The HERO in Family Enterprise: The Mindset to Guide the Rising Generation

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 Doug Gray, Ph.D., Founder and CEO of Action Learning Associates, LLC and co-Founder of Assess Next Gen, LLC. With over 25 years of experience and a doctorate in Leadership and Professional Practice from Trevecca Nazarene University, Doug brings profound expertise as an executive coach and leadership consultant. His experience across healthcare, finance, manufacturing, and education sectors informs his comprehensive approach to leadership development and organizational success. As an advocate for leadership excellence and community service, he is dedicated to helping leaders and teams achieve measurable business outcomes while mentoring the next generation of organizational leaders.

My goal is to be the most curious person in today’s conversation with Doug Gray as we explore his remarkable evolution from wilderness instructor to a thought leader in family enterprise development. His journey offers compelling insights into how families navigate change, build trust, and create lasting impact across generations. Together, we’ll explore perspectives that challenge how we think about family dynamics and potential.

Now, let’s dive in!

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

Doug: Absolutely. Glad to be here. Thanks for the invitation!

Cory: Doug, 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?

Doug: Well, I wouldn’t start with such pretensions. I think what I’d do, frankly, is, not face the audience, but face the graduates. And I think the reason is that they’re the intended audience. And also they’re more important than their loved ones who are in the audience. I suppose what I’d say is that they are the champions of change. We know that historically, and it’s terrifying to older folks. But it’s necessary for younger folks to feel that they’ve got agency. And that’s just a nerdy psychological word for choice, that they have the capacity to create their futures or design their careers. So that’s probably what I’d say.

Cory: When you talk about change and having that agency to be able to make that change, what does that mean to you and how do you feel like that would inspire the graduating class based on the work that you do?

Doug: Well, I’d love to say I’ve done this 20 times so I can give you based on historical evidence or a small data set. But I don’t have that data. So I think, so we’re speculating. But when I look at historical facts the years, I’m a little bit older than you. So since the 1960s, we now have doubled the workforce and doubled the intellectual capacity of knowledge of people, of workers, as a result of women joining the workforce and then all kinds of technological advances. So I anticipate that half of the audience might be interested in being endorsed and supported. Go, women! And I’d love to be able to say that our two daughters, who are 29 and 30, always listen to everything I say with enthusiasm and agreement. But that’s just not my experience. People get back. And I suppose that’s because we resist change. Not the fact of it. We all know it exists, but we resist the idea of being changed.

So a lot of graduates at any commencement ceremony would probably say, Don’t tell me what to do. So I wouldn’t want to do that. I wouldn’t want to be like a preacher or something. And I should add that I worked in prep schools for 10 years. So I had to wear the gowns, and I had to, you know, all the colors and crowns and all that stuff, the memorabilia, and address those audiences in various ways. And I found myself often, this is a long time ago, but I remember calming them down and calming their parents down and saying things like, Of course, we’ll be okay. Where’s your optimism? Because optimism defines our careers.

It’s as simple as choosing to have a positive affect, choosing the future, or believing that the future would be better than the past. A lot of folks have that belief, but not everybody has that belief. The socioeconomic disparities are profound. So I suppose I’d encourage them to be as optimistic as possible.

Cory: And so calming them down, when you know, that work, and you mentioned in prep schools. And now, maybe looking at the work that you do today, how does that dynamic between the parents and their children, and helping them with that calmness, to be able to maybe find some of that optimism? How do you do that?

Doug: Well, I wish there was a green M&M or a certain pill that I could, you know, say this always works, but that’d be silly. There are no silver bullets in our work of parenting and of advising. When I think about anyone, we all struggle with those two things. What is family? How do we support our family? How do we support our loved ones? And wealth, how do we manage our assets, current and future? So, maybe you’ve got such clients, but I don’t. Family and wealth are two topics that overlap and often create anxiety. I’m sure it’s true in Canada.

I’m told that in the US, 40% of the US population is on some form of medication for anxiety or depression? Well, as a psychologist, I’m not a clinician, but as an organizational leadership and business psychologist, I look at that stat and I say, what does that really mean? Am I dealing with the unmedicated person who’s filled with anxiety and depression? We have family members who are ADHD. When they’re not on their meds, they’re different people. Very entertaining. But can’t finish the sentence. And will interrupt yours. That spontaneity is a beautiful thing, and we know neurobiologically that they’re divergent, that they’re responding in a similar way or a different way. The same thing happens with all forms of education, whether it’s financial literacy or teaching high school English.

