From Within Outward: Embracing Advisors and Peer Insights for Family Enterprise Growth

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 Steve Legler, Senior Consultant at Blackwood Family Enterprise Services. Steve is a distinguished figure in the family enterprise field, known for his unique approach to family legacy and wealth transition. Steve is an accomplished author, penning two influential books: “SHIFT your Family Business” and “Interdependent Wealth,” which have significantly contributed to thought leadership in family enterprise management. He serves as a faculty member for the Family Firm Institute’s global education network program and is a member of the Wisdom Expedition for the Purposeful Planning Institute. Steve’s expertise is further showcased as one of the hosts of Family Enterprise Canada’s “Let’s Talk Family Enterprise” podcast. Balancing his role as a consultant, facilitator, and coach, Steve is deeply committed to helping families navigate the complexities of wealth management and intergenerational transitions.

My goal is to be the most curious person in today’s conversation with Steve Legler, where we explore his journey from a family business successor to a pioneering family enterprise advisor. We’ll discuss how Steve’s work has led him to reimagine the role of coaching and facilitation in guiding family enterprises through complex transitions. Together, we’ll learn Steve’s approach to uncovering family dynamics, the role of peer groups and outside advisors, and the importance of proactive family governance. Through these discussions, we’ll highlight strategies for sustaining wealth and familial bonds across generations.

Now let’s dive in!

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

Steve: Alright Cory. Thanks for inviting me and let’s see where this goes.

Cory: Steve, imagine you’re delivering the commencement speech to the graduating class of 2024, and you have the chance to inspire them with your story.

How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Steve: Wow. You’re bringing me back to when I was sitting there listening to some old guy give a speech. I don’t remember who it was or what it was, but, I have children well, they’re adult children now, which might be an oxymoron in some people’s books, but who have recently graduated.

I got to sit in some of these, and I don’t remember what the people said, either, but you’re giving me a chance to share my life lessons.

The biggest one that’s been tickling my brain the last little while is how we have no idea what path is ahead of us. Often, I think that people who graduate and they’re there, and they’ve been studying some subject for a few years, have this great idea that I’m going to become a this, or I’m going to go into this field.

For a lot of them, the first part of that journey will be something like what they’re expecting. But for a lot of them, if you fast forward enough years, they will all end up doing things that they never expected.

You hear people say, boy, I studied this stuff, and I never use it because now I’m doing that. There’s a lot more of that. There’s more of that than there ever has been.

So, I would encourage people to keep an open mind about what opportunities are coming in front of them and not be afraid to ask other people in their circle, whether it be their family or mentors or friends, about, hey, I’m seeing this idea, and I’ve been doing this, and I don’t love it.

What do you think about that? Just to get other perspectives. Too many people remain stuck in their heads. They remain married to that idea that they thought, I’m going to become a this or a that.

And they don’t because of that, they have blinders on, and they don’t notice some of the opportunities that are out there that just might be the grass that is greener on the other side of the fence.

So, to keep people’s minds open and eyes open to recognizing that we don’t have as much control over so many things as we like to think we do. Take the signals that the universe is sending us and at least entertain an exploration of some other fields that are different from what you thought you were going to do.

When I hear people a couple of decades later than those typical graduates and you ask them about their career path, one thing that almost always occurs is a couple of deviations and bifurcations along the way.

I used to do this, and then this happened, and then I started to do that. I think, the younger people today don’t recognize that’s a common reality, and so they remain married to a certain path maybe longer than they should.

Cory: Well Steve, there’s so much in there, and I can tell that your approach here really comes from a coaching style. Like talking about blinders and talking to those around you.

It doesn’t require a coach to ask you that question, but just ask the people around what they’re seeing. So, from that and your approach and, of course, you don’t wear just one hat, and you’re not a coach solely, but I know that you do have that educational and those letters behind your name.

So in that, and young people who maybe don’t have the opportunity, they don’t have a coach like you and I do to challenge us on some of those thoughts. How do you see that as an opportunity to put some of what we’re talking about here in place for themselves?

Steve: It’s unfortunate that too many people don’t get coaching or understand what it is.

That is changing. It continues to evolve, and I think more and more younger people get it and understand the benefits of having a coach. I coach a lot of people. Sometimes, I don’t even call it coaching, but I do it anyway.

It is a field that I discovered right after I finished the FEA program. Somebody had suggested coach training, and that was the biggest inflection point in my life. I remember after doing the first 3-day coaching course that I did, I came home and said to my wife, I don’t care if this ever helps me in my career.

