is one relationship that I invest in every day. How can I learn from others around me, and how can I share, maybe any of the mistakes that I’ve made, so that others don’t have to make them?

So I guess that’s what I would think about, is building a life based on what’s possible, not what scares us.

Cory: Amazing! Kathy, as you mentioned, the expectations that people have as they reach milestones in their life for moments, where do you see that show up in relationships, the families, and business executives that you’re working with?

Kathy: I think that those milestones are incredibly important. It does give us the opportunity to take a pause and to think a little bit and reflect. Sometimes we talk about them as precipitating events, because we do look to them to sometimes set us off on our next adventure, or doing the next piece of work that is before us. So I do think that milestones are important.

But I also think that oftentimes, we put off living today, because there is some milestone coming tomorrow. And that’s the piece where I think that we get a little bit caught up perhaps, in delaying our lives instead of living them today. So those milestones are important, but I wouldn’t put off the living, and I wouldn’t put so much expectations on ourselves and on others around those milestones.

Cory: I sense a lot of pressure from people around those milestones. Around themselves.

Kathy: And it’s so interesting this time that we’re in, because we’re talking about the older or the younger millennials and our Gen z’s as being the anxious generation. And so we see these lives, that for whatever reason, whether it is the way that these kids have been parented, or whether it is the omnipresence of social media, or the crazy political environment we’re in, or COVID, there are a million contributing factors, but we do see this rise of anxiety. And I think that we put so much pressure, and there is such a microscope on these events, and everything has to be perfect and worthy of Pinterest and social media. I think if we can dial it back just a little bit by being really curious instead of judgy, and being really focused on being fully ourselves and just dial it back a little bit, we’ll have a healthier, happier group of kids.

Cory: Kathy, as you were saying that, I was thinking about our relationship as generations. I don’t think it’s one generation. I think it’s been a while, but our relationship with ceremony. And as you were talking about those expectations, I wonder if it’s that we aren’t practicing that ceremony enough. And so we put that expectation on this one moment, because we haven’t done that moment, or celebrated those little moments in such a grandiose way, or such a way that we can mark that.

Kathy: That’s a really interesting idea, Cory. I think that we do get so caught up in being busy, and we are an increasingly secular society. Not that all ceremonies are religious, but it is a place of ceremony. And so if you start stripping out those opportunities, it does heighten the focus on the ones that we have left. And maybe that’s part of our journey, to figure out how to celebrate the everyday, as opposed to needing that religious moment or that lifetime milepost.

Cory: Absolutely. One of the things that I was struck by is when you talked about that word, certainty, and then you rolled into talking about the curiosity of boards, around how they can support management. I often think of corporate governance as a risk management mechanism, and that curiosity, we’re talking about some tension here. How do we support that tension and allow our brains to get to that point of curiosity?

Kathy: To me, learning to live in that tension is actually, the role of a board is to exist in that space where we both hold the line and have that oversight, and hold people to account, and support, inspire, question, and probe.

Early in my career, I read, Built to Last and From Good to Great, the Jim Collins, Porras books. And they always talk about how we as humans have a unique ability to hold two completely contrasting thoughts and tensions and realities, and live in the space in between those two. And I think, as really honestly dry and possibly sometimes soul-suckingly boring governance can be, it is the framework that gives us that structure to allow us to be intentional, and do the risk management, and provide the oversight and all the compliance and things that boards need to do, and push for exploration, seek new opportunity, and be super curious. So to me, those things go together really nicely, but it is a muscle we have to develop.

Cory: Right. And, Kathy, when you think of the mindset of the individual and the collective, how do we prepare ourselves to be there in that moment to be able to show up in the way that you describe there?

Kathy: I think that it is a muscle we develop. I don’t think that we as humans come fully formed. I think that our natural inclination, as I said earlier, is a pull towards certainty. And if we look wider in the political spectrum, we see that pull toward black-and-white thinking. We see that desire to have simplistic answers because it requires less of us. So I do believe that it is a skill that is developed with a lot of intention.

If I think about the businesses and the families that I work with, that really is the place that we are trying to guide them, to develop that skill set and those muscles that allow them to exist in this space of contrast, and exist within the end of risk and opportunity of compliance and curiosity, in that space of my sister and my colleague. And I think that those are the spaces that we are really working with our families, our clients, ourselves, our colleagues, to get into and get comfortable.