I think anxiety is a trigger because we’re all motivated by fear. It’s the biggest motivator in human nature. Psychologists often talk about avoidance or approach, which simplifies things. But the fear of losing x is the biggest fear known to man, and you and I see that playing out in family dynamics regularly. The elder gens will fear the loss of their legacy, or their reputation, or their impact in a business or their assets, or their beautiful things that they’ve done in their career. And the next gens will fear their inability to prove adequate. So there’s plenty of anxiety, plenty of sleep loss and such. So I think calming down is perhaps something we could all do more of. Not in a parental kind of way, but in a “let’s be straight, let’s be practical” kind of way. So I find myself doing that a lot. I did it a few minutes ago, but that’s a different topic.

Cory: And thinking about the overlap here, the fears that the elder generation, that “now” generation have, and the fears that that rising gen have, some similarities and differences. How do they work to start to understand each other better?

Doug: I suppose we just modeled it, didn’t we? They improved their listening and communication skills. And I don’t mean to simplify or minimize that process because I think it’s endless. So, an example, last weekend, I flew up to Northern Minnesota, where my family is, family of origin. And parents are in their eighties. My brother and sister and their spouses are there. And it was one of those rare occasions Cory where everybody felt comfortable wearing a Christmas elf hat or a Santa hat or whatever, and having photos and gift exchange and telling stories. And I appreciated it in the moment as a time when people did a pretty good job of listening and then sharing. Well, I assure you that’s not my memory as a child.

I’m the eldest, but the three of us were within three years. And subsequently, we compete for attention, dessert. Who knows what we competed for? But it defined us as people, I’m sure.

As adults, we’re in a different place, and our interactions with our parents in their eighties is also quite different than it used to be. So I suppose that’s an example of us listening, and reflecting, and learning, and communicating differently now than we did 60 years ago. And, my hope is that anybody can learn those skills.

So another comment back to your question is if there’s a thread line in my career, in my life, it’s always been, how do I act as a champion for next gen leaders? In other words, how do I foster leadership development for people who are younger typically than me? And I did that in my twenties as an outbound instructor in various wilderness environments, seasonally and then in prep schools as a teacher, and then running a nonprofit in DC for 10 years and working as an executive coach forever. 30 years, yes. And working with family enterprises.

So when I think about how do leaders develop, I think it’s kinda the same answer, poorly. Because we don’t have a script. There’s no rubric or academic lexicon or ladder that we need to subscribe to and jump. That notion thankfully has been displaced by the reality that all of us have our own career paths, and our capacity to grow and learn and such, and that’s exciting to me. So in the last 20 years, psychology has really flipped away from anxiety and depression. Those were the things after the world wars that we needed to explore. And there’s plenty of research on those things, and they’re super important. Don’t get me wrong. But in the last 20 years, we’ve begun to focus on how do we flourish? A word that really wasn’t used as much 20 years ago and now is used frequently. You probably do in a daily practice with your clients. Is that true?

Cory: Absolutely, yep!

Doug: My take is that wealth advisors didn’t do that 10 or 20 years ago. What do you think?

Cory: I would say so. I think that focusing on the fear of loss would be very much rooted in a lot of those conversations.

Doug: And I also think we’ve got this new vision that’s more positive, but we’ve also got more vocabulary around how to get there. We certainly got access to the tools, family meetings, and statements, and governance stuff. That’s easy to replicate. But we’re just beginning, I think, to use some of the applications from psychology in family wealth advising. And that includes the psychological capital stuff. Are you familiar with PsyCap?

Yesterday, I published an article that your viewers or listeners might like at familybusiness.org. And the title is something about HERO, that acronym, which is clever, but it’s also descriptive for four competencies. And they’re easy for us to apply at individual and family levels. Hope, efficacy, resilience, and optimism. And I know they sound nerdy maybe, but if we could just embrace them as vocabulary words and ask simple questions like, to what extent do you have the will and the way to hope for a better future? That’s a simple diagnostic. 1 to 10. And in a millisecond, somebody can answer it. An individual level or a family level. And I suspect you know what the patriarch’s answer would be. How helpful is that patriarch or matriarch? I don’t want to pick on a certain gender.

