The Fear of Ugly: Reframing Conflict in Family Enterprise Communication
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In this episode, Jane Beddall, founder of Dovetail Resolutions, helps us reframe how conflict shows up in family enterprises. Drawing on her experience as a mediator, consultant, and conflict coach, Jane shares why not all conflict is the same—and how the fear of escalation often prevents families from addressing tension early. We explore the distinction between healthy disagreement and deeper dysfunction, and why timing, environment, and tone matter more than we often realize.
Jane offers a fresh lens on how families can turn conflict into connection. From the “ugly kind” of conflict to the kind that builds trust, she shares insights that might shift how you approach tough conversations. Whether you’re navigating legacy, leadership, or long-held patterns, this conversation opens up practical, surprising ways to move forward—without losing what matters most.
About Jane Beddall
Jane Beddall, M.A., J.D., is the founder and principal of Dovetail Resolutions, LLC. She is a seasoned mediator, consultant, and certified CINERGY® Conflict Management Coach. Jane works with legacy families, family enterprises, and family offices to help individuals and families handle communication and conflict better. Her expertise in using conflict coaching with transformative mediation is especially effective in these circumstances.
In January 2019, Jane launched the weekly podcast Crafting Solutions to Conflict, providing a practical and positive perspective on conflict. She graduated from Trinity College (Hartford, CT) with a B.A. in Economics. She earned her law degree, cum laude, and her M.A. in Public Policy Analysis, with a concentration in Conflict Resolution, from the University of Pennsylvania. Jane is a Conflict Dynamics Profile® Certified Practitioner and holds Family Firm Institute Certificates in Family Business Advising and Family Wealth Advising. She lives in Naples, Florida.
Resources discussed in this episode:
Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.
- Website: BeaconFamilyOffice.com
- LinkedIn: Cory Gagnon
- LinkedIn: Beacon Family Office
- Email: beaconfamilyoffice@assante.com
Contact Jane Beddall | Dovetail Resolutions, LLC:
- Website: dovetailresolutions.com
- Podcast: Crafting Solutions to Conflict
- LinkedIn: Jane Beddall
- Email: jb@dovetailresolutions.com
- Phone: (203) 887-1160
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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 Jane Beddall, founder and principal of Dovetail Resolutions, LLC. Jane brings deep expertise in navigating communication and conflict within legacy families and enterprise settings. A certified conflict coach and mediator, she integrates transformative practices to help families move through challenges with clarity and care. Jane hosts the long-running podcast Crafting Solutions to Conflict, where she explores practical approaches to conflict. She holds degrees in economics, law, and public policy from Trinity College and the University of Pennsylvania, and is certified by the Family Firm Institute in both Family Business and Family Wealth Advising.
My goal is to be the most curious person in today’s conversation with Jane, as we look at how conflict shows up in family enterprises and why it’s often misunderstood. Jane brings a grounded perspective on how families can navigate disagreements with intention and respect. We’ll touch on how families can distinguish between healthy disagreement and deeper dysfunction, explore the role of timing and environment in tough conversations, and look at what it really means to build a culture where every voice matters.
Now, let’s dive in!
Cory: Welcome, Jane. We’re excited to have you here today to share your wealth of knowledge and experiences. Let’s dive in, shall we?
Jane: Thank you. I’d love to.
Cory: Imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?
Jane: Well, as you know, my career is all about helping families deal better with conflict and communication. So that would be my focus. And I would say conflict is a part of life. Always has been, always will be, but it doesn’t need to be nasty. And you would serve yourself well in your personal life, in your professional life, in your community life to figure out how to get better at dealing with it. Be more competent, be more confident, and it will help you and those around you in so many ways.
Cory: Amazing! And so when you say conflict is a part of life, what is it that makes positive conflict versus negative conflict?
Jane: Great question! And part of it is the perspective. There are people who believe that every disagreement is an opportunity to fight, to draw lines in the sand, or to not fight and give in, or to pretend nothing is happening at all. Of course, we agree. We just won’t talk about the fact that we can’t talk to each other.
I think part of the problem and the challenge is we are encouraged to see nasty conflict because it’s interesting and exciting, and that’s what gets into the newspapers to the extent they still exist. And, of course, Succession, the show in my mind, completely captures the concept of nasty conflict. And I think of conflict as coming in three flavors, good, bad, and ugly.