Cory: You make the comment of how dry corporate governance can be. I think of showing up in that room, and we need to make quorum, and you have expectations as a fiduciary to be there, or maybe we’re advisory and you still made a commitment. But I think of all those other things that are going on. You talked about how full the mind is, and maybe some of that anxiety as you mentioned, the current generation that’s kind of starting to take ownership and take leadership. Where are you finding that boards are able to leave the things at the door, the politics that you mentioned and all those pressures, and be able to actually show up as here’s what I’m here for, and the world is demanding a lot from me.

Kathy: Well, some of that just comes from getting old. You start to have a little bit more perspective that most things really just are not that dire. And many of the decisions we make are not going to, in and of themselves, going to make or break the company or the environment or the trust. I think that if we can give ourselves a little bit more perspective, we can identify those very few decision points that actually are critical, and the rest kind of like the rest of life. We’re all just kind of figuring it out as we go along. There is no manual.

I think that as boards, we can also work to really identify what are the risks here. And for those that are not significant, we can delegate some of those decisions. We can make them quickly, because, quite frankly, they’re not as dire.

I think one of the other things that I talk to my clients, talk to my children about, is anxiety and excitement physiologically feel the same. Heart rate increases, blood flow increases, cheeks may flush, we may start to perspire in sweat. It is the mental game that determines whether we are anxious or whether we are excited. And so if we can start to think through and use our prefrontal cortex a little bit more to help us manage the way that we think about, talk about, and experience these different situations that we’re in and maybe start to reassign some of that anxiety into opportunity, start to reassign some of this risk into possibility, we may have a bit of a different experience.

Cory: Kathy, I’m going to bring up the salad story again here for a moment. We’ve talked a lot about curiosity. I think about creativity, and where creativity lives in the life of executives and board members. In strategic planning, I hear a lot of copy and paste, adjust the numbers, and not a lot of creativity. I’ve listened to numerous podcasts about amazing founders, creativity, and pushing the mold. And you get to this point of maturity, and you add these different layers on to protect what’s been created. And then people aren’t willing to take the risk, but they’re also not really exercising that muscle of creativity.

Kathy: I would say boards are not known for being the hotbed of creative thought. It is often more about compliance and risk. I really think that that’s part of the art, though, of being in an inspired place, is to make sure you get all that work done. It’s part of our fiduciary duty. But if I really want to add value as a board, I think that moving into that space of curiosity and creativity and thinking about what is possible and where the opportunities lie, that’s a much more productive space. And as you said, those entrepreneurs who are building incredible things aren’t looking at their compliance. They are looking at what is possible. Where are the gaps? How can I fill them? They’re artists. It’s just their medium is a little bit different.

Cory: Absolutely. You think of Steve Jobs and how much he bet the entire farm, or Walt Disney and what he took to build those films in those early days. And they really were artists in many different ways.

Kathy: That same sense of creativity, of pushing boundaries, of looking at old problems with new eyes, seeing what is possible as opposed to what’s already there.

Cory: Kathy, if you were speaking to a family member, or maybe a non-family member who’s in that executive position, and they’re seeing opportunity, and they feel the creativity and passion, and they’re just trying to figure out, how do I pitch this? How do I show this vision that I have, this opportunity, to a group of people whose job is to make sure we don’t sink the ship? How could they approach that?

Kathy: So, Cory, you’re taking me back a long time. I used to work with one of my mentors. I’ve been very fortunate. I’ve had a few in my career. But we actually taught a class called opportunity recognition, and we taught this in the MBA program, and I taught it in undergraduate. I taught it in executive education. We did it for years. It was great fun. And we talked about how you frame opportunity to bring it to life.

And so, there’s the coaching of here’s how we think about it, and here’s how we can frame it, and here’s how you bring it to life, and here’s the data that you need to show. But I think that one of the things that I’ve learned in working with so many entrepreneurs and so many really inspired business founders or next-generation successors is around how do we build the culture that embraces opportunity? How do we build a culture that embraces failure? Because that’s the dark side of opportunity.

And so, how do we figure out how to fail fast so that we can recover and build that culture of creativity, opportunity seeking, tolerance for small failures, as we go along. I think that that’s actually the place where I would start, as opposed to the technical, here are all the elements that you need in a good pitch deck. Instead, how do we build that culture of opportunistic market scanning, creative risk-taking, within boundaries for a family.