I know that this is going to make me a better father, a better husband, a better person.

And so I continued with those courses, and it was a complete change of mindset and way of of looking at things and a way of, I hate to use the word helping, but helping people, being a resource for people, because too many too many of the people in our lives have all the answers for us and are not shy to share what they think we should be doing.

If that were the best way to get people to do things, boy, the world would be a lot more efficient because there would be a lot of people telling people what to do. And if you just listen to all those people, the world would be great, but that only sometimes works so well.

Tell people what they should do is not the best way to get them to do it. Just think about what your grandfather might have thought and the way he might have operated, or even your dad.

Cory: Absolutely. And so, when we’re talking about the journey that people are taking through life and family enterprises, there are a lot of complexities.

And as that journey is being forged by any member of that enterprise, how do they take some of those opinions of others?

As you say, there are so many opinions about what that person should be doing versus an opportunity that comes knocking.

Steve: Well, my backstory is that I went into my dad’s business because I was told from an early age that that was my duty, and I followed that path of least resistance for longer than I care to admit.

And now, when I see people who are in a rising generation of some kind of family enterprise and are sort of blindly following, I can easily identify with them and understand the ones who don’t really think that that’s where they want to be but feel like that’s where they have to be.

So, to answer your question, the unconflicted advice is the part that’s hard to get because many people think I still remember.

We had our 25th anniversary of the business that my dad had started, and we had this big event. I was between my undergrad and my MBA, and all these people, suppliers, bankers, and customers were all coming, and they were patting me on the back.

Customers were all coming, and they were all patting me on the back. This is going to be yours to take over and all of that and I was all pumped up on it too, because it was like, this is this must be where I’m supposed to be.

Less than five years later, we sold the operations, and we were down to 4 people instead of 300. And all of a sudden, my outlook on things changed.

But it was actually more of a relief than anything else because I recognized afterward that I didn’t really want to run a steel fabrication company. I didn’t really know that I was going to be running a small family office for 20 years either, but I kind of accepted that role.

It took me a while before I finally found my calling, and that was in the FAA program, where I realized that, my god.

There are people who work with families to guide them and bring them on this journey to do all this stuff in the family circle that has nothing to do with the business circle.

I had thought that the business circle was the only circle, but then I realized it’s not the only circle, but it’s certainly the most important circle. And then I recognized, wait a sec. This is this family circle; a lot of stuff goes off the rails here, and families need more support from outside professionals in this circle.

Then, the other part was that I’m actually more comfortable here in this family circle. My grandmother, my mother’s mother who lived with us when I was growing up, used to say, you should become a priest.

And I would laugh at her and laugh at her and think, that’s crazy. Less than ten years ago, I was at the Bowen Center in Georgetown, where all these people were studying family systems theory.

I looked around the room for one day and a half. The people there were clergy—ministers and rabbis. And I was like, I guess she saw something in me that my dad didn’t see, but he had the blinders on. He needed someone to take over his business, so the fact that I could have done it.

It kept me in that rut, and with the blinders on, I thought, well, I can do this. I don’t love it, but somebody will do it, and it may as well be me.

It was a relief to not have to do that, and it was a calling to finally discover that working with families on these kinds of challenges gives them a different perspective than the one that they grew up with.

Whether they end, I’m not the kind of guy who comes in there and tells people to quit their family business and do something else. It’s not bad.

But there are a lot of areas in between where people are guided to the right seats on the bus. You might not have to take over as an operator of the business, or you might just be on the board and an owner, though these are options that I think a lot of people don’t see.

And so if we can hold up a mirror and show them different opportunities, that’s a huge value added for them.

Cory: Absolutely. Steve, you mentioned getting other perspectives, and then you also mentioned unconflicted advice. So, how do people know when that advice is conflicted?

Steve: If I had an easy answer to that, I think we have to put this on people’s radars so they can ask themselves the question. I was talking to some people yesterday and mentioned who should be running the family meeting.

And so we’ve got to talk about, well, the lawyer who draws up the estate plan can then have a family meeting and explain it to the rising generation, and that all sounds lovely and better than no explanation.

But if I just drew up this estate plan with Mom and Dad and now I’m introducing it to the people who are affected by it, would I want to hear their opinion on it to tell me where and why you didn’t do this?

Why am I going to be there trying to sell what I just did? I’m so smart, and I did this and this is how it’s going to work.