Good is the collaborative, creative kind, innovative. Wouldn’t we be going nowhere fast if we all thought the same way about everything? Thank goodness we don’t. We have different perspective, different life experiences, different skills, talents. So we do disagree, and that’s the good kind. And then the bad kind is, well, we start pointing fingers. We might try to convince other people in a heavy handed way that our way is the only way. That’s the bad kind. And then the ugly kind is things like Succession. We stop speaking. We go to court against each other. We blast each other in public. And I think it’s the fear of ugly that can drive so much unproductive behavior.
Cory: Fear of ugly. I love that. And so where do you see those fears? Is it because we have examples like those TV shows that people fear that? Or do you think that it’s inherent, or maybe it comes from previous generations and experience in childhood? Where does that come from?
Jane: I think we’ll go with all of the above. It is a collection of challenges. Certainly in families, there can be a carryover. The brothers didn’t get along, and now the cousins, just by default, seem to feel, well, we can’t get along. That’s the way we do things in this family, fighting with the other branch.
More generally, I think there’s a fear of if we grapple with, if we address things that aren’t going well, will that make things worse? Isn’t it better to just skate on by, do the minimum, not risk things getting out of hand? And a piece of that, I think, is we’re just not very good at these difficult conversations. We don’t learn really how to do that very well. We learn other things, and of course, you know the lines about the most important things I learned, I learned in kindergarten. There may be some truth to that, and then we don’t learn more of it and practice it as we go through school, and we go through other important skill-building experiences.
Cory: And when you talked about that spectrum of people who see any form of conflict as that opportunity to fight, and then on the other end was people who hide from the fact that there is conflict. Where do you think that fear, or what do you think it looks like in those two ends of the spectrum?
Jane: What’s interesting Cory, part of it is we don’t all stay in the same place all the time. We change. We also may be in different places in different parts of our lives. I can absolutely have a civil spirited disagreement at the neighborhood association I belong to. But when I get into my family business, brother, there are, of course, as we know, ultimately far more challenges there, because it is my family and it is my business.
Some of it is certainly that the fear can exhibit itself with, I just won’t say anything. I’ll just be quiet. And what is dangerous there, of course, is sometimes that frustration in a volcanic sense is building and building, and there’s no release until it’s too big a release. And then we have a complete mess with the lava flowing in every direction, hurting everything, and damaging people in its path. So there can be that.
Looking for a fight is sometimes the way people will react, and they can pick at anything. If we try, we can certainly find some way to be offended. How dare you say it to me like that? We can make assumptions. And of course, we can rely on old wounds. And families? Well, you damaged my bike when we were preteens, and I will still be angry about that, although we’re in our fifties.
Cory: Absolutely! And, Jane, the the work that you do with conflict coaching, what if if there’s a family member listening right now who’s recognized some of the behavior that you’ve demonstrated, I hope they have because if not, they’re they’re probably living under a rock, because we all see and experience different forms of of conflict throughout our our day to day in in so many different systems and and areas of our life. And so if they’re listening right now and saying, you know, maybe that isn’t as healthy as I thought it was. How does the conflict coaching work that you do help?
Jane: So I learned a few years back now, a conflict coaching model, a woman named Cinnie Noble, who is based in Toronto, created this model. And it is so thoughtful. It is so careful. It is so clear. She put a lot of effort into putting it together and lots of research, a lot of testing behind it. And it is fabulous in my mind for situations where people know each other. It’s good in any circumstance, but with family members who are in a rut, they’re in a track of this is the way we behave with each other. It is extremely helpful there, and I will just hit some of the highlights of it.
Certainly, the very first piece of it is it’s a seven stage model. And the first thing is what is it you want to accomplish? Why do you want to put time, effort, and money into this? And sometimes that’s challenging. It’s, well, I just want everything to be better. Don’t we all? But a little opportunity to talk through, what is it I’m hoping for? Is it this particular dispute we’re having? Is it a recognition that this is our challenge now, but there will be others down the road? And I’m a huge fan, I’ll say, as an aside of anything that relates to skill building. Usually, when people contact me, there is something that’s not going well right now, but there will be something in the future. So I really enjoy working with people on that. When I’m not here to help, let’s have you be in a better place.
