Rewriting the Script: Revitalizing Stalled Family Enterprise Relationships

In this episode, Darrin Hotte, a certified Family Mediator and Family Enterprise Advisor at New Solution Mediation, shares insights from his 35 years of experience in conflict resolution, family business dynamics, and complex relationships. Darrin emphasizes the importance of curiosity, empathy, and clarity in navigating difficult conversations and decision-making processes within families. He highlights the therapeutic value of mediation, which enables participants to discover their true interests and desires while fostering understanding and collaboration.

Darrin discusses the role of generational patterns in family conflicts and the significance of preparing for important conversations with a focus on personal growth and effective communication. He also touches on the catalysts that motivate families to seek mediation, such as financial or legal pressures, and the stress that arises from a lack of clarity about the future. Darrin concludes by expressing his gratitude for the opportunity to help families find order amidst chaos and move forward with their businesses and relationships.

About Darrin Hotte

Darrin Hotte is a certified Family Mediator and Family Enterprise Advisor at New Solution Mediation with over 35 years of experience and specialized training in the areas of conflict, family business, leadership, de-escalation, complex family systems, and relationships. He has used this background to mediate, coach, or facilitate over 900 disputes in private practice since 2010. He teaches at Simon Fraser University’s Beedie School of Business, the Justice Institute of BC, and coaches and trains lawyers at Continuing Legal Education BC. Partnering as an Associate with David Bentall and Next Step Advisors, Darrin supports families in making the crucial transitions that accelerate growth and prosperity.

Darrin also specializes in de-escalating hostile interactions and trains organizations to become safer and more skilled in this area. He has become increasingly known for his work defusing emotional intensity in family meetings. In his spare time, Darrin is a paid-on-call firefighter and brings this experience of managing high emotion and trauma to his work with people in conflict. He enjoys running/weight training, cycling, and photography and is also an occasional jazz drummer. However, his greatest joy is found in his wife and two children.

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

Contact Darrin Hotte | New Solution Mediation: 

Cory: 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 Darrin Hotte, a certified Family Mediator and Family Enterprise Advisor at New Solution Mediation. With over 35 years of experience and specialized training in conflict resolution, family business, leadership, and de-escalation, Darrin has successfully mediated, coached, and facilitated more than 900 disputes since 2010. As an Associate with Next Step Advisors, he supports families through crucial transitions, accelerating growth and prosperity. Known for his ability to defuse emotional intensity in family meetings, Darrin specializes in de-escalating hostile interactions and navigating complex family systems and relationships.

My goal is to be the most curious person in today’s conversation with Darrin Hotte, where we delve into his wealth of experience as a mediator and family advisor. We’ll explore the insights he has gained from guiding families through challenging times, focusing on the power of curiosity, empathy, and intentional communication in transforming conflicts into opportunities for growth and understanding. Together, we’ll uncover the intricacies of navigating complex family dynamics, the importance of being open to new perspectives, and the therapeutic value of mediation in fostering durable agreements and personal growth.

Now let’s dive in!

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

Darrin: Sounds good.

Cory: Darrin, imagine you’re delivering a commencement speech to the graduating class of 2024 you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise you’ve gained along your career?

Darrin: Thanks for that question and by the way, thanks for having me on and it’s good to be with you. Great to get to know you when we met before but this stuff happened to me early on.

The seeds of where I am now started at the beginning, my mom and my dad loved people and they had lots of great friends.  My mom was an especially extreme extrovert and that’s what I am too so I’ve always been interested in people.

I remember early on; I had many good friends and I’m grateful for all the good friendships that I had in my life. When I was younger, I noticed by the time I was in my mid-teens or early teens even that, when I had friends that were struggling with something, they had some issue that they were dealing with.

I cared a lot about that and I was interested in talking to them about having conversations. And so, we’re talking about things and in the times where I thought I was helpful, I just found immense privilege in that.

It was on I felt in honour that people would trust me with something that’s really personal, really important, and so on. It starts there and then I thought, well, I’m going to be a psychologist.

I want to work with people that are struggling with things and so, that’s where I was pointing initially. But then I got involved in working with kids and teens at summer camp and at a church that I was connected to. I started to get a and for leadership in those places because it was more of that stuff.

I was engaging with people about what’s important to them and an important life thing so I really love that. I still went on to, get a psychology, and social sociology degree, because that was important, and I wanted to do that.

So that’s what I did. I worked with, people in those settings, young adults and teens, and, then once one of some camps I worked at, I was one of the senior staff there, and they asked me to take some pretty intense first aid training to then establish a trauma team at this camp and so that’s what I did.

I had some first aid training back in high school, and I was always stopping at accident scenes and things and trying to help people whenever I could so it seemed like a good fit for me to take this 1st day training and get this team together. And again, it’s just another way a new version of helping people when there’s a problem or trouble and so that’s what I did.

