From Silent Agreements to Shared Intentions: Revealing the Patterns That Shape Families

Cory: Welcome, everyone. Thank you for joining us for Silent Agreements, Shared Intentions, Revealing the Patterns That Shape Families. My name is Cory Gagnon, I’m a Senior Wealth Advisor at Beacon Family Office at CI Asante Wealth Management Limited, and I work alongside successful families as they navigate the 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 today for what’s going to be another fantastic conversation.

Legacy Builders Live is produced by Beacon Family Office at CAI Asante, where we support successful families to design integrated strategies for their wealth, business, and legacy. Through a values-first planning and intentional stewardship approach, we support enterprising families in creating successful successors and securing multi-generational peace of mind. This webcast extends that mission, bringing together forward-thinking leaders and proven frameworks to help families and their advisors lead with clarity, confidence, and purpose across generations.

If you have any questions during today’s session, please feel free to drop them in the Q&A box, and if time permits, we’ll address a few questions live, and if not, we’ll follow up afterwards with you one-on-one.

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

Now, introducing today’s panelists. First, Steve Legler is an advisor at Blackwood Family Enterprise Services, supporting enterprising families through the relational challenges of wealth ownership and transition, drawing from experience from his own business family and family office work, and he’s also the author of two books, Shift Your Family Business and Interdependent Wealth. He helps families clarify rules and strengthen how they work together across generations. Welcome, Steve!

Steve: Thank you, Cory, good to be here.

Cory: And Dave Speck is the founder and president of Advising Generations, LLC, and a long-time advocate for family-owned businesses and advisors who serve them. He’s the author of The Family Business Whisper, and an educator who helps families and professionals understand the dynamics that shape generational decision-making and enterprise longevity. Welcome, Dave!

Dave: Good to be here, Cory, thanks for the invite.

Cory: During today’s webcast, our goal is to explore five key questions about what we’re calling silent agreements, and how they shape families’ behavior, how habits and control can limit contribution, and how conversation and learning can help families move towards greater clarity, shared intent, and healthier ways of working together over time.

Now, let’s dive into our first question. How do the same patterns help showing up in families, even when circumstances change? Often I hear families say, we’ve dealt with this before, so why does this keep coming back? And from an advisor’s perspective, that question usually points to something deeper than the issue at hand. Decisions, roles, and expectations, tend to follow familiar paths shaped by history and habit, even when the family grows.

Steve, when you’re working with families, what patterns do you see forming quietly around authority, responsibility, or contribution that families may not immediately recognize?

Steve: Good question. The biggest difference I often see is the speed at which the different members of the family are accepting change. And so, you might have the senior members of a family that are entrenched in leadership roles, where they’ve always been the ones deciding, and they tend to look at their offspring, the next generation, as kind of frozen in time at a younger age, where they don’t have the ability.

So that pattern of “I decide, you do what I say,” can extend way further into the future than is really realistically necessary. And so that having the older generation have that moment where it clicks in their head. That not only should they be downloading some of the decision-making to the others, but that they kind of have to do it. It is the next step, but somehow, for some people, allowing or delegating some of those decisions downstream is kind of an admission that maybe they’ve lost their fastball. And so some of them will go kicking and screaming before they will allow others to have the room. And so, you have the younger people who want more and can take on more, but they aren’t necessarily given the space. to take on bigger roles and to grow into bigger leadership positions.

Cory: I like that phrase, lost their fastball. That’s a good one, Steve. Dave, when families bring you a specific challenge, what helps you look beyond the surface issue to understand what’s really shaping how decisions are being made?

Dave: Well, one of the first things that I have to do when I’m showing up to a family, is show up, kind of, with the beginner’s mind, and not reflect on what I’m doing with other families, because as I think about approaches that others have taken, oftentimes those can actually stand in the way of the creativity that a family will need. So, beginning with a curiosity and with an open mind as to what families can need, what processes can work for them.