Cory: I think of companies like 3M, or even Alphabet, and all the amazing things that Google has been able to develop because of that culture of assigning a certain amount of resources for that creativity. What is it about those cultures that allows that to function so well?

Kathy: I think that it really is that idea that for us to move forward, we need to be constantly reinventing ourselves. And I think that as humans, that speaks to a real primal urge to be authentic and be able to recreate ourselves and reinvent ourselves.

And so whether we’re doing it through exploration of product, or whether we are doing it through education and growth of our own minds and abilities, or whether we’re doing it through redefining relationships, I think that it just speaks to a bit of the human condition. I think cultures without creativity wither, and that’s where you see, you know, the old IBM that almost imploded due to their own bureaucracy and inability to reinvent itself. So I think that that’s a big part of it.

Even Elon Musk, think of him as a person, a leader, his companies, whatever you will. I know that that’s particularly now a bit inflammatory. But one of the things he talks about is his tolerance for failure. And by any measure, by any psychological measure or by any monetary measure, his tolerance for failure is pretty high. As long as we don’t make the same mistakes twice, we now know way better what to fix. And I think getting really comfortable with that culture of we try things. We don’t expect them all to work, but we try them and we learn, and then we move on to the next thing.

Cory: Yes. And, Kathy, when you think of maybe a little bit outside of the business circle here, in family cultures where families are reinventing themselves, and are not only curious, and I love the remaining curious of those who we think that we know, thinking about some of those rituals and celebrations, and things that actually keep the family together. Because as much as they might not think it, families have that choice to remain connected through business and ownership. And so, how have you seen that reinvestment into family culture and relationship succeed?

Kathy: I have a family right now that I’m working with, and one of the remarkable things about them is that they actually have had a number of cutoffs inside the family, a large number of cutoffs across multiple branches. And yet the majority continues to show up and reinvest and recommit. And one of the things that I’ve been talking with them about is that you have the choice, and we need to come to the party ready and willing to make the choice to be there, to be open, to be willing to hear the good things and the hard things. And we can’t force anybody else to that party. I think that this idea of divorcing your parents is having a moment. There’s a lot in the media and social media about using boundaries to kind of wall oneself off from what may be perceived as past injustices. And for sure, we have to have boundaries. But I see the weaponization of boundaries as something that is really detrimental to families.

So when I’m working with these families that have these cutoffs, we’re talking about how does one maintain boundary, but also maintain relationship, because I don’t think that it is an on-off switch. I think that we don’t need to weaponize our boundaries. We can maintain, but also stay in relationship and be open to hearing some things that we may not love to hear, but that help us grow closer over time.

Cory: Absolutely. I so appreciate that the family hasn’t defined themselves by those past experiences with that cutoff. That it takes a lot to dust yourself off and say, no, we’re choosing to be here. And as much as maybe those members are choosing not to be here, we can still invest in those that have stuck around.

Kathy: It’s pretty great. And helping them redefine what success looks like, because success does not look like everybody together around the dining room table for Thanksgiving. If that is our definition of success, we’ll fall short every time because we can’t control whether or not Uncle Tom wishes to reengage with the family.

So our definition of success has to be that we let people make their choices, and we celebrate those who choose to be together. And that has been a real mind shift for this family. And I wouldn’t say they’re all the way there yet. I would say we’re opening up the door to find what success looks like.

Cory: I think of that in the context of, you mentioned those events and those moments that hit social media, and that not everything needs to be perfect or appear the way that others create these images of success. Our success can be different and defined by us.

Kathy, a double-edged sword, that boundaries, as well as as that weaponization, how do we take what this current generation is standing for and say, we accept that, and here’s some moderation from this, and here’s the intention, or really what what we’re hoping to get out of it, versus, if you don’t comply the way I I’ve set my boundary, I’m gone, or you can’t see your grandkids, or whatever sort of weaponization. I’ve definitely seen those around as well.

Kathy: I think that whenever we embrace any philosophy too strongly, we risk pulling it into the dark side. And so, this is just one recent example. We’ll go back in history and be able to come up with 500 more. I kind of see it as the development of each generation as they go through their own experience. What new areas are we going to test out, and how are they going to work for us, and are we going to take it too far? And then the pendulum swings back a little bit more towards center.

