Cultivating Resilience: From Resistance to Openness

In this episode, Judi Cunningham shares insights on building resilience when faced with adversity during strategic planning for family enterprises. We explore the importance of facilitating open and curious dialogue to understand differing perspectives, giving family members agency in conversations, and assessing what’s truly important to make clearer decisions.

Hear Judi’s perspective on transforming unproductive communication into a constructive discussion over time, establishing clear family versus business roles to reduce confusion, and implementing information-sharing protocols as more households take ownership. She offers examples of leaning on wider communities or specialists like her Trella Advisory Group when alignment remains elusive internally.

Throughout our discussion, Judi offers insightful takeaways to put into action – make room for open dialogue even when uncomfortable, clearly delineate family versus business roles, implement structures around information flow and decisions as ownership broadens, and don’t hesitate to access outside help when stuck.

About Judi Cunningham

Judi Cunningham is the founder of Trella Advisory Group, a consulting firm that works with family enterprises and families of wealth. With a Master’s in Family Systems Counseling and over 25 years of experience, she excels in navigating complex family dynamics and business challenges. Judi’s strategic insight and facilitation skills help families find alignment and address tough decisions. Judi is known for her innovative educational initiatives. She pioneered the Family Enterprise Advisor Program, establishing global standards for professional advisors. In addition to her for-profit work, Judi volunteers her time to support multi-generational family success. She serves as the Chair of the Board for the Purposeful Planning Institute which helps advisors serve families of wealth and families in business.

Resources discussed in this episode:

Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.

Contact Judi Cunningham | Family Enterprise Consultant and Educator: 

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 Judi Cunningham, founder of Trella Advisory Group. With over 25 years of experience navigating the complex dynamics of family enterprises, Judi excels at guiding business families towards alignment and progress. As a thought leader in the field, Judi continues advancing the understanding of family enterprise complexities as Chair of the Board for the Purposeful Planning Institute. Harnessing her sharp strategic vision and innovative educational initiatives, her pioneering work has set global standards for advisors serving families of wealth across generations.

My goal is to be the most curious person in today’s conversation with Judi Cunningham, where we explore building family resilience when faced with adversity during strategic planning. Judi emphasizes delicately understanding individuals’ differing perspectives on adversity and managing it with care. We’ll highlight facilitating open dialogue by encouraging questions rather than assumptions, giving family members agency to opt into conversations, assess what’s important, and say “no” to get to clearer “yeses.” We’ll also explore how transforming unproductive communication into constructive dialogue gradually bears positive results for family enterprises. 

Cory: Welcome, Judi. We’re excited to have you here today to share your wealth of knowledge and experiences. Let’s dive in, shall we?

Judi: Sure. Sounds good.

Cory Alright. Judi, imagine you’re delivering a commencement speech to the graduating class of 2024 and you have the chance to inspire them with your story.  How would you begin your speech to convey the incredible lessons and experiences that you’ve gained throughout your career?

Judi: Well, that’s an interesting question. I think, Cory, I would start by saying something like the best of life is not in the planning, that It’s all the opportunities that present themselves along the way, which is where the richness of life actually exists.

And I think that when I was younger, I used to think that if I planned everything, if I was organized if I had goals, if I had everything mapped out, that that was going to that was going to create the quality of my life. And is that important? Yes. I think it is important.

Like, it’s important to know where you’re going and to have goals and to have direction and all those things.

However, I think sometimes there’s this kind of session or focus on planning to the exclusion of everything else. When I think about my own experiences, my own life, and my career, It’s really been in the opportunities that have presented themselves along the way that I could have easily ignored because they weren’t on the plan. They weren’t taking me where I thought I wanted to go.

But when I said yes to those things, they opened up a whole new opportunity. I just think that’s so important.

Even things that have happened in my life that have I been just listening to something yesterday about sometimes it’s the adversity that has us change direction. And so, things that I might have said in my life, that was a failure. When I look back on it, it created a new trajectory for my life that completely changed how I think and change what I’m doing. I think about those times now as a real gift. As opposed to, they have kind of some negative, experience behind them. Right?

That’s why I think I would want to impart something like that if I was doing a commencement speech, something like that. I think it’s hard when you’re young, everything’s in front of you and you just think, okay, I want to plan it all. I want to go after it. Right?

Cory: Right, focusing on the planning but having the room for the opportunities is really what I’m hearing. How does that shape the work that you do with families?

