The Next Chair: Governing Tomorrow, Next Generation Leadership in Family Enterprises

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at CI Assante Wealth Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. On this show, we explore global ideas, concepts, and models that help family enterprises navigate the complexities of family wealth.

Today’s episode is a special one. For the first time on Legacy Builders, we’re bringing together multiple guests in a panel-style conversation to explore a topic from different professional perspectives.

After more than 70 episodes and conversations with family enterprise leaders, advisors, and researchers from around the world, one thing has become increasingly clear: the most important decisions facing families are rarely solved through a single lens. They require thoughtful dialogue across disciplines, experiences, and generations.

Joining me today are two voices that will already be familiar to many of our listeners.

Barb Schimnowsky, Partner at Watson and leader of their board director and executive search practice, and James Grieve, Principal at Catalyst Strategies Consulting and co-creator of Succession Ready, have both joined us previously on Legacy Builders to share their expertise. Today, we’re bringing them together to explore one of the most important challenges facing family enterprises: preparing the next generation of leadership.

Through the combined lenses of governance, executive search, strategy, and succession planning, we discuss why leadership transitions often become urgent before families are ready, how governance creates clarity during periods of change, what readiness really looks like in the rising generation, and why preparing both future leaders and current leaders is essential to long-term success.

Whether you’re a founder, a member of the rising generation, a board member, or an advisor serving enterprising families, this conversation offers a unique opportunity to hear how different disciplines approach the same challenge and where those perspectives align.

Now let’s dive in!

Cory: Welcome, everyone, and thank you for joining us today for Legacy Builders Live, Governing Tomorrow, Next Generation Leadership in Family Enterprises. My name is Cory Gagnon, and I’m a senior wealth advisor at Beacon Family Office. I work with successful families, navigating complex transitions of wealth, business, and leadership, helping them align vision, values, and legacy. I’m excited to have you here for our inaugural live conversation.

Legacy Builders Live is produced by Beacon Family Office at Assante Financial Management Limited, where we help successful families design integrated strategies for their wealth, business, and legacy. Through values first, planning, and intentional stewardship, we support enterprising families in creating successful successors and securing multigenerational peace of mind. This webcast is an extension of that mission. It brings together forward thinking leaders and trusted frameworks to equip families and their advisors with the clarity and confidence to lead with purpose today and generations to come.

If you have questions during today’s session, please feel free to drop them in the Q and A box. If time allows, we’ll do our best to answer some of those live at the end of our session. And if we don’t get to your question during the webcast, we’ll make sure to follow-up with you afterwards. We’ll also be sharing the panelists’ contact information after the session if you’d like to reach out to us directly for a follow-up conversation.

Before we begin, a quick note. The content shared during this webcast is intended for informational purposes only, and does not constitute professional advice of any kind. The views and opinions expressed by our panelists are their own, and do not necessarily reflect the views or positions of the organizations that they’re affiliated with. We encourage viewers to consult with qualified professionals regarding their own specific circumstances.

Now to introduce our panelists for our conversation. Barb Schwonofsky is a partner at Watson and leader of their board director and executive search practice. With over twenty five years of experience in executive search and human resources, she holds both the certified management consultant and family enterprise advisor designations. Barb is known for her ability to deeply understand client needs and match them with exceptional leadership talent. She has hundreds of successful placements across sectors, and is a two time honoree of the top 100 most influential people in Abbotsford. Welcome, Barb.

Barb: Thanks!

Cory: James Grieve is principal at Catalyst Strategies Consulting, and co-creator of Succession Ready, a practical approach to succession planning for founder-led businesses. He holds the Certified Management Consultant, Family Enterprise Advisor, and Certified Exit Planning Advisor designations. A former president of CMCBC, James helps organizations uncover blind spots, mitigate risk, and build long-term value, especially in family enterprises and indigenous-owned businesses. His approach blends strategy, customer service, and systems thinking for sustainable impact. As you can see, we’re in great hands today.

The insights shared by Barb and James come from years of working directly with families and boards, navigating real challenges of leadership transition. We’ll be exploring five core questions during today’s conversation, each one focused on a key piece of the succession puzzle. These will appear on screen as we go, and I’ll also be contributing some of my own perspective as a moderator and fellow panelist.

Now let’s jump into our first question. What does strong governance look like in a family enterprise preparing for leadership transition? In our work, we’ve seen that governance often starts as reactive, but most successful families treat it as a leadership system. It’s about future proofing, not control. Now, Barb, in your experience working with boards and directors, what are the key governance structures or conversations that support a smooth and thoughtful leadership transition?