Personally, I have a lot of patience for all of it, because I just see it as part of our journey as humans. We think about something. We cut out a little pattern and make the coat, and we try it on and look in the mirror, and we’re like, I don’t know if I like this coat. Maybe I make some alterations. And then maybe at the end of the day, that cut and fabric and kind of coat just isn’t going to fit, and so we take it off. So I think that it happens generation after generation. And part of just the way that I have chosen to go through life is to give lots of grace to people as they are trying to figure this stuff out. And I have a belief, again, if we live in integrity and we are just living our values and we are fully ourselves, and our goal is to create acceptance and create space for others to be exactly who they are, those little kinks work themselves out of the system.

Cory: Yes. Kathy, I think of your metaphor of trying on the jacket, taking it off. I think of that repair, that declaration that I’ve made, I tried it on, and now I need to repair from something that wasn’t I thought it was, in line with my integrity. Uncle thought he was better off leaving the family, and now he wants to come back. How can we be welcoming to somebody who says, maybe that wasn’t what I wanted after all?

Kathy: I mean, to live life with compassion, I just think I am constantly making mistakes, trying to recover, trying to learn, and just do a little bit better next time. And so having the humility to own up, take responsibility, be accountable, and do my own work, that’s on me. And how others choose to accept or not accept is on them. Right. But that’s that, commitment to integrity, commitment to being accountable, commitment to doing my own work, taking responsibility, showing up the way I want to show up, and when I don’t, reflecting on it and going back and trying to fix it.

There’s another culture point that I find is quite successful with families, is that commitment to doing my own work. If we can build that into our family culture, we can go far together, because we’ve done that work on our health. And that work both helps us become better, but it also allows us to make mistakes, because we are fallible, imperfect humans, and we will make mistakes just like in business. We will fail fast to do better sooner. And so, I think that it is coming full circle to that. Let’s tone down the anxiety. Let’s reprogram ourselves to think about it as opportunity and excitement, not anxiety and risk. It all fits together if we allow it.

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

Kathy: Here we go.

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

Kathy: Well, I think that it goes back to what we’ve been chatting about here for the last little bit, which is around how do we invest in the development of our people? And our people include ourselves and our families. So if we are very intentional in that investment in human capital, I think that that is the most important strategy. And from that investment comes whatever topic area it is we need to focus on at that time. So it may be that we recognize that we’ve got an accountability gap, and that’s where we’re going to focus our attention. Or it may be that we recognize that we’ve really got to build our skill set in terms of dealing with uncomfortable conversations so that we can push through and get back into alignment. It may be that we need to spend some time and energy and thought and governance, and just pry our eyelids open while we try to stay awake and read that book, or that document, or engage in that meeting one more time. I think that there really isn’t a silver bullet for families. There really is not a “follow this path, and you will come to enlightenment and success.” I think the only thing we can do is invest in our human capital.

Cory: I appreciate the way that you describe that, because if we’re doing that together, there’s some relational capital that’s being developed at the same time.

Kathy: Always.

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

Kathy: Well, research has indicated, has told us pretty clearly, that if we look at either the enterprise being broken apart, or bankruptcies, or however you want to call failure of that multigenerational view, 62% of the time, it comes from unresolved conflict in communication. So that kind of is the bucket that says, with unresolved conflict, with an inability to build skills around communication, and an inability to gain alignment between family members, we know that, statistically speaking, that is going to be the most common challenge for a family. And categorically, I would agree. I also think that that’s a bit of a catch-all. It’s a big bucket.

So if I were to piece it down much more finely, I would honestly say that it comes from doing the work, showing up the way we want to show up, and being accountable for not only what comes out of our mouths, but the impact it has on others around us. And so that piece around being in integrity, I think, really is the core of that. Learning how to self-manage, becoming very good friends with your prefrontal cortex, and understanding how we need to show up for ourselves, for others, for our business, for the long term, how we need to inspire those around us to continue to do better and to be better, and be unafraid and unabashedly ourselves. It starts with us. It’s us doing the work.

Cory: Absolutely. I think it’s something that I want to highlight there. The says and do’s. So many people judge themselves based on their intentions, not the result of their actions and what they say. And as much as it might have been great intentions, we still need to see what is the impact of how that was delivered.