Judi: Well, I think it’s important because one of the things when we work with families, it’s really easy to get focus. Like, even a family will come in and they’ll say we’re going through transition or we want to transition wealth. Or we want to get the next generation educated or whatever the goals are that they have, you have to pay attention to that. You can’t ignore that. That’s what they want.

You’re moving along, but what will happen inevitably is things will happen in a way that crop up that either they weren’t aware of but you certainly know that they weren’t on your radar.

I think sometimes we can ignore those things as advisors if we’re so focused on the end goal like, well, we just have to deliver this thing, this plan, this exit this, whatever it is. I think it’s really easy to ignore things that are popping up all over the place. Like, that’s just life. Right?

It’s really easy to get so focused on things that you miss those things. And to me, those are my favorite things that come up with families because that’s where all the richness lives. That’s where the pause happens and the going deeper in conversations about meaning and purpose and why they’re doing this.

I find with families, sometimes they’re so focused on the result of where they’re trying to go that they’re not thinking about, the quality of their relationships. They’re not thinking about the depth of their relationships. They’re not thinking about, what their actual fundamental goal is.

Sometimes that’ll talk about money being the goal, and it’s rarely the money. it’s usually all about family and just about every family I work with. If you pull everything away and get to the core of it, it’s about family. Those are the conversations that I love to have and really, help people get closer and more connected to their purpose and what’s meaningful to them because then everything else falls into line.

And even when there’s conflict that’s the other thing. Even getting them more connected to purpose and what their ultimate desires are will also help them manage conflict. That to me is the real richness of working with families.

Cory: Now, Judi, going back, you use the word of adversity and when working with families and families thinking about strategic planning and being focused, how can they build that resilience to be able to adapt as that adversity comes to be?

Judi: The tricky thing in working with families more than any other kind of consulting client is that adversity for one person is not adversity for another. You can’t, it’s not like this blanket thing that the family feels sometimes there might be things that are going on that they are struggling with, but often, it’s one person that’s struggling with a family right now where one member of the family, the whole process feels like adversity for this person.

The whole family having to have these conversations creates so much stress and difficulty for this person that just going into meetings is a challenge for them. Right? They just go, I’d rather be doing something else. Other family members, embrace it. They go, I want to go in. I want to resolve these things. I want to get clear about where we’re going and what the next phase of our lives is and our existence as a business and as a family, I want to get clear about those things.

I think that adversity has to be managed in a very delicate way. There’s time spent with individuals, sometimes we will spend more time with individuals in the system, which is one of the reasons why we always work in teams.

There might be some team members who are working with individuals, the other team members who are attending to the entire system, and the whole family. That kind of building resilience really happens over time.

And it’s sometimes I wouldn’t say by accident, but they sort of point it out. Look at the difference of where you were. Where you are now in terms of how you’re managing through these things, how you’re making decisions, how much clarity you have, etc. They will say, I didn’t realize that because when you’re in the process, you can get lost.

I mean, if you have somebody coaching you, or you were in counseling or whatever it is that you’re doing to help you get clear about your own life, sometimes you don’t know the distance that you’ve traveled. And so, it’s the same thing when we work with families is sometimes, they don’t.

They’re not aware of all the things. So we often point out things that have changed in the family.

I was facilitating a family meeting and then on the 1st day of 2 days of meetings and the 1st day, there were, eight people in the meeting and the family, and in the first day, probably 3 of them dominated the conversation. We kept trying to bring other people in but sometimes they’re not comfortable because it’s just not part of their family culture. You get 3 of the 8 who are dominating. Well, by the next day, it’s really balanced. When we point that out they don’t realize that that has happened, right?

They don’t realize that now everybody’s talking and that everybody is engaged in the conversation, and it’s a much more balanced conversation. They’re not aware of it until you point it out.

That’s sometimes how resilience gets built in those little tiny places that sometimes they’re not even really aware of.  And then they start to go right.

We can have a balanced conversation in our family when their experience before was it’s always the three people that are dominating the conversation and for the rest of the family, that doesn’t feel good to them. They do start to really feel better as it’s more balanced.

Cory: Now, Judi, let’s go back to the individuals that make up the pieces of the puzzle and the work that’s being done on the collective versus the individual. You used the example of the person who feels like everything in the process is adversity. How does that person or as you work with them how do they know that this is the right direction?