One of the most powerful aspects of the model is what’s called the not-so-merry-go-round of conflict. And it recognizes and actually graphically shows how we tend to get ourselves into this cycle of, well, my brother said such and such a thing to me. And what do you know? He said it the way he always says it. And I reacted the way I always do. And we’re off to the races off-track immediately. Pointless. So the idea is, and what I love in this coaching model is because it’s really about two people, it’s about yourself and the other person or the OP, as we’d like to say. The client gets to play both roles. So how would I say what needs to be said to lead us to a productive conversation in a way that does not immediately set off my brother?
Because I really know how to do that if I give myself a moment to think about that. I’m very good at that. Literally practicing how to say it so it rolls off your tongue. And sometimes a client will say to me, well, what should I say? Then my response is it’s really not at all relevant what I think. I don’t know your brother, and I’m not going to be there when you’re having this conversation. So it’s practicing. How do I say it? What do I expect comes next? And then reversing roles. I have to think about how to not set off my brother. I have to also know that he’s going to say those things that make me crazy. wait a minute. He’s going to say those things that don’t have to make me crazy.
Cory: I love that because you can’t control the other person, so to switch those seats, Jane is fantastic.
Jane: And to just say, alright. I know he’s been saying these things to me with that tone or that face or the rolling eye, whatever it is, does not mean I have to lose my mind. I’m not required because he’s doing what he has always done, and I can anticipate, does not require me to go crazy. Maybe I can step back.
Cory: I love that! And so, when you said when you’re not there to help, I’d love that because so often, people become dependent on the advisers, coaches, or consultants that they work with. And so can you help me understand the difference between what you’re talking about here and your role as a mediator when you step in that function?
Jane: That’s a great question. And in fact, they can overlap a little bit. So one reason, I had done mediation for years and years and started out way back when I was practicing law. I would do some co-mediation with a senior lawyer at the firm where I was. And what we did then was very much what’s called evaluative. It’s all about the money. What’s the value of this case? It’s in litigation. What’s the value of this case? One side says x, and the other side says y, and the mediator will help them not just split the difference, because then you don’t need to pay anybody if you’re going to do that. But it’s a little more nuanced of, well, let’s talk about the fact that you have a fascinating and novel theory. This state has never recognized that theory. So maybe that’s not a winning idea, and you may not do as well as you think. Or, yes, you’re going to win in the sense that the verdict’s going to go your way. You’re not going to get the money you think you are. Let’s get a little more realistic. So that’s one kind. It’s called evaluative.
The next kind is called facilitative. And that is we have to figure something out. And they may, as is true with evaluative, there may be people who don’t know each other at all. There’s just I don’t know you. The example I like to give is there is an established neighborhood, and then across the road, there is a vacant lot, which is going to be built up with houses. Every morning begins with the beep beep beep of the trucks going backward into this new development that’s being built. The people across the street find this to be a horrible way to start every single day. A facilitated agreement that could happen through mediation would be something like, alright, until 9AM, those trucks go the long way around. It takes them more time. It’s not as convenient, but the beep beep beep doesn’t begin until most people are at work, most people are at school. We can just find a way to make this less miserable. So that would be the second kind.
And then the least well known actually is what I prefer, and it’s called transformative mediation. And the focus there is truly on the relationship, where the relationship matters. So you don’t do this with strangers. You do this with people who are in a family together, who work together, and, of course, work together and are in a family. It’s perfect. Because, for example, there could be a situation where my coworker and cousin says things to me that absolutely make no sense to me. And I could honestly say in a very civil way to the other person, I don’t truly understand how you see it that way. And if I were in your shoes, I cannot imagine that I would see it that way. Nonetheless, what matters to me is this relationship.
And because of that, I respect how important this is to you, and that you truly see these things this way, which is a foundation for them going forward to try to work things out. And, of course, it creates a wonderful cycle when the person on the receiving end hears that. So much easier for them to do the same. Well, Jane, I don’t understand how you can be so nuts. However, I do care about our relationship, and I will respect that you genuinely believe what you were telling me you believe. So much better than, well, we’re just going to try to force these people to figure something out. We need that foundation of what the heck, what matters here, while the relationship matters a lot.
