Beyond Inheritance: Creating Space for Rising Generations to Thrive

Cory: Welcome, everyone! Thank you for joining us for Beyond Inheritance, Creating Space for Rising Generations to Thrive. My name is Cory Gagnon, and I’m a Senior Wealth Advisor at Beacon Family Office at CI Asante Wealth Management. I work alongside successful families as they navigate complexities of wealth, business, and leadership transitions, helping them align vision, values, and legacy, with clarity and purpose. I’m excited to have you here to join us for what will be another fantastic conversation.

Legacy Builders Live is produced by Beacon Family Office at CISante Wealth Management, where we help successful families design integrated strategies for their wealth, business, and legacy. Through values-first planning and intentional stewardship, we support enterprising families in creating successful successors and securing multi-generational peace of mind.

This webcast extends that mission, bringing together forward-thinking leaders and proven frameworks to help families and their advisors lead with clarity, confidence, and purpose across generations. If you have any questions during today’s session, please feel free to drop them in the Q&A box, and if time permits, we’ll address a few questions live, and if not, we’ll be sure to follow up with you afterwards.

Before we begin, just a quick note. The content shared during today’s webcast is intended for informational and educational purposes only, and does not constitute professional advice of any kind. The views and opinions expressed by our panelists are their own, and do not necessarily reflect the views and positions of their organizations that they’re affiliated with. We encourage viewers to consult qualified professionals regarding their own specific circumstances.

Now, let me introduce today’s panelists.

Vincent Valeri is Managing Director at Valerian Associates. He’s a trusted advisor to enterprising families, known for his integrative approach that bridges the gap between wealth management and family dynamics. First-hand experience in his own family’s business and training as a family enterprise advisor, Vincent focuses on legacy planning, leadership coaching, and helping families navigate complex relational challenges. Welcome, Vincent.

Vincent: Cory, good to see you. Kristen, always a pleasure.

Cory: And Kristen Heaney is founder and coach at In Three Generations. With a deep understanding of family wealth challenges, Kristen brings a unique voice to her work as an unprepared inheritor in recovery. She is a valued coach and consultant helping families implement practical strategies for wealth transition, while also supporting professional advisors in engaging with the full complexity of family systems. Welcome, Kristen.

Kristen: Thanks for having me, excited to be here.

Cory: During today’s webcast, our goal is to explore five key questions that help families uncover what really shapes successful wealth transitions. Drawing from lived experience, we’ll look at the mindsets, money scripts, and missing conversations that can either support or sabotage generational wealth transfer. This webcast will go far beyond inheritance, and look at the emotional and educational work required to steward wealth wisely.

So, jumping into our first question. How do we help the next generation figure out who they are without forcing them to become who we expect them to be. And I’ve seen this play out in families where the next generation is deeply grateful, and also quietly stuck. And when we’ve identified this and define for somebody really where they are, with them, that resentment or loss of confidence can really start to be identified. And that can be a risk to the individual, the enterprise, and the full system.

So, Kristen. Over to you first. Bringing up that unprepared inheritor in recovery, what identity pressures did you experience personally, and how do you see those play out in the families that you work with and today?

Kristen: So much, I think, especially for people who do have this image in their mind of what it looks like to thrive as an inheritor, to thrive as a business successor, whatever the role is. We all have some mindsets to overcome in order to become confident. And for me, that image looked like, well, and the backstory is, I was an early inheritor, and so I was not prepared at all on the technical side. And in my mind, that’s what was required. And so in order to do it successfully, I needed to be doing it like my dad was doing it. So having a lot of financial savvy. 

Honestly, I would define this as, in your free time, you read, like Kiplinger or the money section of the US News, and I was like, I read it because I have to. So, I feel like, in my mind, there was a real stumbling block around, well, I’m not the person who knows or is comfortable with the realm of things that I need to know in order to thrive in this role. I was a psychology major, specifically avoided business school because I found things like accounting bored me to tears.

And so, for me, there was a real mindset shift to say, okay, if I’m going to be successful here, I’m going to have to do this in my own way, because I did have confidence in myself in other areas, and so, I mean, this is me kind of struggling through it, but now what I know is that there’s a whole body of research from the field of positive psychology and the Gallup organization that literally would support the notion of figure out who you are, and then lean into those strengths to do the things, the side of things that doesn’t come natural.

And so now, of course, with our clients, we have all sorts of people who are from various fields, and maybe don’t consider themselves to be a numbers person, or are familiar at all with the world of business, and have found a way to absolutely rock their role, and they end up on the investment committee, on their family, and feel really proud of the ways that they’ve been able to overcome, I guess, really, the ways that we stand in our own way.

Cory: And, Vincent, in your experience coming from a family business. What inherited roles or expectations do you most often see holding people back from becoming who they really are?

