Wealth Beyond Money: Cultivating Trust, Identity, and Connection in Family Enterprises

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 Emily Bouchard, Chief Learning Officer at 10×10 Learning Roadmap & Founder of Bouchard Bespoke Consulting. Her dedication to unlocking the full potential of individuals and families stems from over 20 years of experience coaching multigenerational families through the complexities of wealth, relationships, and leadership. Emily’s transition to fractional Chief Learning Officer reflects her expertise in designing personalized learning experiences focused on lifelong growth, emotional intelligence, and financial acumen. As an accomplished author and speaker, Emily is uniquely positioned to guide families on their journey toward fulfillment and prosperity. 

My goal is to be the most curious person in today’s conversation with Emily Bouchard, where we explore the journey of a dedicated family coach developing innovative approaches to wealth communication. Emily will share insights on supporting families as they navigate wealth transfer, identity formation, and cross-generational relationships. We’ll explore how advisors can transform difficult conversations about prenuptials and inheritance into opportunities for strengthening family bonds while reducing shame around wealth. Through Emily’s lens, we’ll discover how families can create deeper trust and authentic connections that endure far beyond financial considerations.

Now, let’s dive in!

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

Emily: Sounds great!

Cory: 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?

Emily: I have to say I’ve really been looking forward to this conversation because of how thoughtful you are and how you ask such an evocative thing right out the gate to really dive in from such a meaningful place, because I think that’s it’s, what life is all about is having these meaningful conversations. So thank you for that. So I think I have to start off with, as you’re getting ready to go off into the world and design your futures and go out, and you know, the world’s your oyster and you’ve got all these ambitions, it’s so important to keep in your awareness how precious each moment is and to make the most of your interactions.

And that comes from the painful experience of suddenly losing my mother when I was 14. So she was completely fine and healthy one minute, and then she had an aneurysm burst and was in a coma within a few minutes. So she never regained consciousness. It was a very shocking, traumatic event in our life as a family, and really set me on a trajectory in terms of what is this life all about and how do we really maximize our time that we have, knowing how precious it is and that it could be gone in each moment.

So it’s this invitation to never forget how precious each day is, what a gift it is to wake up in the morning, and that you have a choice about your orientation to your day and your life. And there’s so many things going on in the world that we can’t control, and the one thing we can control is our intention, our mood, who we’re going to be in relation to our lives, especially when we don’t know if we’re going to have this conversation with this person tomorrow. Right?

If we treat, not from a neurotic place, but if we treat each moment as, wow, what if I am not going to see this person again? It makes it so that in the foreground, you’re really focused on what matters most, and the trivial stuff doesn’t get to have the kind of mischief and impact that it can often have in families. So that’s one I would share. And I’d say that also set me on a path of really being very curious about what has us be resilient and antifragile based on what can happen in our lives. And that I became fascinated by the concept of post traumatic growth rather than stress and being disabled by it. So that’s the understanding that as human beings, we have a tremendous capacity to grow from whatever trauma we experience.

The next one I would say is I really understand, and want everybody to understand that family is a choice, and it requires attention and intention to have a deep experience of what family means. And I grew up with a stepfamily right from the get go. I never met my maternal grandfather. I only knew my maternal step grandfather. I always knew that he wasn’t my mom’s biological dad, but he was my grandpa. And his daughters were my aunts, and they were no different in my mind than my uncle that was my mom’s biological brother. So I had this experience growing up in a family with differences, the step family, and this step into I want my family to be strong and nurtured and whole, and what does that look like?

And so then when my mother passed away, my father remarried about eighteen months later. My stepmother was a very kind and loving person, and she came from a very kind family that adopted us, which was really quite something because we basically lost my mom’s family. They didn’t put any energy into nurturing their relationships with us. We made attempts to, and I tried to in different ways. But my stepmom’s family, I went to spring break in Florida with my new grandparents every spring break when I was in college. I ended up with six new cousins, three new aunts and uncles, and they just completely embraced us. It was never a question that we were as much a part of the family as everybody else. And that brings tears to my eyes just thinking about it because it’s a choice. They didn’t have to do that. And it’s made a huge difference in my life. And I’ll share that my father just had his ninetieth birthday. We had a huge party. He decided he wanted to have a celebration of his life while he was alive.

Cory: Amazing!