So the conflict coaching is something I started doing more recently. And one of the reasons is a family member would contact me and would be so excited. We’re going to make some progress. We’re actually going to get some things figured out. And then at least one other essential person wants nothing to do with it. They’re not doing this. So, obviously, very deflating for the person who contacted me. And sometimes they won’t even talk to me, the other person, about anything because no. And not infrequently, that other person feels I have the upper hand. Why would I be making any changes? And perhaps the relationship does not matter enough for that person, or they are not in enough pain yet. They may later be in real pain over, wait a minute. Is it money? Is it my spouse saying “work this out, I’m sick to death of you coming home angry every day from work.” So in those instances where we can’t get everyone necessary on board, an option is for me to work one one-on-one with whoever is willing to do that.
And then we can do the coaching, which is you could make some progress by having conversations that don’t go off the rails. So that would be the conflict coaching. I can stand alone. If I am involved in a mediation where there is some kind of actual dispute right now, usually, I will insist on at least a little bit of coaching so that there can be a recognition of, we are really not going about this in an effective way, getting a little venting out of the way if that’s important, and starting on that skill building idea. I’m here to help you with this issue right now, but I would like to see everyone leave a little better off in handling things on their own.
Cory: And so, imagining somebody who’s in the family system. You mentioned going home and venting to a spouse. Maybe it’s a parent. Somebody who’s protective of that person, and they’re seeing this conflict. How could that person maybe approach these two, or approach the person who they’re supporting and protective of, and suggest one of these two approaches that you’re mentioning?
Jane: Well, I would say unless there’s a strong relationship with both, I would not encourage approaching the other person, but only the one that you were quite close with.
Cory: Yeah. And in that, I was thinking maybe, you know, a mother and her two children.
Jane: And it’s so tough because she’s then in a tough, crazy position sometimes. So that is really hard. And sometimes that’s the mother who reaches out to someone like me, and says, this is not working. We’re going to destroy the business and they hate each other and we can’t do Thanksgiving anymore. So this is not working for me as a mother, or as a person who has, and as you say, it can be quite interesting.
We’ve talked sometimes about shareholders and stakeholders. There may be the person who does not have a vote, but they have influence. They really care what’s happening in the business. So what I like to do as a suggestion is if you are aware of this conflict going on, and you care deeply about how this thing rolls out and you care about the damage it’s causing, the people who are in it may have gotten themselves into this for so long or so deeply. They’re not really thinking about the damage. They are holding on to their positions, and sometimes they’re very, if you will, objective things. They’re data driven. I’m right because of x y z. They are not taking in the fact that this is truly doing me harm. And I would encourage the supportive person as calmly as possible to have a conversation about, I’m worried about you. I would like you to live the best life you can. From what I’m seeing, you’re not there right now. You’re in a tough spot.
So let me digress for a second and say one thing I like people to really think through, is if you’re going to have a challenging conversation, or you think it might be, set things up as well as you can for success. For example, there are people who there’s no way they should be having important conversations at 09:00 in the morning. They ran into the office. They are beyond frazzled. They don’t know which end is up, and which child got dressed for school appropriately, and which one didn’t, and it’s all they can do to make it until 10:00 without breaking too many things. The other end of the spectrum, there are people, and it certainly tends to be true with older people, who may be having a little bit of cognitive decline. They’re not gone. End of the day is a tough time. That’s not the time to have a particularly emotional conversation, or one that requires some very serious thought about important issues.
More generally, where are you going to have this tough conversation? Are you going to be able to do it in person? Well, maybe not. Sometimes that’s not possible. They’re on opposite sides of a big country. What’s the best way with this particular person? Is it phone? Is it video? We’re all different about what works. And if it’s someone you know, think about that. Think about the day of the week, the month of the week. If it’s a family business, you may have an awareness that, no, we don’t do anything complicated the third week of the month. That’s the month where we get the product out the door. We revamp. We do something, and we don’t need to take this on then. But those were just some ideas about you just don’t jump into it and say, okay. I’ve had it. I’ve got to do something.
Cory: Right! And so, thinking about the pain, you mentioned, there’s nothing immediate in my face that’s saying it hurts enough. how do we create that urgency n in a way to maybe stop the collision? We can see that coming, and we really just want to ensure that it doesn’t get to that point where things become destructive.