Later on, I continued my work with people and worked in as a minister in some of these faith-based places and now I’m working with broader families and people of all ages and that’s an amazing place where you’re celebrating some of the great things in life with people like new births that joined families, new children doing weddings. graduations. All these great things are celebrated.

Also, there’s the other end of it to where you’re working with people and trying to support people that are going through terrible illnesses or they’ve lost somebody significant to them and then you’re doing funerals and things. And so, being with people through important stages and important parts of their family history with me was really amazing, but I know it’s something.

I noticed that I loved doing weddings, but I found it as a special satisfaction in doing funerals and it was because there was a real sense of need there. Like, weddings are such great celebrations and such an important milestone in a person’s life for a couple and for an entire family set of families but when some families are grieving and you’ve lost somebody, that feels like there’s a real need there.

I found real satisfaction in that and I’ve always loved helping when people are in trouble. There was a time when I was thinking about, well, how else I help people beyond the way I was doing it.

My wife and I talked a fair bit about implantable conflict resolution thought that was probably a good fit for my personality, also I thought that’d be interesting because I’d never really had any comfort training ever.

I mean, which is to me is crazy that we don’t have more conflict training out there and so we thought about this and thought about mediation or maybe becoming a mediator. Of course, family mediation would be natural because I worked with families for so long.

So that’s what I did. I opened up my private practice as a separation divorce mediator and then very quickly got involved with David Bentall who is, he was I knew him from the past and he reached out and we connected and we started to do family business work together, which we still do and that was a natural for me too, because I got an extended family that have had family businesses all through my life growing up and my family got involved in those things.

And so, there’s that part of the background that was important as well. It’s as a mediator now, separation, divorce, and family business and then I still go back to those faith-based places to do the conflict of work and to teach conflict and so I get so much satisfaction out of coming alongside people that are stuck or in real trouble.

And so then to carry on with the story, a number of years ago, I joined the firearm department here where I live and I’m a paid-on-call firefighter and that continues that theme of people are in trouble and I can help in those situations and here’s how we describe it.

It’s like I have always gotten so much satisfaction out of bringing order out of chaos or being part of that process. So as a firefighter, someone has a car accident on the highway. their house catches fire.

They have a medical emergency and they call 911 and we come on our trucks and we come we help, we can’t stop, we can’t fix it or erase what happened. But we can stop it from getting worse and we can get people on the road to get better. It is immediate, it’s the same thing for family advisors, people are stuck.

Sometimes there’s real chaos and real conflict but even in a family business situation where things are going really well, and then maybe they’re adding new generations into the business, they’re stuck. How do we make that work?

And if they don’t do it well, it’s possible that people are going to get bitter and leave and do all those things but there’s a trouble or stuck something that people have there. So, I can get involved in that.

I can’t erase bad things that have happened or difficulty if it’s happened but I could stop it from getting worse and we can get on the route on the road or the path to something better.  It’s something that’s clearer, a clear future and so it’s the same.

It’s order of chaos in that sense too and that’s what I love about it. I took a step further in the last, probably, I guess, about 7 years, I’ve been teaching a fair bit on, de-escalating hostility and hostile interactions and that’s another part of my practice.

It’s important to me to work with people and training organizations and families and people family businesses on how to de-escalate when they’ve got clients and members of the public. Again, order out of chaos and that would be a theme for what I have found the most satisfaction throughout my career even before I had a career.

The sense of honour and privileges never left me that when someone calls me, when the pages go off and we get on fire trucks, what an honour and a privilege to be there at somebody’s family or their own personal life turning point, to be there and to be trusted at that moment and trusted as part of that journey.

Privilege and massive privilege, are something that I found satisfaction in all my life and continue to do. That’s how it got to where we are now and it starts way back with my DNA all the way up to where my life experience and my friendships and I’m just so grateful.

I’m with family and friends and relationships and create mentors and yes, I have so much to be grateful for and all that. I love being able to do what I do.

Cory: Awesome Darrin, I’d like to go back to the comment that you made about celebrating life events and seeing people at their best and then seeing people at their worst. You talked about funerals and the difference in those emotional states. So, I just want to talk about the differences and similarities between some of those events.

Darrin: Yes, the similarities that are really important, that’s what I mean. That’s where the key that these are these are really important moments for people. How do we navigate those times that are difficult and do them as if we’re at our best?

Wouldn’t that be interesting if we’re at our best at weddings and those celebrations and although they can be stressful? I’ve seen not people a lot of their best at those too. Those moments are celebrating and really having fun and enjoying life and you feel like you’re on top of the world.

How can we be like that in the tough moments when it’s really challenging to be at your best self or really challenging to think strategically and properly?