If everything feels like adversity it just feels like an uphill challenge, where they don’t just throw in the towel and say this isn’t the right direction. It’s not feeling right where maybe everyone else is saying we’re still doing we’re still going in the right direction.

Judi: I think that I mean, our job is to facilitate dialogue. It’s not to direct them in any particular direction. It is our job to help them clarify that direction. They are at the end of it, they have a direction, but we’re not pushing them in one direction or another. That’s their choice and I think for individuals that are going, I don’t know.

That’s why individual work is so important. One of the things that I believe when we work with individuals, it’s really understanding what is hard about this. One of the things we will ask them is, what would make this easier?

Is there something that we could do around the structure of the conversation, around the topics of conversation, are there things that you could talk to your other family members that if you clarified some things with them, it would make it easier for you?

Do you need to say no to some things? Do you need some of the conversations and let other people come to an agreement, and then you’ll join after the agreement is made? Do you want to exit? Because sometimes people will say, I don’t want to be a part of that conversation. It’s too stressful for me, and I’m actually okay if my voice is not in there, and I’m willing to live with what they decide. They can exit and then they can come back in.

It’s not an all-or-nothing thing. They can exit for one conversation and come back in in the next conversation. They can exit for part of a conversation. One of the things that I find with individuals, is the moment you give them options and they know that they are choosing rather than feeling like they have to. I have to be in there. I’m a family member. I have to be in there.

If you give it, they start to feel like they have a choice and then they start to say, well, do I want to be in there, not necessarily I have to be in there, then they start to really think about what’s important to them.

What I find is the moment they start to feel like they have a choice, most often, they will choose to be in. Not always, sometimes they will choose to be out because they don’t, they’re not comfortable with where things are going, and they don’t want to be part of it. But a lot of times, they will once they start feeling like you mean I could exit.

And for at least for this conversation. And if they feel that way, then they will say, okay. I’m not going to do that. I’m going to participate in this.

Cory: Judi, in some cases, I would think that this could be the first time that person would be given that permission to feel the way that they’re feeling and be okay with the way they are thinking about things because, in a lot of family systems, there’s a lot of pressure on individuals, maybe the pressure that they think keeps the family together.

But it also could be the pressure that’s pushing somebody away. How have you seen that work really allows individuals and families to thrive?

Judi: Well, I think that we pay a lot of attention to how the individuals spend time with each other. To understand how they’re feeling, to understand where their lines and their boundaries are.

Because to your point, one of the challenges in families is that often people don’t know where their boundaries are because they’ve been pressured to get along, to go along, and sometimes people will go along to get along.

They’ll just be like, “I don’t want to cause conflict, I’ll just go along with this”. Even when inside, they disagree. That to me is a recipe for disaster because in the future, that will always come out.

“I never wanted to do this. I never agreed with this in the first place.”  “I just went along with it because I felt like I had to any number of things like that. Where they’re just but it will come out later. I guarantee you it always does. They will say no.

One of the things that I think in working with families, we give a lot of individuals a lot of license to say no and allow that to work inside the family. The more licensed people feel to say no, the more agency they have over their choices, the more they can find their yeses, the more they will move forward and say, yes.

I want this, but they sometimes need to explore those. Which is why we do a lot of individual work while we’re working with the family. Sometimes, it’s the first time that this kind of dynamic of family and individual is being managed together because they’re used to do, it’s not that family members don’t listen to each other. They do, but what happens when it’s your own family? Sometimes we listen for the things that we want to listen for. We hear the things that we want to hear.

Sometimes, when we hear something that we don’t want to hear, we just either ignore it or we just say, I don’t know what to do with that. I’m just going to pretend I didn’t hear it. Well, our job is to help them hear it and to really hear all of the things. That ties into your original question about resilience.

That’s where resilience gets built. Because over time, they learn how to have these harder conversations with each other. They don’t avoid the difficult things, they start to address them face to face. They start to go, “Okay, we have an experience of talking about hard things openly, and it was okay.”

“We didn’t fall apart and end up in a massive conflict. It was okay. We did it!”

Cory: Yes. Judi, the stakes are high in family enterprises. We mentioned the pressure that’s whether it’s the pressure they feel is holding them together. I want to go back to your comment of pretending that I didn’t hear that because oftentimes, that much too often, that is the case and how to do families, it’s really an individual thing is building the skill-set to be able to hear those and to deal with them.

How do families begin to do that? Whether or not they’re working with somebody such as yourself and your team or they’re just being aware of the fact that they’re doing that and pretending.