Jane: Great question, and tough. It is tough, especially if you feel like you are if you’re conscious of, or have some inkling that you’re winning in some way. Why would I change a thing? Everything’s working for me right now. And it may require taking some time on your own, or with someone else helping you to look at all those intangibles. It could be, okay, we’re making money, but if we keep up like this, it’s not going to work. It could be, I just missed something really important in the family because I was so wound up at the office. It could be, I’m kind of just coasting now, and maybe that’s not a good long-term plan, but it is challenging. And sometimes people will come to me and say, no, Jane. They’re really angry. They would never work with you. It’s too late. And my response may be it might be too early because no one’s paying a price yet.
But I do want to share one thing about the intangibles, the non-money things. This is way, way back, and it did not involve a family, but it involved a group of doctors who were very close. They all attended each other’s kids’ weddings. They just were really close. And a disagreement evolved, don’t think it happened overnight, with one of them taking clients that the others thought didn’t pay enough. Well, they tried to force him out over the money. Well, he was forced out, and everything worked out for him. The rest of them then tried to force out somebody else because he was also not making enough money. Well, what do you know? Not only did they start wasting a lot of time and money on the fighting, at least two of them developed significant health problems. The stress of it all was really a problem, and that may be the little crack to get into, which is, what do you know? I do lie awake at night, fretting or taking a lot more antacids than I used to, or I freeze when I realize it’s my brother on the phone. Is that a way to live?
Cory: I want to just switch gears a little bit and go back to good form healthy conflict. And thinking about, maybe we’ve got somebody on the family council who’s listening, or maybe on the boards, and they’re saying, I want to cultivate healthy conflict. I want to make sure that everyone’s not just agreeing because they’re avoiding conflict. And so thinking about maybe some systemic change and creating that environment where the stakes don’t seem so high that we can’t have that healthy banter. How can we cultivate that environment?
Jane: I think you’re hitting all the right words, Cory. It’s environment, and it’s cultivating. To me, it’s a culture of this is the way we do things in this family. If the culture is the patriarch makes decisions, period. Everybody else can be quiet. And it can then evolve to the next generation. Well, we have two people make all the decisions, or three people, and nobody else really needs to weigh in because it doesn’t matter. If you set that kind of culture, it’s going to be very hard to allow anyone to even dare to raise their hand, because it’s going to be slapped down and maybe you pay a price for speaking out.
I think a couple of things are important. One is having that whole concept of we’re allowed to talk. Sometimes we talk about how everyone wants to have a voice, don’t we all? We want to be heard. We want to be heard in a respectful way. And that’s more than active listening. That’s a bigger picture than the skill of active listening. It’s “we really do want to hear from everyone.” And, of course, what’s fascinating then is sometimes, never thought of it from that perspective. That person who I was tempted to shut down has a really great idea. That person may also become someone who down the road is going to be a big decision maker.
Let’s let them start to have a voice now. In a structural sense, it can be valuable to start to give roles to people who are younger, and not younger is sometimes not exactly what we mean. What we mean is the next generation. And in some of the larger families, they’re not younger. They’re older. The way it’s rolling out in that family. But allowing people to be involved in some way, to get to see some things, and it doesn’t mean they needed to know every detail that they are not in some sense entitled to know. But having a role, because once we have a role of some kind, we have a vested interest in the success of this family and of this family enterprise, which is a great thing. And, certainly, there’s nothing that could ever be bad about that.
I’m very keen on creating opportunities, spaces for communication. Frequent communication is a great thing. And sometimes it doesn’t have to be terribly complicated. It doesn’t have to be terribly profound, but just this ongoing “okay, I remember you. I know you. I know what you’re like when you’re really irritated about something. So because we’ve had those ongoing communications and exchanges, I don’t have to be freaked out about the possibility that this is going to go beyond irritation to full-blown anger because I know you a bit. We have this foundation.”
Cory: Thinking about that culture, thinking about voice and vote, that vote is centralized or concentrated in some way. Maybe we’ve got some siblings listening and saying, just because our parents did it this way, doesn’t mean that we need to do it. You mentioned that sometimes that next generation isn’t young. And so maybe we’re embedded in some of those behaviors. Some of those are very much entrenched in our learning. How can they say, “maybe these cousins that are here that we’re really working hard to have them involved, we want to give them some voice.” Where would they start? Where have you seen a good example where they’ve given something that maybe the risk seems low?