And we do the same thing with efficacy, our capacity to get the job done, our capacity to perpetuate family, enterprise. Some people are good at destroying. Unintentionally, sometimes. But maybe if they’re not effective, that’s something that a family could begin to address. Family wealth advisors used to ignore all that stuff. We just want to protect the assets. And I see a massive shift toward providing a more multidisciplinary and supportive comprehensive way to look at organizational change.

The last two are familiar. Resilience, capacity to return to a previous level or higher. But we’re known as a resilient species, thankfully. You live in a much colder environment than I do in Nashville, Tennessee. Well, okay! It’s a measure, perhaps, of resilience. And, optimism, I’ve already mentioned, is a generalized positive effect. People can learn to be pessimistic, but can also learn to be optimistic. And to the extent they do, they’re good hires. I assure you, lots of my clients reward loyalty when they should reward optimism, or they should reward PsyCap. If we took those four measures as the best way to compensate our employees over time, it would be better than rewarding based on loyalty. And yet some family businesses really struggle with that.

Cory: Now, Doug, as a champion of the rising gen, looking at your acronym there, what is it that the rising gen, or let’s talk more of the family together, can be doing to building that hope and efficacy, resilience, optimism, starting to do the reps, starting to exercise those muscles, you know, get that development early? How can they do that?

Doug: I think the short answer is, today, and slap away; just get started and start playing. You know, how do you learn to jump on a pogo stick, or ride a bicycle, or shoot a hockey puck? We all learn physical skills in the same way. Infants are tremendous, and the brain development is commensurate with that growth. They explore and take risks in beautiful ways. And then we’re all subjugated to schools and churches and elders who say, don’t do things in a certain manner. Well, that’s oppressive. Let’s assume that people of any age can learn hope, efficacy, resilience, and optimism. If you start with that assumption, that’s called a learning mindset. It’s quantifiable, and it leads to all kinds of massive outcomes.

100% of my clients are high on learning mindset versus a fixed mindset. I’m sure that’s true for you, and I’m sure that’s true for anybody listening to this podcast. If not, they wouldn’t listen. They wouldn’t be curious. They wouldn’t be interested. And it’s easy to ask if I wanted to have a better year in 2025, if I’m hopeful, in other words, how do I quantify that? There’s typically all kinds of measures, but numerical, and then non numerical and non financial measures of that.

You’ve probably got clients who say we value our family. How many times a year do they meet? Who pays for the travel? And where do they choose to meet? Is it convenient for the eldest or the youngest? Is it warm and comfortable? What’s going on there? Well, those are sort of quantifiable measures of hope within a family. They’re pretty simple.

What about the non-financial measures of hope? Hope is a word. If we recorded a family meeting, we can use AI to quickly assess how many times are those four words used? And that’s a quantifiable measure of PsyCap in a meeting. AI can do that immediately, and we can do it repeatedly. And we could track, I did this with several clients, track those four measures, over time. Because I know the outcomes are phenomenal. 65% of job satisfaction is tied to. And I can train people on how to develop their PsyCap in 90 minutes. So if it’s that dynamic and that impactful, I hope you and I, and everybody in our careers will use the model of PsyCap as an umbrella, more comprehensive model because it’s simpler and it’s more impactful.

You probably studied the Five Views of Capital that are sometimes described by many people, who have adopted Jay Hughes’ stuff. And that’s marvellous. It’s good. It’s descriptive and useful. But I’m not here to say that that’s the only model, or that any model’s necessary. If we came to that family event last weekend and told my brother that we were going to have a conversation about family harmony, the four components of it, he’d say, screw you and walk away. So I think sometimes people resist being changed in that way, which is critically important at self preservation. But we also love to change. Our kids are 29 and 30. They have agency. I think you’ve got kids, don’t you? How old are they?

Cory: I do, yes two. They are 5 and, well, newborn.

Doug: So you are in the mix to this. So you’ve seen the 5 year old evolve so quickly. Think about the plasticity in their brain, that person’s brain. And you’re about to repeat that story. As a dad, you’ll facilitate the environment to generate PsyCap. 

