Practice Makes Stewards: How Families Develop Decision-Makers Across Generations

Cory: Welcome, everyone. Thank you for joining us for what we’ve named Practice How Families Develop Decision Makers Across Generations. My name is Cory Gagnon. I’m a Senior Wealth Advisor with Beacon Family Office at CI Assante Wealth Management Limited, and 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 join us for what will be another fantastic and very lively conversation, I’m sure.

Legacy Builders Live is produced by Beacon Family Office at CI Assante, where we support successful families designing an integrated strategy 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 today, please feel free to drop them in the Q&A box. And if time permits, we’ll address a few of those live and, might also do so as we go. So please feel free to put those in the Q&A. And if we don’t get to them, we will make sure that we are following up afterwards.

Important disclaimer for our legal friends. Just a quick note, the content shared during our webcast is intended for informational and educational purposes only, and it 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 or positions of the organizations that they’re affiliated with. We encourage viewers to consult with qualified professionals regarding their own specific circumstances.

Now, let me introduce today’s panelists.

Doug Gray is the founder and CEO of Action Learning Associates LLC and co-founder of AssessNextGen LLC. He is a leadership consultant and executive coach who specializes in succession and next generation development with family enterprises. Through his three sixty assessment work and peer development groups, he helps rising leaders build communication, decision-making, and feedback skills before transition pressure escalates. Welcome, Doug.

Doug: Thanks. Glad to be here.

Cory: And Torri Holley is the chief learning officer at Tamron Learning, where she leads learning strategy and designs wealth education experiences for enterprising families and their advisors. She focuses on building confidence and stewardship capacity through intentional adult-centered learning design, helping families approach learning as a long term succession strategy. Welcome, Torri.

Torri: Hi. So excited to be here with you and Doug.

Cory: During today’s webcast, our goal is to explore five key questions about how adult learning strengthens stewardship, and how repeatable practice builds leaders who are prepared before transition pressure forces performance.

Now, let’s dive into our first question. Why does next generation development look like progress on the surface, yet still leave families feeling unprepared. And exposure can look like preparation. I actually had this conversation yesterday with an advisor peer group that I’m a part of, and I found that it’s not all the same. And what often is missing is that intentional experience, that real accountability and decision-making. We’re not doing this as a mock. We need to actually, have people look like they’re progressing, and fill that gap between confidence on both sides. Now, Doug, where do you most often see potential mistaken for real readiness?

Doug: There’s probably two extremes. One is when somebody’s promoted too early, they may not be qualified for whatever they’re doing, and that’s often because elders have rose colored glasses. We tend to always think our children are above average. The second example is paralysis, when elders in particular might not know what to do, and might not be willing to promote somebody. And both of them, I think, are driven by fear.

Humans are biologically programmed from back here, the oldest part of our brains, to deal with aversive stimuli from market demands to aging children, to AI, to all the economic and global uncertainty that we could focus on. So how do we deal with that? The short answer is we use our prefrontal cortex, and we use objective measures.

Cory: Torri, I think I owe you money because we had a bet on how long before Doug said AI. So, less than two minutes.

Doug: Well, that’s an example of how we’re forced to think in different ways that we’re not evolutionally prepared to do. Two of us have had these things. We’ve all got assisted body parts now. And well, I don’t, but most folks do. And when I think about our adaptation capacity, that pace, we’re really not sure how to process the amount of information that’s available to us now. So I’m glad to have exceeded that little expectation, and Tory won her bet.

Torri: I’m glad you brought up fear, Doug, because I see fear on both sides. I see fear on all sides. The way that parents, decision-makers, and sponsors of learning are responding to rising gen, next gen. I see fear from the family office around preparedness, and I see fear in the rising generation about how they’re supposed to show up, and what they’re supposed to be doing as well. So I’m glad that it surfaced so early because I think if we can honestly talk about this in a family office, in an operating enterprise, we can move forward because family makes things a little bit scary. And so I actually talk about and think about safety and learning all the time.

Doug: Ever do the fear box? Take a post x, write down some of your fears, put them in the box, and then try to not discern who actually wrote what. Pull them out of the box and then surface them. Let’s talk about some of these things.

Cory: What a great exercise. It works. I want to bring up the assisted action. I really like that body parts analogy there, Doug. Because before we jumped on, we were talking about communication across different cultures, and how technology today, I’m a bit curious, masks capability so well, allows people to look like they’re capable of doing something, although it might be technology that’s assisted and they really don’t have that comprehension. And so how do we how do we decipher that?