I will often ask questions, how has this been addressed in the past, or what pattern is there in your family currently for navigating something like this, whether in this generation or the generation before. And so, having them reflect on their own patterns, and then name their own patterns, can then open up an opportunity for me to ask if they would be open to a pattern interrupt, and to alternatives as to the path forward.

Cory: Do you have any comments, what Dave mentioned there?

Steve: Well, I like what he said about inviting them to, would you like to try to interrupt that? And it made me think about the way we do this work with families. We do spend time where it’s us and a bunch of family members, but we also normally spend some one-on-one time. Sometimes there are certain things that are addressable or more easily addressed in the one-on-ones, and then brought to the family meeting to do it in a group setting. So there’s just some importance of, yes, showing up with a beginner’s mind, but also making sure that you’re creating the safe space for the one-on-one conversations before you bring them to the bigger group.

One thing I would add to that, Steve, is oftentimes I’ll ask permission before asking the really hard question, and often those are happening in the one-on-one, where it’s, look, when we get to this point in the family meeting, I need your voice here, and can I lean on you to ask you this question, and are you open to sharing what you really feel? So, a lot of it is in the pre-work, like you said, Steve, in those one-on-ones, laying the groundwork, seeing what they’re comfortable talking about, and even role-playing. How would you describe what you’re going to say in this part? And making sure that they’re comfortable, and that it can land well.

I think no family likes surprises, especially in family meetings, and so it is, it is the pre-work that helps remove as much anxiety in those family interactions, especially when there are strong patterns that need to be interrupted. Like, you’re asking for permission, right? And sort of role-playing it, because I often say that much of what we’re doing in this work with families is helping them have the conversations that they know they need to have. They’re just not able to do them. Or to have those conversations left to themselves. So really, what we are doing is coaching and facilitating having these conversations, and if they were easy conversations to have, they wouldn’t need us.

So anything we can do to help them prepare, to help them feel ready, to give them the confidence and the courage to address these subjects that, without us, they might not be able to even go down that road. That’s all part of the work that we’re doing.

Cory: I appreciate that one, Steve. As Dave Said, like, we’re giving that autonomy to the family. We’re not taking that away by facilitating, as well as a coach, holding them capable. As you both mentioned, the family members know that this isn’t serving them, they know that something needs to be done. And so to be able to help facilitate that individual growth in service of the greater system, sure can help. And in the end, it’s their family, it’s their family meeting, we’re asked to participate and facilitate, but ultimately, we need to keep all of their issues and their agenda at the center of the table, and we just need to be in service. And I think sometimes, as advisors, we can kind of get in the way of some of that.

Steve: And whatever answers they come up with by the family, for the family, are going to be better than any solutions we could invent or borrow from the Jones family that we met with two weeks ago.

Cory: Moving on to our next question. What happens when families realize they’re operating on assumptions that were never clearly discussed? And in our work, those moments of confusion or tension often point to exactly what those assumptions are that were developed over time. I find that it can be things like loyalty, fairness, responsibility. And even though they weren’t explicitly agreed to, somehow the system operates and morphs to accept them in some way until there’s some disruptions and they don’t serve.

So, Dave, coming to you first on this one. How do you help families surface these assumptions in a way that supports understanding rather than defensiveness?

Dave: Well, I’ll go back to what Steve said earlier. A lot of the groundwork is laid in the individual interactions. So, allowing individual family members to have space to talk about the assumptions, and to ask them, where did those assumptions come from? What are those based on? Were those explicit, or were those implied? And oftentimes, it’s in those one-on-one interactions that they can unpack, they can gain a comfort level with. Actually, I just made that up. I don’t know that. I was never told that. And for them to be able to verbalize that, brings a level of humility into what then will be the family meeting space for us to be able to address. There’s been assumptions made. Some of these assumptions have been based on communication, others of these assumptions have been made based on the lack of knowledge, and so what can we do to close the gap between our expectations and reality?