Cory: I did. One of the most important jobs as a parent actually, I would say. 

Doug: I think so too, and I suppose we all do that, right? We take the models that we think are relevant, and then we try to reinforce the boundaries. That’s called deliberate mastery. Plenty of science on that. We know it works.

Cory: And, Doug, in this society, you talked about all these different things that we’ve established, to control people in a way, and that rising gen is looking to prove that they’re adequate. How can we help them feel that optimism, and feel adequate as they are in this world? As parents, we want to create the atmosphere, but there’s so many external factors as well. So how can we balance that without living in a bubble?

Doug: Well, I suppose we always live in bubbles. And the image that comes to my mind when you say that is, we’ve got daughters. So as a father, I wanted to put them in the castle, in the bubble, have them sit in the garden and be protected. Can’t do that. It’s naive to assume I can. But I also thought as you describe that, of when you held your infant, when all of us hold an infant, we all do the same thing. We project our hopes and optimism and such on that individual, full of blessings and positive, and then something doesn’t happen over time. We forget to show our love. And I suspect that’s what you’re really talking about.

So, as examples of ways to show our love that we know work, the gratitude habit of 3 good things every day, that we could state out loud or write in a journal at the end of the day is an example of what social scientists call The Gold Standard. It’s scalable, repeatable, and, when you do it, there is better self description, from individuals as well as their loved ones, about them as persons. They have higher self esteem in various measures. And if you don’t do it, the opposite happens. That’s a great example of a simple thing that anybody can do at any time. There’s no cost.

But a better one is when we ask for feedback, like the Reflected Best Self Activity. Cory, you probably have done this in your career. Ask somebody, a mentor perhaps, or a person you admire, what are three things you like about what I do when I’m at my best? And you might be delighted. You might be surprised by whatever they choose to share. Well, I don’t think we do that enough within families.

I think another example would be writing legacy letters. For decades, I’ve written love letters to my wife and our daughters and give them to them at Christmas. And it’s, by far, the most emotional aspect of the holidays. And my wife regularly tears up and says this is my favorite part of the Christmas tradition. Obviously I’m going to continue doing so. But I recently realized when I was facilitating a family session that I don’t do that for the elders, my elders, because I find myself saying to the next gens that they could do this for their elders. And I don’t want to be a hypocrite. So of course I did it, and traveled, and shared it. And of course I got the expected response. You know, one parent is able to express love and appreciation and the other is not so much.

Cory: There’s no gender bias here, though, right?

Doug: You might be thinking one direction and I assure you it’s not that. The point is not gender bias. The point is modelling the values we want to share. Showing our love. Well, if we did that for our elders more, it might be a good thing. I have a URL called elder peer groups, but I don’t use it. I’d love to create one. Maybe you and I can do so. As a way for folks to share their stories, not only about what they’ve done and their legacy, but also, do you know the phrase, “ghosts of legacy?” Next gen struggle with this sometimes. If a matriarch did x in a certain way, the notion is that others need to honor that past. There’s a ghost of the matriarch, or somebody was around generations ago. I think that’s an important thing to address sometimes, but we don’t. Typically, we tend to avoid whatever we don’t understand. That’s human nature. It’s self preservation. But what if we created opportunities to do so?

As an example, and without being too vulnerable or personal, when I was in my twenties, my grandmother was born in Scotland, and I had this desire to go to Scotland. She had no desire. She was terrified as a child when she sailed over and nearly died by her descriptions. But I wanted to see the place and meet relatives, so I did so. And I was given this photo of my great-grandfather in this building that he had built in the factory that he had owned, which has subsequently been converted to a boarding house, or guest house, or airbnb place or whatever. Well, I didn’t think that photo was particularly important.

In my twenties I wrote some stuff and I gave it to my family, and we created a bit of a family tree. But I hadn’t touched it since. And in a recent conversation, my dad asked about it. Well, you know this Cory, when somebody’s 87 years old and they ask about something, you try to do what you can. So I ripped through the closet over here trying to find the dugout photo. It took hours. And I thought it was here; it wasn’t. I thought it was there, and it wasn’t. But I finally found the thing, and it was so big I had to bring a bigger suitcase to transport it safely. So when I gave it to him on Sunday, it sparked for him stories about his parents, and the rest of us, six or seven of us, were spellbound. It was like a trigger. It was like something had triggered in him an opportunity to share the legacy and the ghost of that. The stuff he knew and stuff he didn’t know. Well, I don’t think we do enough of that in family wealth. And I think the stories define us in ways that are incredibly important.

