Finding Yourself After Leadership: The Missing Chapter in Succession

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 Russel Baskin, Consultant and Certified Executive Coach with Trella Advisory Group. With a background in human development and two decades of experience in advising business families, coaching professionals in transition, and leading educational programming, Russel brings a thoughtful lens to the human dynamics at the heart of family enterprise. Formerly the National Director of Education and Programming at Family Enterprise Canada, she now specialises in governance, continuity, and individual development work, approaching it with compassion, clarity, and a deep belief in the connection between personal growth and family well-being.

My goal is to be the most curious person in today’s conversation with Russel, as we explore what happens when family enterprises slow down long enough to really listen to themselves and to each other. We touch on the quiet patterns that shape family dynamics, the stories we carry, and the moments when legacy and identity start to blur. Russel invites us to consider how thoughtful transitions begin not with answers, but with space to reflect, ask new questions, and move forward with intention.

Now, let’s dive in!

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

Russel: That would be great. I’m really excited to be here.

Cory: Russel, 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?

Russel: That’s a great question. One of the things I would want to share in hindsight when I look back on my life, and something that’s made a big impact for me, maybe more later on in life, but it’s definitely been a life journey of learning, is becoming more self aware about the thoughts, the thought process that I have, my thoughts, and how they’re connected with emotions and feelings. And I was thinking how we spend a lot of time, especially when we’re younger, and rightfully so, on things outside of ourselves.

We’re getting educated. As we get older, even more importantly, we’re trying to stay fit, we’re exercising, we’re eating well, we’re reading the right books, going to the right events, connecting with people for, our career path, whatever we’re learning, a lot of it is, or most of it is outside of ourselves. And we sometimes don’t pay enough attention to what’s going on in our own minds, in our own heads, and the patterns that get enforced because of the way we are thinking, the thoughts that we’re having that are left unchecked as if we have no say in the matter.

And so it was probably about ten years ago that I got much more serious about wanting to, take the self awareness that I have inherently had, and not my interest in personal development and human nature to start to strengthen that witness that I believe we all have, and to step back from my thoughts and to watch them as if on a TV screen or on a film in a movie, and give myself an opportunity to choose what I continue thinking about, and observing the patterned and maybe at times obsessive thinking that goes round in a circle, so that I begin to have a choice and don’t feel like I’m trapped in this cycle of either story that’s going on in my head that’s making me feel angry or sad, or whatever the emotion is that then feeds the story, that then feeds the emotion. And I think as human beings, we get trapped in that cycle, and it doesn’t do us any service. It’s not great for us, and it’s not great for the people around us.

So I think about being able to widen the space between our thoughts and our actions. So even if it’s ten seconds or fifteen seconds, we have that moment of consciousness of thinking, here something has happened. I’ve read this email. I’ve got off the phone with this person, and I can feel something is starting to bubble up. Either I’m feeling hot or I’m starting to make up a story about what that person said and what it meant, and decide on whether it’s beneficial to keep feeding that and fueling that fire, and to understand that we do have, we can have more control and more mastery of what we are thinking about. And that in turn helps us to manage our feelings and emotions and not feel that sometimes we feel out of control, or we become reactive, either through email, or the phone, or in person. So I think I put a lot of weight on self-awareness and bearing witness to our own thoughts and processes.

Cory: And, Russel, as you mentioned that input from external sources. The work that you’ve done with family enterprises, where do you see some of those external sources that fuel that cycle that you talked about?

Russel: Well, a couple of things. One is, I think it’s really important as advisors, especially when you’re working with families, to understand what is your process, what are your biases, which takes self-awareness to be able to understand what those are, so you can separate those from what’s going on in the room or with the family or with the individual family members.

And then I think it’s a way sometimes of helping individual family members who have got stuck in a pattern of reactivity with one or maybe more members of their family, or scenarios where there is this repetitive conflict, or repetitive backwards and forwards that is less about what is being said in the moment, and more about the stories that each person is telling themselves that is rooted in the past, and they just bring it forward. And sometimes we’re not even listening to the people.

It’s the minute somebody we know, especially like a family member, starts to talk about something, we think we’ve heard it all before, and so we’re already in reaction mode. So slowing things down, having people take a breath, and start to have some awareness of their contribution to the dynamic that’s happening in the room, I think is really important, and that everybody owns a piece of it. Whatever’s going on, we like to blame one person, but it’s my belief that everybody contributes in some way. And it’s exploring what part is yours, and then how you can change that dance.