Vincent: I think it’s a lot what Kristen said, too, inherited roles and expectations. Expectations are a big one. There’s an expectation to work in the business. And in my family, I have a sister, similar to Kristen’s dynamic in her family, where the expectation was I was going to work for dad, and I was going to learn the business. We see that a lot still today, where mom and dad have a successful enterprise, widget maker, and the unspoken word is, you’re going to come work in the company. And if you don’t, sometimes that downloaded messaging can equate to a rising gen, if I don’t work in mom and dad’s company, then I’m not worthy, or I’m a loser, let’s say, even inherited roles.

So in my particular case, because I have a twin sister, ironically, so there isn’t this hierarchy of age, per se, but definitely gender. Coming from a very Italian family, the role that I inherited early on was successor to dad. So my experiences growing up were very different to my sister’s inside the company. And we still see that a lot today. We were talking earlier on about some of the labels we put on our small kids. This one’s capable, this one isn’t, and they’re 16, and they have a whole life to learn and grow. We see that still in a lot of the work that we do with families. There’s this expectation to work in the company, and then already early labels on, they don’t like it, or they’re not capable. Therefore, they’re assumed to do something else.

I think it’s what you said, Cory, and that’s where the stunting comes in, that failure to launch. If mom and dad already think of me this way, or I’m already being told to go down this path. I don’t like that path, because I’m not, I don’t identify with accounting. Then who am I? What is my worth? And that can be a real conundrum as families move through their life cycle together. These unexpected roles and deemed expectations that nobody speaks about. It’s this void that sometimes we find ourselves as rising gen, falling into.

Cory: And, Kristen, what about expectations on oneself? What do you see some of the rising gen members that you work with, where they’ve got that expectation coming from within?

Kristen: I think it is often really cloudy in a coaching session, for example, when we ask them, okay, you’re feeling like you’re not ever going to be what your dad expects you to be, or you’re not ever going to be capable of filling these shoes. Do you know exactly what it is? Like, what role you’ll be carrying out? And it turns out, no, they have absolutely no idea what roles they’ll be stepping into across the areas of philanthropy, or investing, or the family business.

And so when you help them to break it down and begin to say, okay, well, how could you learn more about that? And how can we get you to a point where you can understand what exact things do you need to know about accounting to thrive? We know that you don’t need to know as much as your accountant does, and thank goodness for that. But I think when you can help them to turn it from this big, scary, I’ll never be good enough, to actually understanding what might the steps be, what might it look like to be good enough and still be who you are, and then what might the steps be to move a little bit closer to that. All of a sudden, it turns from kind of this big, scary thing that you try not to think about to something that actually you could make a pretty achievable plan around, and still get to be the beautiful person that you are without having to become someone else entirely.

Vincenti: Can I add to that, Cory?

Cory: Please.

Vincent: What I wrote down was, while as Kristen was speaking, is, gratitude equals compliance. The irony of that is, a lot of these entrepreneurs grow up a little wild, and have a business idea, and create a company, and chart their own path. And then in some families, not all, obviously, every case is unique, where the expectation is you’re going to fall in line and follow mom and dad’s footsteps into business. So by not speaking up and carving your own path, it’s almost like I’m doing what I’m told, that’s by way of expressing I’m grateful. And that’s where that stunting comes in.

It’s almost like, as parents, we want our kids to be themselves and happy and thrive. And yet, as business owners with our kids, there sometimes is this unexplained or unspoken expectation that you’re going to follow along, because we’re giving stuff to you, we’re providing you a lifestyle, so it can be really scary for a rising gen, regardless of their age, to step out of line and say, hey, I want to try something different for my life, because the system that mom and dad have built financially affords us this lifestyle, and to deviate from that path can really scare people into compliance, which we know from a continuity perspective is not good for the family wealth, to just comply your way through life and hope it works out.

Kristen: And Vincent, in my case, it didn’t scare me into compliance, but I did feel like a jerk. Like, for my dad, I was invited to work in the family business in the summer. And my dad almost lost his mind when I got a temp job with another kind of business. And he literally said, why would you bite the hand that feeds you? I think just not understanding, because we weren’t communicating well with me as a college student, and him as a parent of a young adult daughter who had her own way of thinking about things, and then when I chose the field of social work, he said, why would anyone choose the hardest work for the least amount of pay? And I guess he had a good point there, but I think to do that, I mean, do you know what caused me to do that? My dad’s entrepreneurial spirit that’s in me. And charting my own path, and in hindsight, you can see how some of those skills are actually useful, knowing what the end of the story was.

So I think that you’ve got people that fall into two categories, one that says, well, I shouldn’t ask any questions because that’s ingratitude, and other people who are like, I’m going to ask all of the questions. I know it’s going to be annoying, but that’s who I am. But, I mean, you do worry, it feels like ingratitude, because that’s certainly not the place that it was coming from.

Vincent: And just to piggyback before we get the question too, Cory.

Cory: Sure.