Barb: That’s a great question, Cory. And I would say it’s an area of work that we’ve been doing quite a bit of lately just with the transition of owner, founder, into a chair role as they’re sort of evolving their business. The real value of having good governance in place is it really lays out the distinct roles of the owner, the board, management, so there’s no confusion. We like to develop an authority, decision making matrix, to help support that clarity. And having the right governance in place really provides the intentional planning structures that ensure things like CEO evaluation and succession planning are staying top of mind. And the good governance also should empower the rising generation, and certainly encourage their voice, so it’s a great mechanism for open dialogue across all generations.

Cory: Awesome! And, James, how do you see governance evolve in the work that you do with families preparing for succession? What elements are most critical for alignment between those generations?

James: Really good question, and Barb had some great thoughts, and I’ll build on them here. So what we’re seeing is governance evolving from being family enterprises and family businesses, or founder-led businesses for that fact, begin with informal decision making. But as the complexity grows and the internal structures are needed, the business are needed, and with intention to guide, the business transitions forward. And what we’re seeing is four key points there, that are evolving here, is alignment.

So good governance frameworks, in my opinion, should create alignment between generations, not just compliance. So in other words, not just who the people are with their birth order. And this includes a shared vision, agreed upon decision-making rights, and strategy and mechanisms for constructive dialogue. So in other words, a baseline to have that going forward.

Secondly is formal roles and accountability. So clarifying the decision making authority through a strategic process, expectations, boundaries in that as well, and then defined roles on the board, a family council or perhaps a leadership team.

Third is that I think that governance should reflect both ownership and operational needs as well. So shareholder agreements, family charters and then advisory boards, independent directors should all be integrated in where the strategy is in the business. You’ll notice that the underpinning of what we do is a lot of strategy-based stuff that then implements.

Fourth and final is that creating the space for difficult conversations. So I believe that good governance and a good structure facilitates open and structuring emotionally safe conversations about legacy, leadership, and the future, especially when decisions are complex or emotionally charged.

Cory: Amazing! And, Barb, you made some comments of new roles within the organization. The founder going from that CEO to chairman, I think, is what you talked about. And, James, you also made some comments of some additional structures and roles. Barb, can you touch a little bit more on some of some of those transitions where the family and the business need to think about not only what they’ve had in the past that’s worked, but maybe what they need in the future?

Barb: That’s a great question, Cory. So, like James says, when a family business first starts out, there’s a board of one. It’s the founder. And then it might evolve where the management team is part of it, or then it might evolve again where they bring in some external advisors, but quite often that’s their lawyer and accountant.

When an owner is truly transitioning out and thinking about the next step of their business, I think it’s important to really look and see where is the business going, where are the gaps, and be very intentional about the skills that you’re going to bring onto the board either in sort of an advisory or a fiduciary role. So moving from the owner founder into serving on the board is a transition. And it’s not just a matter of saying, now we’re going to have a board. You actually have to have some governance policies and a good framework in place to create that sort of rigor, and what board meetings will look like in terms of agenda, minutes, that sort of thing.

Also, it’s really important that the management team is brought along, because now they’re perhaps going to have to report a little bit differently. Reporting on a business to the operator versus reporting on the business to a board can be a little bit different. And so helping them to understand what the board needs and, and evolving that reporting so that when decisions come to the board, things are laid out in a way that they can make good decisions.

Cory: And, James, you made comment of strategy, and sometimes strategy can look like it’s complicated. How can we make sure that we have the right governance as Barb just mentioned, and strategize something that’s right fit for the organization and the people?

James: Really good question. I think the approach that we take and I find is most impactful is when we have a very collaborative approach to the strategy of business, so it’s not this daunting task. But as consultants and trusted advisers, we hold the pen, and our clients tell the story. So they and we take into account other key collaborators that work with these people, so the accountants, the lawyers, everything at the front end, and right size the strategy of the business for where they came from, where they are now, and where they’re going. If you take that all into consideration, where they’re going looks a lot different than as to Barb’s point. It was a board of one as to where it’s going now, and to ensure that that governance reflects actually what the priorities are for the business, and what they’re actually capable of moving forward to going forward. So I think that you can over-govern or under-govern, but the key is to find the right sweet spot there that aligns with the strategic objectives of the company.

And just the last point on strategy, it doesn’t have to be this completely innovative strategy. It could just be getting things down on paper and having alignment and clarity amongst the people who are within that family or that business.

Cory: Fantastic! And I love that point because I often see governance become that bridge between strategy and relationships. And when families start to formalize some of this, it can allow those conversations that haven’t been had to open up and be unburied. So, great points on that.

