Perfectionism Paralysis: Crafting Adaptive Governance for Family Business Longevity

In this episode, Leah Tolton shares insights on business governance and ownership transitions for family enterprises. We explore the importance of flexibility in shareholder agreements, setting clear expectations around participation to prevent disputes, formalizing information flow as more households get involved, and not letting perfect planning delay progress. Hear Leah’s perspective on navigating fair vs. equal dynamics, protecting assets in marriages, and bridging generational risk profiles.

How can transitioning from first- to third-generation ownership be smooth? Leah offers examples of family and ownership meetings to align on goals. We also discuss prenuptial agreements, estate freezes, and special shares to balance liquidity needs across generations invested in the business.

About Leah Tolton

Leah has practiced corporate law for 30 years, with extensive experience advising family-owned businesses, lending clients, and real estate clients on a broad range of matters, including business agreements, tax planning, equipment leasing, mergers and acquisitions, real estate joint ventures, business structuring, and reorganizations. Her practice emphasizes serving ultra-high-net-worth families and their companies across critical areas such as corporate governance, succession planning, reorganizations, strategic planning, risk management, and navigating mergers, acquisitions, and sales transactions.

Additionally, Leah negotiates and drafts commercial contracts, advises on private financing and syndicated lending arrangements, earned the Family Enterprise Advisor designation in 2023, and sits on the Board of Advisors of the Alberta Business Family Institute. This wide-ranging expertise and dedication to serving family enterprises equips Leah to provide tailored legal advice and counsel to family businesses seeking to establish continuity across generations.

Resources discussed in this episode:

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

Contact Leah Tolton | Partner at Bennett Jones: 

Email: [email protected]

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 Leah Tolton, an accomplished corporate lawyer with nearly 30 years of experience, focusing on business structures, tax planning, mergers and acquisitions, partnerships, and other co-ownership structures. In her practice, she emphasizes providing tailored legal services for family-owned businesses, their owners, and boards of directors. Leah holds the Family Enterprise Advisor designation and has been appointed to the Board of Advisors of the Alberta Business Family Institute.

My goal is to be the most curious person in today’s conversation with Leah Tolton, where we explore the foundations to good business governance and how to get started with a shareholder agreement that can adapt as the enterprise grows. Leah shares the barriers families have that result in resistance to doing this work with their legal team. She emphasizes doing the best with the facts you have today and making sure intentions are as clear as possible and there is flexibility built into agreements, so people can adapt.

Now, let’s dive in!

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

Leah: Great. Thanks for having me, Cory.

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

Leah: Well, I think I’d give the graduates a lot of the advice I give to my family enterprise clients. I’d say there’s more than one way to achieve success I would say that there is more than one pathway that you can take through your career. You may think you’re heading off in one direction, but an opportunity presents itself and suddenly you find yourself going in another direction. Things change. Facts in your life can change and you need to adapt to that.

But I think I would say that you need to expect that there’ll be bins on the road. You’ll need to adapt to what you encounter at those bins on the road you’ll need to be prepared to accept change and uncertainty really is a constant.

Cory: I love that. Uncertainty is a constant. And Leah relates it to your field of work as a corporate lawyer and some of us don’t like that uncertainty. As a human, it’s something that makes us feel a little uneasy. How do you in the work that you do, bring some certainty to the very uncertain world that we live in?

Leah: Well, my job as a corporate lawyer is to try to get people to be as clear as they can be in expressing what it is that they want to accomplish in whatever business transaction they’re engaged in. The business transaction could be of short duration, or it could be something that is going to create a relationship that will last for decades. That is why I encourage my clients and the people I deal with.

That includes people who are negotiating with my clients to be as clear as possible about what they’re trying to accomplish in whatever transaction they’re undertaking. And people come to a lawyer and they expect a lawyer to have the answer.

They expect that there are some precise results or decisions that they can make or advice that they can get that will make everything clear, and there will be no dispute. That doesn’t happen. we deal with real people. We deal with real situations, facts change, and circumstances change.

People the business encounters have been on the road. Suddenly, things don’t look like we expected them to.