Torri: Can I respond to this? Because I’m super excited about it. So I have been on this whole journey. My Apple news feed just will not stop sharing information with me about AI. The more I read about it, the more it wants to share with me. And as we talked about in prep for this, if you are feeling exhausted hearing about AI, you are not alone.

In any event, AI as a masking tool for capability and decision-making is really interesting, because of this lens actually that AI is most helpful if you already have good decision-making capability, and it is a tool that assists that, because you can differentiate between a good decision and a bad decision. So, really, that artificial intelligence in learning and how it’s showing up. People are saying, why do I need to invest in education? I can just go to choose your provider and learn.

But what that doesn’t teach is the ability to understand what is happening on the page, to practice that unless you prompt your AI to assist with that. And that really AI is a fantastic tool for the leading generation because they already have those skills and abilities. And it’s not such a good tool for middle schoolers who are trying to learn their multiplication tables, that this learning is much more about the journey than it is the destination or handing something in which we’re seeing across learning, whether it is selective learning, like something like Tamarind, or in schools where the the goal was never to hand something in and complete something, or at least from my perspective.

Doug: You had a cool statistic from Pew. Could you share that?

Torri: So this is actually a Gallup poll that just went out on the twelfth. One third of gen z say that AI makes them angry. And if you dig into it a little bit as well, it’s that we’re pushing AI as this amazing tool, but at the same time, we’re saying this is going to take your jobs and you better figure this out. And so we’re seeing a lot of resistance and frustration with AI. And also, I think go on to any social media platform, and whether it’s visuals that are being created, or posts that are being created, or ways that we are taking the social Internet, and we are stripping the humanity out of it a little bit. I think it’s a little bit uncomfortable for gen z who are increasingly going back to analog music, and manual cars, and records, and reading tangible books. So we’re sort of seeing this, push and pull response, and I think it comes back to fear a little bit in learning.

Doug: You might be interested in this, because it relates to cultural variability, Cory, and also technological adoption, Torri.

I was part of a program last week that looked at the International Positive Psychology Association, and how AI is perpetuating flourishing behaviors or not, like reality-distorting behaviors. And the gist from most of the academics was we need friction, which is commonly defined as human interaction.

So let’s take it to family wealth and succession issues over next gen or leadership development. Let’s assume that Torri needs to be an active facilitator of that process, so that even if the digitally trusting folks go online and they find some information, Torri needs to facilitate that meeting. Why? Because it needs to have human friction, and things are never as seamless. 

The cultural example that came to my mind, Cory, is an Asian g one founder family, very successful. G twos are in the US and not restricted by the Asian beliefs of disclosure, for instance, and and deference for elders.What does that mean? It commonly means that the younger ones are more inclined to say whatever’s on their minds, And the older ones will never talk about an estate plan, or share a will, or do a live reading of a will with their children while still alive, because it culturally is inappropriate. It escalates ghost behavior. That’s a word that I heard from this client. And the main point is it would be culturally inappropriate for us to push in a certain way when there’s resistance to that cultural belief. Makes sense?

Cory: It does. I love the positive side of it, Doug, and whether or not you last week found the positive side through those conversations. I think of the informal learning that can happen. I think of when I was growing up, all those encyclopedias where my curiosity would have me pulling them out and looking up neat things. What that looks like today, or maybe there’s not intentionality in that educational plan, but there’s curiosity driving it with tools that are so much more accessible. Any thoughts on that one, Torri?

Torri: So what I see in families a little bit, is that the informal learning, there’s some assumptions about what is being learned, and so that knowledge is lumpy, and particularly if we’re trying to educate a large age range once a year, which is often how families do this, they do a single learning event. It’s a little bit different if we’re talking about an individual who’s being groomed for succession or something like that. But most often, that curiosity piece is how someone is going to learn outside of the family. And we even talk about concerns that the rising gen are gonna ask questions, and we don’t want to answer those questions.

I recently had a conversation with an adviser, and they said, I love your investment content. It’s comprehensive and it’s amazing, but could you pull out anything that talks about ESG or impact investing for my client? They keep asking questions about this, but we don’t want to create space for it. And I said, well, if they’re already asking the questions, they’re doing their own research, and you’ve now lost the opportunity to have a contained conversation in the way of, here’s our family office, here’s our investment policy statement, let me enable you to invest how you want to and educate.

So that’s what I sort of see with informal learning, is it can go in a thousand different directions, and there’s no way to sort of contain the narrative in the family, in the family office, or the enterprise. And when you’re thinking about it structured, at least you can create spaces for safe conversation and understanding, and importantly, how you want to articulate even things like values in a family setting, saying, I want you to communicate with me with respect. I am your elder, and here’s what that means and feels like when you are doing x y z. So does that answer?