Vincent: It’s that focus, too, that if success equals financial capital, right? So, because a lot of us are born into these already-made situations of mom and dad being successful, to your point, being a social worker early on in your career, there’s impact there. You’re creating an impact in people’s lives that doesn’t necessarily equate to a high financial reward, so then dads would say, what’s the point?

The other thing I hear, we’ll pick on dads a little bit, is say to their kids, why would you want to work there when you can work here? It’s like, maybe I want to experience something on my own. Just food for thought.

Cory: We’ve created the best thing here, so what? If we’ve got the best, why would you go anywhere else?

Vincent: Company you can work for.

Cory: And what was coming up for me is permission to ask questions. That’s kind of what I was hearing you both say, is how do we just give ourselves permission to challenge everything freely, without judgment?

Kristen: And there’s something in there in, it’s not creating a completely new framework, it’s really building on the beautiful foundational definition, as you shared, Vincent, of success that the generation before you defined, but how can you put your own imprint on it and expand that definition in the example you were using?

Vincent, for me, is expanding it to include impact and making a difference. So I think, to be allowed to shape the larger narrative of your family’s success and what that looks like is a gift, but sometimes it takes the tension of expanding that thinking as the next generation is growing into adulthood and the people that they are. That part is the hard part, I think.

Cory: Absolutely. Moving to our second question, we want participation, not pressure, but what does that actually look like? And many families that I work with want the rising gen to be involved. They’re also not sure where those boundaries are. We already touched on that a little bit, and in some of the coaching work that I’ve done, I see people either over-function out of fear, that compliance that Vincent talked about, or under-function, because they’re just confused. And this idea of minimum value, or minimum viable participation, what are we seeking here? And making that not just a framework, some box that we check, but really that permission that that we’re looking to create, and some sort of structure that doesn’t have too much rigidity, but also provides that clarity.

And so, Vincent, looking for your take on this. How can families create flexible frameworks that are based on their values and support that autonomy, while also creating some alignment for the family.

Vincent: I think the first step is to move away from role clarity to values-based clarity. So it’s talking more about who we are as individuals, who we are as a family, what do we stand for, what are our principles. And they don’t have to be complicated. I think it’s having a conversation about, again, like I said earlier, how do we want to show up as a family? How are we going to govern each other in certain situations from a values-based perspective? Let the values drive more of the decision-making, versus, we need a guy in the back operations because so-and-so is retiring, and you’re next in line, go to work. And so that’s part of it. So I think it’s moving from role clarity to more values-based clarity.

So then the framework is, let’s have a values-based conversation, let’s actually co-create some agreements as a family, how we want to show up, how we want to talk about these things, what does the future look like when we co-create it? Those types of conversations, and move away from, you must do this.

I think the other one, too, and Christian and I talk about this a lot, just in our own conversations, the work we do with families, is helping define what responsible participation looks like at different life stages. There can be too much pressure on a young adult to assume too much responsibility too soon. Kristen’s example, where, unfortunately, her dad passed very young.

In my example, we make the joke, I was told too much too soon, and it didn’t serve. Again, those values weren’t talked about first. We’re thrust into a role of “got to get this done.” So I think for families, how do we create it? Slow down, and start with values-based conversations, and a set of guiding principles, agreements that the family works towards to help guide more of those conversations.

The other point I’ll make before I pass it on to Kristen, is stepping back for a moment and really looking at the family business more as a family enterprise. We don’t all have to work in ABC corporation to “be successful,” or to feel like we’re contributing to the family. There’s a ton of roles we can play, including being a healthy family member that adds value and wealth, our definition of wealth, Cory and Kristen, beyond financial capital, to the family. And that’s important. The family is what, hopefully, is going to continue for generations. The wealth creation tool, the business, most likely will change. At the core of it, there’s a family, hopefully working together with a set of values and agreements that guides them through these conversations.

Kristen: I love all of that, Vincent. And just to build on it, I love that you brought up roles, because I feel like the conversation about roles, and the clarity about roles, and then not having that, not just be something that’s on a piece of paper that you can kind of live into, I think is one of the things that families really struggle with.

I think it’s easy to do in business. But it feels a little bit weird, like, I’m going to make a job description for my son for what it means to be an engaged beneficiary of wealth. That feels odd, but actually, I think that that’s the answer, because then you’re kind of starting with the end in mind of defining the role and what it would look like to thrive in it. But then, to write down the details of, okay, help me know what things I need to know, what things I need to do. Usually what comes out of it is, like, oh, thank god, I thought there were so many more things that I need to do that we’re just kind of assuming are part of it. I mean, how many of our rising gen clients, Vincent, have this unspoken belief that they need to make, like if dad made $20 million, then I need to make $40 million. If dad made $200 million, I need to make $400 million. No one ever said that, so that’s no one’s expectation, but whatever pressure you’re putting on your shoulders.