Cory: Right. And, Russel, when you think about family members who make that comment, I’ve heard it all before, what are some of those scripts that you’ve heard?

Russel: Yes. There’s the “I’ve heard it all before.” Sometimes they’re not even saying it. It’s just happening. They’re not even necessarily conscious that that’s maybe the words that are going on internally. But they’re already thinking about their response and their answer and how they can counteract it, or there could be body language, like rolling the eyes or sighing. Sometimes people turn away from each other. So those are some of the signs. And then it’s about breaking it down, getting them to voice the inside thoughts to a certain extent in the outside. So what is it you’re actually thinking, and where does that come from?

Cory: Right. And thinking of different members in the family where maybe this cycle has started and continued, we’ve spent years or or months, and I’m sure it’s a slow pace in which these stories that were going on in the mind come about. What do you see as a contributor, and what are some of the things that tend to be missed because of that?

Russel: I think there’s a few things that contribute to this. When I’m working with my colleagues, with families, we’re we’re looking at the structures that are in place, shareholders’ agreements, some of the technical pieces, trusts, where ownership lies, some of the more technical parts of it, and how are they contributing to, or are they contributing to some of the discourse that’s going on that is conflictual, or where there’s resentment has been built. So sometimes it’s rooted there, or it’s contributing from that, which is why we explore that area as well.

A lot of it will be just from growing up together, especially if you’re working with g two, or g one and g two. There’s the parent and the child dynamic. There’s a sibling dynamic. So there’s that part of it. And you have to take all of those things into account. And coming from a place of empathy and understanding, I believe that if people had the capacity in that moment to act differently or to be able to reach across the table, they would. And so something is getting in the way of that.

Now I’m not a saint, and I don’t believe in “there’s good everywhere.” But certainly to start with, that’s the premise I begin with, that people are angry, or confrontational, or wrapped up in themselves, or can’t see what’s going on with the other person, because something’s going on for them that might not have anything to do with the person they’re trying to have a conversation with.

Cory: Right. I love the visual of watching my life through a TV screen and being that observer to my own life. When you’ve seen family members implement that strategy, what are some of the “aha’s” that have come about for them?

Russel: I think what happens is that they start to connect the dots between what they’re feeling in the moment and where it is actually coming from. Because if somebody says something and suddenly you’re having a lot of feelings, whether it’s sadness, or anger, or frustration, it can sometimes seem that it seems larger and bigger than maybe the incident warrants. Some people feel more than others, but sometimes even ourselves, we can turn around and go, you know, I don’t know why I’m just so angry right now. And that it can be without therapizing people. It’s more about looking back and going, you know, this situation just reminds me of when we were kids, or it could even be what happened last week and we didn’t get resolved, and now it’s being carried over.

So, yeah, that’s definitely something where people have moments. And often, it’s not when you’re actually in the room with people. It can be afterwards. Things take time to percolate and integrate, and then people could come back and talk about what’s come up for them in between the times that we’ve been working together.

Cory: And you mentioned the work that is done through some of the technical understanding, and that maybe some of the feelings that are unexplained come from just what is there, or maybe what’s unknown. Are there other aspects that you see as people are really navigating different points in their life, where maybe some of that starts to come up, where they’re maybe not able to necessarily put their finger on where those feelings are coming from?

Russel: I think one of the tensions that are present with family enterprises for certain is the tension between the generation that is about to exit out or at some point will, and the generation that’s stepping into their shoes or into their place and will start to take control. So there often can be tension around that. The younger generation or the rising generation are, you know, wanting more and more responsibility. They want to have equity. They want to feel like they can start making decisions.

We often talk about them being children or kids, but they could be 50 years old. And then the generation that often, especially in Canada, that were still working a lot with g one, transitioning to g two, they started the, if it’s a business or growing their wealth, from nothing, and it’s become part of their identity, a part of how they value themselves and how they feel they’re valued by others, and they just have a very close relationship with what they do and building this business, or these assets for the family. And there may have been a point where they wanted to retire, step back, and they have the talk, they have the conversation, but the actual actions don’t necessarily meet what is being said or being promised because it is so much more difficult than they thought, and then they have nobody to talk to about that. It can be quite challenging for everybody in the family.

Cory: And, Russel, somebody who’s listening to us right now, who’s battling with that idea of what is the value I’m bringing and how much control do I want, or that desire for control. And I think situational, there’s probably a different level of control that is desired. But what might they start to think about, and how could they bring that to different support in their life to really understand what that struggle is for them?