And in terms of getting people to be comfortable with the level of anxiety, I say you do the best you can with what you understand will be the fact you confront when you look at it right here right now, but we need to build enough flexibility into the agreement so that people can adapt as they need to.

Things can change if they have to. We can come back and renegotiate or amend if we have to. In my world, people think things are going to be perfect.

They come to me for the perfect answer, but really perfection can be the enemy of the good. What I encourage people to think of is doing the best they can with the facts that they have, making their intentions as clear as possible.

There’s ever something that arises in the future where we have to look at that, we know what we intended at the beginning, and then we work from there.

Cory: That’s great then. Let’s go back to the comment that perfection can be the enemy of the good because I see that often with clients where it might show up and appear on the surface as procrastination. That seems daunting, how would we even accomplish that?

And it’s just too much of a hassle. Let’s not go there. In your world, Leah, what does that look like? Or what would be the situations where you see people maybe not coming to you because they’re feeling that way?

Leah: I work with a lot of family-owned businesses. The kind of things that get tangled in people’s thinking before they come to see someone like me are things like the idea that they have to have, a plan for their business and their estate all thought out in perfect detail before they ever talk to a lawyer, whether it’s a corporate lawyer or a state lawyer.

They have the idea that if they don’t have these thoughts in perfect order or in perfect clarity that’s not worth wasting the time and quite frankly spending the money. They wait until they think they’re ready and it becomes bigger as time goes on. The business becomes more valuable. It becomes more complicated to run.

There are more things that are involved in running it such as perhaps some real estate or maybe there’s operations in more than one country. There’s maybe a complicated employee structure that now didn’t exist before. Maybe it was simpler and now it’s bigger, so they need more people. A lot more families are dependent on it now.

Meanwhile, perhaps some of the kids are working in the business and some of them aren’t. And now, if the people who own the business or the parents, they’re struggling with the idea about how do we divide this up now when this business isn’t liquid and someone has contributed in working in the business or as an owner of the business to the value of the business. Is it fair that that person gets an equal share, or should we find another way to do that?

And suddenly it becomes really big and really complicated, and paralysis sets in. At that point, that’s where I say that perfection becomes the enemy of the good. We’re never going to get this probably perfect. We can probably start. We can pick a thing that is probably the burning issue or something that’s perceived to be the biggest priority and deal with that.

We’ll figure out how that connects to other pea other pieces of it. And then we’ll work on the pieces that connect to it and build it out gradually. But if we wait until we’ve got the perfect plan, we’ll never get going.

Cory: Let’s go back to the pieces for a second, Leah, what are the pieces that connect? Because you mentioned business and you mentioned the state and people typically think of okay. I need a will, it’s about transition.

I need a will, but they don’t think of all the other aspects or there’s, as you said, there’s expanding into another country or employee, issues and things become big on that side of things and they think about the world in silos. How do you approach it by connecting those pieces?

Leah: To give some thought about the pieces that might be important. When you have an organization that’s that complicated and that many things going on. You’ll often see that, a family or a family business consults, for example, with its accounting or its tax advisor, and there will be some kind of plan that’s put into place that sets out where parts of the business should be operated or some of the assets that the business or the family-owned should be put to preserve the tax.

That’s one piece. You’ve already mentioned another piece, which is the piece that most people think about, which is how we transition our wealth and our property after we die. We go through this process of planning for our estate that’s called. And what pieces do we need to put that into place?

Usually, we think about a will. That’s what happens, that’s the document that governs what happens to your property when you die. Also, we would think about it in lawyer terms. We would think about pieces that include how you manage your property and your personal decisions before you die, by way of an enduring power of attorney or a personal directive. Rather than during power of attorney, appoint someone to make financial decisions for you, a personal directive, appoint someone to make personal decisions for you before you die.

Those are pieces most people are familiar with. A piece that I work with a lot that can be really effective in dealing with this paralysis and this concern about perfection being the enemy of the good is a shareholder agreement.

As a corporate lawyer, I advise companies and their owners, how about all kinds of governance matters and about all kinds of transition matters. And a shareholder agreement is a tool, a piece that can be added to that combination that creates the bridge between the plan, that puts assets in a certain place. And what happens to those assets until you need your will when you die? Those are the pieces that I think are the predominant pieces.