Cory: It does. Yep. Doug, you had some thoughts there?

Doug: Academics and learning and development people talk about two different approaches to schooling, which is really what you’re talking about, informal and formal learning.

So informal would be, what does Torri do when she’s curious about something? Well, I suspect she writes a prompt, or asks a friend, or calls a friend. In other words, our curiosity is the determinant of, I call it the cure currency of our learning. Curiosity is, psychologists know, one of the key drivers of human behavior, but certainly of schooling. The more formalized stuff is under attack. When we look at the power of universities and didactic programs that say, here’s the only way to do financial planning, law, family succession work. The younger ones will say, really? That’s odd. And when they get multiple conflicting perspectives, they’ll say, do I really need this graduate degree, or this bachelor’s, or this certificate program?

I had a 60 year old client yesterday say essentially that. I could go to Stanford. I could go to Wharton, and I could get this certificate program, but I’m not sure I need it. And this is a guy who’s running multiple businesses. So we explored what he did need. And his next stage in leadership development, frankly, meant reducing some of the sectors that he’s invested in, so that instead of having five, they have three. And there are compelling reasons for that. Well, that would have only happened if we had an informal conversation, and that’s the role of executive coaching, I think, in skillfully moving that schooling ahead.

One more thought. You probably know this phrase, Torri. I think there’s only three things we do, all of us. Torri, you do the same thing. And that’s, I think, we create space for clients to meet. They meet with us. They meet with each other. They have the space. And then we manage the pace, whatever that looks like. It could be quarterly, could be annual, could be weekly, could be every hour until you get through the crisis. But it’s the space and the pace so that we can practice grace. And those not only rhyme, space, pace, and grace, but I think they nutshell some of the work we do when we’re at our best.

Cory: I love the rhyming.

Doug: Credit goes to somebody at Stanford. One of those pods I’ve listened to.

Cory: Moving us forward, what shifts when families move from hoping readiness will emerge, to intentionally designing for it? And, Doug, you just mentioned something, that gap can become visible. But then the next question is not just what we build, but what is that process that needs to be there? And so how do we design that structure that is flexible enough, but also is intentional and reactive to where we are, where we’re going, rather than it just being one person’s approach? And, Torri, coming to you first, from an adult learning perspective, what changes when development is intentionally designed, rather than left to experience?

Torri: So I actually prepared an answer for this, but I want to bounce off of what we’ve been talking about a little bit. And it’s, what is the intention of learning? Is the intention of learning in a family meeting connectivity? That then is going to drive the structure of what you’re going to cover. If the intention of learning, for rising gen members, adults to participate in governance, to become the CEO of an operating business, to inherit $100,000,000. So when we create a really clear pattern around why and we communicate that to adults, they’re going to be more engaged around learning just from the get go.

If you say, I want you to come to Tamarind, or I want you to partner with Doug, and I want you to learn about this, and you don’t say why, there’s immediately going to be resistance and pushback and disengagement, and all this sort of icky emotion around it. When instead we say, here’s this opportunity. Do you want to engage with it? Here’s why we’re learning. There’s a real opportunity to kind of do things differently.

The other thing in adult learning strategy that I talk about every single day, is your learning has to be practical, and it has to be actionable. And so what families often do, for worse or for better, is they bring in a subject matter expert, and that subject matter expert lectures about something that is complex. And then they say, great. We taught income statements today. We taught the spaghetti diagram of our ownership structure. Super glad everyone understands that. There is no reinforcement. There is no application. There is nothing to do sort of with that learning. And I feel like the really unfortunate thing, and I’m a rising gen member myself. I’ve been going to family meetings since I was, like, 16 years old. It is that you build this energy and this momentum and this engagement in that learning time, and then you don’t give a so what. You don’t give the opportunity to practice. You don’t give the opportunity to build confidence or apply it to something that’s going to impact them.

And so what you see is just sort of frustration built up, and that’s what I see frequently in families, is both from rising gen members and from the people who are sponsoring learning, is frustration with it. So then it becomes something that they tack at the end, or they don’t want to do, and it becomes this thing like, ugh. Even when we’re a learning family, ugh, we don’t like it. So I think when we move to something more intentional and structured, we can deal with a lot of that frustration. We can give it purpose, and we can engage in a meaningful way.

Cory: Can I add one thing that I learned from you, Torri?

Torri: Please.

Cory: What’s in it for me? I think if we haven’t defined that for each individual in a way that they’re invested in their own outcome, it’s pretty hard to be engaged in any of it.