Now moving on to our second question, how can families assess if the next generation is truly ready to lead? And, James, you made a bit of a comment about this. But what I find is readiness really isn’t about age, it’s about mindset. And mindset, not only by the leading generation, but also the rising generation, ensuring that they have the capabilities and the context around what that readiness really looks like. And, James, you’ve built a full framework around this at Succession Ready. Can you walk us through how you assess leadership readiness in the rising generation?

James: Absolutely! Thanks, Cory. And you mentioned Succession Ready in it. I would be remiss if I didn’t mention the co-creator of that as well as Ashka Work. She’s a great colleague of mine, fellow CMC, and we co-created this very purposeful and intentionally in a tightly scoped way that meets owners where they’re at and kind of just fuels the getting them ready for succession.

So to your question there, what we do is use a really structured approach, based on four key areas, when we’re looking to the next generation.

So first of all, we look at the competency of the people who are looking to move forward. So a lot of times, people believe that they can evolve into roles, but we have to really look at what they’re competent and able to do. So the technical skills in order to make that happen.

Secondly is the character. And this draws the values of the organization as well, but also the emotional intelligence of the people that are going to lead coming forward. Again, as we mentioned earlier, and Barb made great points, as the business becomes more sophisticated, and it’s not just aligned by birthright or birth order, you look at the character of the people. So the resilience, how well it aligns with values and then their capacity.

What bandwidth do they have to take the business to the next level or sustain it the way it is running right now, and their awareness to handle complexity. We’re in the year 2025 right now, technology is evolving, new systems are evolving, how we work with people, that type of thing. So the new generation or the new leader has to be able to handle that type of complexity.

And finally is the commitment, the commitment to have a genuine interest in the business and accountability toward the family enterprise going forward.

So those are the four things we look at. And quickly, the way that we do this is that we use assessments, not assumptions in this case. Again, building professionalism into this. So tools like 360 degree feedback, leadership simulations, scenario-based planning, and to help separate that from potential to preparedness. So people have potential, but how do you prepare that for it?

One thing that’s very important is that we realize at Succession Ready where our skill sets stop, and then we may have to pass this along to someone who’s special, skills in HR or boards like Barb is or something like that. So we take it to a point where we have these assessments, and then move it forward.

Another thing that’s really important is that the readiness for succession with people is not static. It’s developmental. So whoever may be ready now may not be ready to lead the company into the future. So what could be done to support these people?

And then finally, as I touched on a little bit earlier, but just to bring it to light, is involving third-party perspectives. So other professionals that could help develop these leaders, provide objectivity, and depersonalize the situation. I think a lot of times, particularly in family businesses, it becomes very personal. And, you know, the most liked sibling, or the most liked cousin, or whatever the case may be, might be seen as the next leader. So we like to bring in people who are professionals that can look at this and depersonalize it based on the best composition of the board, or the great work that Barb and her firm does that would have better exact subject matter expertise than we have. So, hopefully, that gives you a little bit of an angle of the intentional process to make that happen.

Cory: Fantastic! And a few things there, James, I’m going to come back to you on, because I think that there’s some points that deserve uncovering. So, Barb, when you’re working with boards or selecting candidates, what signals tell you that someone is actually ready to step into a senior leadership role?

Barb: Right, and I agree with everything that James said, and even you said it, Cory. It’s not about age. It’s definitely about competencies and technical skills. We, too, will use assessment tools. But before we do anything, we develop what we call a CEO Success Profile. Because if that transition is happening, yes, you need a CEO for today, but you also need a CEO or leader who is going to be able to move the firm forward of where you see it going over the next five years. So that’s one thing that we have in place. So if you’re looking at that CEO success profile and all the things that you’re looking for, how have they demonstrated that so far in their role?

And, sometimes we hear a lot from the founder. They’ll say they’re not ready. Well, based on what? It’s sort of just their gut reaction, and we will say, have you tested them to see if they’re able to make complex decisions or lead a team or what have you. So, maybe giving them a special project, or putting them into a role where you can see in action whether or not they have the competencies that are needed, and see how they perform.

I think another thing that’s really important is that somebody demonstrates a willingness to learn, and that they’re coachable. That’s huge, because the last thing you want is somebody coming in and, you know, like, “I know it all, I don’t need you telling me what to do.” That isn’t going to fly at all.

And what I do see quite often is when a founder says that they don’t think their kids are ready, it’s because their kids are looking at the business through a different lens. They might be more tech-savvy. They see opportunities that maybe don’t align with where the founder wants to go. So that creates its own little challenge.