So, again, I’m a big fan of doing that pre-work with the one-on-one, gaining the confidence of the individual family members, allowing them to have a voice, and to not have to worry about where they fall in the family dynamic, whether they’re younger, or older, or the loud one, or the quiet one, or the peacemaker. In those one-on-ones, they can just be who they are. We can ask them great questions, we can encourage them. And we can also challenge them in one-on-one settings where it wouldn’t be appropriate in the family setting. So, again, I’m a huge fan of the one-on-one work.

But again, it goes back to, am I genuinely curious about them? Do I genuinely care for their well-being and what they’re trying to accomplish? And then, am I courageous enough as an advisor to ask them hard questions?

Cory: Steve, if a family starts to become aware of these unspoken agreements, what shifts do you notice in how they understand roles, expectations, or authority.

Steve: The kinds of assumptions that I see are often that the older generation will assume that the younger generation, because we raised them this way, believe all the same things that we do in terms of work ethic and responsibility, and putting in the 80-hour weeks, which generally are not always there in the younger generation, especially these days.

And so, ideas about work-life balance, which might send the older generation into, like, “oh my god, what is this, I had to get up at 5.” This happens in all kinds of families, and it is never discussed, and just having the opportunity to talk about it, first one-on-one, and then as a group, to normalize for these families that it was the same with me and my dad, and it’s the same all over the place, to just let them know that they’re not the only family going through this. But just having the opportunity to address the questions of the assumptions and having a discussion around it, they’re already miles ahead of most families that will just continue to leave these things as never discussed.

So, giving them the opportunity to talk about it, not to shame them, to be humble with them, and talk about how this is normal, and it’s good that we’re talking about it, because now at least we can make some progress.

Dave: Cory, I have one thing to add before you move on. I think asking families about the roles that they play in the business, and asking them, do they have a defined role? Most family members that I meet don’t have clear job descriptions, and oftentimes don’t get direct feedback on how they’re performing. And while this may seem like a benefit, for the rising generation to maybe skip the end-of-year meeting, it’s actually terrible for them, because they don’t know. Am I performing? Am I not? They’re held to a higher standard than non-family employees. But if they don’t get feedback on how they’re performing, then they don’t actually know, and it can be really tough on them and their development.

And then the other one is, just for me, I like to call out the informality. As families, we typically lean towards informal, because we’re family. And at some point in family enterprises, the informality stops working, and we just need to call it that. The informality worked for us for a long time, and now there’s just too many of us. There’s too many shared roles we have, and we just need to lean on more formality. And most families hate formality. But ultimately, when you get from generation to generation, you need to start incorporating formality, so that people understand what they’re responsible for.

And those performance evaluations, you made me flash back more than half my life ago. The most awkward 15 minutes of the year was when my dad would sit me down and try to give me some sort of performance review. It was nice later on when we had somebody between him and I to do that instead, although that was still a bit awkward, but we can all benefit from the feedback. And if it’s done properly, it’s very helpful. And too often in family businesses, there’s not enough of it.

Cory: Absolutely. That’d be a great other discussion, our relationship with feedback. We won’t go there today, but I think that that’s such a good one. And kindness and clarity. Having defined roles, having scorecards, things that people can actually measure themselves against, so they know if they’re doing a good job before somebody else tells them, is great.

Dave, you mentioned the one-on-one discussions, and the three of us all do this work. I’m curious for each of you, what does it mean for a family member to show up to those one-on-ones, prepared to get the most out of that work that you do with them?

Dave: Well, I feel like we, as advisors, have to take responsibility for helping them show up that way. I never want to surprise a client. So even in our one-on-ones, preemptively, I’m going to send them some questions. These are some areas I would like to explore. I’d love for you to have a chance to think about them beforehand so that you can be comfortable, and we can have a great conversation. So, again, there’s even pre-work to the one-on-ones that needs to happen, so that you can make great use of the one-on-one time.