Torri: Something that actually came up in my most recent adviser training, we call it, the wealth education facilitator training, which is how Cory and I met way back when. There’s a gentleman in the course right now, and his name is Joel Wood, and he said, just continually ask so that, what’s in it for me? Well, I’m going to get $5,000,000. Okay. What are you going to do with that $5,000,000? I’m going to go on vacation for the rest of my life. Okay. Great. And then what? and that’s actually added a fair amount of richness to this learning process, is we we no longer kind of just stop at what’s in it for me, but what really truly fundamentally is going to be different if I show up with this education in a meaningful way? And so that’s actually been leading to some really fantastic conversations with families as they’re thinking about learning, as well as individuals.

Cory: Amazing. So much from the coaching world there that is very rich. Doug, any thoughts on what Tory said before I pop over?

Doug: There’s two levels of behavioral change. I’m trained as a psychologist, so it’s the individual and the team. And when we think about the individual changes, Torri didn’t talk about assessments, but behavioral assessments are often useful, whether they’re self reports like the EI and the DISC stuff. There’s some that are not reliable and not valid. And then there’s other persons rating my behavior. Those are called three sixty assessments, and those are incredibly predictive, super valuable, and the best accelerants of behavioral change known to psychologists. We’ve got over a hundred years of data on that. Hogan is pretty good self-assessment as well to look at leadership changes.

But I think the main point is the individual changes are fairly easy to track and and measure. The team changes are harder. So we use surveys, we use interviews, and we look at milestones quarterly for instance. And sometimes, a decision-making matrix, or a racy structure, or some structure that helps the team manage how they’re moving forward. And the analogy is often repeated that I wouldn’t go to a doctor or nurse who didn’t do my vitals, or take the vitals and look at my past records. Same with the wealth advisor, same with the legal advisor. And yet, family systems don’t have that database. Even if they’ve got a cool repository like leaf planner or some archives that go back a 100 years. How we make decisions is really what we’re talking about today. How we learn. And that’s often the place for individual journals and team records. It’s the reason why top down decision making is evolving and objectives and key results.

Our leadership is evolving. Gen z’s of every age and every ethnicity are embracing the fact that we’ve got agency. We want to express our opinions. And that’s based on a bunch of my research as well. So that’s why I wrote the OKR leadership book, and that’s why we created assessnextgen.com. And Individual tools, we need team tools, and we need ways to track it over time.

Cory: And when you use those tools, specifically the three sixty, Doug, how can we measure like, do we go back to that as our measurement, or are we looking at behavioral change of how the system has evolved once we’ve baselined where we’re at?

Doug: Both is the short answer. But let’s imagine we did a three sixty assessment of Cory’s interactions with any number of people, or Torri’s, because she’s got a bunch of sisters, I think, and you’re g five or whatever. So there’s dynamics, emotional conflict, and sometimes people don’t often express what they need to. So the model we use is here’s Torri, and here’s the family system, business system, ownership system, and learning system, because we’re all part of these five systems. And for each of those five, there are 10 behaviors that we’ve validated. So then we ask a bunch of people in different rater groups, like seven different rater groups. Well, what do you think of Torri’s dot dot dot. And then, she also does it. So the self rater is compared to those six other rater groups. And there’s a gap always, and that’s a learning point.

So if Torri thinks she’s up here, but others say you’re down here, that’s an inflated view of whatever that behavior is. And the inverse is certainly true. If Tory thinks, she’s down here, but they say, you got it. You’re a rock star. And the short answer to your question is if there’s one thing I could wish any listener or viewer of this to do, it’s behavior number one. So there’s 50 behaviors that are ranked, but number one is please express your thoughts and your emotions on whatever you think is an important topic. Silence does not aid. Family systems are too emotionally complex. So, Torri, I know you to be articulate and expressive. Please do not hold back. Express your thoughts and feelings on important topics.

Torri: The feedback that I’ve gotten is I could do a little bit less expressing, frankly. They would like to pick the time and place, I’m sure. But honestly, Doug, this is a lesson that I have learned and developed in my family system, is create space, and for others to communicate. And that actually has been really helpful for developing my family. It’s being an outspoken individual and learning to take a back seat, but that required a degree of painful self awareness.

Doug: In my experience, it doesn’t matter whether you’re in your twenties or sixties. My last call was with a client in his fifties. His dad’s in his seventies. He’s still struggling with the things he needs to change, and he’s become more articulate. He’s able to express them. And, of course, I’ve worked with him for several years, so I get some behavioral feedback from other people. Now what about this?

Cory: Yes. And overfunctioning. It’s a wonderful thing. Where are you overfunctioning?