Because a lot of my teaching and stuff is around to fight or flight and freeze process and what happens when we make limit fires?  We feel under threat and so in some way, I’m trying to enable people as much as I can. I can’t control people but enable them to be at their best in the tough moments which is that’s the escalation that’s setting up the right process for people that say they could be at their best preparation.

People show up to meetings and they’re ready to go. They’ve got the right headspace and they’re ready to do that well and they’re wildly different kinds of things. The great moments in life and the worst moments of our lives and yet they’re both important.

How can we help somebody be their best selves in a tough time as a challenge for me to hear a family advisor for sure.

Cory: Now during the decision you talked about your education, your psychology education, and just some of the base knowledge there can you help us understand the difference or, again, differences in similarities of the work you do and, yes, having that background in psychology, and what a family psychologist would be doing?

Darrin: Yes. Do you mean the difference between what I do? Is it a mediator as opposed to a status psychologist? That’s a pretty good question. I’m not a therapist. I make that clear regularly that I don’t do therapy remediation or as a family advisor and yet, when we do this stuff, well, there’s therapeutic value.

For people to be able to reflect deeply and to become curious first all about themselves and what’s going on for them, and I can lead that conversation with them and check in with those places.

And again, it’s not to do therapy, it’s not to fix their family background and all of that. It’s for them to discover what they really want and get right down to their interests. We talk about interests all the time, there’s a therapeutic set of values in that.

So we do that and then people are together in meetings and having the right conversation together and if I can help, I can’t control this, but if I can enable them, put them in the best possible place, be curious about each other, and then some empathy can build, and we get to some other different places.

There’s some therapeutic value there and so that’s what’s one of the things that is really nice of what I do. There’s that benefit too, but I’m not going to do therapy. The process that I lead in whatever way with the family business and separation or mediating whatever context, it’s a forward-focused process.

We’re looking forward, we talk about the past sum because sometimes we have to or there are times when people show up to mediation sessions. They haven’t talked to each other for a year and a half and now we’re face to face and they’re going to talk to each other about parenting time and child support and all of those things and asset division and pensions and child support, or a family business that has been in a conflict.

Some people are coming together to talk after months of not talking to each other, not communicating. We need to attend to some of the emotional things there and let them move that ruble away so that we can get on to then negotiating and talking and some forward-looking stuff.

The past stuff comes up we’re not afraid of that but we’re also not dwelling on it and staying there. We do it often as a way to try to understand each other and that could sometimes be helpful. Somebody did something that created a conflict.

I think the other person that they hurt, the hurt person doesn’t know why they did it and they often make assumption that there’s something that’s interesting. I’ve found throughout my career doing this that when there’s conversely people pull apart and they stop communicating or they communicate less.

What’s left then is it is assumptions. Now these two people looking at each other assuming that they did something for a certain reason or didn’t do something for a certain reason. What’s normally the case overwhelmingly is that our assumptions never favor the other person. They always favor us.

The other person had bad motivation, they hate me, they’re evil. How did we paint this picture of somebody who is it’s never really great? So, bringing people together for the first time to talk is really helpful to talk about.

So why did you do that? Let’s say I want to understand that. If someone can be curious enough to want to listen to something amazing and that can really change things. So yes, that’s some things about therapy and psychology in the way we look at this.

I’m going to make another point actually, just about this. What’s interesting is that I talk to people about this fairly regularly especially other mediators and lawyers who are doing this work is it a separation of a legal problem with relationship aspects or is it a relationship problem with legal aspects?

Well, how you approach it depends on what you think of that and so my strong view is that this is a relationship problem. This a family that’s not working well anymore. Now they’ve decided to go in different directions and yes, there are some legal aspects to that for sure that they need to attend to.

They need to formalize things and they need to get legal advice and do all those but that’s a relationship problem with legal aspects. So you will think about family enterprise and these are relationships and this relationship stuff.

There are some business aspects to it and some all that but your family vision and all of where you want to go as a family and your legacy, It’s all about relationships and conversations.

Cory: Absolutely. And the thing is we’re born humans, we’re born without anything. We’re not a business owner that happens to be born. We’re humans born that happen to be a business owner or happens to be in a marriage or happens to be in whatever relationship. So I like that Darrin, that’s awesome.

Darrin: Yes. I like what you said too. 

Cory: Now going back to it, I just want to ask another question about therapeutic benefits that sometimes come out with regard to mediation because the way that I’m thinking of it is that, if we take time to reflect on a situation, our thoughts, our reactions, that there might be an opportunity to change behavior going forward. Do you find that it’s sometimes a byproduct of mediation?

Darrin: Yes. Absolutely. 2 things happen in terms of changing the way a person is moving forward. I’ll tell you that when I’m working with a family business or in some of the mediation context.