So I think that you’ve got two things, the pressure we put on our own shoulders, even though no one asked us to do that. But then we have the, I guess, confusing role challenges. And some of this happens for all the right reasons. I have several clients where the parents, the leading generation, are very inclusive. And so, every meeting that they’re having with their family advisors, they’re inviting the kids too. But the kids are not kids, they’re, like, 37, with 3 kids of their own, 2 careers, and juggling so much, and to come to those meetings, you’re actually taking PTO from work, or missing your kid’s soccer game, or whatever it is. Balancing all the responsibilities of life, when actually, it’s not clear whether it’s necessary for that person to be in that meeting.

The parents, with the best of intentions, are saying, you’re welcome to come to the meeting. But then it actually would be more helpful if there was more intention around, okay, am I going to be stepping into a family office role, or a family foundation role? In which case, let me really shadow you, mom, as you’re leading our family foundation. Or, dad, if I’m going to step onto the board of our family business, there’s some of these meetings I really need to be going to. So it’s kind of just this big inclusive invite, which is not always really helpful, because then it feels like if the rising gen can’t go to meetings, they’re being disinterested and ungrateful, but at the same time, it’s too much pressure, they can’t do all of the things well.

Cory: I love that. It’s almost like, Vincent, we loaded the basis, and Kristen just hit it out of the park, so, awesome. Love that. And I think of how do we create those freedoms that we all desire? If we can do this well, it’s not just the rising gen, it’s everyone. That leading gen also feels some freedom from this.

Vincent: We see pressure, too. I know I experienced it. We see a lot with the folks that we coach. A lot of wealthy people come from humble beginnings. Especially up in Canada, the US, our dear friend Kristen is a little bit older than us, so there’s a little bit more of those 3, 4, 5 generations in Canada. We’re still young and developing. A lot of the wealth here is first, second generational wealth. A lot of immigrant families.

So one of the conundrums I found myself in, a word that Kristen coined years ago, a tangle, well, if dad can come here as an immigrant and make financial capital, therefore, Kristen said it earlier, I should be able to be making exorbitant amounts of money. And if I don’t, therefore, I’m not good enough. And so then there’s that pressure. It’s even about mom and dad creating space for the rising gen to lean into a role, but it’s also giving space to yourself, that if you don’t want to be in that role, the self-imposed pressure to, I must step into a role that I think I need to be into because of the work mom and dad did before me, that’s unhealthy. Not only personally, but from a continuity financial perspective, it doesn’t serve the wealth to get stuck in these labels. “I must do this because of,” It’s a big challenge we see with the families we work with.

Cory: Dad didn’t, didn’t start the business to add more commas. It was to create that well-being, and so to use that as a measurement is easy, but so often, not helpful in any way.

Vincent: We’re all coaches on this call, right? So we talk about when we coach our clients, who are you comparing yourself to? Same thing is true in the family. You’re comparing yourself to the generation before. Well, if they did it, I must be able to do it. You will, but in your own way, whatever that means to you.

So I think we don’t talk about that enough, is that we compare ourselves to others. Johnny graduated from the same class I did, he’s so much further ahead, therefore I must not be good enough. I know with myself, I used to have this ticking timer. Dad started the company at 35. By 45, he was here. 55 years here. Well, I’m 47, and I’m nowhere near the size and scale of what he created from a business perspective. I mean, I could argue, but my life, I’m very happy with what I’ve built and the life I’m living. Two completely different stories that serve each other, I think that’s more of a healthy mindset to try to adopt for us and for the families we serve.

Kristen: I have a silly metaphor for this that we use in our cohort program, about, even though it’s not a perfect metaphor, because rarely is there a baton pass moment. Actually, for my life, there was, but most of the time, it’s like this decades-long baton pass.But we’ll use the metaphor anyways, because I do think it ties into what you’re identifying here, this idea of, do people really have a lot of pressure on their shoulders, and how is that getting in the way, is this notion of a lot of times for some people. It’s not the case for everyone. They feel the weight of the baton in their hands, and they’re looking at the leg of the race that somebody else is running, grandma, or my brother, whoever it is, and totally forget that you’re supposed to be running.

So I think that sometimes in coaching, for Vincent and I, that’s what it feels like, where we’ll kind of listen to where they’re at, and then go, okay, did you want to get started in running your leg of the race, given who you are and your strengths? And it’s almost like a weird relief for them that they have when you kind of explain it to them that way, where they go, okay, that’s right, I’m supposed to be running. And that feels like I could do that. I could start running my own leg of the race. I probably can’t do it like they did, but maybe I could begin with the first couple of steps.

Cory: I love that. It makes me think of junior hockey, where, when I started, it was like, I had the best seat in the house, I was spectator on the ice, and forgot that I wasn’t there to watch the game, I was there to play the game, and we see that so often. So, good metaphor.