Jane: I think being involved in planning an event, or a part of an event can be helpful. Certainly, we know families that get involved with philanthropy, and they find ways to allow the younger folks to have a role in learning the process, learning how you do this, which is not just we’re going to give you however many thousand dollars. We’re going to say, how did you decide it was puppies and kittens? We weren’t surprised, but how did you make the decision? Allowing people to learn as they go. And I think what can be so challenging sometimes is with this idea of, I individually think, well, maybe we should make a change. We should open things up a little bit, but we’ve always done it this other way. And I don’t even know how to start the conversation. Well, maybe I know who my kindred spirit is, and the two of us talk about, well, how would we go there? How do we even raise this?
Honestly, Cory, if someone is listening to your podcast, that can be the catalyst. So what do you know, whether that’s a man or a woman? I just happen to be listening to this cool podcast about family enterprises. And I was thinking that maybe it’d be appropriate for us to take another look at the way we do things because sometimes there needs to be a reason to bring this forward, to put the energy in, and to avoid a “wait a minute, should I be suspicious? Because we’re not on great terms that Joe and Jody have decided to bring something up. What are they up to? Well, now we heard this.” There are just a lot of people out there who work in this advisor consultant world who recognize families don’t have to be miserable.
Cory: Right, absolutely! And thinking about our listeners, and I love that you brought that up, they tend to be lifelong learners. And so thinking about somebody who really wants to maybe dive a little bit deeper into healthy conflict and some of their tendencies when it comes to conflict, and identifying biases and patterns, are there resources available?
Jane: There are so many. I wouldn’t know where to begin. So I would say if you are someone who is a reader more than a listener, do a Google search, as simple as that, and take a look at, well, this one seems to be speaking to what’s of interest to me. There are wonderful books. There are wonderful articles out there. And, of course, the shameless plug is if you are a listener kind of person, then you should be listening to my podcast, which touches on all kinds of different things, all of it related to conflict and communication in some way.
Some of my guests do the type of work that we do, and they have insights about conflict from that perspective. And some of my other guests have no idea what we do and don’t do anything like it, but they are conflict specialists who have particular thoughts, experiences, and theories to share about how we do this being human thing without blowing everything up. And then I also have very short, host on mic, as we call it, episodes that are on a specific topic, which are a few thoughts on something that I have been learning along the way, I’ve been exposed to along the way, meant to be thought-provoking.
Cory: Fantastic! On that note, 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?
Jane: Bring them on!
Cory: Alright. What is one key strategy that you believe is most essential for building a successful family enterprise?
Jane: One word, communication.
Cory: Great. And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?
Jane: You know my perspective. So it’s going to be the conflict that’s happening that is unnecessarily nasty. There can be tough things out there. Sometimes, it really is going to be a tough situation, but is it even possible to split up the business without destroying the business and hating everyone? So that’s the real challenge. And I think what you need to do is talk more, talk more often, talk more openly, create a regular space for communication, which is to say, don’t wait until everything is gone absolutely to hell before you start engaging.
Cory: I love that! Jane, you mentioned something that I’d love to just touch on, potential outcomes. You made mention that the business could possibly split. And where do you see that come up as a strategy where maybe the conflict is happening, but they haven’t really dove into what are the opportunities here, or potential outcomes that could be a win for everyone.
Jane: And I think partly there is fear right there. If we start talking about this, my goodness. What does that mean, and what are we going to do? So there needs to be an understanding that we’re not pointing fingers. We’re not saying we’re a bad family. And sometimes people will contact me, and they say, my goodness. I can’t believe we’re fighting. We should be so grateful. But there can also be that emotional overlay of, we could never sell it. We could never split it. So they hang on in an inappropriate way.
I will just briefly tell you of a family where the two people who were running the show were 89 year old twins, and one had pancreatic cancer, and the other one was just not very competent at almost anything. And the competent one with cancer was distraught over the idea that they might have to sell the business, and that would be failure. They have let down their grandfather. Well, how many years ago the grandfather died? These two are 89. I had to work with them about the fact that there is no failure here. Your children have not entered the business, but they followed their passion and their love, and the resources this family has created allowed them to do that. There’s no failure here. And by the way, you have a fabulous management team who you honor and respect. Let’s get a little more creative. I’m not an expert on ESOPs or anything like that, but I think you need to look a little farther afield than “we just hang on forever in misery until we manage to tank the whole thing.”