But I would say the biggest thing, beyond the technical and the competencies about whether or not somebody’s ready, is whether or not they have followership. Because you can have somebody that can do all the great things, but if the rest of the family and the rest of the team don’t follow them, you can’t really develop that. They either have it or they don’t. And a lot of that is developed as they’ve sort of been working in the business.

Cory: Right! And so you both talked about some tools and assessments. And, Barb, I love the CEO Success Profile and being very clear about what that person looks like. And, James, you talked about third party objectives, but specifically 360 feedbacks. And so I want to just bring it to somebody who’s been in the business, somebody who’s demonstrated that willingness to learn. They’ve been in the organization. What does a good 360 assessment look like? Because there’s a lot of them on the street. And if somebody wanted to say, this is what I’m going to use to put the next leader in the chair. What does that 360 need to be telling them? And who is it that is reading that to make sure that it’s accurate?

James: That’s a really good question, Cory. And as I mentioned earlier, a lot of times, we defer these to the CPHRs, so Canadian Professional Human Resource people, or the leadership coaches and that type of thing, to really dive into this. But I can give some feedback of what I believe a good 360 is that we see here.

So it all starts, as I mentioned, to bring it back to where the organization is going and what’s their key people that this person is going to be interacting with going forward. The team that they have, their customers, and where they would interact with those key collaborators within the business, and to get objective feedback. And sometimes it’s not exactly what people want to hear. So really understanding and and and keying in on what’s working well, what the areas of improvements are, and then what the plans are going forward from that.

So I’m giving you generalities of what I’d like to see in this and the value of $3.60 as far as specific types, I would defer to the subject matter experts on there that we inter interface with, like recruiting firms or CPHRs or HR professionals, whatever the case may be.

But I think what’s really important here is to have this aligned with everybody that person’s working into, so they’re not just coming into a position. They’re coming into a position of authority or a title. They’re coming into a situation where they’re actually going to be leading people. How do the people they’re leading feel about them? Where do these gaps come in through? And it has to be a real objective, humble place for them to accept that feedback, and a safe space of culture where people can actually provide that feedback so they can move it forward.

And the underpinning of this, and, Barb, you’d probably know better than me, but having a strong culture in order to bring that forward is critical, so that people can provide this feedback and they’re not just formally compliant. I hope that answers.

Barb: Having a third party do that kind of creates that safe space. If we sort of wind it back a bit, when you have a board, succession planning should be on the agenda every year. And so at that point in time, you’re looking at who are the potential successors within the firm. Are they ready now? If not, when are they going to be ready? Is it one, two, three? What are the gaps, and how are you going to close those gaps? And then getting the feedback from others to see how they’re progressing in terms of closing those gaps.

The other thing that we’ve used, and this is really useful when it’s a tricky situation, perhaps where you have two siblings that are vying for the same job, or just one that’s clearly not a successor and not ready to accept it. Quite often, we have also engaged, we have a really good relationship with an industrial psychologist who will do a really robust assessment to further substantiate whether or not they are able to, move up into that role. And if not, coaching them and getting them to realize that although you’re not going to be leading the company, at some point in time, you’re going to be an owner, and you’re still going to have a say, but just in a different way.

Cory: Right, I love that! And, so many parts that we can jump into. And, as we go through our questions, I think some more will be related back to some of the points there. I’ve I’ve seen families hesitate to engage in this readiness conversation, and I think you both brought it up well in that safe space, because it is personal. We’re talking about people who were also related to, and we see at the dinner table on Sundays. And so bringing in these structured tools, external perspectives, actually gives everyone permission to talk about growth areas without judgment. And I think that that’s key when we’re talking about this.

Now our next question, what’s one mistake that often families make when navigating leadership succession, and how can they avoid it? I find that it’s great to talk about best practices, but it’s also great to learn from maybe how others haven’t done it well. As humans, we’re kind of a creature that we need to learn for ourselves. I think that there’s an opportunity here to make some headway from what others have done, maybe incorrectly. And for me, I find that it’s rarely that technical side of things. It’s often that emotional, structural, you know, lack of clarity, which we’ve kind of touched on, and decisions that are being made in isolation.

So we’ve talked about boards. We’ve talked about councils, and really just those avenues to have those structured conversations. Now, Barb, when it comes to a common mistake that you see in how boards or ownership groups approach succession, how might they take a more structured approach to avoid those mistakes that you see?