And also, you need to know the personalities that you’re dealing with, because some are like Steve and can react and be fine on the fly, and are comfortable just going with it. And there’s others that want and require more time to process their thoughts, their feelings, and they may even have to take notes and bring those notes to the meeting so that they can convey what they feel. And so I think it’s unfair if we think that everyone is like Steve, and can just show up and move along with the conversation. So, again, it’s about pre-work.

Steve: Well, you know, that’s a good segue. To me, you’re right, they’re not the same, and different family members, once we get to know them, and we can relate to them in ways they like to be related to. try not to give extra homework to people who I already sense are not that engaged. I try to keep the one-on-ones very loose, and it’s just a check-in, and how did that last meeting go for you, and very informal. But there are some times when we’re preparing for something at an upcoming meeting where they need to do some homework. But I will always be prefacing it or sending them an email, please, before we speak again next week, I hope you’ll have a chance to review this and be prepared to discuss it.

I never want to be someone who’s giving them more homework, because one thing that some people don’t recognize that is a challenge for us in some of these families we’re working with is they are in a very busy part of their lives, raising kids, and kids doing homework after dinner, and finding the time, you can’t do all these interviews from 9 to 5, Monday to Friday. Some of them have to be on weekends and evenings.

And so always recognizing that we are perhaps impinging on some other family time and not abusing that, and recognizing the flexibility that they are showing and we are showing, to keep them wanting to keep coming and being engaged, and being able to have them relate to us as a relatable person who’s there for them, not for their parents, but for them. To help them have their voice heard in the family meetings is something you never forget.

Cory: I think that’s a good reminder. And even as we think of what it takes to do this work with facilitators and coaches, it’s a big investment in time and energy, not just financial resources, to move the family forward with this work.

Moving on to our next question here, how do families move from patterns of control to shared contribution over time? Steve mentioned this a little bit, as we grow up, and not just seeing somebody as the way they were, just because we raised them this way. I’ve seen this in my work where family members start to notice that responsibility and authority is becoming unsettled, and people carry more of that decision-making weight, where others are on the sidelines, and there’s this recognition that contribution is uneven, but that responsibility maybe is desired, and some of the decision-making as well, as the family evolves, changes, and and grows up.

And so, Steve, when you begin to work with families, and they look at these dynamics more closely, what shifts do you see in how roles or authority start to take shape?

Steve: You used the word a minute or so ago, evolve. And I really think that these changes within a family system don’t happen quickly. And we have to normalize the fact for them, that it takes a while before some of these things start to move, and then start to stick. And so, if you have an expectation that we’re going to go and say, okay, from now on, we want, you know, Bobby and Susie to take over this and be in charge of it, if we expect that that’s going to happen at the next meeting, we’re probably setting ourselves up for disappointment. And so, just having the people recognize that slow changes, and that often the same people who are lamenting the fact that they don’t have a voice, when you try to put out a call for who wants to step up and do something, they’re not necessarily recognizing that that’s a message for them.

I always talk about how, in most families, when people like us come in, we’re dealing with what was more or less an autocratic decision-making system, and we’re trying to move it towards a more democratic one. But that takes months, quarters, and years before it happens, and so you have to look for every little opportunity where somebody has a desire for change, and somebody’s willing to let something go, and just take those small wins wherever you can, because if you have an expectation that this is going to go quickly, and that you’re just going to make some pronouncement, and everything is going to change, it really doesn’t happen that way very often.

Cory: Dave, what do you find helps families expand contribution while still maintaining clarity, trust, and direction?

Dave: I do think it starts at the top, so whoever’s leading the organization kind of sets the tone for control or delegation. And I have had to lovingly challenge founders about this dichotomy of continuity, versus control. They’ll come and they’ll engage me because they say they want continuity in the business. But their actions will likely be modeled after control behavior. And so, oftentimes, I have to ask them, do you want continuity, or do you want control? Because ultimately, you can’t have both. Again, that takes a relationship to ask a hard question, but if you truly want continuity, at some point, you have to begin to let go of some control.