Vincent: I’ll just piggyback, I know we got to get to question number three, but you look at sports, right? So look at hockey players. Their players play a different style, they have different skating attributes. Some are physical, some aren’t, but yet they’re successful. So if we can just use that simple analogy, run your own race, you look at athletes, they all look different, there’s different sizes, different styles, but yet they achieve a level of success. The same is true in family enterprise. Your race is going to look different than mom and dad’s. It must look different. Embrace it. Embrace your style, embrace your thinking and your hopes, and to Kristen’s point, get running.

Kristen: It requires a little resilience, though, because sometimes mom and dad are the coach, and they’re going, why are you doing it that way? And it takes some resilience to be like, because it’s my way. Because it’s how I run. So it’s not like everything is magically better as soon as you start running. You have to believe it in your own heart. You have to deeply believe that your way of running the race is your strengths on display.

Cory: Absolutely. Vincent, you, brought this up earlier, the definition of wealth, coming from the root of well-being. We talk about financial capital, and so this question, often people use the word wealth, and being very intentional about using financial capital. And so, how do we build that emotional capital? I think it fits well into the conversation we’ve already had here.

Oftentimes, I’ll see family situations, and we all know it, that money doesn’t erase any problem, it just amplifies it, and it also fits very well within emotions, in that room where all we can hear or all we can see, it definitely amplifies things. So those feelings of fear and guilt and pride and love, it doesn’t just need to be negative feelings that we’re amplifying. We can also have some of those positives. But oftentimes, I see that this gets left out of the conversation. People aren’t planning around what are we doing for that emotional well-being.

And so, building that emotional literacy. Vincent, you talked about that coach approach. The three of us have that background. What is it, about 9 different emotions that people can name? And there’s so many more.  What can we bring to them as far as just being able to name some of those emotions? It can definitely do wonders.

So, Kristen. When it comes to emotional questions, what do you see that needs to be addressed before families tackle big things like governance and transition planning?

Kristen: In a weird way, governance and transition planning can feel safe. Like, we’re going to put words on a page, and it’s going to be a very concrete thing to do. But you don’t spend very much time doing that before you realize, if you haven’t addressed a couple of other things before, it can kind of feel like it kind of maybe is a waste of time, even. And I think that a couple of questions that are important to answer, number one is often skipped, surprisingly, but why are we doing this? Or what is the intended purpose of our business? Growing wealth? Because that’s what brings people to the table, and that is kind of the values questions that Vincent was talking about. And that’s something as a family that you can rally around.

Maybe for a family business, it’s like, we make an impact on our local community and provide jobs for local people, whatever that is for your wealth. Maybe it’s, we’re trying to make sure all of our family members in the future have a safety net, and can take care of one another. Whatever it is for your family, it’s going to be unique for everyone. But I think some families, especially when wealth grows quickly, really haven’t stopped to define that or have conversation about that together. And I think when that hasn’t happened, then everyone’s coming to the table with different expectations and understanding of what it is that you’re trying to do. And you might have some family members who would say, I don’t know if I’m on the same page. I don’t know if I’m aligned with what we’re trying to accomplish across generations, because I see it causing a lot of friction in our family relationships. So whatever the intended purpose is, it’s not worth what we’re dealing with. And so, I think getting clear about that can be essential.

But then, I think what’s underneath of that, once you have that defined, and whether or not you have it defined, a relevant question that is a hard one is, do we trust each other to be able to get there and carry out the intended purpose of our business or wealth? And there’s a couple of different ways that that pops into your mind. One is, like a reliability trust. Do I trust my sibling to step into these roles with me one day after? Grandma is gone, or mom and dad are gone, or whatever. And if not, maybe that’s an education gap, or maybe that’s a skills gap. We don’t know how to make decisions together, so how is that going to work? And you can close that gap with education or experiences together.

But sometimes it’s a relational trust issue, where you’ve got some stuff to work out from when you guys were 16 and 14, and that’s still getting in the way. And so, regardless, I think there’s always a way to close the trust gap. But if you think about it, if you don’t address that, it might be, like fiction or fantasy, that you’ll ever get to a place of carrying out that intended purpose, if you’re not able to get to some of those trust matters.

Cory: And Vincent, We talked a little bit about unspoken rules. What unspoken rules do you often see within families, and how do you help them name those and see what’s maybe standing in the way?

Vincent: I think there’s a big one, we all see it. Every family has a version of it. It’s “don’t rock the boat.” At some degree, there’s a “don’t upset the apple cart.” I recently had two family meetings I did in December before the holidays. And everybody was very explicit how much they love each other. We love each other, I love my family, we want to continue this legacy. But then when you ask them a little bit of a deeper question about, well, have you expressed your unhappiness with XYZ with your mom. Well, no, I haven’t done that yet. Well, why not? Well, because I don’t want to make her or him upset.