Russel: I think that what’s really helpful for business owners or wealth creators as they get to a certain point is to be able to talk to somebody, or do some coaching, or maybe it’s with a sort of, like a tech group, but a place where they can feel free to explore what it is they may want to do after they step back or step aside from what they’re doing now. And it’s not to say that they have to. A lot of owners will stay in their eighties and nineties, and that’s just the way it is. But being able to do that because it’s your choice, and not because you don’t know what else you would possibly do and you can’t see a life for yourself outside of the one that you’ve got, doesn’t really mean you’re choosing your life. You’ve become almost a victim to it because you’re trapped in a way.

And then you’ve got the next generation that are sort of waiting and don’t have an opportunity to really sort of make their mistakes and show up fully in what they can do, and also have that parent or the senior generation be there as mentors or to fall back on. So really exploring, who am I outside of what I’m doing today? What other things maybe would I love to do that I’ve never had an opportunity to do? Because I think it’s the generations coming after the baby boomers that have much more interest in life-work balance and family, and not at all be climbing the ladder and work, work, work. I don’t know that necessarily they’re going to face the same problems or the same challenges, let’s say, as business owners and wealth creators that are now presently in between their sixties and their eighties.

Cory: And, Russel, I find it so surprising when discussing this topic with entrepreneurs. They choose to be in business to create this freedom for themselves and their family, and find themselves in this position where they’re trapped. And so you mentioned a couple different resources. In previous episodes, we’ve explored peer groups, and you mentioned tech, which we’ve talked about. And I want to get into a little bit around the concept of coaching. You mentioned baby boomers, and there’s maybe a generational understanding of what some of the resources available are. What might that conversation look like from the beginning?

Russel: Well, interestingly enough, in terms of coaching, and I think you’ve just completed your executive coaching program at Royal Roads University. Now there’s a whole another avenue of coaching, which is retirement coaching, that has really taken off, especially in the in the US, but also here, which is trying to help not just business owners and entrepreneurs, but people that have to retire from accounting firms, sometimes from legal professions, doctors, take the next step in their in their lives, because we’ve lived in a in a world where sixty five is the retirement age, so that’s our culture, and then you go and have these golden years. 

Well, we’re now talking about thirty years, not five to ten years. That’s a lot of golf, and a lot of sailing into the sunset and grandparenting. And not that we shouldn’t enjoy those things, but especially for entrepreneurs and people who have had careers with a lot of responsibility, and where they’ve devoted the best part of their lives to that, it’s very hard to suddenly put that aside.

Now often, like the first year, the first eighteen months, two years, it’s fantastic for people because they’re tired, they’re burnt out or worn out, and they’re doing all these things. But then they wake up one morning and go, now what? The vacation’s over. And what am I going to do now? And so, do they start another business? It is very challenging because nobody’s really mapped out that part of our life journey. 

We all know about school, about university, about the career path, but nobody has started to map out what that retirement, or really that next part of our lives, could look like. And I think people are forging the path now and exploring, and finding out what works and what doesn’t. And a lot of that means understanding what makes you happy, what gives you purpose, what gives you meaning in life, how do you find joy, how do you feel like you’re doing something meaningful, so that you don’t end up falling into this depression and feeling of uselessness, which is very hard to get out of once you start sliding down that road.

Cory: And, Russel, speaking to the rising gen member who’ve maybe seen that senior generation successfully take that vacation, but now they’re back. Maybe there’s some of that push-pull for control. And what is it that you would say to that rising gen member to help them support the family as a whole, to allow them to find value that they’re providing themselves, but also the space for that member who’s maybe still in search for what their next act looks like?

Russel: Well, when we’re doing transition planning or any kind of succession planning for a family, there’s always a focus on the next generation. I mean, in every way you look and turn, and quite rightly, they’re the future. And so training, education, experience, starting really young, and helping them understand the responsibility, if it’s stewardship or if it’s ownership, or whatever it’s going to look like. At the same time, to start to help the exiting generation to think about and plan in the same way, and perhaps find mentors that have done that and can offer some guidance and advice, because we focus in on what’s coming next. I mean, we have a whole culture that is focused on youth and staying young and active, which is great. We all want to be healthy for as long as we can, but we also have to put some time and attention into the generation that is about to step out and step onto a different path.

And so it’s not just what are we going to do with mom and dad, it’s more like, well, how is this going to work so everybody can can thrive, not just with token positions on the board or volunteering somewhere, but to put the same kind of time, effort, resources, and really helping the exiting generation think through what they would like maybe the next ten to twenty years to look like. And is it part of the family enterprise? Is there another area? Is there a foundation they want to start? What is it that they would like? And I don’t think that there is an age where somebody needs to exit. It is a conversation to be had with the next generation and with your spouse to decide what that might look like. 