Other things may be added in certain circumstances, but those are the big ones that I would describe.

Cory: Okay. And I want to circle back to your comment of fair versus equal. And how do you deal with that as the world becomes more complicated and the business or the estates of the family becomes, bigger and harder to understand of how that contribution from one family member is different from another and how parents are thinking of that?

Leah: Well, my job as a corporate lawyer is to try to get people to be as clear as they can be in expressing what it is that they want to accomplish in whatever business transaction they’re engaged in. The business transaction could be of short duration, or it could be something that is going to create a relationship that will last for decades.

I encourage my clients and the people I deal with and that includes people who are negotiating with my clients to be as clear as possible about what they’re trying to accomplish in whatever transaction they’re undertaking. And so, people come to a lawyer and they expect a lawyer to have the answer.

They expect that there are some precise results or decisions that they can make or advice that they can get that will make everything clear, and there will be no dispute. That doesn’t happen. we deal with real people. We deal with real situations, facts change, and circumstances change.

People in business encounters have been on the road. Suddenly, things don’t look like we expected them to.

And so, in terms of getting people to be comfortable with the level of anxiety, I say you do the best you can with what you understand will be the fact you confront when you look at it right here right now. Still, we need to build enough flexibility into the agreement so that people can adapt as they need to.

Things can change if they have to. We can come back and renegotiate or amend if we have to so in my world, people think going to be perfect. They come to me for the perfect answer, but really perfection can be the enemy of the good. What I encourage people to think of is doing the best they can with the facts that they have, making their intentions as clear as possible.

There’s ever something that arises in the future where we have to look at that, we know what we intended at the beginning, and then we work from there.

Cory: Right. And Leah, is it typical when somebody walks into to law office and thinks they’re talking to a corporate lawyer that they start talking about the voice versus vote and what happens with the family cottage and heirloom assets is that typical or is that something that your way that you approach your practice is different from a family enterprise perspective.

Leah: I think it probably is unusual in the experience that most people would have with a corporate lawyer. I think it’s fair to say that most professionals, not just corporate lawyers, that people operate in their area of expertise.

And they’re highly trained in that area, and they are accustomed to dealing with the concerns that they usually see there. Over the course of time, having seen a number of these kinds of situations evolve, it’s the addition of those things I listed over and above that make the pile even bigger and make it harder to start because it’s become more complicated.

And if you can pull off some of those things, that can make it easier. I do have a designation. I think Cory as a family enterprise advisor, has also broadened my thinking over and above my corporate legal knowledge to come at these questions, in a different way than I think most people would experience in their relationship with a corporate lawyer.

Cory: Right. Now Leah, going back, you mentioned the fact that things change. And I’m thinking about the fact that in a family enterprise, specifically, when we’re thinking about a corporation, their corporations can last beyond a generation beyond many generations from inception to the current day could be many owners have come and gone. And some of the things that are set up along the way might be fitting for that time, but not for others.

I wanted to go back and just ask about how you approach things from, let’s say, a 1st generation ownership to how it could be different from a 3rd to 4th generation transition and how getting those players to agree or see the vision and understand how to adapt as things change. How do you approach that?

Leah: Well, that’s a big question. okay. I’m going to break that down, and I’m going to start with what it would look like to transition from 1st generation to the next one because I think it becomes more complicated in many ways you transition from generation to beyond. Let’s start with the first one. What has to happen?

When you’re talking about the 1st generation, they’re used to, making decisions without probably extensive consultation. There might be some key management people or key employees or people like that who would have some input.

Probably spouses in a combination there. We’re probably talking about a handful of people and maybe fewer who have input into what direction are we taking this. How are we going to finance this? Where are we going to put this?

How much money are we going to make? Do we need to change the pricing? Right? All that kind of stuff can be done with a pretty tight group of people. Let’s say those spouses have 2 kids and let’s say both of those kids are involved in the business just to keep this as simple as possible.

The kids watch that whole process evolve, and they’re they both have a role to play in the business, and they’ve grown up in it. They’ve fulfilled several roles. Maybe they’ve even gone outside the family business. Did they work somewhere else?