I’m out for 2 things. I’m off one for durable agreements. We want to do that. That’s why we’re there for us to make durable agreements.

And then the second thing is for people to be better off because of the process. One of the ways that happens is just the way you’re talking about this. People reflect. I ask them some questions. I give them a format and a forum, on one usually at first and then together in groups and meetings and things where people can reflect and they can ponder. Why did I do that? Where did that come from? And to be curious about themselves and then curious about somebody else. And so that could be a massive behavior change.

And the other thing that I’m trying to do as well is I’m trying to model something different. The way that people have had a conversation is up to when I meet with them, usually, those conversations are dysfunctional. They’re not helpful. Many of them are destructive. And so, the way that I ask questions, the way I demonstrate curiosity, the way that I pause and give time for reflection, or, the way that I have people ask clarifying questions to each other. Like, it models something that can bring a shift as well, but, like, the people that I work with Cory are these are smart, good people right across the board.

They just and know what they need. Really deep down, I believe that they know what they need for their families, for their businesses, and their life, all of that, their kids, and so my goal and my task is then just to bring that out of them and help them discover that.

And so, certainly there’s transformation that they place in their agreements and clarity moving forward. By the way, clarity is usually the most stressful thing about all of this stuff with family and with conflict. Not knowing what the future looks like, your wealth, your business, your relationships with your kids. Like, that’s so stressful to stare into a fog bank on that stuff. Getting clarity is helpful, it’s very good for people. They can transform their futures.

Also when they experience a different meeting, a different conversation, not therapy, and not doing therapy and have just a different way of doing it. That could just change things. And they take those back to their boards and their leadership teams and back into their families and have different conversations. And that’s amazing when that can happen.

Cory: Now Darrin, let’s talk a little bit of the proactive side. Maybe I want to go back to the comment how people have not having talked for months because I think that there’s something there. But thinking about the clarity and where somebody is on a moving forward basis.

Maybe they’re proactively coming to this and saying there’s a situation and you talked about the training you do in de-escalation. Thinking about how there’s an opportunity here to de-escalate a situation proactively rather than getting to that situation where we’ve stopped talking for months. How can people approach that?

Darrin: My biggest bit of advice for people is to be curious so because I think that’s what you’re talking about, isn’t it?

People some are in conflict and they’re moving forward in whatever direction and they haven’t talked for a long time. There’s a lot of heightened emotion there. How do we deal with that to be able to have the right conversation?

If a person can be curious and force themselves to wonder what’s going on for that person and with open-mindedness about it because often we’d make assumptions about the people we know the best quite easily.

You’re in conflict with a family member and you’ve grown up with it. This your sibling for instance, you assume why they did what they did or you assume what they’re experiencing when they didn’t get to be the CEO, how the company and you did. All those things make assumptions.

But to be open, even a little bit just to crack the door open and still keep. I’m 95% know what’s going on in here but I’m going to be 5% open-minded about learning something new. I’m going to be curious. I’m going to find out and I’m just going to stop my mind from that inner chatter. I’m just going to wipe that away. I’m just going to really try to listen to understand.

That does a lot to bring down the temperature in a conversation and someone that’s leading up to a conversation. I think it was Chris Boss who said that curiosity is like a self-management hack and if you’re curious, it changes your mindset, it changes the way you feel.

That’s what I would encourage in people and that’s a conflict thing. That’s what we teach that in conflict all the time. You go from defensiveness to curiosity and if you could do that, that just changes things dramatically across the board.

So that’s where I start.

Cory: Now Darrin, can you give an example I think that it’s wanted to really get into and define what curiosity looks like and sounds like because as you mentioned, internal chatter and just opening that door. What would you say look like to be truly curious?

Darrin:  I was working with some siblings in a family business, and one of them in particular, I’m going to mention. I’ll tell you a little bit about it now. There was so much animosity between them, that they could barely work together and their conversation with each other, they both considered to be very disrespectful. They both felt offended and it was just difficult for them. And so, when I started my work with them, I met with them separately, got to know them, find what was going on.

And in that early time, part of that process, I’m prompting them to think about what their sibling is feeling and experiencing and I would ask the question, “So what do you think? Why do you think they said that? Tell me about that.” they might have an assumption about why they did it, like they’re a bad person or they’re mean or whatever it is. And I want to push it a bit further and go, “So are you sure about that? Like, could it mean something else? Imagine, liking them better than I do, but what could it be? Anything else?” And then I might list some examples. “Well, I wonder if this is going on. I wonder how their relationship with a significant other is. I wonder if their health’s okay. I wonder if they’re stressed financially. What could it be?”