Now I find myself selling it as a, which is completely vast and awkward. I always talk about the tail-wagging dog and families who go to see professionals like lawyers, accountants, and tax specialists to figure out how they want to plan their transition.

And then they assume that the plans that are drawn up for them will magically perfectly match what the family wants and needs and I say, wait a second. Can you not take some time to talk to your family and figure out what makes sense for them?

Then you can see those professionals. They’ll be happy to know exactly what you want, and they’ll be able to serve you even better because they’ll be responding to your exact needs.

However too many people don’t do that because they don’t know how or they don’t know where to get the help. A lot of professionals are in too much of a hurry.

Somebody comes in; we need this. I know how to do that. I can do it quickly. I can send the bill, get it done, and move on to the next one. It’s so convenient because the family that just came in was almost the same as the Smith Family from two weeks ago.

So all I have to do is pull those documents out, change a few names, and off I go. I’m doing all this business, and I’m the big guy in this town, and I’m cranking out all these things, and all the people are coming to me.

And next thing, everyone has all these. I went to see the best lawyer in town for this, so my plan must be great. And what? It is great until it isn’t.

You won’t know that until somewhere down the line, hopefully sooner rather than later. Sometimes, families only discover their shortcomings and plans when it’s too late to change them.

And I’m hoping that people are starting to wake up to the fact that just taking the advice as given without a full attempt to involve the people for whom the plans are being made is an oversight.

Cory: Right. And, Steve, I want to go back to your comment about clergy because I think that is a great way to reflect on a new person in the room, a different person than the lawyers, accountants, and tax specialists.

And it doesn’t need to be somebody from a religious background, although it might be the right person for that family or that member.

But I do want to almost compare, and I know that you do a lot of mentorship within the professional space. and thinking about those people in our corner who help us identify blind spots, whether professionals, family members, or church members.

How is that coaching mentorship role in somebody’s life? How do they build that, seek it out, and ask for it?

Steve: So, are you talking about a person within a family who can play that role or someone who’s looking for that role?

Cory: Maybe they’re saying, look. I’ve educated myself, and I’m on this journey and doing what I was supposed to do. But now I’m seeing these opportunities and looking for a bit of guidance and be it a coach, as we talked about.

Maybe it’s just me. I’m looking for those, call it, unconflicted people are in my corner.

Steve: Right. So, I think one area to consider is peer groups. If you’re part of a family business and you can join a peer group through Family Enterprise Canada or any other group where you can then meet with people who are going through the same thing as you, that’s pretty unconflicted.

But I just want to go back to the clergy thing. There is a video that I saw years ago from the Business Families Foundation with John Davis, the guy who came up with the three-circle model.

At one point, he says this is the kind of work with families that used to be done by priests and rabbis. And I thought, wow. That just ticks the box of what I was thinking about getting myself into.

A couple of years ago, somebody from the US contacted me on LinkedIn. He was trained as a CPA, but he also used to be a pastor in a church. And he was even a chaplain at a hospital.

I set up a call with this guy, and it was like he got hired by a multifamily office. I think that was a master hire because if you want someone to walk in and be comfortable in a family meeting, picture this guy. His job was at the hospital, where the whole room was gathering while someone was dying, and he had to walk in there and connect with these people, listen to them, and try to make them feel better.

Like, that guy could go around a family meeting tomorrow morning —I don’t care—because he knows how to do that. And so many people in our industry are learning how to do more of the family circle stuff.

Learning how to do it is the hardest part for many of them or many of us because it’s not about having the answer. As I often say, it’s actually more about who I am than what I do and my ability to respond in the right way.

So if you’re part of a family and recognize that, wow, our family could be or should be talking about this stuff, but we don’t know how.

You know, what you were asking about almost made me think of a family champion, like the person in the family who really drives the need to bring someone in to help us with this stuff. Those are the people who typically reach out to me.

I had someone reach out from a local business in Montreal a couple of weeks ago, and as she was talking to me, I went. So why are you contacting me?

Well, I told my dad to do it, but he wouldn’t do it. I just started to look, and I said, I’m going to go and talk to you first, and now I’m going to, So there are people in a lot of families, and this this comes from Dennis Jaffe’s research of the 100 families that have lasted a 100 years.

One of the things they discovered, the ones who succeeded in making multiple transitions, was that there was always someone in the family who took it upon themselves because it’s typically not a paid role.