As long as everybody knows and there’s some kind of trajectory, or actually a written plan that everybody is on board with. Now not everybody may like it, but there’s agreement, and it’s transparent. It’s not your mom or dad is going to step out. I think it’s going to be in five years, but I’m not sure. I think what drives people crazy is just the unknown, and the shifting dates, and the topics of conversations that don’t get to the table to be discussed.

Cory: Right. And from a society perspective, there’s this talk of age 65 as mentioned. And what is it that could be done differently to support the generation as they’re looking further in the way that we do that rising generation member? And you mentioned the journey through university and learning, and all the things that we do to prepare people from childhood into adulthood. What is it that is missing that we could possibly do to support as a societ,y and maybe looking kind of broader?

Russel: I do think advisors are starting to offer, especially financial advisors, and advisors that are managing the wealth, financial planners, on helping the senior generation to explore what kind of life they want to create for themselves, what does it look like. So that’s definitely happening as well. There’s coaches that are specializing in this area, which I do too, but usually more in a consultative role. Things like being able to think about, if they took themselves out of the role they were in now, what is it that they would start to miss? Like, what would they have to replace?

One of the things that, it seems especially true for men, is around the social component. Because the minute you’re going somewhere to work, in an office, family office, or an office in the business, even if you’re not actually doing that much. You’re having that social interaction and that social contact. Also, how do you see yourself? How do you get value and get validated if you’re not overseeing employees, or you’re not meeting with business partners, or you’re not sort of maybe even mentoring the next generation coming in. Where are you going to get that satisfaction and meaning? 

And how do you take the purpose that has driven your life, which is often to build wealth in order to take care of the family, take care of the community, how are you then going to find that if you decide to step out of the business? So it takes exploration, and I don’t think we can do this on our own. It’s very hard. So we need to find somebody we feel comfortable with that has some expertise and is able to listen and to direct without there being some kind of ulterior motive behind it.

Cory: And you mentioned playing golf. There are many people who have great hobbies, and many people who really struggle to find what is in that hobby. I had a client years ago who we were having these conversations, and he said, you know, I walk into the coffee shop, and I see that group that sits there in the corner every morning, and that’s not for me. And I’ll never be the one sitting there. And he’s continued into his eighties now, building and selling businesses, and continues to do that because that’s the activity where he finds the most joy, and that’s become the hobby. And so how do we allow ourselves to define what that success is without the shame associated with “I need to get on the golf course?”

Russel: I think that, realizing it’s an open book, really, I don’t think that we want to be telling people how they should live their lives. I think what’s most important is there’s a sense of being able to explore and find out what works, and then discuss that with your family, you know, with your spouse, because that’s a changing relationship. Couples have been together for thirty, forty years, and most of that time, they’ve both gone their separate ways during the day. And suddenly, they’re thrown together again, and it’s not always a good thing. It takes some working out. And it’s the same with the family.

If there’s a family business, if that creator wants to stay on and keep doing that with this business, then how do you make that work with the rising generation? So it’s not sort of maturing yourself and leaving the business because you’ve got to give it to your kids, and you don’t have a choice. Here’s the problem. Here are some options and possibilities, and how are we going to make this work for everybody? And I do think that your client found what worked that helped him thrive. And I think we hear the word retirement, and then it has a certain picture for us. And that’s what we need to dispel, because it’s no longer really relevant anymore.

So there may be people that will just enjoy lots of different kinds of leisure, or participating in the world that isn’t buying and selling businesses, or running a business, or even doing volunteer work. And there are other people like your client that that’s to him, it’s like train building, that’s his thing, except for he doesn’t have to worry anymore, I would imagine, about whether those businesses are successful or not. There’s not the same pressure. It’s more coming as a hobby, as something that he enjoys doing that’s challenging, that connects him with people. And so in some ways, the activity might be the same, but the purpose that’s driving him is different.

Cory: Yes. And I think redefining or maybe even finding new words, Russel. The term retirement means to be put out of use. So why do we want to be put out of use?

Russel: We don’t. And when I went through the retirement coaching program that I did a few years ago, there were people trying to change that name, rewiring, all those sorts of things. But they need to catch on and take hold. And I don’t think that whole movement around it has really become where it has expanded and become big enough that people are just automatically calling it something different. So nothing else has come up. And because it’s so embedded in our culture. Even when you’re talking about, like our government, your retirement pension and all that, it’s still there. And you look at somewhere like France where it’s a different kind of setup, but they’re rebelling against the retirement age being put up.