Barb: Well, first of all, I think it’s something that many families push off, and two fold, I mean it’s forcing people to sort of face their own mortality. And, second of all, it’s an emotional journey. And there’s probably going to be some difficult discussions, and nobody sort of rushes to the front of the room to have those. And so, it gets delayed. And then sometimes what happens is there’s an event and that drives the process, and that’s never a good thing. So, the more you can be planful about it, the better off you’re going to be.

And I think you also need to realize that it’s not a one time event, it’s a multi-year phased approach. It doesn’t happen overnight, and it’s sometimes two steps forward, one step back, because there’s going to be bumps along the way for sure.

I think the biggest mistakes that I see is not having really open dialogue with facilitated discussions with a wide group of people. It can’t just be the owner deciding what he’s going to do. I had a call with a client not too long ago where we were talking about this. And I said, well, you know, what do your siblings think about this? I don’t know. I haven’t had that conversation with them. And so I said, well, I think that should be the first step that you have. So you have to include key voices, and also as we’ve sort of touched on earlier, it’s not just about the technical skills. It’s sort of like the full picture, and just looking at what’s needed in the future, and really making sure that you have a plan.

Cory: Right! And, James, in your consulting work, what people related or relational pitfalls do you see derail even the best laid succession plans?

James: It’s really interesting, a great question! As I was listening to Barb, there’s so much alignment with what she was saying. I think a couple of things here. The biggest pitfall is avoidance. I think these conversations about succession are delayed because they’re emotionally complex. They’re not simple conversations. So that’s important. And this can either lead to avoiding the question entirely, or making rushed decisions under pressure or unplanned exits. The key thing is really being intentional about that.

I think too, the lack of role clarity that comes through with this. So in family businesses, we talked about this, that it has to move to a sense of intentionality. We talked about the start of our time together today. And without these clear rules and expectations which formalize a business, transitions become ambiguous. So it’s hard to say who’s doing what, and what they’re going to be doing. And this leads to maybe some tension for people who feel they both should be in the same role, or people become disengaged when they don’t get the role they want. So in some cases, we see that, which then leads to some confusion about ownership and leadership. So who’s doing what? And just because someone’s a shareholder in a company doesn’t mean that they’re ready or want to lead. So some people just want to be a shareholder and hold back.

We look at the different, you know, people want to be part of the family, and they’re part of the shareholder group, and the ownership group, and who’s actually running the business. And then assuming this alignment that people have without verifying it. And the whole premise of our business is getting people clear with where they’re going with the strategy and alignment. And a lot of times, it’s just assumed, and that’s never really a great plan because it’s not well intentioned.

The businesses or the families that we’ve seen doing it well are well intentioned. They have a shared value set. They have a shared mission and vision of what they’re doing. And without some structured dialogue that suits that plan, things can get a little messy and tricky there. So I’ll close by saying a good way to mitigate this, and a good avoidance strategy is to just create a phased plan to make this happen. It doesn’t happen overnight, but using facilitated family meetings, structured development programs that we talked about for the competency of where people are at, what their capabilities are, and some timelines associated with that. So you have accountability agreements that really could make it manageable and proactive. So we are dealing with humans here. Things are going to be going in a tricky way, but putting the guide rails around it the best we can without being too prescriptive, I think, is really important.

Cory: Fantastic! And one of the things that I’ve heard both of you say is there needs to be foresight. And, James, you made an excellent comment, and both of us kind of share this language, as CEPA’s, certified exit planning advisors, that unplanned exit. You know, somebody might be there. And, Barb, you talked about assessing the competencies of more than just one person in the organization. And I think that that’s key, we might have a great plan, but all great plans need to still have a contingency plan involved, and having that backup is key.

James: Yes!

Cory: Now onto our next question, how can families balance the decision to promote from within versus bringing in external leadership? And I think this is one of the toughest calls, and we’ve heard this in our discussion already, around assessing that next person. You know, the decision carries legacy weight, the future impact of both the values and vision of the business, but if it’s always been led by somebody within the family, it’s a very hard decision to say, we don’t have somebody from within. So, Barb, starting with you, when helping families recruit or consider external candidates, how do you guide them through the internal versus external decision? And what criteria do you use to help them assess this is the best fit?

Barb: That’s a great question. Well, the first thing that we do before we even start is we have a very deep consultation process. We will talk with the owner, the family members that are involved with the business. We talk to the leadership team and really get a good understanding of where the business is at, what’s working well, where there’s opportunities for improvement, what are some of the headwinds that are coming, looking at the current leader, what do people like about them, and if they were having to pick a different leader, what would they like to see done differently, and a whole host of other questions.