Emily: He’s like, “I want to see my friends. I don’t want to have them celebrating me that I’m not there.” And so because he’s been going to a lot of these funerals recently. And so we invited all of my stepmom’s family. She’s passed away in 2019, and they all came. My cousins all came. Their kids came. So we had three generations. And it was our family reunion again, and we would have that every Thanksgiving for years. We’ve lost that when my stepmom passed away, but we still stay in touch.

So that was really special. And, again, that cultivating of our relationships. So that message would be really strong in my heart in terms of you get to make your family what it is by the attention and intention you put towards it. James Hughes often talks about the family of affinity. And I’ve been living that since I was born, and I definitely channeled that into my work with complex family dynamics and with step families in particular. That’s been a real specialty of mine.

And then I think that the last thing I’ll share, which I also speaks to that post traumatic growth is, when I was 18, I volunteered as a camp counselor at a brand new camp for children that had cancer and their siblings. This story means so much to me because it completely changed my life where I was in a cabin with two teenage girls, who had both lost a leg to osteosarcoma. One lost her right leg, and one lost her left leg. One of them was about six foot tall, beautiful African American young woman from the inner city of Houston. And then the other one was this petite, maybe four foot nine girl from way out in the country. She came, like, six hours to come and be at the camp, and she was, Caucasian. And they’re sitting across from me, and they’re both swinging their one leg, and we’re just having a great time talking.

And then, Tara, the little girl from the outskirts, looks at their feet, and she’s like, dang, Cassandra, if we had the same size feet, we could go shoe shopping together. I was like, what? And I just again, it’s like that embodiment of what does it mean to claim whatever your life has, the cards you’ve been dealt, and have the best experience playing that hand. Again, you never know what life is going to deal you, but you have a lot of say about how you respond to it. And that really informed my work with families, with kids, with couples, around how to be resilient in the face of adversity.

Cory: I love that! It would be a much better deal if they could have bought those shoes together. But what a great laugh, and what a great memory that is, seeing people who were thrown a curveball and absolutely made the best of what they had. That’s terrific. I love that.

When it comes to those precious moments, there’s a lot from the stories that you’ve told us where you really have found these moments where there’s gifts in everything. And so the work that you do with families and the experiences that you’ve had helping them from where they’re at, how have you seen others take those gifts and really maximize each day?

Emily: It’s so important to consider. When I first was introduced to this work, I wasn’t familiar with it at all. I needed to do a bunch of research, and I found this research out of Columbia University that really showed that young people in affluent families were greatly at risk, even more so sometimes than children from disenfranchised families because they had access to things that could really take them down the wrong path. They also didn’t necessarily have access to the kinds of services that would support them because there’s a presumption that if you have money and wealth, you’re fine. And so I got really interested in the impact of wealth and growing up in an affluent environment on these young people.

I’ve done a lot of research and have been trained in the human potential, human development, child development, and, really looking at what are the most important essential ingredients for having a fulfilling life that is oriented towards the possibilities and what’s good, and not having the pitfalls of what can happen with the wealth, really take you out. We have a lot of cultural pressures, memes, and presumptions about what being wealthy is supposed to look like that can actually have a dramatic impact on somebody’s life, and they can get really caught in that momentum and that sway in that direction. And so supporting people in having a really clear sense of their identity, who they are, not in relationship to the money and the wealth, but to their core purpose values, their kind of intrinsic strengths, and then also honouring the family legacy that’s brought them to this point.

I think the biggest issue is the shame, guilt, confusion, and overwhelm that can happen with wealth, especially when there’s not the greatest communication about it within the family because of fear of it doing harm. So that often keeps people from speaking about it. So using those, the orientation of what how life is a gift, and each day is so precious, and what is it to be grateful for, and really tapping into the kind of the intangible things where true wealth lies seems to be very helpful for people that want to break away from the the trappings that can happen with it.

Cory: Right! And as you talk about identity, it leads me to think of identity of self. But then back to your comments about family of choice, what is your identity as a family, and how do you perceive yourself. And so how have you found in the work that you’ve done with families, that stepfamily and how people can emulate some of what your stepmother was able to bring, the family that she brought that had such open arms. How did they do that? Was it by fluke? Was it by very much intention? And how have you been able to help other families harness some of that energy?