So like all challenges, there’s not a simple answer to it. It’s complex, and it has sort of different ways, and different sorts of consequences of changing. So for some people, they wanted the age to stay at 65 because of what they received from the government. And as entrepreneurs, or even maybe people in different sorts of public companies where they want to stay on longer, those that would like to see the age sort of raised for sure.

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

Russel: I’m ready for the tough one. Well, the interesting one.

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

Russel: I think that, a few things. One is I think having empathy. I think being able to put yourself in other people’s shoes and understand other people, because you need to manage your family, outside stakeholders, and employees, if it’s an operating business. So, really understanding people and having the capacity to see where maybe they’re coming from. Being inclusive and collaborating. I think we’re moving away from this “one person leads the way.” You can’t really get much done that’s going to be sustainable if you’re not bringing other people along with you.

Cory: Right. That saying, “if you want to go fast, go alone. If you want to go far…”

Russel: Exactly.

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

Russel: I think one is transparency. Not talking about what’s being transitioned, not being open, and making sure everybody knows what’s going to happen rather than plan it on your own, and then it’s a surprise when somebody passes. Again, collaboration, your transition is going to involve other people, and bringing those people again along with you. They don’t necessarily have a vote, but let them have a voice, and understand your thinking behind what you’re executing. And then education, helping people understand, especially in larger, more complex family enterprises. There’s a lot of moving parts. And so having people understand what they are actually going to be responsible for, and what that’s going to look like.

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

Russel: Well, continuing on from our conversation, is knowing when to let go. When is it time to step away or to step down? So that’s in terms of transition and exiting, but also in terms of harbouring maybe grudges or resentments, letting go in that way, not carrying that burden with you throughout your life.

Self-awareness, like understanding yourself and being able to master your thoughts and your emotions, and surrounding yourself, especially in a family-run business, with outside non-family executives or advisers that can help balance that, your knowledge and the family’s knowledge, but also bring some professionalism and structure to what is going on. And I don’t mean that family members aren’t professional, but there’s less likelihood of disagreements where family members get stuck. If there’s non-family outside, maybe board directors that are bringing a different perspective, it just creates more space for people to show up differently.

Cory: And before we conclude our discussion, I’d like to highlight where our listeners can engage in more of the conversations you’re having, or more of the conversations that are relevant and helpful to the conversation that we had today.

Russel: So I can be found on LinkedIn. You can contact me through LinkedIn, and also through, I’m a consultant with Trella Advisory Group. We’re a boutique family enterprise firm of consultants across Canada. And we also have resources on our website, and advisors across the country that you’re more than welcome to reach out to. And even if it’s just some advice or some kind of direction somewhere, we’re always happy to talk to advisers and family members.

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

Russel: Well, there’s always more to talk about in this field because it’s so dynamic, and so variable and changing all the time that I think we captured everything that I thought we were going to capture today. So thank you. I appreciate conversation and curious questions.

Cory: Awesome. Well, thank you, Russel. I appreciate you taking the time to share your experiences, your expertise with us, and your insights have been incredibly valuable. I’m grateful for your contribution, and I know our audience will as well. So thank you.

Russel: Thank you, Cory.

As we wrap up this episode, we invite you to reflect on Russel’s reminder that meaningful transitions begin with honest reflection on what we carry, how we react, and the stories that may be holding us back. Whether stepping into leadership or stepping away, clarity begins by slowing down and asking what’s really driving us.

Whether you’re part of a family enterprise or work alongside enterprising families, her lens offers a way to navigate tension with empathy and hold space for both legacy and change. Russel reframes transition as more than a technical shift, it’s a human process shaped by courage and compassion.

Throughout our conversation, Russel named what often goes unspoken in transition, how control, identity, and legacy can become tangled in ways that quietly shape family dynamics. She explored the internal stories we carry, the habits we repeat without realising, and how those patterns can hold back both rising and exiting generations. With insight and compassion, she offered a view of succession that starts with self-awareness, deepens through empathy, and invites every generation to co-create a future where both continuity and personal growth are possible.

If you’re in a season of transition, stepping back, stepping up, or guiding others, Russel Baskin offers a thoughtful, grounded approach to the work of family enterprise. You can find her on LinkedIn or through Trella Advisory Group. Links and resources are in the show notes to help with your next step.

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 BeaconFamilyOffice@Assante.com or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.