So we really get under the hood to understand what’s going on in the organization. And from there, this is where we develop this CEO success profile, and that is the benchmark that we’re going to use now to evaluate candidates. And if there’s somebody internal, then we assess them just the same way that we would from somebody from the outside. And a lot of it can really depend on where a company is at in sort of their whole evolution.

What we have found is organizations that are really kinda stuck, and there’s a lot of resistance to change. Sometimes an internal candidate is what they need at that point in time. But if they’re looking for somebody who’s going to be innovative and maybe take them to the next level, quite often, that requires somebody external. So it’s really having a look at, sort of where the business is at in its life cycle, and where they’re moving to. Maybe they are looking to do an exit. Maybe they want to continue as a legacy. So all of that sort of comes into play about internal versus external.

And then it’s making sure that there’s cultural alignment, which if they’re an internal candidate, usually there is. As we’ve touched on earlier, having a very robust evaluation process, typically from somebody that’s external to the organization. And if you are going to promote from within, really being aware of where the gaps are, and having the right support to help elevate them. And that’s quite often where an advisory board can come in, they can be a good coach to the next leader. You can get them their own personal coach. Sometimes people will have them join, sort of a peer support group or or what have you. But you can’t just throw somebody in and say they’ll kind of figure it out along the way. You have to support them, and really make sure that they’re onboarded well, even if they’re an internal candidate. Again, you have to treat them the same way as you would someone from the outside, and provide support.

Cory: Fantastic! And, James, the work that you do with families, when an internal successor wants the role, you made comment about this in one of your previous comments, but they may not be fully ready. What are some of the steps to develop them or prepare the family for alternatives?

James: Thanks, Cory. Barb set the table really nicely by saying that planning is so critical here, and that it’s getting the strategy going, and make sure there’s a plan going forward with this, and understanding objectively what’s there. So I think it’s really important to balance the aspiration of the next gen’s interest with their development. So when we look at this and we develop plans of people, and look at the vision where the company is going, and what they actually do, and what it takes to get there, talk to the people and see if they actually want those roles, and then be honest about where the gaps are.

As you know, the best plans are ones that are minimum one year or three, sometimes five up to ten years out. So understanding what that roadmap looks like. And one of the key things we provide with this is to develop a roadmap for the client to simply see what this looks like, and find out where the gaps are. So they may have the right people. They’re just not ready yet, which is okay.

And then what do we do to support them within that? So bridging the gap with interim support. Again, if it’s a good culture and people are willing to understand that that is a good step in here, there could be things like interim external leadership, bringing in someone who’s seasoned from the industry, or who has worked in a family business or something within that particular marketplace is really helpful. Not a threat. In other words, it’s a mentorship, and it could be two way mentorship. They could be learning on both sides, which I think is really important. A dual leadership with the mentorship phase. So just having, like I said, both sides in that.

And then maybe some informal, Barb had mentioned some informal advisory roles that could be there that could change that. And that’s where if we saw this evolving, and be very clear with our succession plan, ready methodology, we would hear this voice coming through, and that’s when I would pick up the phone or email someone as a subject matter expert as Barb would be, and say, I think there’s a governance issue here, hand it over, and then they’re in good hands. It takes all of it. It’s a unique ecosystem.

And then within that, with the governance piece is defining what success looks like, and have that really clearly articulated for the role, for the company, and for the future. I think that’s really important to look at those things going forward. And what are those key milestones along the way for the internal successors to reach, and then close those gaps over time, or it may open new gaps, then how do we deal with that?

And then lastly is supporting both the leader and the system. I think we can run the risk of focusing it too much on the individual, which is a real risk because then we’re creating the next owner’s trap within this. But how does this person evolve with the system? It’s dynamic. It’s a process. That’s why it takes all of us in this multidisciplinary advisory space, to ensure that the business and the family system are ready for this person, and that person is ready for what’s next, if that makes sense.

Cory: Absolutely! And you both have mentioned coaches. And, Barb, you also mentioned a peer group. So when we think of the support that can be given to these people in leadership roles, how do we assess those two things? Is a coach essential for everyone in a leadership position? Or maybe that peer group is the better place to get the support. So, Barb, how do you see those as support mechanisms for senior leadership?

Barb: There are so many options. Sometimes we’ll recruit a CEO, and part of their mandate is mentorship of the next generation. They’ve got a short timeline. They might have a two or three year runway. They know that they’re going to be gone after that, and that’s how they’re developing the next gen.