With these siblings, I had to do a fair bit of that, and, again, privileged that they would ask me to be part of their journey. I’m grateful for that and I really enjoyed these people. They were good people enjoyed them. Over time, I met them separately a little bit. Then they came together to have conversations. For that, it went back to the old sibling rivalry and they were just really defensive and attacking. They felt like they were being attacked by the other.

I went back to some of that stuff that I did when I was with them separately to say, “Hey, let’s change the way we’re doing this, and let’s try to make this a curious conversation more than what’s happening now because what I’m noticing now is this is not working. This hasn’t been working. This is a new day, we’re going to start over. This is a new day for you as a sibling partnership in this business.” And so, when they started to ask questions and pause and listen, you can see the transformation happening. You can see the change in it and the temperature in the room came down. There’s more speaking and they felt less threatened and then when you feel less threatened, you feel maybe a little more trust. Maybe not a lot more trust at that point, but maybe a bit more.

They’re willing to be a little bit more transparent, to talk about what they were struggling with and why they felt stressed about this or that, or why they reacted strongly to this. And then over, I mean, it was over quite a long time, lots of meetings over time where it shifted so that they became way more curious and they could have conversations together that were more productive. It’s you who have to imagine what could be going on here that I don’t know.

I’ll give you an example of this in my own life. It’s a little different, but it illustrates the idea. I was driving down the road one day, and this car in front of me, it was starting to swerve around on the road a bit. It wasn’t really staying in the lane and I got instantly furious because I thought this was a drunk driver, I was so mad yet, I was just curious.

I’m ready to pass this car and drive past and offer some feedback and I look inside the car at the driver. It was a gentleman who was maybe mid-forties, dressed in a suit, and he was driving the car, he’s just leaning to one side and slumped down a little bit. He looked really upset. He looked really sad and then looking at the passenger seat, it was another gentleman about the same age, dressed about the same way. It looked like there might be brothers and he was sitting in the chair, he had his elbow up on the side of the window, his hand up against the window and his head leaning into his hand. There’s something bad that has happened. Instantly, I thought, “My goodness. These are brothers who have just come back from the hospital. Maybe they’ve lost their mom.”

Or they’ve come back from a funeral for their mom or a sibling or somebody, so they’re grieving. This is not a drunk driver, this is a family that’s in heavy grief. As I kept driving, I totally changed my attitude and now I want to wish them well, and I want to pray for them. I hope they’re going to be okay.

But the lesson for me in that was that my assumption drove my attitude. At first, I was ready to phone the police. Then after that, I was ready to pray, just because of an assumption. Now granted, I still don’t know what happened in that situation. I don’t know what was going on. That’s not the point. The point was I had an assumption. It drove my actions, my mentality, all my emotion and when it changed, it changed me dramatically.

If we can be curious in those moments of conflict with the sibling in the family business and say, “Okay, I want to know more about why this is happening. I want to know more about what this person’s needs are. I want to know why they did what they did or what they said to me.” I’m going to put my hurt aside if I can and just try to understand. That opens things up. It just changes the world.

Cory: I love that example Darrin because it resonates so well with me. I’m sure you don’t have drivers like this where you live but here in Calgary, there’s people who drive way too fast and are quite aggressive. Sometimes, cut us in half. So how the things that my wife and I have done and said if they’re driving like that, maybe they’re driving to the rush.

They didn’t have time. They decided not to call the ambulance, and they’re driving like that because there’s an emergency. The last couple of years, I’ve been doing that and it’s been such a great privilege to just pull over to the side. “Let them go by. It’s okay,” they’re in a hurry for a reason and it’s their reason, not mine. I love that because it resonates so well.

Darrin: That’s a that’s a good one.

Cory: Now, I wanted to go back to the modeling conversations because I have a bit of a belief here from our conversation that somehow this behavior that comes to results that almost like where you see people is on the top of the mountain, but the mountain’s been climbed for a long time. It might even be generations; this has been learned from. Is that a fair assumption there?

Darren: Generations of behavioral patterns that persist and keep on going. I mean, it’s long enough, it’s been, say, 40 years between siblings. You’ve got 3 or 4 siblings together that live together for 40 years and they know everything about where they grew up. They have patterns that they show up.

I certainly noticed in family businesses that’s a place where people can behave poorly because they revert to the way they treat each other as kids. The disrespectful things that they might say to each other in the workplace, it’s like what happened in the backyard when they were fourteen, and it’s not appropriate in the workplace, but it shows up there.

All those patterns can be there like that but I absolutely believe that patterns go back generations, just exactly what you said. The way people behave, their values, and the lenses that they see life through are affected by the families that they grew up in and those that came before.

And so, no question, generations. We’re humble in this work to know that we’re not going to, we don’t have the power to change people. We can only put them in a position where they can make changes themselves. But, yes, modeling something different, can be really powerful, to go into their situation.