I would say from the perspective of the rising generation, many of them are pursuing rights and not necessarily responsibilities. And so, if we can help them to change their mindset around what is it about more that you want in terms of contribution? Do you want a title? Do you want a bigger title? Do you want more compensation? Or do you really want a bigger responsibility? If you want more responsibility, there’s usually opportunities for that. And founders that are busy, likely have parts and pieces of their jobs that they don’t like to do, and are typically not good at, that can be taken over by someone that is willing to take on responsibility.

So I think it’s a bit of a mindset shift from the rising generation to seek responsibility, rather than trying to necessarily grasp control, and then from a senior generation perspective, understanding that there’s always going to be healthy tension between this desire for continuity, but the natural inclination to control something.

Steve: I like your rights. They’re trying to have, it’s my right to have this, as opposed to, there’s an opportunity for me to take on some responsibility. And often, each one is waiting for the other side to go first. And that’s where we, in our one-on-ones, can sort of normalize that and encourage each one of them to move an inch towards the other one at the same time, and then each one will hopefully perceive some movement from the other side, and then once we get over that inertia, and there’s desire from both directions to have, okay, let’s see if we can move this in a better direction, then we can start to make progress.

That subtle shift in attitude towards “this is my right, I’m demanding this,” as opposed to “here’s a place where I can show some goodwill,” and moving in a direction to take something off someone else’s plate, so I can show that I’m good at this, and at the same time relieve them of a responsibility that they don’t like, let’s help these families find those little win-wins, and once we start moving, the evolution can proceed. But as long as we’re baked in and everyone’s dug in, we’re not gonna move very far.

Dave: I have one other addition there. Language matters. So I think as advisors, a lot of the work that we need to do is helping them with their language and how they speak to each other. How a rising gen talks to a senior generation, it’s completely correlated with how that’s going to land on them.

And so, again, going back to that individual work, some of that coaching work, language matters. If it’s a rising gen that is genuinely curious, that wants more responsibility, that wants to honor the legacy of their parents, that wants to shoulder some burden, if we can give them the proper language and help them practice what that would sound like, then it will likely be received in a much better way. But we can’t assume that they have that language. We have to work with them on it. And, again, we may need to have a pattern interrupt if there is a pattern of speaking in a way that doesn’t land well between the generations.

Steve: You’re making me think of a rising gen person in a one-on-one says something to me, and I’ll say, well, that’s great, and I love the way you said it so frankly to me. Do you think if you said it in the same way to your dad, it would land the same way? Oh, of course not. Okay, so maybe we should take some time to think about a way that you can verbalize this in a way that recognizes his expectation, and practice saying it in a way that you think that, and if we have to work through a few iterations of it until we get the words just right, it’s probably worth doing this, because your chances of success will go up markedly.

Cory: Absolutely. I want to go back to that, the gap between, well, you know what, I offered this before, and they never took me up on it, so why am I going to try that again? And I think, oftentimes, we see that in relationships, where both sides can feel that if this has been going on for a long time. And language is a key in it, if you offer it the same way you did before, it might not land again, and so what can we do to make the same offer, maybe, and deliver it in a way that resonates with that other person.

Steve: Sometimes they don’t hear each other, and the person will typically blame the other person for not delivering the message properly. But there’s two sides to the communication, and sometimes we assume that what we’ve said has been understood.

My favorite expression about communication is, and it is George Bernard Shaw, the biggest problem with this communication is the illusion that it has taken place. So you’ve said something, and this happens with my wife all the time. I’ll say something, and then I’ll say, did you hear me? No. Well, I have to make sure, because otherwise then I’m assuming she heard me, she’s assuming I never said it, and here we go again.

Part of the role of a facilitator is to make sure that the communication has been delivered in the best way possible, but that it’s also been received, and that there’s common understanding around things.