They accumulated some skills there or some observation and some knowledge there. Maybe they’ve gone off and got some formal education. Now it’s time for generations 1, and 2, to transition out of the business. So now we move from a situation where we have a tight group of people who make decisions to now two people, let’s say, and let’s add in a couple of spouses there and maybe a couple of family units there.

So now we have not just one little handful of people. We’ve got 2 hands full of people who are now whether they’re directly involved in the business or not, they’re may they are affected by what goes on there. It’s also harder for those people once you have more than one to be aware of what the other one is doing and what decisions they might be making that are affecting the whole operation or the other one.

Maybe somebody already did it or maybe someone forgot. Who knows?

Communication becomes more challenging once you have more people involved in the mix. The way we need to deal with that is to deal with how information is obtained by each of the new parties, however many there are, how it is exchanged, and who gets it on cadence so that everyone is kept in the loop about things that are important and how the new groups make decisions about matters relating to the family, the ownership, and the business based on that information.

So there needs to be more intention applied. There needs to be more formality to it.

Usually, at this time, you start seeing formal meetings, perhaps family meetings, perhaps ownership meetings, and management meetings that deal specifically with items that arise and apply to the group and the family who may or may not be the same group who are owners, who may or may not be the same group who are running the business.

Now let’s transition that to multi-generations as per your original question. You’ll know we’re at this to the 3rd, and 5th, however many powers, depending on how many family units we have and how many people may be involved in receiving information.

The further along that that organization progresses, the more likely it is that there will be people who may be owners and not even involved in the business on a day-to-day basis. And so now, and maybe not even all of the people who are in the next generation have anything to do with the but are entitled to receive reporting.

So back to intentionality about sharing information, about making it clear, on what cadence that information will be shared if there are decisions to be made, what decisions, those extended participants will have input into, and how that’s going to happen. It becomes more complicated as time goes on and more people are added.

Cory: That was a big question. And I have a few things on that. Leah, when you talk about sharing information and how decisions are made, I think of decision-making as a collective group and governance on boards and boards of directors and you have formal processes in place. Is that what you’re talking about as it gets bigger is that we’re putting those processes in place, or can you have a little, I guess, less formal than you’ve now got a board because you have more than one household’s a part of it?

Or another way is do you always have a board and, it’s now just as you have more than 1 or 2 people, you need to formalize that.

Leah: I’ll answer the question in a strictly legalistic way first, and then we’ll add the layers. The strict legalistic answer to your question, but whether a company or a corporation always has a board is in law, it always does.

Someone is always appointed age director. There must be at least one person on the board. There may be more than that, but there’s at least one on the legal board. And that’s a requirement of the law. Now the layers that I’m talking about here, you heard from my description that some of those layers relate to things that go on in the family. How the spouses be affected how this will impact the kids and are they expected to participate in the business?

And if so, on what terms and how does this affect the family trip how does money come out to the family, etc? That’s family stuff, and there might be a meeting or some formal forum for discussion of those matters in the family. That’s different from the board.

There could be some process that the family employs to talk about those things. That process that the family uses to talk about those things can also talk about what direction they might like to see the business take for the reasons we’ve described. I’d like to be able to have these opportunities, I’d like to generate this income.

I would like this, to be a legacy for my kids to participate, etc. Those kids are all in the family world. Now the family, presumably for our example, will also have at least some members as owners. They’re the ones who own the business or own the assets that are used to make the money in the business. That’s where the owners would also have some kind of structure that would say, okay. And now we’re going to tell the business we would like it to go in this direction. We’re comfortable with this level of risk. Perhaps we’re okay with this much borrowing. Otherwise, they need to come back to us and ask permission for that.

We want to make sure that the underlying value of our shares is pre-preserved, so we don’t want to buy any of this or sell any of that, those are owner decisions. There would maybe after there or a process where those owners get together to talk about those things. Then those owners would appoint perhaps more members to that board of directors who would be the actual overseers of the business to whom the management would report.

There will always be one director, but depending on what that whole process looks like and all those layers I’ve described, You could end up actually with the board that’s got more formality, or maybe you only have her have the one who takes direction from the group as a result of that process.