Emily: To me, it’s like, wow, how did they do that? Right? My birth mom’s family disappears. And then this other family that’s not related to me by blood at all completely embraces us. So you can imagine, as a teenager, how it’s confusing, it’s quite something, and you have to grapple with different things too. I just kept really going to that place of appreciation and gratitude for what we were able to build together as a family, and make the most of that while also trying to stay connected in other ways to the other members of the family.

I think it had to do a lot with intentionality and operationalizing the value of family. We oftentimes will have families determine what their values are, and they’ll say, family is a top value. And the most exciting part for me in the work I do with families is, how do you operationalize that? If I were a reporter standing in the corner and I was just observing the facts, how you operate, how you behave with each other, and how you talk with each other, what would be the things I would be witnessing that I’d be jotting down that would be like, family is a top value for this family. Like, what are the consistent things that happen? And then what are the things I might see that give me pause and wonder how much they actually value family? It’s a helpful way to take that lens out a bit and really think about what we are actually doing to further what family means to us.

And then I love with the stepfamily work that I do especially, I developed this process of doing their own coat of arms, showing them some examples from history and finding out what they like. Oftentimes, there might be gamers in the family. I love when they bring theirs. And then I work with them on clarifying and defining their core values as a family that they all really want that they definitely operationalize. Like, we might not always like each other, but we’re always going to choose each other with respect. What does respect look like? Or, you know, we’re going to have each other’s back. What does that look like? So they can choose how they want to describe it, but it’s all about putting it into action. And then they each take time to create their own version of their coat of arms, and they can have a lot of fun with that. And some of them make it look just like a shield, and other ones, I had one family, she made a big giant fish on a picture, and she had bubbles coming out of the fish’s mouth. And she wrote the values in each of the bubbles. And the fish was like the family. So really allowing for that creativity. And then the idea is that they put that up around the house, especially when the kids are younger, and then they get to true back to that. They get to look at, when things start to, they forget or they fall into old habits, they can look at those and remember, and it keeps it kind of alive for them.

And then, also recommend they have at least one family dinner a week, ideally more, because research has shown the one thing that makes more of a difference in family success long term is family dinner where you’re together sitting at the family dinner table, not with your phones on and actually connecting, like, what was your high and low for the day? Or what’s one great question you asked today? Or, how did you find yourself helping somebody today? Something that, again, furthers the values with questions that they know they’re going to be answering. So it has them kind of orient to that as they’re living their lives, and the parents need to share it too, so they get to give that example.

Cory: I love that! The family dinner is so impactful. Even from a young age, when I look at my own family, we do something very similar. We call it rose and thorn. What’s your roses for the day? What are the things that contributed? And where were some of those struggles? We then also ask, whose bucket did you fill today? And how do you feel about that? So how did you contribute to somebody else’s life? And it’s a really great way to, when you ask a kid, what did they do today at school, you have to get the blank stare, and the answer is nothing. And if you can get them to really answer, you know, something positive. And they know it’s coming. I think it’s great what you’ve just said there for sure.

Emily: I love that! And I think the other thing too is you’re also helping them develop some really important social skills that they need. No phones at the table. You have to look at each other in the eye when you’re saying these things. You get a chance to be seen and heard. People reflect back what they’ve heard. People are curious about it. You have these standards that you start to develop as a family and how you relate with each other. And then they begin to be able to articulate their experiences and their feelings, and being able to do that is so important for resilience based on what’s happening in your life.

Cory: Right, absolutely! Going back to, you were talking about the coat of arms, the values exercise, and bringing families together. And I’m thinking about, you know, we have families that are connected by choice. And now when we’re bringing people together and wealth is involved, you talked about that identity and what it means for younger folks as they’re growing up with wealth. But what happens when people marry in? Or maybe they’re brought in through marriage, and they’re now looking at their identity of, well, is this really my family? Is this really me? And some of those privileged thoughts, and the guilt and shame around that can change from “I was born into this.” So how have you experienced that?

Emily: Oh my Gosh! We could have a very in-depth conversation about this, there’s so many things to say about it. Oftentimes, there’s this moment where they decide to bring somebody home to meet their family. And that’s often a very pivotal time when if they haven’t been upfront about their wealth or their background, the person they’re bringing might be quite shocked. Or they might be so like, it’s no big deal. They don’t even think to say it. And then when they see where they live, it’s like, “wait, what?” And so that’s one.