The flip side of that is we now have technological tools to capture the stories better than we ever have. And I told him at the time, wait. Let me get my phone, and let me record this. And we thought I didn’t do so. I should have. Just discreetly. And clients do that. Forever, clients would put on a little play or a show, or invite the youngest ones to show off some kind of a family talent, show some kind of a satire, or spoof, or mockery of someone in the year. And it’s delightful. It’s a way to entertain but also perpetuate the values of that family. In a similar way, you know people, I do too, who create books and storytelling videos of the history. There’s now software that can capture all that and create a timeline with a photo in a text box and automate all that digitization.

To me, that means we’ve got more tools than ever to capture some of the artifacts and on assumptions that were not stated in ways that we’ve never been able to before. So that begs a question, if we’ve got holograms of Corey’s grandfather or grandmother or both that could be created, what would happen if we went back to the founders of a business or an enterprise and ask the hologram what really triggered this investment or this capital expenditure, and how did that really play out? What were some of the variables at the time? If it was during the depression or a war or whatever the variables were that are external that we can’t manage. Well, maybe we could have some of that as a part of a family system.

Another visualization of that is when we have family gatherings, there’s often an empty seat at the table for the elders who are not able to attend, or the legacy that’s not able, or a religious figure. You might want to join that dinner or that celebration. Now, what if they were a Star Trek-like image that could be tapped verbally or with a click of a button to provide some contribution to current challenges for the next gens?

Cory: Interesting! You know, as you talk about that efficacy component and as these stories and the ability to reflect on some of that wealth creation, why was that decision made? How do I, in current times, be better at deploying capital? Because oftentimes we see where the wealth has been created, and those who inherit it just fear losing as you mentioned. And so being able to share those stories and allow maybe some freedom in that sense. So, Doug, you’ve given a lot of examples there, and and and the ability to relay those stories. How do families do this well? As you mentioned, there’s all these tools now, but it can be overwhelming. So how have you seen them do it well to be able to ensure that some of those stories remain within the family?

Doug: It’s important that they remain behind closed doors, that they’re confidential, that they’re private. I think people, especially with financial conversations, dismiss that fact. It is also something I’m not just sharing as an opinion.

So when we created the 360 Assessment Process and looked at five different systems, one of which is the family system. One of the two behaviours that we found that was most important is to talk about family investing and decisions and such in a confidential way behind a closed door. So I think that’s rule one. Make sure that family stuff remains family stuff. There’s absolutely no reason to share that you got a windfall or a legacy, or that your cousin is travelling through Italy unescorted and the family home is empty. Those are targets for the cousin to be vandalized or attacked or whatever, be a victim of some sort of violence. We need to be prudent. We need to be careful about the stories we choose to share. That’s one.

The second point that’s related is we also need safe places and spaces to practice graces. I didn’t make that up. But I think it’s really important because, as a family wealth advisor, I manage the process. So I create the spaces and the places. It could be quarterly meetings. It could be annual events. It could be, how do we deal with Johnny, who just went into a detox program and didn’t tell anybody that he had a chemical addiction problem? I might have known that he had it. The sibling might have known he had it. But the family might not have known. And they certainly don’t know how to address it. So that’s the space.

And the grace is, I think, what we don’t do a great job of. Religious groups, pick any religion, talk about grace as if it’s an easy thing. We say it before a meal. The serenity of prayer, in my opinion, ought to be renamed the courage for air. The courage to know the difference. Because if we’re not courageous, and “le coeur” is a French word that comes from the belief. The blood, the willingness to share. Those are things that we don’t do a great job. And I think we could do a better job. So to create the safety for a sibling to tell another in a way that they know is going to be sacred. To me, there’s no other word. The reason I host the next-gen peer groups is because it’s a sacred gift. It’s a promise to that cohort that everything’s going to remain confidential, and that they can learn from one another, and they should; we want them to, between the sessions. And they can learn from all the facilitators. That’s an example of an artificial structure. Families can do the same thing. And I don’t think we do a great job of that.