But you make sure that the family addresses things, gets together, has gatherings, brings in resources, and starts to create something like a family council or regular family meetings.

Someone has to drive that, and it is only sometimes someone from the leading generation. In fact, it’s often someone from a rising generation, but they need to get the buy-in from the generation above because that’s who makes the ultimate decisions and pays the bills.

I can’t tell you how often people contact me who are not the senior generation of their family business and want to hire me.

Cory: That’s right.

Steve: Our biggest stumbling block is, well, can someone pay me? I love this work, but I prefer to do it for a fee. But if I can’t help them convince someone who can sign a check to pay me, it won’t go very far.

And that’s actually one of the surprises, a negative surprise when I started this work that I didn’t expect to happen as often as it sometimes does.

Cory: Wow. And so that champion who’s listening to us, Steve, who just realized I’m that person in my family. Other than picking up the phone, what’s the next step?

What does it look like to champion this and sell it to the family?

Steve: It’s hard because even the idea of a family champion—when I discovered the existence of this term—I think it was 2018 when Joshua Knox’s book came out, in which he took his PhD research and turned it into a book.

As soon as I heard it, I contacted him, and he and I presented about it together at the Purposeful Planning Institute Rendezvous. Then I thought there was this niche here of coaching family champions, and I figured out how to turn that into something.

And it’s just that it’s such a niche within a niche that it’s hard. So, if someone is listening and they don’t have a copy of that book, the first thing they should do is order it from Josh O’Nacht.

It’s called Family Champions and Champion Families. Read that, and you will at least have a better understanding of how to describe yourself. Then find peer groups, join associations, start finding meetings and resources, go out there, and find like-minded people because other people are going through similar challenges, and everyone thinks they’re the only one and they’re not the only one.

In this day and age, it has never been easier to find other people who are facing challenges similar to ours. There’s going to be a way with the interwebs that you can find people or whatever.

And you have it’s not it’s not easy. It’s because you must start convincing people in your family that this is needed. But most families who do actually have success in doing this, it’s because someone has recognized this need and has started to push and has started to say, wait a sec. We need to start to work on some family stuff.

Cory: Right. Absolutely. And so, going back to deviations, Steve, this is a fundamental shift in the way that a family thinks about bringing some of this conversation.

It’s only sometimes on an individual basis. We started with the commencement speech and talking to people as individuals, now thinking about a family. Now, we have a group of people who are occupying their individual roles within a system.

Now we’re talking about a deviation, and it might be the deviation that you had in your family, where one day you had an operating business and one day you didn’t.

That’s a big shift, but there are many within, and you brought up the 100-year families. There are many deviations that happen within that. How, within that system of thinking are we able to guide ourselves through that?

Steve: Well, I answered a previous question by recognizing. It was about being conflicted. You have to recognize that there might be someone who is conflicted.

I think families need to recognize that events that happen to their family affect all the members of the family differently. And if the family can recognize that they will face whatever meteor comes in better together than separately, that’s a big moment.

If the family has gotten to the point where they are meeting regularly and have good relationships, then anything that happens is if they have a forum where they get together to discuss things.

I remember when the pandemic hit, and Jim Grubman said that this was a really great test of family governance. Because the ones the families who had not gotten used to having meetings together when the crap hit the fan, they didn’t know what to do, and they were scrambling.

The families had already started to instill some kind of regular meeting, some kind of family governance, and some kind of forum where stuff happens. Okay, we know what to do. We come together, and we talk about things like this.

The arrival of the pandemic was a huge test, and some families were well prepared and succeeded through it, while others were exposed to what was lacking.

So that’s the biggest thing. I always mention to families when they come to me before they have a problem, I always congratulate them to say the best time to make these plans is before the house is on fire.

Too often, people wait until that little blister turns into a big thing, and then they get rushed to the hospital. And now, their options could have been better.

Part of what I often am called in to do with the family is to help them learn to set up a series of regular family meetings so that they can plan and understand, clarify and have dialogues about expectations and where the family wants to go, where the family can go, what the family values are so that if there’s a conflict later, we can rely back on the values to help us figure it out, learn how to work together, learn how to plan together, learn how to have 1 generation download certain operations and expectations to others so that they can learn.

Families work better when they actually have a mechanism and a structure for doing all these things. But getting them to realize they need to do that takes intention and time.

It takes preparation. It takes leadership. It takes all these things that don’t you don’t just snap your fingers and say, what? We should have family meetings. Let’s start having them. We’ll have one next week, and then it takes a while.