Cory: Great. Now, Leah, you’ve got a couple of times mentioned spouses in your in your answers. And I want to go back to that because some families want to protect that legacy and what they’ve created from it going off in other directions. So be it, the breakdown of marriage is a common way attributed in a way that we didn’t intend. As a corporate lawyer, how can you assist families that are different from what family lawyers can do?

Leah: Well back to my comments about trying to make things as clear in intent at the outset as possible. I think as a corporate lawyer, one of the things that is a tool available to me is to attempt to get clarity usually from that 1st generation, but not necessarily about how they would like to see, usually ownership, but can also be participation in the business unfold.  And if they can be clear about that with their kids, discussions get a lot easier with the spouses.

Back to the point, I also made in respect of how these agreements are actually quite flexible and can include whatever terms you want. If the family decides that they agree that spouses should never be owners of shares or that spouses will not be employed in the business or they will only be entitled to receive distributions into their households of dividends or whatever, then the agreement can say that. It can preserve relationships if there’s clarity that that is the expectation at the outset.

A corporate shareholder agreement can certainly say that ownership will be limited to blood members of the family only that, spouses are not going to participate as employees, etcetera. And if that’s all been communicated, then that’s fine. Where the problem comes into your point about marriage breakdown and things like that is when people avoid that kind of clarity. There is no doubt it is not a very romantic conversation, to have.

When a decision has been made and a partner has been introduced but it is kinder to be clear about that and to reduce the likelihood that there’s a dispute about that because of lack of clarity or because no one said anything, it can actually be in the best interest of the company and of the family to be that clear.

The time I would submit to do that is when the family is discussing what they want their governance agreements to say and not to wait until a new partner has been presented.

So, going back to my comment that families have meetings about things that matter to the family.

If a family has been communicating about those kinds of concepts and has reached an agreement on how they would like those concepts to play out in their family, then no one is offended. This is just the way the family has governed the business and governs its assets, and you’re marrying into the family.

Welcome. Right? It’s not to exclude you. It’s not personal. It’s not about you at all. It’s just what we’ve all agreed are the rules of engagement, and we’re happy to have you.

Cory: Right. That’s the sort of thing where you can plan and you don’t need to adapt to that if you’ve planned appropriately and had some of that vision up front.

Leah: That’s the best way to do it. Now if people don’t do that and a lot of people don’t. If people all did that then I wouldn’t have a job. Right? I’ve already mentioned shareholder agreements that can contain some of those terms.

Other tools are part of the pieces, I guess, that I know, we talked about earlier that might also be useful in that context. Sometimes those plans put together the legal structures that hold assets and then operate the business. Sometimes you’ll see in that plan a concept called a family trust.

Sometimes that family trust will hold some of the assets or some of the investments or things like that. It’s a separate legal entity from the company that runs the business or whoever is the owner of the real estate. The trust then may hold some of the value that the family has accumulated. There would be people appointed to make decisions about it called trustees and they would hold that property for the benefit of people who are called beneficiaries.

Depending on what that trust says about what those trustees can do with that property, that property may never come into a matrimonial dispute because the property never became the property of a person who might have been named as a possible beneficiary. So that can be a tool that we can use if families have not had that ideal discussion. That’s not a perfect tool.

I think certainly some matrimonial lawyers who came to the game late might look at that and suggest perhaps they would attack that. Another tool we can use is things like pre or postnuptial agreements where a spouse is now on the scene or a new proposed spouse is on the scene and that person agrees with their engaged partner that they will not claim any part of the family assets whatever are the assets that the family wishes to preserve and so there are ways to do it at various stages.

The best is to be clear and communicate in advance. There are legal agreements and processes we can put in place to build it up if that conversation has not been had or those agreements have not been reached and those are the kinds of things we can attempt to do to protect.

The family assets and those kinds of situations.

Cory: We’re changing gears a little bit towards the passing of shares from one generation to another. And let’s say that we’re not talking specifically about the state’s situation. But let’s talk about what’s coming to the point where the succession of management has happened.

We’ve got the next generation running the business, and we’re looking at changing ownership and maybe the tax people have done some amazing work. And you look at it and say, okay, there’s some holes here that we need to protect things.