So it’s about “how do you feel,” have a narrative, an internal narrative about who you are, your life, what your relationship is to where you’re coming from that would make it so it’s a non-issue in how you bring it up, and the other person is also prepared for it. I think that I ended up writing my little beginner’s guide to purposeful prenups as a result of talking to hundreds of people who, in their interviews with me, as part of a listening coach and their practice of the the family meetings that I would do, they would share, it didn’t matter what part of the country. It didn’t matter their race, religion. How the prenup conversation was handled had dramatic impacts on their experience of the family they were marrying into, how they felt being treated as an outlaw before they even came in, taking it so personally. How it was done was so disrespectful, all kinds of different things. And lawyers often have a very kind of protection adversarial bent, which can really take things in the wrong direction.

So I thought, this is a pain point that, it’s insidious. It creates a crack in your marriage and your foundation before you’re even married. So what can we do to change that? And I was just talking with Kirby Rosplock, from Tamarind Learning, and she and I are going to be doing a master class on purposeful prenups. And a part of that’s going to be onboarding the new spouse as well, to really change this because that’s how passionate I am about it. And she’s like, yeah, I’ve got two families that need that right now.

I think that you ask such an important question because families want to be welcoming, and yet there is such a bent towards protection and all the what ifs of what could happen. And, I like to bring forward the concept of “marriage is the most important contract you’re going to enter into in your life,” and every contract has an exit strategy that you want to have in that contract. It’s a very wise thing to do. And the way it’s set up is that your place where you’re getting married will determine what your exit strategy is if it comes to divorce or even death. Your laws are going to be determining a lot of what this is going to look like. And so why not determine it for yourselves why you love each other, why you’re totally committed to each other, and really having each other’s backs. And instead of taking it personally, and you’re planning for divorce and you don’t love, or you think I’m wanting you for your money. It’s like, no,I want to make sure that no matter what happens, if we divorce, if I die before you, if I become disabled, that you and our kids are going to be okay, because there are structures that are already set up that I don’t have any say in. And we also need to make sure that our life and our livelihood, what we’re building as a family is in keeping with our values and what we want, and it might be different than what my family’s is. So this is a chance for us to do that as well. So you can reframe conversation that can be much more respectful and honoring of the we and who we are. And it’s not just because I have money and you don’t.

And it’s very challenging. I mean, sometimes the person who’s marrying doesn’t even have enough money to afford the attorney. If the family is paying for their attorney, does that attorney really have their best interest? There are so many nuances to it. So I often recommend doing the Purposeful Prenup Process, working with a collaborative attorney, working with a mediator first as a couple and really getting clear on it, and then advocating for yourselves with the individual attorneys as “This is what we’ve come up with. This is what we really care about, and do not think of us as adversaries.” You could set the tone for what it needs to look like, and that can be helpful too.

Cory: One thing that you just said there that I think many people don’t understand is the concept of collaborative law. And it exists, and it is very different as far as a process that you go through, and really looking at that as an option, and making that investment into starting it off right. On that note, I was thinking, you talked about going through a purposeful process, not from a legal perspective of a clause, but more an intention. What’s the most beautiful part of a prenuptial agreement that you’ve seen where somebody’s really brought their values together and said, here’s something that we’re putting our intentions forward and agreeing on this?

Emily: Well, I’m all about context and process rather than outcome and product. So, for me, I created the Purposeful Prenups Process as a way to support couples in being able to have challenging, important conversations, especially about finances, and come out the other side feeling like their relationships strengthened, that they can have these conversations and have them go well. They’re very much grounded in their values, their money stories, their personalities around money so that they have more self awareness about it. They understand how to do their emotional regulation when they start to get discomfort related to it based on their historical background. If they have very different views in terms of spending and saving, how do we need to think about our finances so that each of us has the freedom to have what we need and want? And neither of us is going to get distressed by the other’s strong need for the other, and come up with really creative solutions.

I had one couple I worked with. This was fascinating. She was an inheritor and was a trustee of her own trust. She had a lot of say and control about it. Didn’t have to work. He was an entertaining performer and was very comfortable having debt, and she was not. And he was very much into building wonderful, entrepreneurial endeavours that he thought would really pay off. And she was much more steady and clear on how to invest, and so they have very different personalities about it. So, they could not agree on their prenup, and they found my Purposeful Prenup Process on the internet, and they reached out to me. And so I did the work with them online, and it was one of those, thank god for Google at one point, because it was like they got through this roadblock that they’d hit.