Doug: Psychologists call it overuse of your strengths. If, for instance, you’re skeptical and you are overly expressive on your skepticism, you come off as being negative, arrogant, snarky, entitled, or whatever. So to this kind of a bidirectional paradigm. Tone it down. Tone it up.

Torri: Can I respond to one more thing before we move on? So Doug said people don’t express what they need to. This is also true in learning. Something that we observe quite frequently, is in this traditional setting where it’s happening once a year, and the CFO comes in and they explain the balance sheet, and then you say, any questions? And everybody just goes, nope. That is not a great learning environment, and it is most importantly not a safe learning environment. Trying to be the cousin like, you have to be so self comfortable to raise your hand and say, sorry. I’m actually an artist, a stay at home parent, I work in HR. I do any number of things, but I don’t understand balance sheets at all. Could you just hit it again from the beginning? So that’s something that I find really important.

Actually, with structured learning led by people who know how to do instructional design to share information in a way that is agent stage and appropriate, that is, you know, scaffolded so we can build confidence so that we don’t just have people sitting and nodding. And it’s also why we use assessments, so that we can create benchmarks and goals, and that it’s not in this big open family setting that feels really unsafe.

Doug: You skipped one more resource, and that’s the married-ins who selected that family for some godawful reason. And they’ve got insights that could contribute to some of the question-asking.

Cory: Absolutely. We won’t forget that group, Doug. Let’s remember them as we go through our next questions here. So next one. Why do capable next generation leaders still struggle if they haven’t had space to practice before responsibility arrives? When I think of that communication, feedback, decision-making that we’ve been talking about, there’s something about that pressure cooker, or that situation that we’ve created, where we really haven’t allowed people to flex those muscles and to actually have that repetition that’s required.

So, Doug, in your peer groups and coaching work, what changes when rising gen leaders have structured space to practice before those expectations increase?

Doug: Never do “mirror mirror on the wall.” You talk to the mirror. You smile in the mirror. You make your sales call. When I was a kid, that’s how I was taught. And yet, it’s not a great behavioral feedback tool. What we’re doing right now, Zoom is a better one. Because when Cory’s in agreement, he would see behavioral stimuli. It reinforces behaviors. So why don’t we do that more? And the short answer, I think, is we don’t practice communication because we don’t know how to. Cameron’s programs are useful in many ways. I have a bunch of communication tools that have been adopted by amazing places, including Georgetown, in their executive coaching program. But I think the other answer is we’re not using the technology available to us.

Torri, you might remember a year and a half ago, I introduced you to jitcoach.com, which is a resource I can give to anybody on there who’s interested. And this is an amazing tool. So you can click on a profile. You could select a role-play like sibling rivalry. You can select an avatar. You can make it skeptical or friendly. And then record your video in confidence. And the AI will assess your interactions and give you coaching feedback and analysis instantaneously. Let’s imagine we want to develop those sales skills. Let’s imagine we want to develop the communication skills within a family system, and there’s 100 shareholders at an event in Pinehurst. It doesn’t matter where the event is, but they’re not inclined to speak, and they need to practice some of those behaviors.

I think those are examples of tools that will become more and more commonplace so that people can practice the skills that they need.

Torri: Yeah. This tool that Doug has is really cool, and he gave me the opportunity to beta test it a little bit. And even in my own sort of facilitation work, being able to talk again in a safe environment to someone who’s not going to judge you for messing it up, and give really specific, articulate feedback, was really helpful, even in just playing around with it, and I I see a lot of practical use to continue to build that safety.

Doug: And I bet you guys do role plays in your training, don’t you? People hate role plays, but I’m imagining you do role plays.

Torri: We definitely provide prompting for it. The learning is self-directed, but definitely, we provide a lot of templates, for example, for interviews with family members, interviews with your trustee, with your wealth adviser, so rather than giving that kind of back and forth. But that’s why I was like, I love this tool. I could see so much use for it, and especially in training wealth advisors to navigate the waters of these complex family systems, having the opportunity to build confidence in a totally safe environment, it feels essential to me.

Cory: Doug, I was thinking about this tool and whether or not it will create the environment that you see those 100 people that you’re speaking up in front of, and maybe that judgmental married-in aunt, see I’m bringing back the married-in, who’s about to to say something, or give you that look, how can you create that environment or practice that one?

Doug: The short answer is any way that would serve the aunt, I imagine. Just like you’d ask somebody else for an opinion, perspective, or feedback. Should I say this way? Most people now use Grammarly or other tools to edit their emails to make sure that it’s professional and appropriate, matches the tone as desired. I suspect we’re going to use even more of those tools ahead.