You’re sitting in their boardroom in their office, and you’re bringing something different into that same table where they have all those other conversations. I think that’s powerful and really important for us to think about doing. It’d be intentional about that.

Cory: Absolutely. Now, thinking about somebody who’s let’s call it rising generation and they’re seeing this conflict around them. Maybe there are previous generations that have had a conflict, they’re in conflict with other family members and they’re listening to us right now and they’re saying, “How do I change this? How do I improve outcomes?  Maybe be the change for our family?” How would they go about doing that?

Darrin: Yes. 2 things come to mind for me. That’s really a great question.

The first thing is they may need some help. They need you to bring in a mediator a family advisor or a trusted person around them who can lead conversations differently or help them to think differently. Maybe they can coach them around having these conversations, and how they can be different. You’re going to start that work personally and see if you can change and evolve as a person, and then you bring that back into the family and that can start to shift the DNA and the culture of your family a little bit. That can be really impactful.

And the other thing I would say is as part of that, people should prepare for important conversations and not just prepare to go, “Okay, here’s what’s on my agenda. Here’s what I want to get through.” But where I teach negotiation at business school and a few of their master’s programs, and then also due busy places we’re always saying prepare for a conversation and negotiation and think about what your needs are. Your deepest, like, where am I? What’s driving this? My solution to these problems? What are my interests?

And then imagine that for the other person. What are their interests? It’s again, it’s just curiosity. It keeps coming back Cory, it’s curiosity, imagine what’s going on for them. You lay that all out and you imagine what their answers are to your questions or what they’re going to say about a certain topic. Spend some time writing out why they would say that or where that’s coming from for them.

If you can imagine what their needs are and their interests are, imagine if you could meet their interests. Imagine that you’re negotiating, you’re assertive about not just making sure you get what you need, but you make sure they get what they need. So assertiveness goes both ways. And it’s pretty amazing when you’re negotiating with somebody, you’re working through something difficult, and you see them concerned about what you’re concerned about for you. They’re concerned about your needs too. That’s pretty disarming. Like, that changes things.

So, yes, if people would get the help, either coaching or somebody that can facilitate the right conversations that’s not easy. I understand it’s difficult. So, bring in some help from somebody they trust. But then secondly, go into conversations much more thoughtfully and mindfully and do some good preparation so that you can go in and it can go in several directions and you can respond to it. You’ve thought through where that’s going to go and you’re especially thinking about being curious. You write the word “curious” on the top of your notes. Just “curious”, “be curious”. That would be a great start.

Cory: I love that. Preparing for the conversations is key and something that you mentioned that I wanted to circle back on. I love that you went a little deeper for us because coming to those win situations, it’s important to know how you’re going to get there and what that win looks like, is very important.

Darrin: Yes. It’s great.

Cory: Now let’s go back, we’ve got people who haven’t been talking for a long period of time and of course, there’s a catalyst and we talked about have the need to touch on the past a little bit but really, it’s how do we get to the future. Now their time has passed and somebody finally says enough is enough, and they call you. It might be that it’s for financial or legal reasons that they’ve said I need this to be over.

What are some of those catalysts? Is it always financial or legal? Or is it sometimes people who are just fed up with the situation?

Darrin: Yes. It’s pain in general. Some people need to be motivated to come to the table and have different conversations. And so that could be legal reasons.

They could have been served with papers and they need to go to court. There’s something there or they’re running out of time. They’re timing out on something that they need to now deal with or they’re going to lose their opportunity.

It could be the financial part of it. There’s something holding up their ability to make a deal to sell the business, sell a family home, and they need to get this done if they’re going to be able to do that. There’s a bunch of financial stress around that.

It’s going to have really dire effects on their finances. So that could be a driver. And, yes, just fed up could be one. They’re just tired of the fighting and I have worked with families that have been in court for years, and finally, they’re just tired of it. Just tired of it. I mean, just think of the time, energy, and money that goes into the court. It’s unbelievable. And yes. It’s so destructive.

People sometimes need to have a bit of pain before they’re ready to sit down and be open to collaborating and doing something like mediation where they go through that process. So, yes, there’s going to be a pain point. There’s going to be a reason why they’re going to want to do it and when they do, these things that we do as family enterprise advisors and as family mediators, it’s such a great way to move forward to solve problems, but there’s going to be a reason. People have to be motivated to do it. They’re going to think that their best deal is doing it that way as opposed to something else. That’s why they would do it. That’s why they would do it.

Cory: Now, the family is in court and they decided that this isn’t working for us. I want to go back to your comment about clarity and not knowing the future because I think how walking into a courtroom, all of the preparation, not even the cost, but now we are putting the decision into somebody else’s hands versus our own hands. How do people come to that difference? What does that clarity how the future look like when they have it versus when they don’t?