One of the things that we discovered was she came with a very large in the black bank account with financial resources, and his was in the red. He was just in debt. But the reverse was also true, that she suffered from chronic depression, and he was one of the only people that could really make her laugh and shift her mood. So he came with a very high in the black emotional bank account, and hers was in the red. And so we were able to talk about the different value that people bring to the marriage and the relationship, and why they were getting married, and also being very clear that who they were in relationship to money wasn’t going to change. She had to go into this with her eyes wide open that he was continually going to be in debt, and he was going to continually take risks, and that wasn’t going to change. And they were able to have great conversations. They really understood each other. It wasn’t from a place of judgment. It was really valuing the strengths that they brought to it. And she could not tolerate the idea of if they were to get divorced, that she would be continuing to have to pay spousal support to the degree he was used to, as he continued to be in debt because of how he chose to move with money. It was so against her value, she couldn’t tolerate it.

So we created something with her financial adviser and her attorney, and then his attorney as well, in terms of a financial agreement that was going to be a gift she was going to give to him in stock when they got married, as a marital gift. And as part of the prenup, with the recep receiving that gift after they got married, that he would not receive any spousal support if they were to get divorced. So that was her insurance policy. She was like, it’s yours. And then we had to be really clear with her. You cannot have an agenda about what he does with this money. He could sell it all the day he gets it, and he could go to Atlantic City and gamble it all. And you have to be completely okay with that. And you can be because you’re not going to have to pay him out if you divorce. That’s what you’re going to have to keep reminding yourself.

So we actually had to do some what-if scenarios and bring laughter to it, but it’s really about “don’t be in denial about what the reality is of this way of behaving.” And that was their solution. And it was fascinating how they did it, and we had to make sure it worked with the law and their state, and they were able to come up with a really wonderful solution to take care of both of their needs.

Cory: I love that! And one of the my favorite things that you just said is equalizing resources and not just focusing on the financial resources. There’s so much that people bring to a relationship that it’s not just about money. And if it is, then that’s probably a recipe for disaster. And so looking at everything that’s being brought in is such a fantastic approach.

Emily: Yeah. And I have to say some couples have gone through the process and chosen not to get married, which on the one hand was sad and not what they anticipated, but on the other hand was so such a blessing for them, because it’s so much worse if you get married and then find out that you’re actually not compatible. So I just strongly recommend it. And couples can do it at any time whether they’re moving in together. You can do a cohabitation agreement. And it’s a great way to start practicing those skills together. You could do a postnap after you get married. Even if it’s not valid in your state, it’s still a great process to do as a couple, especially if you’ve been having difficulty with money, and this is a big deal in couples that financial infidelity is becoming quite known now, where they basically cheat on each other with how they’re spending, or getting into debt, like getting another credit card, or it might be gambling. It’s so many different things. And so if you’ve encountered something like that, doing a postnup is a really useful thing to get on a new page together as a couple with the reality of, given the fact that this behavior happened, what do we need to do as agreement as a couple that you have freedom to do these kinds of things and it’s not going to disrupt our marriage, and I’m not going to be impacted by the choices you’re making if I’m not included in them? What does that look like for us? So that’s another recommendation for couples that are in that situation.

Cory: I think that could be quite a conversation, because how can somebody not be impacted by that? I think coming to terms with the impact and the concept of the insurance policy, how do you give yourself that, whatever each person needs to be able to be happy together and be okay with that.

Emily: Having authentic trust in relationships is so key to overall satisfaction and ability to make great decisions together. And in situations where there’s been a breakdown in trust, it’s really important for couples to understand, and for family members too, how to repair it. And I’m working with, Charles Feltman, the author of The Thin Book of Trust, and we’re writing a new version of it, trust in families for wealthy families that have a co ownership of things together, where some family members are maybe working in the business and others aren’t, or some are in the family office and others aren’t. How do you make sure that that trust is really solid? Because we often have these trust vehicles for the money, but how are we managing, maintaining, and deepening the trust within the family? Because that’s such a key component.