Cory: I wonder about that friction that you talked about, Doug, if we’re in a room together, I can’t just pop open Grammarly over here, or Claude, to say, what’s going on? And how do I do that? I guess we’re all on our phones.

Torri: But I think what’s interesting here is that this is a step in a line of practice.

Doug: Try this one. Whisper into it. You can do it instantly.

Torri: Doug always has the best tools.

Cory: I know.

Doug: I learned a lot.

Torri: When educating around financial literacy, specifically around a topic that people have emotional responses to, for example, like financial statements, there’s a lot tied up in it. Identity, capability, confidence, all of these things. You can only start with awareness. You can only start with safe failure, and then you can build enough sort of understanding to then you might show up as a junior board member. And so creating sort of, again, this scaffolded experience. So tools like DUGGER sharing are not going to be able to simulate the adrenaline spike that you might have in conflict with a family member, but they give you the ability to practice and build that skill. So then you’re flexing that muscle so that at least when the time comes and you’re experiencing that conflict, you at least have some preparation for it. So it doesn’t give you, again, the destination. It certainly can be part of the journey.

Doug: In good days, don’t we all do that? We self-reflect. We bite our tongues. We would rewrite the email.

Cory: Sometimes you wait a day to hit send as well.

Doug: Exactly.

Cory: Torri, I want to go back to the financial statements and asking the CFO questions. How do we create practice and some sort of learning environment that allows us to build that capability without just dumping a bunch of complexity on top of the family?

Torri: So I come back to this idea that failure is actually essential. It’s important. We need the opportunity to practice things and to not do well at them, and to not be discouraged. So comfort with a little bit of failure, without getting discouraged and totally miserable, is an essential life skill, I think, for young people. And practice needs to feel real. It has to have stakes, but without feeling risky and terrifying. It shouldn’t be, I was invited into the boardroom and spoke up and then was, like, laughed out of the room, but it should be, I met with the CFO ahead of time, and I came prepared, and I asked questions. And this is a skill that we say is essential for beneficiaries is to show up prepared and engaged. So I think having that awareness, building some knowledge, and then seeking out places that are safe.

In my own family, I usually start with my sister who kind of acts as a liaison between the family office and my family. And I talk to her, and then we all build alignment. And then when we show up in the boardroom and we have something to share as a family, we have practiced that together. And so, I think to the hero’s journey a little bit. Find your allies in the room wherever possible, and practice with those people as well. Taking bite sized pieces, not jumping into the deep end.

I think about my very first board meeting. I was, I think, maybe a sophomore in college. My grandfather said, you can come. We’re having it in town by where your college is. And I was taking notes on my Blackberry, and he stopped the meeting. And he said, everyone look, my granddaughter is disengaged and looking on her phone. Why would I invite her? And I was angry and emotional and embarrassed. And fortunately, I’m me, and I was like, I’m happy to not take notes. I’ll just sit here and chill. But I can imagine if you were someone who is a little bit less like me, would never show up again. So I think just those little opportunities for setting stages. So I really like opportunities like junior boards, having a mentor, all those kinds of different opportunities.

Doug: Ground rules or guardrails come to mind too.

Torri: Yes. That assumes that everybody will participate in the guardrails and the ground rules, which is not always my experience in advance. What about you, Doug? Does everyone follow the rules that are laid out?

Doug: You know the answer. But they can be re-reviewed or previewed, as needed. I had a new client family yesterday, and dad and two kids were on this call, and I’d already met mom and dad. And one of the kids said, is it okay for me to have a sidebar with my sister who’s not on the call? And I thought, of course. Why wouldn’t you? And he wanted me to give permission for him to do so. And it reminded me how important ground rules are, whatever they might be. Go sidebars. Go open communication.

Torri: Gather your allies.

Cory: Yes. Well and as Torri was talking about those side conversations, making sure that they’re productive conversations and we’re not creating some sort of triangulation, and creating a poor communication environment that it’s encouraged and part of what’s accepted, rather than somebody doing it because they’re unsure, or it feels risky.

Torri: I think back to Doug’s point earlier as well, feedback, reflection, benchmarking, that helps all of this as well. We don’t start you, again, being the CEO of a company, and sometimes this happens in family operated businesses. We throw the family member who’s kind of been groomed into this situation because mom or dad are ready to retire. But if along the way we can provide structure and feedback, here’s where you’re at.

I’m a big advocate for non-family feedback as well. Creating that 60 environment, it’s really helpful for knowing where you are as a rising gen member. There’s a ton of self doubt about capability. I, for example, will not work in my family enterprise because I can’t handle the ego death of not knowing that what I’m doing is real and legitimate. And I hate the idea that someone is just patting me on the back, and it was just an environment that I could not hack it in. So I think knowing that about yourself as well, and trusting the feedback that you get, is really essential.