Darrin: Yes. The lack of clarity is so stressful. Like I said, it’s the most stressful aspect for my clients right across the board. They just don’t know what the future looks like. So stressful. And the court is a roll of the dice. You go there and you get a human being that makes a decision. Then you’re going to live with it. Then you can appeal it and all that stuff. But it’s out of your hands, and it’s not clear how it’s going to turn out.

I talked to some clients the other day who did mediation and then they decided to go to court. The one-party thought, “What? I’ve got a better deal going to court. I think we’re just going to do it.” And they went there, and it was a disaster. Their lawyer was not at all correct about what was going to happen there, because lawyers have opinions about what’s going to happen in court. And they can disagree. And these are, I love working with lawyers. These are good people. They’re trying to help families and people move forward and all of that. But they can disagree. And this one lawyer was certainly not correct about what was going to happen in court. It was a disaster for the client.

So, it’s one of those things where everybody goes into court because they think they’re going to do well. But everybody can’t do well in court if they’re after different things. Like, somebody’s going to have to suffer, and maybe both of them. It’s like, “Okay, why would you spend all that time and money to go get an outcome you don’t want?” That’s some of what we say to people about doing that instead of doing mediation or some process where you’re working together.

I don’t know if that answers your question.

Cory: Yes it does and it as you say, lawyers, some great people but we all we all have assumptions as humans. We all have those beliefs and biases that drive those decisions. The judge was making that decision also would be biased in some way based on their own history.

Darrin: That’s tough. I mean these poor judges, they don’t know this family, they don’t know the situation. The family knows their situation, they know their history, they know the traditions, they know their values.

They know what’s important to them and they should be the ones making decisions. I mean, that’s why we want to keep things the courts feel the same way. They don’t want to see people, they’re only there because people have to go there. There’s a few that do, there’s some courts there for a reason.

There are also some people that really have to go there. That’s going to be their best situation, and resolving the problem but it’s still not a nice place to go and people don’t need to go there very often and that’s very rare.

Cory: Now, Darrin, as we near the end of our conversation today, there are a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Darrin: Go for it, alright.

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

Darrin: Well, it’s not going to surprise you with my answer here but, I think that if people can become intentional and courageous about engaging in important conversations, that’s a key right there.

A key strategy that will change and make them successful. The things that statistically make businesses successful family businesses are having a shared vision as a family having found meetings together, having a strategic plan, and having an independent board.

Those are the things that are made statistically that will make 500 businesses more successful, more sustainable, and growing value. All how that’s really important but if you think how all those things, all how those things that involve by nature, really important conversations.

Honesty, and getting down to real value are what people want, like a shared vision for a future family. That takes some brave and important conversations to share family meetings that you’re having family meetings to have these important conversations.

An independent board and having a board at board meetings, we have those really great conversations where people can be honest and we can get down to some things that independent board members outside perspective that can bring a different perspective and value to what’s going on and the decisions that are making.

A strategic plan, how do we come to a strategic plan if we don’t know what’s going on together? What’s our analysis of who we are, wherever we’re going, what we have of our weaknesses and threats, and all of those things? Those are really thoughtful conversations that people need to have about meaningful topics. I think that’s a key strategy, a key part of what has to be it’s the DNA of your business.

Cory: Great. Well, I’m going to ask the next one in a different way because we talk about seeing people at their best and their worst. With that in mind, what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Darrin: To me, it’s incompatible and unmet expectations. People have expectations and ideas how what that’s all going to look like, whether it’s becoming involved in the business or whether it’s a transition of wealth, all of that. People have ideas how what that’s going to look like and it’s not all the same.

If those ideas are your expectations are unmet or they’re incompatible with reality or with your other family members expectations. That’s where the problems biggest problems, I think, show up, and all of that, that’s where I see it.

Cory: Awesome. And one strategy to overcome that?

Darrin: Take a guess. I’ll let you guess. Have a great conversation.

Cory: I was going to say curiosity, Darrin.

Darrin: Yes. That’s how you care, it’s the same.

Cory: Awesome. And in your experience, what are the top 3 qualities that successful family enterprise leaders possess?

Darrin: Yes. I love that question. There are so many ways to look at this, but here’s what’s coming to me. Number 1, being great listeners and being curious, even when they feel attacked by leaders in family businesses to be able to overcome that defensiveness and to be curious and then be really good listeners, is key.

Another one is if people can be collaborators and consensus builders, collaboration is magical and it works well and it normally works well. People bring their diverse ideas experiences and perspectives together and create something that’s even better than what happens.

Also, doing things by consensus that families to say, okay. We’re going to we’re all going to agree. Even if you don’t love the idea, if you can at least say “Okay, I’m going to support this”, rather than voting and ending up being 3 to 2, and then you make a wild big decision, basically, that’s pretty tough. I don’t like consensus, that’s a good way to look at it.