We could have quarterly meetings, family meetings. We could have a family council, which affects, or a family office, which typically focuses more on financial matters than the non-financial. But I’m here to tell you, the non-financial is much more important. And I don’t know if you think of it this way, but all the family office clients I’ve got struggle with the interpersonal conflicts. There’s nothing soft about that world. WWhen the US military called it soft just because they didn’t know what else to call it. You know, the hard objects. The hard skills were how do you load a gun and shoot a tank. But everything else is really what defines our careers. So I think that’s why we need models. I think that’s why we need safe spaces to have the conversations.

Last point that’s related to me is the word practice. Physicians get to practice their medicine. Isn’t that a lovely gift? Lawyers get to practice their work. Isn’t that lovely? Wealth advisors do not get to practice. Leaders do not really get to practice. We’re not given permission to practice. I think that’s a shame. The reality is you and I are practicing every day, especially when we try new things. Maybe try new things in safety and confidence with one another. And to the extent we’re able to express our love, well, that’s a communication skill. It’s something that can be taught and can be developed.

Cory: I love that, and so much ties back. So, you know, I think with that, Doug, as we start to wrap up our conversation near the end, there’s a few questions that I ask each guest before wrapping up. Are you ready for the tough ones?

Doug: Yes. So I should have listened to one of your previous recordings. All good. 

Cory: Now the first one, what is one key strategy you believe is most essential for building a successful family enterprise?

Doug: Maintaining the long-term hope.

Cory: And what does that look like?

Doug: Strategy needs to be aspirational. It needs to be up and to the right. But it’s like looking at a star and asking me, what does it look like on the backside of that star? Hope is to find every good prosocial. That’s another nerdy term. But every good collaborative event, activity in human history, every university, every church, every town, every business, every family was a hopeful endeavour by a bunch of people who shared a similar vision for whatever. At one level, it’s presumptuous and fairly silly. Why do we think this business is gonna thrive or flourish, or survive even? And yet we do it again and again. Why do we assume this newborn of yours is gonna be extraordinary? We assume that because we don’t expect our children to be average or below average. They’re going to be superior in some manner. Hope defines us, and thank goodness it does!

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

Doug: Fear of loss. And I’ve already addressed that a little bit. It’s easy to say if I don’t have access to the trust or I don’t know the terms, and I’m not clear about the distributions and how they might affect me. But it’s harder to say; I’m really not sure what it would be like if we didn’t have the family business anymore. If we sold it and now have all these assets. I hear the concept of a family office. I really don’t know what that means. What’s the glue that’s going to bring the family together three times a year? And we lack it. We lose it. And that terrifies a lot of people.

Durable family harmony is sort of a flag we fly like any other aspirational flag, but it’s elusive, blows in the wind, and it falls down when the flagpole is shattered. So I think we need to be attentive to the ways in which we protect our assets and share our assets. And you see this every day. Next gens are looking at donor-assisted funds. Marvellous example of massive opportunities for them to practice agency. Terrifying to many elders. You want to support what political group? Or what ecological interest? Or what DEI initiative? And why would you do such a thing, honey? Well, those to me are tremendous examples of agency. So the fear of loss plays out in all kinds of ways.

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

Doug: PsyCap, humility, and curiosity. And what I’ll add is that humility and curiosity cannot be taught by AI. They will never be displaced by AI. Your curiosity is a currency of learning. But it will never write the prompt. Cory writes the prompt. Cory looks through perplexity or ChatGPT and uses that question to lead to the next question. Your curiosity drives your learning. Why do you spend any time on YouTube? The number one search engine is Google. What is? And number two is YouTube. How do I dot… dot… dot… So curiosity and humility is another one that will never be displaced by AI. Thank goodness there are two. But when we remain humble and show publicly our humility, it uniquely describes us as people, and it can become one of the premier family values. We see this in philanthropy. And when you think about any entity that’s benefited from philanthropy, we tend to focus on the bigger ones.

The colleges and universities and the hospitals for instance, that have the capacity to deal with your $10,000,000 donation. And we don’t often look at the park downtown or the rotary investment in that clock on the park. Well, maybe we should. Maybe humility can play out in a hundred different ways. Maybe anonymous gifts will displace the Gagnon gift… Family gift. I’m putting you under the bus here, sorry. In other words, anonymous philanthropy is an example of humility.