Cory: Absolutely. Moving us along, what tends to break down when leadership is tested under pressure before skills and confidence are fully built? And, Torri, when wealth education is used as a succession strategy, where do you see rising gen leaders struggle most when responsibility arrives before that preparation?

Torri: So I actually was thinking about Paul Edelman’s work on parallel readiness, and maybe Doug will have some insights into this, that often readiness is put on the rising gen member, put on this individual, and there’s not this conversation, again, that the family office isn’t ready, that the leading generation members aren’t ready. And it creates this kind of icky system and this negative feedback loop where they say, you’re not ready? Well, you must be entitled then, or you must be this negative descriptor. So then the rising gen member gets kind of discouraged, and that is the feedback loop, because then you’re sort of seeing the affirmation of the behavior that you thought you were observing.

And so I think being able to build up to confidence over time and get both sides to understand that this is a process. Again, I keep saying journey and not the destination. We never stop learning, whether we are that 19 year old in a boardroom, or that 70 year old who’s trying to navigate succession with their children. And at the end of the day, we are all our parents’ children, and so we have all these scripts to overcome. And so you could be the best leader in the world, but you are still, mom’s daughter who stayed up too late and didn’t do her homework in ninth grade.

And so I find that when we’re sort of pressure testing leadership in a family setting, it can be hard to overcome those family scripts. So, again, I will tell you from an HR perspective, I’m actually against outside employment policies from a personal development perspective. It’s definitely an amazing opportunity to go and pressure test outside of your family.

Doug: And it could be a template or script that you can edit and adapt, like an employment guideline, for instance, or communication guideline.

Cory: Absolutely. Doug, through your work, what patterns show up most clearly when readiness is assumed rather than built?

Doug: Well, psychologists call it overusing our strengths. One of my strengths is that I’m excitable. One of the reasons I’m doing this gesture is so I don’t speak when Torri is. And that’s an example, intentionally, of managing our strengths so we don’t overuse them. One of the trends that nobody’s talked about yet is psychological capital, which has been researched in the last twenty years, and it’s a way to look at four variables that overlap and that perpetuate families. Hope, efficacy, which is agency, the capacity to do what you need to do. Resilience and optimism, so it’s h e r o. So the hero within is a thing that can be taught, measured, quantified, developed in ninety minutes. And it will be a skill which then will perpetuate legacies. Nobody’s doing that. It’s an example of in positive psychology, what’s called a positivity spiral rather than a downward spiral. And I think that this is another good example of where AI reinforcement will, in fact, shape better behaviors. We can teach sci cap. We can develop it. And in my opinion, advisors need to do a better job of using these tools in ways that are intentional to accelerate the positivity spirals.

Cory: I think Doug, when you say nobody’s using that framework

Doug: I’m open stating. Not many. 

Cory: So what do you see when it is used?

Doug: It goes back to decision-making. Let’s assume that you’re going to consider a number of scenarios and ask what’s the most hopeful one for the Hawley family or the Gagland family. And hope then becomes a determinant of that decision-making. That’s a simple example. Then add efficacy and resilience and optimism. And then add skills that help people develop those. And then over time, make sure that that provides a foundation for what is now being described as brain capital.

I don’t want to sound nerdy, but I’m going to be nerdy a little bit. If you look at Mackenzie and the Davos Summit and some of the recent research, I’ve written a bunch about this. We are now in an information glut, and we’ve got so much content. The question becomes, how do we make those decisions? It used to be that decision-making and strategy was based on physical assets, but they’re not anymore. And they’re certainly not in legacy and transfer and assets. They’re based on intellectual capacity or psychosocial capacity. In other words, if Torri can talk to her sister, that’s great, and she’ll practice those skills. If she can’t talk to her other sister, that’s not so great, and it’ll lead to that downward spiral. Well, those are skills that affect our decision-making.

According to Mackenzie and others, how we implement AI, how we add friction, is going to define our legacy in the future. So let’s imagine that McKinsey’s got to adapt. Let’s remember that they created this term called management consulting from their accounting practice, codified it and said that they were the only ones who were capable of charging their day rates or their week rates. I think that’s silly. What if instead, collaborative teams of advisers were better at using AI, and those multidisciplinary teams to focus not just on the financial, which is pretty straightforward? And it’s been based on AI for twenty or thirty years anyways. Certainly, their security. And then we add the legal stuff, which has already been disrupted. And then we ask, well, what’s the Torri factor? How can we make sure that Torri’s strengths are implemented in this family meeting? I think that’s exciting. That’s one reason why I created the AI for advisors program, so we can implement some of these over six months and practice what tools are going to be useful. That was a bit of a rant, but no excuses.