I think the third thing for a leader is a really big picture of how the situation of the family’s long-term legacy. Do you just see the most important things in the big picture?

That includes knowing when your vision is the right vision for everybody or not. That’s not always the case that the business leader is, generation 1, their vision for the business and family. It’s not necessarily the case that their vision is the right one or a good one for everybody and so it’s being able to look at the big picture and say, okay.

Is this going to work for everybody and then find out how those conversations and we dig into that with families all the time? Because there are situations where the family members at the 1st generation, impose a vision. On the next generations and people could sometimes go along with it. And they okay, well, then I’ll do all of them.

The county business is what they want and then they end up seeing enough seen it bitterness and people really just fade out because it’s not where they want to be.

It’s not what they want and like leaders that have a big picture of you and they see everything that’s important and they can even their own view how what reality is, they’ll question that and they’ll wonder and they’re open-handed with their vision of the future so that it’s right for everybody.

Cory: I like that and just because that that vision was established generations ago, doesn’t mean that it can’t be adapted for what the current situation is.

Darrin: Sure. Yes, absolutely or maybe that vision needs to die. The vision ends with your generation and now it’s going to be something new is going to be birth out how. It’s possible that’s it’s hard for people, especially visionaries and that’s because vision and having a vision is a great gift.

You like to see that in leadership but have a big-picture view to go. Maybe this is not compatible with everything for everybody at all times.

Cory: Absolutely. Yes, and before we conclude our discussion today, I’d like to highlight where our listeners can engage in more conversations you’re having or just more information that you’re digesting. Could you provide or guess where they can do that?

Darrin: Yes, I would say my website’s the primary place, they can go check out what’s going on there. It’s going to be revamped soon and I’m also going to be launching some new stuff around de-escalating hostile interactions and some offers for people that might find that helpful because it we’re post COVID and through COVID, not only do we get more annoyed with each other and more stressed, but we also lost some social skills because were part for a couple how years.

And that’s really showing itself is we see that you go to businesses that have those signs up saying, please be respectful or else we’ll ask you to leave. I mean, that’s it just didn’t see that a few years ago, hardly ever.  Now it’s you see it a lot and so we’ve there’s something there. But anyway, as I said at the very beginning, I think I’m just so grateful to be part of what people are going through and to help bring some order out of their chaos and see them move forward.

These good people are doing good things. They’ve got good businesses and they’ve got families and these are all such important things. So anyway, people want to reach out and find me there and how to connect with me there. I’d love to have conversations with people if they’d like to, I’m happy to chat.

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

Darrin: Thank you for asking, but nothing that we’re going to wrap up in the next 3 hours.  There’s so much more, correct? Anyway, thanks for the opportunity to have the conversation with you.

I appreciate what you’re doing. I love it that you’re doing what I’m talking about. You’re having curious conversations with people and then making that available to others to take advantage of. So, thanks for doing that. That’s an important thing you’re doing and thanks for allowing me to be part of it, but keep it up.

Cory: Awesome. Well, thank you and I know that your time is valuable. Thank you for sharing your time with us and sharing your expertise and just somehow your experiences.

I know that there’s so much more, as you said, we could we could talk for hours. I’m grateful for your contribution to this episode and I know that our listeners will find some nuggets. If it’s just one thing, I’m sure there’ll be one or a few from what we’ve discussed today. So, thank you.

Darrin: Yes. Thanks, Cory, I appreciate it.

As we wrap up this episode, we invite you to reflect on the lessons Darrin has shared about the significance of curiosity, open communication, and proactive conflict resolution in navigating family business dynamics.

Whether you are part of a family business or provide consulting to them, Darrin’s experiences highlight the importance of being curious, preparing for important conversations, and seeking help when needed to break generational patterns of conflict.

Throughout our discussion, Darrin emphasized the significance of curiosity and open-mindedness in navigating difficult conversations and conflicts, particularly within family businesses. He underscored the power of setting aside assumptions and genuinely seeking to understand the perspectives and experiences of others. By embracing curiosity, preparing thoughtfully for important conversations, and being willing to engage in collaborative processes, families can find clarity, resolve conflicts, and chart a path forward that aligns with their shared values and aspirations. Ultimately, Darrin’s message highlights the importance of intentional communication and the role of skilled facilitators in helping families navigate the complex dynamics of their interconnected lives and enterprises.

For those seeking additional guidance on navigating the complexities of interpersonal relationships and other business challenges, Darrin is always eager to connect directly. You can reach out to him via his website and we’ve included his contact information together with additional resources in the show notes to support you on your journey.


This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Howfice 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 how 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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