So that’s an unspoken rule that we see in a lot of families. I’m guilty of it, too. We don’t want to upset. Harmony takes precedent. I always smile when we do values with family, and they go, harmony? And you go, well, what does that actually mean? Families want to stay together, they want to be in harmony, and yet, that sometimes can be the glue that gets unstuck. So there’s this unspoken rule that we don’t challenge the norm, or mom and dad, especially in families that have a really strong culture, you know, dad’s right. Even if he’s wrong, he’s right. I think that only works for so long. So that’s a big unspoken rule that we see.

Part of it, too, another unspoken rule is if I disagree with you, it’s a lack of loyalty. I think that’s something that we see oftentimes. Well, again, dad thinks, or mom thinks, my older brother or sister is the chosen one. Who am I to disagree? What we know to be true in families is that conflict, these unspoken rules, they’re always present. And it’s not necessarily bad or good. It’s how we deal with it Because it is the unspoken word. And unspoken expectations that we have of one another, that will ruin the relationships. And the research shows that when relationships break down in family enterprise, that’s what usually is the problem for financial transition. So that’s a big one.

Cory: Thinking of resilience from a systems perspective, what have we done difficult together? And bringing back what Kristen said, trust each other. If the boat tips over, do we trust each other that we’ll be able to all have the skills and ability to get in that rescue boat and do the tough things together?

Vincent: I’ll just add to that, it’s, again, it’s not clarifying expectations. So don’t rock the boat, and then, like, parents automatically think, oh, of course my kids know what I’m thinking and feeling and what I want. They’re my kids. They’ve heard me say it a thousand times. And then, to your point, a situation arises where we need deep trust with each other, and we haven’t had that. We haven’t worked that muscle. And then, things break down. Part of your role, folks that are listening and hopefully family champions, is to find that muscle and the courage to ask the questions that you want to ask, even if it might rock the boat. Maybe rocking the boat gently, I emphasize gently, is what’s needed to help families have different, deeper conversations with respect to their planning.

Kristen: And get honest about it if you don’t have it. For my brother and I, it was clear to me that I should not be involved in the business, because I would only get in my brother’s way. I had no business skills associated with the industry of our family business. We had no skills to make decisions together, and how it was when my dad died is there were certain areas where I was intermingled into the business. The last thing that I wanted to be doing was making things more difficult for my brother to keep our family business afloat. If we go back to the boat metaphor, by me keeping myself inserted in that situation, I hadn’t earned the reliability trust of being involved in that, and so I would have brought that boat down and knew it.

So I think it’s not this idea that everyone needs to have this high degree of trust. Some families don’t, and that is what it is, and that’s okay, and you make your decisions based on that. So if you can send one family member to one arm of the family enterprise, and another where you’re not reinforcing more chances to have to collaborate together and make decisions when there’s already shaky trust going on. That’s okay. That’s the family that you have, and the family enterprise that you have, and that’s something to embrace as well.

Vincent: I have another one that Kristen brought up before. All of us siblings were treated equally, not fairly, as another. So, 3 kids, 2 kids, everyone’s working. Everyone’s equal. That’s not Kristen’s example. Her brother’s probably not a very good social worker. Maybe he is, I’m not going to speak to that at all.

And we’re not equal. Our hope for families is a fair process, and that really involves having… you’ve heard me say it, Kristen and I use these words ad nauseum, having the courage and confidence to step into a conversation. If there’s one major takeaway from this call today for families that are playing together, it’s to really lean in on those uncomfortable conversations that you know you should be having, but don’t want to have because of these unspoken rules. Call it culture, that’s been downloaded from us, even to our parents, from their parents, we don’t say negative things about the family and the path we’re going on, even at your own personal detriment.

Cory: Awesome. Moving us along, the next question, how do we move from protecting the legacy to co-creating it across generations? We kind of talked about that, living in the shadows of the giants, that this legacy thing is something that we need to protect, and for me, when I think of creating Legacy Builders and these conversations that we’ve been having for years, my own personal opinion is we’re co-creating this legacy, and taking it, and continuing to build on it. And so, it’s more about that collaboration than it is about compliance. And so often those pressures that we have talked about already, comes with that.

We talk about continuity of wealth, of financial capital, but that wealth component, what is the story? Vincent, from you, what mindset shifts do you see are most essential for that leading generation to make room for sharing this stewardship?

Vincent: I’ll give two, you said one, making room, so I think it’s going from hero or founder. Leader of the family enterprise to a guide. You hear it with all the leadership courses and stuff. A great book that I always reference, it’s called The All Blacks. It’s about the 12 principles of the New Zealand All-Black rugby team, and number one is “leave the jersey in a better place.” So I think that’s a mindset that we can take on as families, we want to leave this situation better than how we found it. So you talked about that, Cory. That means creating space, moms and dads, for the rising gen to have deeper, more difficult conversations.

And the other one that I wrote down here as we’re talking, is moving from control, holding the reins too tightly, shifting to a mindset of continuity. Maybe the control today is what’s needed because of the life cycle of people and where they’re at, but knowing that holding the reins too tightly into the future, it’s not a good recipe for continuity of your family wealth.