Judi: I think I mean, it’s exactly the same thing that happens with advisors. Sometimes advisors want to ignore things that they hear because they don’t know how to deal with it. Often what I find, it’s not out of malicious intent by family members. They’re not ignoring things because they think, “I don’t care about you”, “so, I’m going to ignore what you just said”. They just don’t know.

They’ve heard it a whole bunch of times, and they’re tired of hearing it, and it’s never changing. Instead of saying why, you say this all the time. “I don’t understand it. I don’t understand the way you think”.

What family members typically do is they’ll just ignore something like that. Well, what we do is, first of all, we slow everything down. I will stop them and say, “Okay, let’s talk about that.” We’ll ask questions that one of the challenges and families is that people speak shorthand to each other. When you’ve been with people your whole life, in your head when they’re talking to you, you are filtering the information through your 30, 40, and 50 years of experience with that person.

What you’re doing is you’re saying, I know what they think I know how they think. I know what they meant by what they just said. Curiosity is not present in a lot of families because they think they already understand because they’ve been working either personally or professionally with this person for so many years.

I had so much experience with them that they just they’re not curious anymore. They don’t go, what do you mean by that? One of the things that we do is get really curious. Then they realize and sometimes we’ll say what do you think they meant by that? They’ll say, “well, I think they meant this and the other person will say, well, actually, that’s not what I meant”.

One of the things that just from a skill building, I think that one of the most important skills that fans need to learn how to do is be curious and check out a lot of the assumptions that they’re making. “So you said this. Did you mean x versus y?”

Check this information mean that when you said that whatever you wanted to do this, “Did that mean forever, or did that mean just for right now?” Or, “what does it actually mean?”

Being curious and questioning and really understanding, I think is a skill that families really need to learn. Often what I say to families, and family members is I’ll say, pretend you’ve never met this person. You probably would be really curious about them. You wouldn’t assume that what they meant when they said that to you.

Cory: Right.

Judi: I think the really important thing is learning how to be curious with one another. Again, after they’ve been together for so many years. It happens in couples that have been together. They’re not curious about each other. And often, that’s when things go off the rails.

Cory: Right. Bringing back to the fact that these are relationships and they do need to be worked on. Let’s talk about the transformation from it’s a cultural transformation within the family to go from the “I’ve known you for decades”, and I assume a lot of things and fill in the blanks.

We’ve now transformed to that curious culture and we’re working on those relationships. What sort of transformations as you’ve worked with people have you seen over time? Because this isn’t an instant thing, this is an over-time.

Judi: It takes time, it’s actually a beautiful thing to watch. That sounds kind of corny, but it’s why I do this work. It’s really gratifying, to watch relationships change, to watch people that have been in long-standing conflict to actually be able to laugh again with one another, to be open to one another.

These are family members that at the poor, they never stop loving each other.  They love each other, but some things have gone on that have just gotten in the way of their relationship, but you can see the love. When you peel away some of these things and they do learn to be curious again. It’s just really it is transformational and it becomes this really beautiful thing.

At the start, I worked with a family down in the States, there were 3 brothers and they ended up through the process. The 2 brothers well, they were all in conflict with one another. Throughout working with them, one of the things that happened was one of the brothers said, “I just want to get by out.”

They were always resistant to him leaving because they were afraid that that was the beginning of the end of their relationship. That if he left their relationship would be fractured because the relationship was already fractured, it was kind of hanging on by a thread.

One of the things that I said to them is what’s what could happen. I can’t guarantee this but what could happen is when he’s able to leave and he exits, he may be able to come back. It took time, but over time, he exited the business. I got an email from one of the brothers, and he said, “I don’t even know how to thank you for this.”

This is like, he said “I never thought this could happen in my lifetime.” I have my brother back and he comes and he spends time with our family. He is at all of the holidays, he never used to come to any of the holidays. He used to spend all his time away from the family, and it completely transformed their family. He was just so happy.

It was just one of those emails when you just go. “That is just so gratifying to hear that they that they have their family back now”. But sometimes it’s paradoxical. Right?

You think, well if you exit, that means you’re just going to go away, but it actually had him feel free to come back. Anyway, you just never know how these things are going to end up right?

Cory: What I’m sensing is there’s a lot of fear that is holding back these decisions.

Judi: Yeah. Families exist, I mean, and often it’s fear around the relationship. Right?