Cory: Absolutely. And I’m sure your wife says things every once in a while that you don’t hear too. Moving us on, really in the spirit of sustainability. So, making a shift is one thing. What helps families stay aligned when new pressures arise? We can talk about beginning to share those responsibilities differently, opening up contributions, and then there becomes that challenge of sustaining the change. And circumstances evolve. Could be leadership transitions, liquidity events, personal milestones, and they all test how steady those new ways of working together really are.

And so, Dave, from your perspective, when familiar patterns start to reappear, what helps families realign clarity and trust without slipping back into those old habits?

Dave: So, I find that when families develop plans together. Not necessarily that everyone has a vote, but if everyone has a voice, then it can be our plan. And then it can be revisited as our plan. It can be revisited as my understanding of our path forward was this, what changed, or something like that. Where I find the biggest challenge is when there is a plan that’s created by a person, and then the plan is, it’s basically like people are being acted upon rather than acting together. And so, as early as I can, I’m trying to get founders to at least engage the voice of spouse, of rising gen to have voice, and then as plans get put in place, then they can say, this is ours.

The other thing I would say is that we have to often remind people that they all have agency. And sometimes the biggest frustration is, my dad is doing this, or my mom won’t let me do that, and people feel trapped. But I think it’s important that we go back to their agency. What choices do you have now? Some people don’t realize that you actually are choosing to work in the failing business. And by choosing it, you may be choosing a situation that offers you less control of a specific situation. But I think oftentimes, too many people forget that they’re still agents, that they can take action, and that they aren’t just being acted upon.

Cory: I like that accountability piece, it’s our plan, not my plan, not your plan. We’ve done this together, and so we’re accountable to the collective on this. That’s a good one to anchor on.

Steve, when families begin operating differently, what seems to support those changes as the family continues to grow and adapt?

Steve: I jotted down the word CRO, Chief Repetition Officer. People have to be reminded of things over and over, and that is a role that we as a facilitator can play to normalize it, and then hopefully we get family members to also start to repeat the things. We decided we weren’t going to do that this way anymore, and that from now on, we would decide these things this way. And to just get them into recognizing, admitting, and sharing amongst themselves what they have agreed to together. But it’s all predicated on what Dave was saying, that it actually is something that they developed and co-created together, and that this is not something that came on the stone tablets from the mountain.

We need to make sure, when we are helping families co-create new realities, that they are all nodding their heads, so that we can go back later when things don’t sort of land with the way we thought it was agreed to, and we can ask the question, well, wait a sec, I remember at our last meeting, I thought we decided this. Did something change, or did I misunderstand it? We can be the dumb guy with the stupid question to give other people the space to jump in and sort of readjust, and where are we? Maybe what we thought we agreed to was suboptimal, and maybe we found a way to do it even better. Wouldn’t that be great? Or if not, who do we have to remind about the fact that we all thought we agreed to this, and so maybe you didn’t understand, but there’s a role for you to play here to step up going forward.

Dave: I’ll give you a concrete example, a family right now that we worked with last year to put together a shared use policy for vacation homes. So, how they would be scheduled, how maintenance would take place if things got broken, how those things would be taken care of. And so, at the end of the meeting, when we kind of solidified what the agreement was, these aren’t legal agreements, but you can take a step as a family to say, at the end of the meeting, everyone just come over and put your initials on this, and let’s decide together that this is what we’ve decided on together, so that when something happens in a way that’s not decided upon, that we have something that we agreed on, and that we can hold each other accountable in a positive way.

And so that can happen with shared use agreements. There was an aviation policy one family put together with how they would access the plane, and how they would use it, and how many hours, and how that would get scheduled. So I think, again, families often fight formality, but when they can decide on something together, when the advisors will document it for them, give them a place to go and find those things they agreed upon, and then also hold them accountable and repeat, like Steve said, to just remind, especially when things aren’t in question, let’s just take 5 minutes as part of this next one, and review what we decided on last year together, in terms of how we’d be in shared ownership or shared use of these specific assets.