Cory: And, Kristen, I’m sure you’ve witnessed this, where that rising gen member or members, realize that they have the ability to shape the legacy, rather than this pressure to inherit it and carry it as it was. What happens when that change is realized?

Kristen: It’s a really beautiful moment, and I say moment because I have the incredible privilege of actually watching the transformation happen, and I know it’s the same for all of us. So, I feel grateful to be in the chair of, sometimes across the Zoom, of literally watching the light bulb go off over someone’s head, and the way that I make sense of it actually comes from their mouths as they’re talking about the transformation that they experience. And the phrase that they use will be some iteration of, I moved from feeling like all of this was happening to me, like you’re stuck in someone else’s machine, to feeling like it’s happening with them. And remarkably, that mindset shift seems to happen, not only when someone’s now on a committee, or a board, or in a leadership role of some kind, it often happens well before that.

But it’s this mindset shift that happens where they realize, I have a contribution to make. That might not be for 10 years, but it is my responsibility to figure out who I am and what imprint that I’m meant to be making on my family legacy. And a lot of times, Vincent, to your point, it is complementary, I guess, to whatever journey the generation before you has made.Focus in one generation on improving process. Maybe the next generation has improving relationship focus as kind of a theme across the generation, but whatever that is, there’s at least one person in that generation that probably has a unique skill or strength to bring to that initiative. I think when they realize that, that’s when they start to get sort of, like, fuel or an engine behind, okay, now, even though maybe accounting or investing or whatever is not my favorite thing, or even it could be philanthropy. Even the philanthropy is not my thing, now I have a reason. Now I have a why behind my own role in this, and it feels like I’m a part of it.

And interestingly, you got to think about the shift. It’s remarkable in the families when that happens. So if you think about, I’ve had the sense that my parents are protecting all of this from me going rogue, and then to come to a place of education and family conversation, to then think, now I’m alongside of you in protecting it, in collaboration, is quite a shift to make. So I think that that speaks to the leading up to that point as well.

Vincent: That reminded me of a conversation we had a little while ago. Another mindset shift, Cory, is about living real responsibility. We give fake responsibility, right? Give our young folks in the family real responsibility, with real consequences, both positive and negative, or else, how are they going to learn? I worked for dad for a long time, and there was a run of me coming to work late. 15 minutes, 20 minutes, I would initial my time card because I was the boss’s son, and only after a period of time was that cut off, and I was reprimanded by the supervisor, hey, you got to stop doing that, because not only is it wrong, you’re setting a bad example for everybody else. But I think we see that a lot still with the families we work with. There’s not this mindset of, I’m going to give you some real responsibility, and it’s on you to sink or swim.

Kristen: And then, when you fail, it’s not the end of the world, because then you learn from it like the rest of the world does. It’s a little bit more pressure, I think. That can make people feel, on both sides, leading gen and rising gen, really nervous about the failure, but we all know the failure is the points at which you learn. So, I think that was a great example.

Cory: I think of it when my oldest, around 3 years old, and we give her these tasks where it was, like, keep her busy, and then we realized, she can set the table. Why wouldn’t we get her to do things that are actually contributing? And that shift in us, we saw it in her, and so, it’s not just 3-year-olds, 30-year-olds, too. Everybody needs that.

Vincent: Great point, Cory.

Cory: All right, so our last one, and we’ll do kind of a quick round on this, because I think we’ve really hammered it well. So, what conversations are we still avoiding, and what are the costs of not having them? Kristen, what haven’t we said already as it relates to this?

Kristen: This is a good question, and the problem is we don’t have enough time to solve these big matters. But I do feel like this is where my areas of, like curiosity and honestly, like writing and doing research are going, just because I’m having clients that are coming with these challenges, and there’s not a book for that yet, or whatever, a podcast. And I’m going to give you one for the leading gen, and one for the rising gen that I’m hearing a lot of. And the one for the leading gen is helping parents of adult children with navigating the complexities of parenting adult children in the context of wealth.

I think there are a lot of boundaries, confusion, when your finances are all kind of shared, and there’s sometimes less privacy, and the power dynamics are tricky in family business. So all of that, I mean, it’s always a transition for parents to parent differently when they have adult children, but I think there’s a lot more stress in the hearts and minds of the leading generation when their adult kids are handling money, handling personal finances irresponsibly, or whatever. Because then you worry, now they’re going to squander the family wealth, and your mind gets away with you, and it just feels like the stakes are higher, and so that can lead parents to have a tighter grip, or be more advice-giving, and actually, that’s doing just the opposite. That’s actually eroding the confidence of your kids. And so, I think when you get stuck in that dynamic, it can be very difficult to get out of. I’m seeing a lot of that. So the nuances of parenting adult children for leading gens, I think we need more conversation about. And I’m working on something, I don’t know what it will be yet.