Cory: Right.

Judi: I mean, these families are so smart around building their businesses. Some of them are so incredibly successful. And you just go, “my gosh”.

Sometimes when I’m working with these families, I’m thinking but they get to be so smart. Like they’ve just built these massive empires. But if you look at what is so important to them and that the business is important to them, they love it. They find it really interesting. They love the challenge of growth.

They love all that stuff but they also really love their families, and they’re very tentative around their families, and they are really wanting it to work well with their families.

I’m working with an entrepreneur right now and his style, like, if you just met this person, you would think he doesn’t really care about his family. Right? But what I know is that he is desperate for them to acknowledge him, to care about him.

It’s they’re everything to him. But if you look at the external behavior, you wouldn’t initially think that.  It’s the family is so important to most of these, enter-family enterprise entrepreneurs. It’s important.

Cory: Now Judi, you used a couple of terms that I want to go back to. When you told the story of the brothers that were in business together.

Judi: Yeah.

Cory: There’s what I’m sensing is there’s a melding of the roles. I’m a business partner and I’m a brother.  Can you talk about a little bit how some of that confusion sets in or where we’re around the dinner table as a family but we see each other not as family members but as we see each other during the day?

Judi: Well, it’s a hard thing in families when you are working together, you’re owning together, and your family members. They get confused as to which conversation, what hat I’m wearing, and who I am in this conversation.

Am I the business owner? Am I the business operator or am I your brother right now? That gets very confusing for families. We do think that by being deliberate about environments that we have that families are meeting in.

For instance, you wouldn’t generally have a business operations meeting sitting around the dining room table. You would typically do that in a business. You would do it around the boardroom table. You might have an ownership meeting in the boardroom, but you also might have that somewhere else. You might have that in a different environment.

Being delivered around where they’re sitting when they’re having these conversations, who’s in the room when they’re having these conversations, and what’s on the agenda. Not mixing the agendas, but trying to really change the agendas.

Cory: Right. And that that goes back. It makes me think of a family that I was having a conversation with. And this was a brother-led business now, and they were bringing the 3rd generation in. He was talking about the conversations that he was having with his nephew. I said, have you thought about instead of on the shop floor, maybe taking him for lunch. And you’ve then gone from being his boss to being his uncle again. In those situations, Judi, you said, “being deliberate about the environment”. Is there anything as far as structure goes I think about, as you said, the agenda and the environment, but things that families can become a little bit more intentional about continuing to cultivate those relationships?

Judi: Well, I think Cory, that example that you just used, like, go and take them for lunch and be his uncle, it depends on what you’re trying to accomplish. If you’re trying to understand, he’s not really performing very well. Do I need to make this a performance conversation or do I need to make this a personal conversation to say, look, how are you doing?

Is this a job? Like, do you want to be working here? How are you doing overall? That’s an uncle conversation. That’s not and to be really candid I’m not your boss right now.

I’m not the owner of this business or whoever he is. I am your uncle, and I want you to just think about that when I’m talking to you.

And so asking questions that are really more of a personal nature and then also creating an environment where whoever the person is reporting to, then it isn’t necessarily the same person getting like, if it’s a big enough business having your nephew report into somebody that isn’t family is going to make it a lot better because they can have a performance conversation a lot easier and it doesn’t get confusing.

Because when you’re the uncle and the boss, it can be a confusing conversation for somebody when you’re doing a when you’re having a performance conversation because you’re going in your head, you’re saying “This is my uncle”.

Even things like “I don’t want to disappoint them”. What if my dad finds out and, he’s going to be upset with me, etcetera.

All these things where a family member might not be able to be really open. Encouraging structures that work. Yes, putting, making sure you’re having the right situations with the right people in the right place at the right time, but it’s also having other structures like making sure that family members aren’t reporting to family members.

Sometimes, it’s not possible, we have a client right now where there’s so at an ownership level, the family members are equal, but at a business level, one reports to the other.

It’s not great because they don’t have a really hard time separating that. Now in our facilitation, we will say to them, this is an ownership conversation, so you’re all equal right now.

Cory: Right.

Judi: And this is a business conversation, and now you report to this person. But that’s where they get really confused and so it’s not perfect. There’s no way that we can kind of fix that. But it’s helping them understand where the lines are around the business and then the ownership, and conversations, right?

And then there are also obviously siblings. You have that whole dynamic and one’s older than the other.  That’s the other interesting dynamic with families is that you have embedded hierarchies, even though a sibling group by nature is they’re equal.