Cory: Right! And when you talk about that, the kids working, maybe they’re working in the business or the involvement, and it might be involvement, or it might be that this is an asset that was a bloodline asset. And the families that you work with where they’ve had that asset or those assets and somebody marries in, maybe there’s kids that come in through marriage.

How have you worked on some of those in deciding how those assets are handled?

Emily: It’s that fair versus equal scenario. It’s so important to, again, be really upfront about, based on how things have been set up, what are our parameters, and then what freedom do we have with what we have access to. So, really, you want to be grounded in reality in terms of what you can and can’t do.

I worked with one family, where there were four daughters that were from a prior relationship, and then two kids that the mom and dad had together. And the dad, because of how the bloodline was set up for his inheritance, when he passes away, his two kids with her will get the principal, his trust will go to them. And the four daughters that he adopted won’t have access to that. And so one of the things that they did early on was they started a very rigorous family education program, and they were completely straight up with the daughters once they turned 18 about how he can continue to distribute money to them during his lifetime, and he’ll do it to the maximum he’s able to. And that is for them to be really smart about investing, growing, saving, building and becoming savvy about their life with money, because he knows that when he dies, he’s not going to be able to keep taking care of them in that way. And it was something that they were like, yeah, we know. And he’s like, no. I want to see how. It’s your money. You can do whatever you want with it. And the expectation is that you’re going to have it last. It’s for you and your kids, and their kids, and I’m going to keep giving you the most I can give you as I see you taking those steps. If you choose to just spend it, treating it like it’s always going to be there, the amount I give you is going to change, because you’re not using it the way that it’s intended.

So that was an important thing for them to have, it’s always like everybody’s going to be getting this amount, and it’s up to you and your choices and what you choose to do with it that determines what amount you’ll continue to get. And then they did great education with them, and it was really fun to develop the education programming with them and do illustrations that really made sense for them in terms of the power of compound interest, and helping them understand the different ways that they can invest. He also did things where he would invest in certain  passive income things, where you could have money coming from it without having to do a lot of work in it. And he would invite them to invest in it with them. They could use some of that money that he gave them to invest in that, which would then be something that could keep giving them resources after he wasn’t there.

So he was really operationalizing his vision of family and value of family, and he was using it as an opportunity to train them, and really have them see what was available and what they could do. And then when one of them wanted to be really entrepreneurial and open up a community related business in where they lived, he and his wife invested in that. And so that was another way to be able to give additional support to one of them and feel really proud about what they were offering to the community, because that was another important value they had. So they were creative about how they did it.

Cory: Absolutely! I love that, the ability to think outside the box and realize there were constraints from an asset gift perspective, or an estate gift perspective, but lifetime gifts could be maximized in a different way. So that’s just that creative thinking, understanding, and communicating it, that “equal versus fair.” That’s such a great story.

Emily: Another one I really like is when they invest in education plans. So that there’s money that’s set aside for the kids and the grandkids, and in perpetuity. And they might have an investment committee with the in-laws focusing on how that money is invested, what they can do to have that grow. And then they learn, with the idea that they’re also having input in the well-being of their children, their education, that sort of thing. And then also the distribution. What are the parameters? What can we give to within this vehicle? What does it not cover? That sort of thing too.

Cory: That’s great! That alignment of values and purpose through what connects them is such a fantastic story.

As we near the end of our conversation today, there’s a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Emily: I’m ready.

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

Emily: I said it a little bit earlier in terms of having a really grounded awareness about trust, what is it that builds it, what is it that maintains it, and what is it that breaks it apart, and then how to repair it. And there’s really four key distinctions to know about related to that. And it’s, do you care about what I care about? Are you sincere in what you’re saying? Do your words meet what you’re doing? Are you reliable? And then, are you competent? And when you understand those, how to maneuver with them, and how to give really healthy feedback, you can do a lot to repair trust. So I think that’s one that I’ve seen make the biggest difference, knowing that distinction.

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

Emily: I think I got into this work twenty years ago because of Roy Williams and his book on Preparing Heirs. And his stance has really played out in it in what I’ve seen, which is families that are proactive in raising very responsible, accountable children to be engaged young people and contributive members of society, and understanding their roles and responsibilities related to the family wealth, and where that’s a part of their life experience, they tend to do the best. And there’s not a fear of talking about it when they’re able to really because there’s so much that’s said about “you have to be transparent.” You have to talk about it. But if you know how to communicate effectively and then really prepare your beneficiaries for what they’re going to have to do, and what this means to be a beneficiary, to work with a trustee. What if you are the trustee? To just support them in this world of wealth and give them the language to understand it.