Cory: And what a great example of that informality and the need to grow into some formality, because it’s no longer serving. I can reference a lot of times where I’ve rented Airbnb or VRBO, and they take a damage deposit, and there’s a whole bunch of policies there, and you have to respect the place, and what’s the difference between the family’s property and somebody else’s.

Moving on to our next question, which conversations help families shift from long-standing habits toward shared intent? That recognition I find of the patterns, and we’ve talked about this a few times throughout our hour already, some of those serve well, and some don’t. And so, it really becomes the act of adjusting how those decisions and responsibilities are shared, that slight shift of attention, and that’s really kind of what we’ve talked about, so far.

Now, Steve, which conversations tend to bring the most clarity or forward movement when patterns and expectations are being reexamined?

Steve: You’re making me flashback to a family meeting I was in a few years ago, where the parents, who were in their 60s, were kind of getting fed up with taking care of certain things around the family vacation home. And the way the mother threw it out there in kind of a, hey guys, can you help me out? I really can’t do all of this anymore. And seeing how all the rising gens sort of just saw this as oh my god, it’s real. And it wasn’t done in admonishing them for not doing enough. It was really kind of a, not quite a cry for help, but just somehow in the attitude that it’s being presented in a different way, and it’s being presented as a genuine need.

And so, if it’s done kind of more as a request as opposed to an order, if it’s, hey, please help me out, I really need somebody to step up, as opposed to, I keep doing this, and you guys don’t, it’s the attitude that usually, I’m thinking the older generation, exhibits a new attitude, but it can come from the younger generation, too. And just somehow a different reality of how genuine something is, and how, personally, you’re feeling it, can somehow land differently, better, than if it’s the same old complaint being voiced again, and then people just tune in. So somehow, just the approach and the tone, kind of, hey, can you help me, please? As opposed to the finger wag.

Cory: It’s amazing how we hear that request for help so much differently. And I think what you also said there that struck me was asking a group versus having those individual questions. We haven’t talked about triangulation, and that’s not really our topic, but that going to the family as a whole and requesting it of everybody versus having individual conversations, and how that can serve us better in that approach.

Dave, looking across your work, which conversations make the greatest difference when they happen earlier rather than later?

Dave: I love to live at the intersection of the past and the future, and inviting families to live there as well is fun. Take for instance, one family I’m working with. There were four brothers that started a business. And they decided it was actually their dad’s business, but the four took it over, and they decided, we’re all in this together. There was no buy-sell, if one of us wanted to get out, we were selling. It was all-in or all-out sort of a situation. Well, now they’re two generations beyond that.

And so, looking at the past of, okay, our philosophy was this then when we were running it. But now our kids and our grandkids are running it. Does that philosophy still serve the family? And what ways can we learn from the past, and the patterns that we established, and what ways do we need to innovate into the future to make sure that our family relationships can be preserved, and the business can be perpetuated?

I love the idea of looking backwards in the rearview mirror, learning. But also, then quickly turning towards the windshield and looking out, and saying, but what do we need now? And I just think there’s great learning there. And again, it’s about that co-creation of our future together, not having to do things exactly how our grandparents did it, but it’s that opportunity to say, these are some great things that our grandparents did, these are some learnings, and what do we want for our future together? So that co-creation, I think, is important.

Steve: I like that, that looking backwards. And looking at some of the good things from the past, but then turning it and saying, okay, a lot of that stuff was great, but that was 50 years ago. A lot of things have changed. What are the good things we can keep, and what are the things we need to add to or do less of, or how do we morph this or turn it in a way that serves us better? Always with the goal to then have the conversation to co-create something.