I have another situation. It was a distribution company, and the dad gave a division to the son to run to see if he was ready to sort of take on the bigger animal, so to speak. And he was great at sales and marketing. He was a natural leader, but he hadn’t really led a large team. And he didn’t really understand, perhaps the supply chain side as well as he could. So in that case, we actually brought in a coach adviser who worked beside him as needed. They had regular, weekly meetings, but if he needed him for other stuff, he could call upon him. And part of that too is he really did not want to emulate his father’s leadership style. His dad was quite top down. So for him, it was finding somebody that really aligned with him.

There’s lots of peer groups. There’s MacKay CEO Forums, TIGER 21, you name it. I think they’re all good, but for me, the the risk that I see sometimes is that when you’re sharing your issues with those peer groups, they are only hearing your perspective. And the perspective of the others back at the office could be quite different. And so perhaps the guidance that they’re getting is  not as valuable, let’s say. So I think you have to look at the individual, what they’re open to, how they learn, and kind of find a happy medium. Maybe it’s a combination of a peer group and a coach, or what have you.

Cory:  Awesome! And, James, anything that you wanted to add as it relates to coaching?

James: No, I think that Barb made a really, sharp point there, that it’s not one size fits all. It’s many sizes fits many. It’s really understanding the organization and just be mindful of the recommendation you make. As you know, what I found really interesting, Barb, and thank you for bringing it up, is when you go to these mentor or peer mentorship forums, it’s one perspective. So you’ve got to have the right size, and it could be intimidating for people to go to that as well. So sometimes there’s individual coachings needed. And full disclosure, I’m not an executive coach, but I understand the value of coaching. And then we defer to those people who could provide that. But to have it right sized with intentionality, I think, is really important. So it builds momentum versus derails, or brings further complexity into the situation.

Barb: Yeah, fascinating! I think one other thing that we haven’t brought up, but, you know, when you’re developing next gen in the organization or someone else, you also have to be very clear from the get go. There are no guarantees. We are helping you be the best prepared for when the opportunity comes, but there are no guarantees because I’ve seen a lot of people interpret that, you know, they’re kind of a slam dunk. The way they behave around other people reflects that. And then when it doesn’t happen, it does a lot of damage.

Cory: I love that, Barb. Thanks for adding that. And when we’ve worked with families where promoting internally felt emotionally right, but the person needed a runway, sometimes the best plan is both. And I think we’ve really heard that, from both of you, is that bridge of that interim leader, getting that support and and not feeling like it’s a failure to the the legacy of of the business and the family because you’ve brought in external support, either that coach or an interim CEO, somebody as a an advisory, to that that developing next gen to really prepare that next leader. So, I think, really making sure that families see that it’s a win to make sure that we’re developing those people in the best way possible, and meeting them where they’re at and where the business is at is key.

James: Yes!

Cory: Now for our next question, what does effective mentorship look like between generations? So we’ve kind of covered on this a little bit, but how can families make it real and not just symbolic? And so I found that mentorship isn’t just a relationship. It’s a system. James has mentioned thinking about the system, and systems theory is very important in a lot of this, but it works best when it’s intentional, cross-generational, and actually anchored on business outcomes. So we’ve talked about strategy here quite a bit so far in our hour. And so, James, how do you structure mentorship or leadership development for that next generation in your succession work, and what helps mentorship stick?

James: Well, thanks for the question. It’s really important. It’s interesting that we come through our time together today, which has been fantastic. We started talking about taking the informal to the intentional. And many business owners have started their businesses with purpose, passion ,and planning. And then the key is to keep that going with mentorship. And in our process with Succession Ready, what we do is we go in there and really anchor it.

Again, the word strategy is coming up here, but building that mentorship plan into the succession plan. So clearly defined roles that align with that goals, timelines, and check-in. So creating intentionality at every stage, including the mentorship side of it that aligns and is clear with what the plan is going forward. And then I think what’s really important is to anchor mentorship to real business outcomes. I don’t want to sound cavalier here, but there’s a lot of times that we don’t need another friend. Well, it’s nice to have friends, but in this case, it’s an accountability partner. So instead of general mentoring, rising next generation leaders, and, of course, now with the way that information is consumed, a generation is no longer twenty years or whatever. It’s really tightly, you know. So maybe getting them to take on strategic projects of tech integration, things that the company values, like environmental, social goals, that type of thing, and new product lines with senior oversight.

So there’s almost some oversight, but make sure the mentorship matches where they’re at. And I think too, is multiple mentors. One mentor doesn’t have all the answers. Just as we mentioned, it’s an ecosystem for all of us here. So how you do one thing is how you do everything. So why would we say on the one side, we have a multidisciplinary advisor, but not have that with a mentorship group? So I think it’s really important for different types of needs.