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

Emily: Love that question! I think it has so much to do with a willingness to be in that not knowing place and to learn with your family and remember that, I’ve never really been in this position before of having to lead people in understanding wealth because I built it, or I I’m in this place. So having that lifelong learning mentality is so huge, and being willing to share about their learning experiences, where they took risks, where they failed, where they innovated, and then allowing for mistakes, failures, and innovation to happen with the younger generation. So that’s one.

The other, I would say, is having an openness to direct feedback and input from other family members, and knowing that it’s coming from their best interest in terms of who they are now and what’s happening now, there’s always respect for how it’s been before. And then also knowing how to provide really effective mentorship and direction for the next generation. That’s really key.

And then, of course, communication. I’ll just throw that in because knowing how to communicate effectively is all about “what did somebody hear from what I said,” not “I told you, so you should know.” It’s like, “hey, what did they actually hear? What was their listening?” That’s the most important thing.

Cory: Absolutely! And communication is nicely weaved through those three qualities that you mentioned. So that’s awesome!

Before we conclude our discussion, I’d like to highlight where our listeners can engage in more of the conversations that you’re having, some of the things that you’d summarize, some of the things that you mentioned today, because there’s a lot that you’re up to. And some of the things that you’re interested in that maybe others are doing. Can you kindly provide where our guests can find you and some of those resources?

Emily: Well, I’m pretty active on LinkedIn. So if they want to know what I’m interested in, they can go there. We were laughing at, before this started, about how I did a post recently about my favorite books on governance, and I had so many responses. I asked people what else there is. So it’s like it became this really robust, sharing of resources, and I love that.

I’m obsessed with the book, Build an Enterprise Family to Last, that I just think is phenomenal, by Sarah Hamilton and Margaret Vaughan Cox. It’s such an accessible, easy to read, beautiful book, for families that have an enterprise. I’m a raving fan.

And then, I was just at the Family Office Exchange. They did a gathering for chief learning officers, and it was so great to share best practices. Jane Flanagan shared her research about next gen education, and I’m really diving into multisensory experiential education options for engaging the family members, and having a really great lifelong learning experience with their money and their wealth. So that’s something I’m really excited about. And my website has all, like, what I do and stuff.

Cory: We’ll link to that in the show notes for sure.

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

Emily: I think the one thing I’ll say here with you is I’m so inspired by financial advisers like yourself that are so committed to a holistic approach to the families that you serve, your clients, and what a difference it makes in their lives when you really embody the fact that true wealth is so much more than just money, and what does it mean to have a truly rich life. So I want to thank you for this and what you provide with the resources that you’re extending out.

Cory: Awesome! Well, I appreciate that, and it’s definitely a work of passion. And so I wanted to thank you for taking the time to share your expertise and your experiences with us today. I learn a lot from the insights that my guests share, and I’m incredibly thankful for the value that you brought. And I know that our listeners will too. So thank you so much.

Emily: Thank you.

As we wrap up this episode, we invite you to reflect on Emily’s insights about transforming difficult conversations around wealth into opportunities for strengthening family bonds.

Whether you are part of a family enterprise or provide consulting to family businesses, Emily’s emphasis on operationalizing values, establishing authentic trust, and balancing fairness with equality provides a framework for creating deeper connections that transcend financial considerations.

Throughout our discussion, we explored the impact of wealth on family identity and relationships, uncovering lessons on communication strategies and purposeful planning. We delved into Emily’s research on challenges faced by affluent families and her approaches to family meetings. Her insights on the Purposeful Prenup Process and collaborative law offer solutions for navigating sensitive financial conversations. These perspectives guide families seeking to balance individual needs with collective wellbeing, emphasizing regular family rituals, inheritance planning, and initiatives that foster financial literacy across generations.

For those seeking expert guidance on family wealth communication, prenuptial planning, and building authentic trust within families, Emily Bouchard is ready to assist. We’ve included Emily’s contact information, along with links to her website and additional resources in the show notes to support you on your journey. 

Disclaimer: 

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