My dad joined CAFE, the forerunner of Family Enterprise Canada, back in the eighties. He heard the message that it’s important to have family meetings. He didn’t hear the part about you should bring in an outside facilitator.

So he was smarter than everybody else, so he ran the meeting himself and that was in 1985, and we didn’t have another family meeting again until 2006. That was only because he was diagnosed with cancer. We have to have a family meeting.

That’s what I say to families. 21 years of defeat between meetings is not the recommended interval. You need to get into the habit of doing this.

But the reason we didn’t have another meeting was because it was not interesting or fun or whatever experience that we wanted to relive again.

He didn’t dare try to call one again because the reaction was not good, because it was not well planned, not well run, and not a dialogue—it was a monologue of that thing. I have this burning desire to tell my family everything I want them to do.

As we said before, telling people what to do is not always the best way to get them to want to do it. That’s how he felt he needed to do it, and it did not go over well. I understand perfectly well, and when families talk to me about it, why do I need you to come in and do this? Because when I do my job well, it doesn’t look very hard at all.

It’s really like, what the hell is that guy doing here? Was this like the referee at the game? If you didn’t notice the referee, it’s because they did a good job. It’s a role that some people appreciate and understand right away, and other people don’t, and sometimes they try it on their own.

I know I’ve worked with families that have self-facilitated their own meetings for a while because someone in the family has that skill set and is stuck in a situation.

I remember going into this one family—there were 14 of them. I was told it was the first time they had brought someone from the outside. The woman who normally used the facility had the biggest smile on her face because I was like; finally, I can just participate like everybody else and not be trying to. You were talking about conflicted situations. You took a lot of time for somebody to be in.

Cory: Absolutely. You took a lot of weight off your shoulders there to be in that room. So, Steve, I want to go back to your comment about the business circle being the most important circle and how many people view that.

Now, we’re talking about the family circle and focusing there. Then you also commented about the pandemic, so contingency planning and planning for the unexpected. I guess what I’m bringing up is the unpopular path. Going down the road that maybe isn’t going to make us a lot of money or strategizing something in a way that isn’t where we’re going but avoiding what we don’t want and having a plan for that.

The unpopular focuses our attention on what’s unpopular. How do we get started there?

Steve: I don’t know if I’m going right to your question, but what’s coming up in my head here is that in my business circles, I like to encourage people to think of the business as an asset that the family owns.

If there’s anything that’s happening in the business circle that is somehow going to compromise the relationships in the family circle, my bias is to figure out a way to cut that off or do whatever or sell the business or whatever.

Don’t have the business be the cause of the problems in the family so take care of making sure that you are looking out for the family members. Some of them are in the business and some aren’t.

I hear these stories about how the son was working in the business, and then suddenly the dad came and said, by the way, I’ve just sold the business and no warning, no nothing. It’s a little bit like my story, but not quite.

The idea that the business circle is more at the top of my mind is often a function of founder-led businesses or early in the first or second generation. I think that families that once they’ve gotten through a few generational transitions, they’ve often morphed their business or sold the business and started another business or started another business and closed some down. So they they recognize it more.

But too often, in early-stage businesses, that business is like it’s another child of the founder, and it occupies a lot of the time. It is the wealth engine and the repository of most of the family’s wealth. Of course, they are paying a lot of attention to that basket.

But when they are focusing so much on that basket to the point where they are neglecting the family part. I think we’ve all heard stories of people who worked so hard and neglected their families. I’m sure we all know people who did that, and they’re doing what they think is best.

They’re just trying to make the best decisions based on what they know at the time. It’s hard to fault them for that. As outside advisers to such enterprises, part of what we need to do is to hold up that flashlight and say, hey. Do you see what’s going on here?

Some will be glad to have it pointed out to them, and others will hear that you’re probably right but do not know how to stop and they might be too far gone.

That’s why my bias is always to value the family circle more, and I will always try to point families to or push them toward resolutions that keep the family intact, even if that means making changes on the business side.

Sometimes they’re receptive to that message, and sometimes they aren’t. A lot of advisers are completely the other way, saying it’s the business that hired me, so I’m going to go and advise the business, and I don’t care about the family.

And that’s fine; those people are out there. For people who took the FDA program, the idea was to expose us to the broader picture.

Where you come down with how you try to advise and guide families is up to each person, and how the leaders of the family take that advice is also up to them. And it would be nice if every story had a happy ending, but they don’t.