Kathy: Yes. And that willingness to be a bit vulnerable and to accept that responsibility and not deflect, I think, is really important. And give ourselves the grace to make mistakes. Jim Collins was so right to embrace the AND. It’s the beauty of the AND. These two polar opposites that create this tension, and managing that tension through all of these different places and iterations and environments, I think, is how we get through.

Cory: Absolutely. And, Kathy, in your experience, what are the top three key qualities that successful family enterprise leaders possess?

Kathy: Well, I think that it is pretty tightly tied to what we talked about earlier, that idea around integrity and curiosity and relationship. But if I were to tighten that up even further, and I’m thinking of family enterprise in the academic sense, like the entire collection of assets, not just an operating company, and not just our investments and our balance sheet, but the entire collection, our human capital, our social capital. I think that those who are most successful do go through life with a measure of humility that really helps with that accountability and that relationship piece and the curiosity piece. For us to have a bit of humility, a bit of humbleness, allows us to be more self-reflective and be more thoughtful, and to recognize that it takes a village. It isn’t just my own brilliance that has gotten us here. There is a little bit of luck and a lot of work from a lot of different people in different ways. So I think that piece about humility is one. I don’t think that we can escape the importance of curiosity because it just changes the landscape from what is to what is possible. It moves us from reaction to inspiration. So I think that that element of curiosity is so important.

The other thing that I really appreciate about the families that I work with, those long-term family enterprises, or just even the view, the anticipation that it could be long-term, is that type of thinking, is the willingness to think about what is possible over the long-term and not be ruled by fear today, not be ruled by what’s expedient, but to be patient for for what is in the best interest of the family enterprise over the long-term. That long term-thinking, I think, creates the space for generational success.

Cory: Kathy, before we conclude, I’d like to highlight where our listeners can engage in more of the conversations you’re having, as well as any resources you think are worth highlighting for our audience.

Kathy: Well, if anybody ever wants to talk to me, the easiest place is through Trella, which is the wonderful firm that my colleague, Judy, started a number of years ago. And there’s a small tribe of us who’ve all been friends and in this space together for an awfully long time. And I just feel so lucky to be able to work with such incredible people. So, always through that medium and LinkedIn.

But I do speak at various events, and I teach in the Family Enterprise Adviser program through Family Enterprise Canada, which is a wonderful organization for both families, practitioners, and advisors. And that group of individuals are just so inspiring, and there are a bunch of people doing way more impactful things than I possibly am, who are really inspiring and a great source of information and wonderful practice.

Cory: Wonderful. And since your friends have been on the show, there is a new newsletter that Trellis put together that takes all these wonderful thought pieces that Kathy and her colleagues have put together, which I believe were being done previously. And now there’s just a wonderful place to have that delivered. So I think that that’s a great resource to highlight as well.

Kathy: Thank you, Cory.

Cory: I wanted to make sure 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?

Kathy: I really appreciate the approach that you take with this, Cory, about being the most curious person in the room. As you can see, that’s a definite theme for me. So thanks to you for the work that you’re doing in highlighting some different approaches and ways to think about things, and allowing people to have space for their personalities to come forward. I think that it’s a real service to families and advisers as we try and find the connections that make this work possible and worthwhile. So thank you very much.

Cory: Thank you, Kathy. I very much appreciated learning alongside you, your expertise, your experiences, your wonderful stories. I found it incredibly valuable, and I know that our listeners will as well. So thank you so much for your contribution.

Kathy: Thanks, Cory.

As we wrap up this episode, we invite you to reflect on Kathy’s reminder that growth often depends on our ability to stay present in tension, to hold responsibility alongside possibility, and to leave room for learning when the path forward is not yet clear.

Whether you’re part of a family enterprise or walk alongside one, this conversation highlights the value of creating cultures where people can question, experiment, and grow. With greater perspective and accountability, uncertainty can become a source of progress rather than something to avoid.

Throughout our conversation, Kathy brought forward the discipline of staying curious when certainty feels more comfortable. She showed how boards can protect what matters while making room for creativity, why learning requires space for mistakes, and how families can remain connected while respecting individual choice. Her perspective reminds us that progress often begins when we shift our focus from anxiety and risk toward possibility, learning, and the courage to keep trying.

If you’d like to learn more about Kathy’s work, you’ll find more about Telos Group in the show notes, along with ways to connect and additional resources related to today’s conversation.

Disclaimer:

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

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