Cory: Yes, not every building needs to be named. And we need to know where we’re headed. But yeah!

Doug: Some next gens do that intentionally in part because they want to hide the asset distributions. But another reason is they don’t want to attract attention to themselves because digital access from their buddies is easy. So if they post the fact that as a beneficiary, they suddenly had 10k, or 50k, or 100k or whatever, the number is to distribute wherever. They certainly don’t want their friends to know about it because they’ll expect them to pick up the bar tab every Saturday night.

Cory: Absolutely, yep. Now Doug, before we conclude our discussion today, I’d like to highlight where our listeners can engage in more of the conversations you’re having or more resources, with regards to some of the topics that we discussed today. Can you let our guests know where to find you and some of those resources?

Doug: I’d be happy to! I do a lot of this, collaborating with wealth advisors like you, Cory. And part because I know my swim lane. I know where I don’t belong. But there’s several URLs or websites, and I guess I’ll send them to you also. I mentioned nextgenpeergroups.com, and that’s pretty extraordinary. In January, we’re launching the next cohort. We’d love to have, and 70% of the current group are renewing, which is common. We’d love to have another cohort for non-family members because it’s a larger group, and family businesses are unique. And what’s unique about that program is that it’s validated. It’s based on the assessment process. And that’s also reflected in the digital content and the book I wrote.

The Success Playbook for Next Gen Family Business Leaders is referenced there. assessnextgen.com is the 2nd URL, which is a 360 assessment process. You and I spoke about that in a different context. And that’s unique to the world because it’s validated and customized for family-owned businesses. Hugely important tool to accelerate succession planning. So I’m often brought in by wealth advisors or family office leaders to say, Help. Can you determine if so-and-so has the chops, and then what capacity should we develop?

Action-learning.com is kind of the mother ship, and there’s a bunch of content there. Everything’s connected to YouTube and LinkedIn and whatnot. So those are great ways to reach out. And I’ll mention also that I’ve got several projects that I’ll be able to announce shortly. But I won’t tell you the URLs. I’ll tell you what they’re about. You and I like technology. Here we are meeting, you know, in this manner. I’ve created an AI-assisted coaching tool to accelerate communication with family wealth advisors. We can all do a better job, and that tool will be launched within weeks and then piloted shortly. So I’m super excited about that. Another one is a not-for-profit for family wealth advisors that will have some master classes and tremendous content. And I’m excited about that, but I’m not going to tell you any more about it today. How’s that?

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

Doug: No. I appreciate your generosity, and I hope that this is useful to someone. 

Cory: Absolutely! I believe that your insights have been incredibly valuable. And I wanted to thank you, Doug, for taking your time to share your expertise and your experiences with us.

The stories were great, and I’m grateful for your contribution. So thank you.

Doug: Thank you. And I love your candour and receptivity to this whole process. I would not ever want to be in your shoes as a host. I’m happy to be a guest. Thank you for asking.

Cory: Awesome! Thank you.

As we wrap up this episode, we invite you to reflect on Doug’s thoughts about psychological capital, creating safe spaces for authentic dialogue, and the transformative potential within family enterprises.

Whether you are part of a family enterprise or provide consulting to family businesses, Doug’s emphasis on building hope, fostering resilience, and nurturing genuine connections across generations offers a fresh perspective on family wealth and legacy.

Throughout our discussion, we discovered how family strengths emerge through deliberate practices and honest communication. We explored Doug’s HERO framework – examining how families can build their capacity for hope, develop confidence in their abilities, strengthen resilience, and cultivate optimism together. We looked into real examples of how creating safe spaces for meaningful dialogue and capturing family stories leads to stronger bonds across generations. These approaches provide concrete ways for families to address challenges, celebrate successes, and grow together while honoring each member’s individual journey in the context of their shared legacy.

For those seeking expert guidance on family enterprise development, leadership coaching, and building psychological capital within family businesses, Doug Gray is ready to assist. We’ve included Doug’s contact information, along with links to resources in the show notes to support you on your journey of strengthening family dynamics and creating lasting impact across generations.