Right? So they’re their peers. But birth order creates an unequal structure that people start going, well, “I’m the older one”, “I get to decide more”, which has nothing to do with being older. Right?

Because we have lots of clients where the youngest is the decision maker there isn’t any hierarchy is just a construct in a family, even with parents and children, I was working with a family and I said in the family system, you’re all equal. There’s no hierarchy and the dad said, “forget about that”. There is a hire.

He’s like, I have a stronger voice than my kids. But when we boiled it down I said, why? He said it was really about the ownership that he had a stronger voice around. So that’s how he kept it because he did. He was in the 4th generation. He owned a ton more of the operations than his children did.

He did have a greater vote in the system, but he had married that with the family system, and then there’s also this idea with parents and children that I as a parent, get a stronger voice, but when everybody’s an adult, at what point does that go away?

When are we having adult-to-adult conversations? Or do you always have a stronger voice as a parent for the rest of your lives?

It’s usually because they have created these leaders, they have created the wealth in in many instances, not always, but they’ve often created the wealth. In their minds, they go, “Well, therefore, I have your voice”. Right? But they think that it’s because they’re a parent.

Cory: Right.

Judi: And it’s not because of that.

Cory: Yes. And in as you mentioned, the adult-to-adult conversations we have in transactional analysis, which is talking about the parent adult, and child, it’s often referred to as the parent-to-child and bringing that. But what about when it comes to cousins? We were raised together. We see each other at holidays, but we’re in different households. And now we’re supposed to have these conversations as adults.

How does that culture change, or how is that different from just a nuclear family?

Judi: I think what happened so the first mistake that I see that families make is they assume that if you grow up in the same household, you all think the same.

You all value the same things. You’re all the same, which we know that’s not the case. I have 7 siblings. Everybody thinks very differently. People have similar values, but they’re not the same. They’re just not the same. And we’re individuals. I think that gets confusing for families.

And then when you go into branches because in a branch, it’s the result of siblings. So those siblings were similar but different. And then they marry someone that brings a whole new culture, and then they have children. Sometimes, the branches are so diverse like night and day difference.

Sometimes they’re just a little bit different, but some of them are completely different. You go, “I can’t even believe that’s the same family”. When you’re trying to work across the cousin group, It is like negotiating.

I mean, there’s a bond because there is a family, connection and sometimes families like those cousins have spent a lot of time together, growing up. And for others so they know them. They know who they are and they know how they think, but they may not feel connected to them because those cousins may have gone off and done very different things in their lives.

And we have families where some of the cousins are really accomplished and the other ones are still living at home. Right? And they’re both in their twenties, but some of them have been off in their super successful and others have barely got their careers off the ground. It’s just the same thing as working within a family.

It’s just spending more time finding those places where they are connected, where what they want, where they want to go. It’s the same work because you’re trying to find alignment across the cousin group and It’s just sometimes a lot more work.

Some families are pretty aligned. We had a client that the 3rd generation of cousins. I think there were, like, 18 of them was remarkable how the line they were. I would say that it was because the 2nd generation was so aligned.

So, there was so much alignment and kind of connection at the 2nd generation level that it showed in the 3rd generation. But every family is so unique. This is why I think sometimes people will come in and they’ll say, well, can you just give me the best practice? And I’m like, “There is no best practice”. There is there really isn’t. I mean, there are things that we would say this is going to be helpful.

Cory: Right.

Judi: And it would be helpful if you did these certain things, but families are so uniquely different that you just, it’s everything’s kind of this custom way of managing through it.

Cory: There’s no flowchart that you’d if this, then that.

Judi: I wish. You just do here are the 12 steps, of the process. This is all of it, you’d be good.

Cory: Yes. Judi, as we near the end of our conversation. There are a few questions that I ask each of our guests. Are you ready for the top ones?

Judi: Yeah. Alright.

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

Judi: I would say, transparency. I think that if family members and the family as a whole can agree and this usually starts with the senior generation if they can start from the fundamental premise of transparency, a lot of things can get accomplished. But the more that they don’t want to be transparent, the harder it is to, build something for the future that actually works oo I’m a big proponent of transparency, and it’s not easy.

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

Judi: I think, there’s a few of them so I think that the courage to address hard stuff, I think that’s a big challenge. I think fundamentally in families, people are afraid that might be too strong a word. They’re nervous. They’re worried about making things worse. I just had a patriarch say to me, “Please don’t make this worse”.