But then for rising generation, we’re hearing a lot of rising gents who are coming to us, feeling, I don’t want to call it uncomfortable, or a lot of tension around being a part of a family with accumulated wealth in the context of the cultural conversation about the wealth gap, and I think there is a need for people who do have family wealth, to really work in their own hearts and minds about how they feel about that, and to get clear about the imprint that they’re making in their family, in the world about that, so that they can be resilient to whatever the cultural conversation is, and it’s not allowing them to kind of get spun around in their own hearts and minds about that.

More rising gens need the space, more advising gens that are concerned about that, and kind of tangled up about that, need the space to be able to work through that in an environment that’s really neutral, politically neutral, and supportive of their developmental process.

Cory: Vincent, what can families prioritize right now?

Vincent: How do I follow that? It goes back to what we talked about earlier. I think what would really help families, a conversation hopefully leads to more conversations. What does responsible ownership look like at this stage of life? Self and our family.

I think there’s so much added pressure in these family enterprises that the rising gen put on themselves, to hit these markers of success and self-imposed metrics. If I don’t do this by a certain age, I’m not winning at life, whatever that means. So I think a healthy conversation for families is actually sitting down and talking about what it looks like at this stage of your life, and the life cycle of where our family is, just so that we can all be on the same page, and then define. So what does responsive ownership look like at this stage of our life cycle? And then what does success actually look like and feel like for you, the individual, and for our family? Because if those two definitions are different, then most likely they are. By definition, that’s conflict.

Then we got to talk about it. We really want to allow, we really want to create space for the individuals and the families, and we’ve gotten away from it. Technology has been a big asset and friend to all of us, and what we’re seeing, my family included, we don’t have Sunday dinners every Sunday like we used to, to talk about stuff. Part of my personal mission is how do we have more of those moments as families, just to talk about what’s going on? Like, what is actually coming up for you in your life as you’re off to university? What are you thinking about? What are the conversations you’re having? And how does that translate into our family system? I think those are some of the missing pieces that families could adopt. Not easily, but they could adopt and try to have within their own family systems.

Cory: And just the comment on technology, I think even as we were talking about building resilience. Today, the fact that we’ve had Google for a long time, now we have AI, there’s not a lot of healthy discussion where people disagree. It’s like, I’m going to prove you wrong, because I’ve got everything in my pocket that’ll back me up here, so we’re not even flexing those muscles to say, let’s just disagree for a moment, and learn from each other, and understand each other’s view, and why you came to that conclusion.

Vincent: I’m smiling.

Kristen: Value of just that, right? That’s valuable in and of itself.

Vincent: Kristen, when we were growing up, I would say, oh, so-and-so told me this. And my dad would say, well, how well do you know this person? To your point, we just default all of our trust to technology, right? Well, Google machine told me it’s true, so therefore. Again, these assumptions that we make about what’s happening, but it’s a good point, Cory. It’s dig deeper.

Kristen: Something I wanted to say in, follow-up to what you shared, Vincent, which I thought was really great. And again, it’s kind of about the comparison, is I’m excited that there are a lot more resources for families in these situations, like Legacy Builders Podcast. But what I’m finding with my clients lately is they’re coming to my coaching session saying, they read this, and they listened to this, and they’re trying to put on another family script to their own family. And this might be a family that’s totally different from yours, or between G4 and G5, and you all actually don’t need that much complex governance. And so I do think that it is a little bit tricky to kind of filter out all of the great ideas, many of them, but then to make them your own, and apply them to your own family, or to you as an individual, or whatever. You prompted that, pinky on me, Vincent.

Cory: Amazing. We had one question, yes, we’re recording today, and it will be posted, probably by the end of the week.

Any quick last comments from either of you? Anything that we didn’t say? Because I think we’ve run a pretty good race today, and just if there’s anything?

Vincent: I have one that we, Kristen, will probably roll her eyes, because we say it all the time. I think the name of the game is to stay in the game. If we keep continuing with the sports analogy, right? Oftentimes, we see families, rising gen, families that work together, just to stop. They stop trying. This is too hard. I think it’s got to stay in the game. I think that’s key, for all the listeners and the rising gen out there. Stay in the game.

Kristen: Make it yours, I think.

Cory: Absolutely. Well, it’s been a great hour with the two of you. Thank you both so much for your contribution. I think that race, there’s a lot that we saw along the way, so much more than just planning, paper, and structure. The power of reflection, and building relationships, and that willingness to engage in meaningful dialogue, and maybe even disagree every once in a while, and practice some of those things that don’t feel so comfortable. Because that’s really how we grow.

If anything today sparked ideas, raised questions for family members on the call, advisors on the call, I invite you to connect with the three of us. We have our Legacy Builders newsletter every second week, our Legacy Builders podcast, which both Kristen and Vincent have also graciously participated in, and stay tuned for next month’s webcast, where we’ve got two amazing guests, just like these two individuals, who will be joining me as well.

Vincent: Thanks, Cory.

Kristen: Thanks, everyone.