And one of the comments that you made about the ownership discussions of how much money you can borrow or you can’t sell that asset and it makes me think that the next generation might have a different risk profile.

They might say I’m looking at this for the long term. And Mom and Dad are saying what? I want to go spend time where it’s warmer, and I want to make sure I have the income that I need from the business, how do you approach that, Leah?

Leah: Well, this is a really good question because this happens all the time. To refer to my earlier comments about a plan that a tax advisor may have put into place very often, you will see that those kinds of plans include certain kinds of shares that would be you to our generation 1 who built up the business to this point. Very commonly, a different kind of shares would be given to generation 2 who are going to take over and run from this point and grow it even bigger. The shares issued to Generation 1 have a set value.

They represent the value that the business has grown to under Generation 1’s watch. In many ways, that generation is in the place of the bank. Right? They’re waiting to get paid. They’ve got value in there.

They’ve got a pretty big interest in what happens with that company or that corporation going forward.  As you say, meanwhile, generation 2 is ready to go. There’s some trust there that generation 1 is ready to pass it on and is convinced that generation 2 is going to take it in the right direction, but there still needs to be some balance between generation 2’s ability to grow the business and the assurance generation 1 wants that it’s going to get its value out.

Some crazy decisions aren’t going to be made that are going to prevent them from getting paid. In my agreements, what I often say to people is that they govern 1 of 2 things. One of which is how shareholders govern their relationship together while they’re in ownership as a group. And that can include things like who’s on that board you asked about.

If mom and dad have not been paid, maybe mom and dad want to have a member on that board. They have a pretty regular finger on the pulse of what’s going on. It can include a list for example of decisions that have to be unanimous, whether mom and dad actually are on the board or not. mom and dad are waiting for money. They still get to weigh in on some things that would maybe impact how fast they can get paid or whether there’s even a chance they might not get paid.

Things that would make a big difference to the asset pool or to the money-generating ability things like borrowing a bunch of money as you’ve mentioned. Things like selling a bunch of assets as you’ve mentioned, things like you’re going off in a different business endeavor. Maybe mom and dad need to approve that.

Because if it’s going to change the likelihood mom and dad are going to get paid, that might be the kind of thing they want to weigh in on until they’re paid. Or maybe they want to weigh in until they’ve received a certain amount of money. After that, they’re comfortable with the risk and all kinds of ways you can make that work.

There may also be a list of decisions that mom and dad don’t need to be consulted on. Maybe the kids get to go off and they get to engage whatever professionals they want. Maybe they get to maybe they set their strategic plan.

Maybe they set business plans. Maybe they arrange their own banking relationships. Maybe mom and dad do not really need to be involved in that every day and mom and dad are comfortable with that. And maybe the kids go off and they do it on their own. There’s always a balance there. Those are the kinds of things I ask people about and say, okay.

If you’re the bank, how much control of this do you want to have for how long? If you’re the one who runs the business, how much flexibility and freedom do you need to accomplish what you want to do over the long term?

Those are the kinds of conversations that I would address with people to build into place that tool, that agreement among them about how they’re going to govern themselves and their relationship as owners.

Cory: Right. And that also underpins the importance of you asking about those other assets because if mom and dad have sufficient assets for their lifestyle maybe those decisions and the amount of control that they require to feel like they have the income and assets to provide for their future isn’t the same as those who maybe have the majority of their wealth tied in into the business at that point.

Leah That’s an excellent point. I’ve referred to regularly receiving input from tax advisors and working with the state planning lawyers, for example, but it’s also often the case that I also engage with the people who manage the investment for the family for exactly that reason so that everyone has an idea about what the big picture is, what the whole pool of assets is.

And while it’s big and messy, to start with. You and everyone will have their part to contribute to figuring out how to make a plan here. It’s really important to have that big picture from advisors like you, for example, who would have visibility into components that I would not necessarily see as a corporate lawyer.

Cory: Right. Yes. Leah, as we transition here and get closer to the end of our conversation, there are a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Leah: For sure.

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

Leah: I think the family enterprises that I have seen the most successful have been based on really deliberate and calculated decision-making, gathering good facts, making the best decision that people had based on the information they had at the time, and people being ready to diversify or pivot.