Cory: It’s a delicate balance for us advisers, who don’t want to lead with fear. But really, what we’re saying here is you can neglect that family capital for some time, and it’ll be okay. If you have it in the dark for a while, it’s alright. There will be a time when it is major and unforeseen.

Steve: I have clients who, unfortunately, waited too long, and some relationships within the family are damaged to the point where I don’t know how well they can be mended, but I will try to bring them the resources that I can to help them do that.

But exactly the one situation I have in mind, the idea of somebody leaving the business who’s there kind of and doesn’t really want to be there, that’s part of the next step of hopefully mending the relationship.

Cory: Steve, 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?

Steve: Go ahead. I’m always ready. I always say that when I walk into a family, and I’m there, I’m the only one with a different last name sitting around the table or around the living room. I never know what’s coming up, and I have to be ready to respond appropriately. I never want to know questions in advance. I think you sent them to me, but I don’t remember reading them. So let’s go.

Cory: Fantastic. So, for the first one, what is one key strategy that you believe is essential for building a successful family enterprise?

Steve: For building the enterprise, If it’s a family enterprise, it’s it has to be involving the people in the family as early as possible in the awareness of the business, not necessarily to bring them in, but to make sure that they’re aware.

So it’s okay to come home from work and sit around the table with your kids and talk about Dad’s business. This is what we’re doing. And, no, you don’t have to come and work in the business, but I want you to know.

Maybe you’ll want to do some other business, and let’s learn about business. So, entrepreneurs who have a love for business and skills, I think transitioning to the children who are ready, willing, and able to learn about business, whether it’s that particular business or another business, I think you can never start too early with that.

So, if you want to have a successful family enterprise, transitioning that business mindset and business skill early on into the kids’ lives will pay dividends, whether it’s in that business or others.

Cory: I love that. Often, we talk about voice and vote, and really, what you’re saying here, Steve, is that the bare bones minimum is just awareness. Give them the opportunity, give them the knowledge of what’s there, and let them make their own decisions.

They don’t know the decisions that are being made or even if they’re involved in them if they don’t have the awareness. So that’s that’s awesome.

Now, what is the most common challenge that you see family enterprises encountering regarding wealth transition and generational continuity?

Steve: They don’t know how to start the conversations that they know they need to have, and so they delay them. There’s not a single person who, when you say you really should be talking to your family about this, says, really?

Why? I mean, they know. They know that these subjects should be discussed among their family members, and yet they delay them. They’re always too busy, but they’re also often scared, and there’s some uncertainty involved. They’re worried that the conversation might not go well, and they’re really not sure what path they want to take.

And so they figure, I can’t talk about it till I figured out exactly what I want to do. That’s exactly wrong. You should have the conversation to involve the people so that you can make an informed decision with some clarity and transparency of what’s involved so that the people who want to raise their hand say, yes.

I’d like to be part of that. Or, no. I don’t want to do that. Or, yes, but I don’t want to be a partner with my sister. Like, I have those conversations so that you can structure things in a way that responds to the need.

But those conversations don’t happen easily, and that’s why people like me, that’s how I’ve started to explain my role: I help people start these conversations and have them go well so that they can have these very important discussions.

If you just delay having the disc discussions, you’re just delaying the problem, and the longer you wait, the less good options you have.

Cory: Yes. I love that. It’s not the awareness of the conversations that need to be had. It’s the skill set and courage to have them.

Steve, in your experience, what are the top three qualities that successful family enterprise leaders possess?

Steve: Humility. The ones who do well are the ones who don’t act like they’re the smartest person in the room. Communication is not just knowing how to be open, transparent, and authentic.

I guess, learning how to let someone else have the space that they need to grow. Too often, leaders are so stuck in their roles that they’re not willing to give them up because they don’t know what will happen after they do.

So that ability to step aside and let a younger person come and fill your shoes and actually be glad if they do a better job than you as opposed to setting them up for failure so that you can walk around and say, well, I was the only one who could do it.

I mean, that’s that, but there are still people who have that attitude. Being able to be humble, communicate, and share, and then know how and when to start to step aside to let others come in and fill that role that you’re filling, knowing that you can then go off and get to another chapter of your life where all kinds of other wonderful things possibly await you if you have the courage to go and look for them.

But you have to have somewhere to go and if you’re stuck and you think you have nowhere to go, then the people behind will come and try and push you out, and that’s not a recipe for anything good.