Torri: I love that you’re nerdy, Doug. That’s why we hang out with you.

Cory: I did like that. So, yes, keep it up. Not that you need my permission to keep going, but it was good.

Let’s, let’s tackle this one quickly, just in the interest of time. How does intentional development change the long-term patterns of decision-making, communication, and continuity in the enterprise? Doug, what long-term patterns improve when next generation capability is built, early and intentionally?

Doug: Laughter. Emotional honesty can be measured by laughter. Comics do this. Teachers do this. When phones are not provided in a classroom, laughter increases. Social interaction increases. When you go to a comedy house, you take your phone and you put it in that secure thing, that sleeve thing. And it doesn’t function, so you can’t record the comedian. Why is that? You know why. We want to practice laughter. We want to practice emotional vulnerability. We want to practice emotional exchanges. So my answer’s laughter.

Cory: And, Torri, through your work, what shifts when learning becomes an ongoing part of stewardship, rather than something families only do when transitions close?

Torri: A lot of different things happen. And what we know is that developing human capital is a strategy for being a 100 plus family. It is one of the ways that we can do this. I think most interestingly, what shows up in my work, is a shift in who we determine is capable and ready. So I’ve seen this pretty frequently where a family learns together and there is very clearly a leader. They are being groomed, and they are sort of the assumed person. And then you start to see some folks who are unexpected crop up, that they have never been given the opportunity to learn and grow and show themselves in the full glory of their strengths. And suddenly, we have people who would never have been considered as a board member, who never would have been considered as a leader starting to lead in the family. And learning is the spark that does that in a family system. I think particularly, learning that is safe and structured, and everyone is given the same opportunities and time, and sometimes given more opportunities for coaching and going deeper.

So that’s my favorite thing. I have a goal. Last year, I had sort of, like two people who were transformed that we worked with, and my goal for this year is to have 10 people who have been transformed by learning.

Cory: Amazing. I’m sure you’ll reach it if we’re probably already at two this year, if you go back and count.

Torri: I’m hoping so.

Cory: Now, before we wrap up, I’d love to give each of you the chance to share one final thought, key takeaway, piece of advice, even a reminder for the audience to carry with them after today. Doug, I’ll start with you.

Doug: Two words. Practice curiosity.

Cory: Tori?

Torri:  Well, now I’m trying to think of two words because I tend to more words. Doug is meeting the space here. I’ll come back to what I’ve said five times today, that learning is this journey and not a destination. It is not something that families can do one time. It is not something that you would expect yourself to do one time. I think about when I started running, I would rather have sawn my leg off than run, and then by the end, I absolutely loved it.

So we can transform. We can do things that we never knew that we were capable of, and it’s all about that patience, showing up, being able to fail, and that’s all part of a journey, as opposed to showing up one time.

Doug: Thank you. Please don’t saw your leg off.

Torri: It would’ve made running harder for sure.

Cory: I know that feeling. I gave running a real go for a summer and realized it is just not for me. I completed the race that I signed up for and I went, no, this it’s okay not to be a runner.

Torri: As any runner will tell you, just keep running and someday it’ll click. It might take twenty years, but someday it’ll click. Same is true for learning. If we’re going to try again, try in a different way, try trail running, try speed walking. Try any number of different things that you don’t have to be contained into the the one particular part of it that you use.

Cory: Yes. Doug, my key that I’m taking forward from today, one was asking you to be brief, because the brilliance that came out when you said laughter is a measurement of pattern change. I’m going to use that in my work going forward. I think that when I look at family systems, that is such a great barometer for us all to look around and say, hey, what’s visible here? Have we achieved it? So thank you.

Doug: Sure. It’s a lagging indicator, and it can be used in recordings as well. And what triggered it for me is, I spent the weekend with our girls in Charleston, South Carolina hanging out on a beach, celebrating one of their birthdays. And the amount of laughter in the dark playing crazy eights with a granddaughter was unbelievable. Laughter became a metric for that event. It doesn’t matter if it’s a kitchen table or a boardroom table.

Cory: Amazing. And let’s continue to fail and get back up and not saw our leg off, because that is an important part of it. Thank you both so much for your time, your contribution today. It was fun. We achieved what we set out to. If we watch it back, hopefully there’s enough laughter to say the lagging indicator here today was achieved. And I look forward to engaging with our audience again next month, where we’ll continue to bring back great guests to share on wonderful topics. So thank you both, and we’ll see you soon.