And that’s a role that we, as facilitators, because we are there to serve the family, we’re not part of it, we are uniquely positioned to be able to lead those conversations, and have them look back, where some people will look back fondly, but then to acknowledge, as we’re now looking to the future, that some of the younger people who didn’t live that past part, but might be seeing different ways that it can change in the future, to just hold that space so that the family can co-create new ways forward. And sometimes it’ll happen quickly, sometimes it’ll take a while, but helping them to have those conversations creates the possibility that as long as we can make sure they’re all hearing each other, a better future can arise, can evolve from where we were before, as we now shine the flashlight down the road and say, but where do we want to go with this?

Cory: Dave, your example there, how important agency is, going back to your comment, of those brothers decided they wanted one off-ramp. Their grandkids maybe deserved to make that decision again to say, how many off-ramps do we want here?

Dave: And the impact of 2,000 employees if they keep that, we’re all in it or we’re all out. The impact is bigger than just on the family.

Cory: Absolutely. The community impact is massive there.

Now, I haven’t seen any questions come up, so before we wrap up, I’d love to give each of you a chance to share one final thought. Could be a takeaway, piece of advice, a reminder of maybe what you learned, or reminded yourself in our conversation, that our audience can take away, with them after today. Steve, I’ll start with you.

Steve: I recognize that people who don’t do this work have trouble conceiving of what it is. I hope we’ve given you a little bit of behind the scenes, or what it really takes to do this work well. It is a privilege to be the only non-family member in a group of family members. We need to be close enough to the family so that we know what’s going on, but we can never be part of the system, because then we lose the ability to act on the system for the family.

The work that we do really is challenging. But we don’t have to come up with the solutions for the family, we just have to help them talk about, co-create, and learn to communicate with each other better. And so it’s been a pleasure exchanging this time with both of you, because I know you both do this same kind of work, and the conversations that we have amongst other people who do this are always very enriching. And so I hope people watching this will get something out of it as well, because I think there’s a huge need for families to have people who can play this role for them. The number of people who want to do this kind of work continues to grow, and hopefully we’re all helping each other do this work better.

Cory: Thanks, Steve. Dave, over to you.

Dave: Well, I would say, as a family member getting into these sorts of conversations, do all you can to assume good intentions of others if we go into conversations, especially if family meetings are new. And if we go in with negative intentions or assumptions that someone’s going to try to take advantage of me, or someone’s going to try to get more, or whatever, we have a negative impact on the system. And so I would encourage all to go in deciding that others are also showing up with good intent. Just making that decision can change the tone of the room.

I would also say, go in with curiosity about others, and about what the needs are, what the concerns are, what the worries are of others. And when we worry and think about others, our concerns oftentimes get solved. But if we’re only thinking about our worries, our concerns, people will feel that spirit of me versus we. And so, I think just considering how we show up is a good start to ultimately having a successful interaction.

Cory: A great way to say how important it is to love one another, I think that’s a lot of what I heard there, Dave, without even using the word, that was, marvelous.

Dave: Thanks.

Cory: Well, thank you both. I enjoyed this hour with each of you. It was informative. Some great takeaways for our audience.

I want to thank our audience for joining us, those who tuned in live, those who are grabbing the recording, because now is the time for them to hear it. I think you both did such a great job at wrapping us up. I think that curiosity is the number one thing for me when it comes to looking at patterns and assumptions, and how to disrupt them. That’s really what we talked about today.

I want to invite everyone to continue to have these conversations, connect with Steve, Dave, and I on LinkedIn. The three of us are there. Send us a message if you have any questions, as I previously mentioned. There’s so many ways that I continue to bring this information to the world, if it be our bi-weekly newsletter, where we’re curating insights from other great people across the industry, our Legacy Builders podcast, which both Dave and Steve have kindly given their time, and we continue to have amazing guests who give that, that as well. You can find those on Apple Podcasts, Spotify, YouTube Music. Stay tuned for our next month’s webcast, and I look forward to seeing everyone then. So, thank you.

Steve: Thank you.

Dave: Thanks, Cory.

Cory: Thanks, guys.