Cory: I love that. Great great story, Jane, and thank you for sharing. Now in your experience, what are the top three key qualities that successful family enterprise leaders possess?
Jane: Number one, recognizing no one is immortal, really hard for a lot of founders, certainly. It could be patriarchs, but it tends to be the patriarchs, the people in charge. I will be here forever. Why would you think otherwise? It’s not going to work out that way. And I get a little annoyed sometimes when people say things like, if something happens to me. Okay, stop right there. When something happens, and it will be death or disability. It’s straight death or it’s disability and then death. Let’s be real. So that would be number one. Just be realistic.
And similar to some things we’ve been talking about, the leader who is both smart enough and confident enough to allow differing opinions to be raised because you can learn great things from them. And you can also let those people talk, and they may be able to really get behind what you want when they’ve had a chance, instead of they’re just simmering with resentment. Not a good thing.
And number three is foresight. Make policies. Make them now before you need them. Do not get into this position of, well, what do you mean? My niece was allowed to have a job at the company, and my son can’t. Just an invitation for trouble, ad hoc decision-making of that kind is, I think, a recipe for disaster.
Cory: Yup. It’s such a great example. Employment policies are a huge point of contention and a great place to start conflict. So let’s avoid that, if we can for sure.
And, Jane, before we conclude our discussion today, I’d love to highlight, you mentioned your podcast. I’d love for you to give another plug and give us the name so people can find it, as well as anything else that you’re maybe having conversations, or listening, reading, engaging with.
Jane: So the podcast is called Crafting Solutions to Conflict. I started it in January 2019. It’s out there on all the apps. It’s also on its own dedicated website. And my company is called Dovetail Resolutions. You can find it at dovetailresolutions.com. And my name is Jane Beddall. And if you can spell it right, which is a challenge sometimes, but it is two d’s and two l’s, you will find I am the only one on LinkedIn in The United States. There are a couple of gals in The UK who are not active, but I’m the main one.
As far as reading and listening, I hop around, to be honest. I go over in this direction, and to some extent, I am guided by my guests. I get wonderful book pitches, and I get immersed in their book at the time. So I have yet to have a podcast guest who had a book to offer that was a clunker. They’re different. Some are very detailed and dense, and some are, woah, read that an hour and a half. But it did have some fun things to think about, presented in a very accessible way. So I’m all over the map.
Cory: Amazing! And I wanted to make sure that we covered everything today. Is there anything else that you came into today wanting to share with our audience that maybe we didn’t get a chance to touch on?
Jane: I think we’ve covered a lot of important things, and I appreciate the opportunity to talk with you.
Cory: Well, thank you, Jane. I also appreciate you taking your time, and all the experiences and expertise that you shared with us today. I’ve learned a lot in this time we’ve spent together and found it valuable. And I know that our guests will also find your contribution very valuable, and we’ll be grateful for it. So thank you.
Jane: Thank you for your kind words.
As we wrap up this episode, we invite you to reflect on Jane’s perspective on conflict as a potential source of clarity when handled with care, rather than something that inevitably leads to division.
Whether you are part of a family enterprise or provide consulting to them, Jane’s approach offers a practical reminder that building a culture of open communication starts well before the tough conversations and often shapes how those conversations unfold.
Throughout our discussion, Jane brought clarity to the often-misunderstood role of conflict in family enterprises. She reminded us that conflict is not all the same. It can be constructive, it can be damaging, and at its worst, it can become what she called the “ugly kind.” Often, it is the fear of reaching that point that causes families to avoid addressing tension altogether. Jane also shared how structured tools such as the CINERGY conflict coaching model and transformative mediation can help families interrupt unproductive patterns and turn conflict into progress. Her emphasis on preparation, from timing to environment to tone, offers a practical approach to more effective communication and stronger long-term alignment.
If you are looking to strengthen how your family approaches disagreement or to address underlying tensions before they escalate, Jane Beddall and Dovetail Resolutions offer guidance rooted in experience and empathy. You can find more about her work, her podcast Crafting Solutions to Conflict, and additional resources in the show notes.
Disclaimer:
This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This not an official program how 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 BeaconFamilyOffice@Assante.com or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.