Like requiring you to make this better, please don’t make it worse. Sometimes, it’s at that law of cure. Sometimes, it does get worse before it gets better. However, we never go in thinking we’re going to make it worse. I think that the courage to address things is a big challenge. The other thing that I think is a challenge is the willingness to include the rising generation. I think that these really strong patriarchs, what I often say to them is what got you here won’t get you there.

Because they think that if I’ve made all the decisions to date, so I’m just going to make all the decisions in the future. And I will design this for, like, 3 generations from now. But you’re not going to have people that want to engage and then they’re perplexed.

Why nobody wants to be involved? So, I’m like, “Because they weren’t part of it”. This willingness to include and to listen and to be open to doing something different than what you thought. And it’s very hard for highly successful people because they will say things like, “But they don’t know what they don’t know”. I know how it’s going to work. Right? Like, I’ve done it, and I know how to make this thing successful. They should just listen to me and I’m like, “But they want they need a voice in this”.

It’s this really big dilemma. and I think that’s a big, challenge. I would say the other thing is the openness to evolve. Sometimes what I find with senior generation members is they’re so dug into how it needs to look that they’re not open to it being different. And in the differences is where we really find a new place for a family to evolve into and find a new level of resilience and change, etcetera.

Cory: Right. And that nicely ties into the fact as you said at the beginning, is so much focus on planning and excluding everything else.

Judi, in your experience, what would you say are the top 3 qualities that successful family enterprise leaders possess and these might be leaders in the new generation, the rising gen, but just those qualities of leadership.

Judi: I think probably the things that I just talked about, it’s that openness to change, the willingness to bring other voices in, the courage to address things, the willingness to exist in the unknown. That is not a comfortable place for a lot of these senior members, they don’t play well in the unknown.

Like, they’re so used to being the decision makers and I have to figure this out.  They’re the fixers. They are the ones that say, the buck stops with me.  And so, I have to figure this out. That’s hard. That is hard for them to say “Okay, maybe it’s not going to be me”. Maybe it’s going to be somebody else.

Cory: Before we conclude our discussion today, I’d like to highlight where our listeners can engage in more conversations that you’re having.

Judi: Our website is and so that’s our website. I would encourage people to go there. Also, if listeners are advisors, I was talking before about the Purposeful Planning Institute, which is the, I’m a big believer. Families need a space for them to talk to other families that’s private, that is advisor free, that is just for them.

Go to places like Family Enterprise Canada, get in peer groups, be in be in an environment where you can talk to other family members. Then I also believe that advisors need their private space to talk to other advisors, to talk about the challenges of working with families because it is challenging. Places like the Purposeful Planning Institute or Family Enterprise Canada. Any of these organizations that really help with these things, I think that those organizations fantastic.

Cory: Perfect. 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?

Judi: I don’t think so. I think, I mean, I’ve enjoyed this conversation. I think it’s great that you’re doing this Cory, and helping the people who are listening, podcasts are so popular now, but helping people who are listening to find resources and learn things that will help them think through what they want to do.

Anyway, I just think it’s been it’s been a good conversation. I’ve enjoyed it.

Cory: I have as well, Judi, and thank you for that. Thank you for sharing your time and expertise with us.

It was definitely an insightful and valuable conversation, and I’m grateful for your contribution to our show in this episode.

Judi: Great. Alright. Well, thank you for having me.

Cory: Thank you.

As we wrap up this episode, we invite you to reflect on the relationship truths Judi has revealed from her rich experience advising multi-generation family enterprises. 

Whether you are part of a family business or provide consulting to them, Judi’s wisdom sheds insight on complex dynamics that can take patience to transform.

Throughout our discussion, Judi offered several insightful takeaways to put into action. Make room for open, curious dialogue between family members, even when conversations get uncomfortable. Clearly establish family roles versus business roles to reduce confusion about which “hat” someone is wearing. Implement structures and protocols around information sharing and decision-making as more households take ownership stakes and don’t be afraid to lean on wider communities or specialists like Judi who can lend an outside perspective when alignment remains elusive internally.  

For those seeking additional guidance on the themes covered today, Judi and her team at Trella have extensive experience guiding families through challenges big and small. Please reach out if you have specific questions. We’ve included Judi’s contact details and other helpful links in the episode notes to aid your journey.

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

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