Cory:  Absolutely. Again, some of that uncertainty may be the barrier there.

Steve: Well, the uncertainty and the fear that comes with the uncertainty. Having the confidence of knowing that it’s okay. I’ve faced uncertainty my whole life, and I’ve always managed to find a way through it in a positive way.

Sometimes they need coaching and they need and the family has to have the right attitude around that too. Because if you’re just they’re trying to push, if my son is pushing me, my first instinct is to push back.

Cory: Absolutely.

Steve: And so it’s helping families to learn how to do that dance together and helping one generation understand why the other generation is acting in this certain way so that we sort of have a little more understanding and forgiveness towards each other and hopefully can come together a little bit.

Cory: Absolutely. And that perspective is key. Now, Steve, before we conclude our discussion, I’d like to highlight where our listeners can engage in more conversations you’re having.

And, no, as far as somebody who’s having those conversations, you’ve mentioned some great thought leaders in the space. I know that you put out some incredible thought leadership.

Can you share with our guests where they can find you and some of the resources that you find useful?

Steve: Yeah, I’m easy to find. My name is Steve Legler. There’s only one vowel, an e, which repeats a few times. It’s easy to spell and say but not common, so anyone can always find me via Google. My LinkedIn is a great place to find my stuff.

Stevelegler.com is my website where my weekly blogs go up, plus other things, all kinds of other content that I’m involved in either as on this end of a podcast or on the other end of a podcast.

The organizations I’m involved in, Family Enterprise Canada and the Purposeful Planning Institute, are wonderful resources for like-minded people like me. The Family Firm Institute is another area where I have a wonderful international network.

I’m connected with lots of people, and my social capital is one of my strong suits, which I never realized I would have. If you’re looking for someone or whatever, hit me up, I love to connect people to other people.

Or if you have a family business situation, with your family, or with a client family, and you want to just chat a little bit to get a perspective, some ideas, and some areas you might want to explore, I’m happy to indulge.

And if you go to my website, there is a link. You can hit my Calendly and book a call with me and that happens to me a lot. More often than not, I’m happy to have these meetings.

Sometimes, they’re not perfect, but I’m willing to take the risk of jumping on a call with just about anybody. If somebody is listening to this and is inspired by anything I’ve said or wants to ask a question, hit me up.

Cory: Perfect. We’ll definitely include those links in the show notes, and as you say, they’re easy to find otherwise. Steve, I wanted to make sure that we’ve covered everything today.

Is there anything else that you’d like to share with our audience that we didn’t get a chance to cover?

Steve: Well, I could go on for hours and hours about all things related to this subject, but I think I’ve said plenty, and I’m glad that I was able to answer your questions coherently.

I’ve also received some questions that I’m not used to getting, which I appreciate, and they made me reflect. So I’m happy to have a chance to share with your audience. Thanks a lot, Cory.

Cory: Well, thank you, Steve. I appreciate you sharing your expertise and experiences with us today. I found it incredibly valuable, and I’m grateful for your contribution to our episode.

I know that our listeners will as well. As you mentioned, many things go unsaid. So many questions that I could have asked. Maybe we’ll do this again in the future.

Steve: Alright. Thanks, Cory.

As we wrap up this episode, we invite you to reflect on the invaluable insights Steve Legler has shared on the nuances of family enterprise dynamics and the importance of fostering open communication within business families.

Whether you are part of a family enterprise or provide consulting to family businesses, Steve emphasizes unconflicted advice, regular family meetings, and the value of external facilitation, offering a fresh approach to navigating the complexities of family wealth and business management.

Throughout our discussion, we reflected on the key aspects of managing family businesses. We talked about the need to balance business goals with family relationships, and how important it is to plan ahead and communicate openly. We also discussed the benefits of getting advice from impartial outsiders and having someone guide family discussions. Above all, we emphasized that keeping the family strong is just as important as growing the business. These insights offer a practical approach for families looking to preserve their legacy and tackle the unique challenges of running a family business over multiple generations.

For those seeking expert guidance on navigating the complexities of family enterprise and intergenerational wealth transitions, Steve Legler and the team at Blackwood Family Enterprise Services are ready to assist. You might also want to pick up your copies of his insightful books, “SHIFT your Family Business” and “Interdependent Wealth,” and we’ve included the information together with additional resources in the show notes to support you on your journey.

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 [email protected] or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.