Those are the successful ones. The people who don’t have their eggs in one basket. They’re they keep their eye open. They realize they might have to make a decision or a change of direction or they need to broaden their appeal and they do that. They’re the ones who I have seen be more successful from a strategic perspective.

Cory: Love it. That’s great. What would you say is the most common challenge that you see in family enterprises when it comes to the transition of wealth and generational continuity?

Leah: The most common challenge most common challenge, I think, is that because people don’t tend to think naturally in terms of sharing information. They’re just used to doing their thing.

Maybe making decisions based on information that they have and doing it the same way they always have. People who are involved in family enterprises that get larger and involve more people, tend to fall victim to the scenario where not everyone has all the information. And when they don’t, they do what people do. They fill in the blanks. They jump to conclusions.

Sometimes they assume the worst. Do they attribute bad motives? Things can get pretty unpleasant pretty quickly because people fill in those gaps for themselves. I find that it’s more effective if people do meet regularly or they have some kind of agreed schedule that they get together and they sit down, they say, okay.

Let’s reset. Where are we at today? Doesn’t have to be complicated. Doesn’t have to be a formal detailed agenda, but they agree that they will meet, let’s say, twice a year and reset. That is an effective strategy to prevent that.

Cory: Awesome. That’s great! In your experience, what would you say are the top 3 qualities that successful family enterprise leaders possess?

Leah: Flexibility, adaptability, and, a level of comfort with uncertainty.

Cory: Perfect. That ties it in very nicely with the way that we started our conversation. Leah as we conclude our discussion today, I’d like to highlight where our listeners can engage in more conversations that you’re having. Can you kindly provide us with where our guests can find you?

Leah: Sure. I would be happy to share my own podcast actually, that’s called Beyond Succession that you can link to either through my firm’s website, through Bennett Jones or you can find it on Apple or Spotify.

There are a series of episodes that we have produced that deal with these transitions and I have talked with several professionals, from tax and estate planning advisors, but also some leadership transition advisors and people who assist with other components of management of the family enterprise and those kinds of topics are all very relevant to what I do.

They have been featured on my podcast and if folks want to hear more, they can find more there.

Cory: Perfect and we’ll be sure to link to your podcast in our show notes I can say that you’ve done an amazing job. I enjoyed all of the episodes that I’ve listened to so far.

Leah: Thank you. I can say the same with yours.

Cory: Well, I appreciate that. I do. Now I want to make sure that we’ve covered everything that you wanted to make sure or you wanted to share with our audience. Is there anything that we didn’t get a chance to touch on in our short time together?

Leah: I don’t think so. I think we’ve covered a lot of ground here. We’ve asked some big questions.  We’ve tried to deal with some big issues, and I think there’s a lot here to chew on. I think we can leave it there for now.

Cory: Sounds great. Well, thank you Leah for taking the time to share your expertise and experiences with us today. Your insights have been extremely valuable and I’m grateful. I know our audience will be grateful for your contribution to this episode.

Leah: Looks great. Well, thank you very much again for having me, Cory. It’s been a pleasure to speak with you today.

Cory: Thank you. Well, that’s a very common thing that parents have to think about.

As we wrap up this episode, we invite you to reflect on the insights Leah has shared from her extensive experience as a corporate lawyer advising family enterprises.

Whether you are part of a family business or provide advisory services, Leah’s expertise sheds light on effectively navigating ownership transitions across generations.

Throughout our discussion, Leah provided some valuable takeaways. Recognizing that change is inevitable, so build flexibility into shareholder agreements to adapt as needed. Clearly set expectations upfront around family member participation to mitigate disputes. Formalize information sharing and decision-making as more households become involved in ownership. And don’t let the perfect plan be the enemy of a good start – begin with priority issues and fill gaps over time.

For those seeking additional guidance on the themes covered today, Leah and her team at Bennett Jones have decades of experience assisting with complex corporate restructurings, growth strategies, and ownership transitions and if you have specific questions, please feel free to reach out to Leah directly. As mentioned, her very own podcast “Beyond Succession”, is accessible through your favorite podcast platform and we’ve put links to this and Leah’s contact information in the show notes.

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

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