And then tracking and adjusting this as time goes on. It’s not a set it and forget it thing here. It’s really dynamic, especially when you’re dealing with the emotional complexity of families, all the dynamics that go on there.

And then the last thing, and I mentioned this a little bit earlier, but, I want to bring it up again, is reverse mentoring. So bringing in a mentor, but also having that maybe that next generation leader to help the mentor to understand going through their, because the person coming into that role is not just a one way conversation. It’s a two way conversation. I believe in a good mentorship relationship where both sides are proactively and productively challenged to provide a great outcome. So I think that reverse mentoring, if that’s easier said than done. But I think when you look at all these things and do it with intention, it could lead to good outcomes.

And again, it’s not one size fits all. It could be used a little bit more and less of the things I talked about. It’s like a recipe. You have to get it right in order to deliver the outcome. So that’s how I think it would really make it, not just symbolic, and actually have it so it has meaningful impact and purpose.

Cory: Fantastic! And I do want to remind everyone, that Q and A box, as we near the end, queue those up, and anything that’s on your mind.

Now, Barb, what role can governance or the board play in supporting or even formalizing that mentorship across generations?

Barb: Well, I think when you have a board, the whole succession planning is something that you’re talking about, at least annually. And so they’re the ones that can make sure that there is a natural plan in place to be developing people, and that that’s being reported back, that you have, like James had had mentioned earlier that you have the mentoring anchored to the business outcomes, and then you’re having a regular sort of evaluation process. And that’s going to be reported back to the board so that you can see that the potential successors are sort of moving up the food chain in terms of their readiness. So that is certainly a a role that they can play.

And all the things that James said, it really hit home for me, kinda stole the thunder. But reciprocity really does matter. And so it works best when there’s that generational view that it’s a two-way street. And so if you’re going to be having goals set for the up-and-coming generation, that this is what we want you to learn in terms of business outcomes, let the leader also have some things that they want to learn. Like, make them be a little bit humble. Now it’s you know, AI would probably be something that they might learn from the next generation. So to make themselves a little bit vulnerable as well is a good thing.

Cory: And one of the things that I want to ask both of you, and, Barb, we’ll start with you. When it comes to ownership of development, you’ve talked about the board and maybe leaders, people who are managing that next generation, are setting goals. But where do you see that ownership, or shared ownership of the development of the person? So talking to the rising gen member right now, of maybe I’m not getting that direction, but how do we balance some of that direction that we need versus taking action and going ahead and developing yourself?

Barb: Well, I think every organization, regardless of whether it’s a family business or not, should be looking at key roles within an organization and figuring out who are the potential successors? Is there anybody ready now? And if something happened to that person tomorrow, who could step in and fill the role, or would it be leaving a huge gap? And so when the board is looking at that on a regular basis, they’re holding management accountable to say, this person over here is, if something happened to them, what’s your plan? And so it’s top of mind.

And that’s one of the biggest values that I see with having an advisory board in place, is they keep things like that top of mind, and they hold management accountable. Because if the owner is not doing it, sometimes it’s hard because then that requires you to be managing up. And if they don’t support it, then then things just fall apart. And one of the approaches that we’ve taken to really get people to focus on succession, is looking at things from the view of what would happen tomorrow if you got hit by the proverbial bus. Do you have a plan, or are you going to be panicking? When they sort of take a step back and think through, you know, how ready they’re not, that sort of leads them to really put a lens on interim leadership and people not being ready, and it sort of lights a little bit of a fire underneath them.

Cory:  Awesome! And, James, any any additional comments from you on that?

James: No, I think what Barb said is really important there. I think the operative words there are just accountability and structure. And I think it’s just so important to, as we professionalize and optimize these businesses here, is bringing people in from the outside and looking at different ways, different angles of how business can be looked at. It should be done by design, not by default. And I’m not just spewing rhetoric here. What I’m saying is that there’s just a really intentional process here, and there’s real value in having your governance set by experts like Barb or others that are in our networks, to just invest in that time to really set the path forward for your business so you can achieve the things that you want to do and and go from there. And it’s an investment in people to provide them with great mentorship.

I’m sure we all can think of four or five people. Maybe it’s more, maybe a little bit less, but who really have made an impact on our life. You just never know if that could be brought in intentionally. It’s just who knows what that could really be. Even if they don’t stay in the family business, they can actually achieve things to move forward and do other things too. So, can’t stress the importance of good mentorship and what that looks like. And the last thing I’ll leave with is that if you provide good mentorship, there’s a good chance that that person who’s the mentee in the future becomes a mentor within the business or otherwise as well. Maybe it’s a trade association or somewhere in the market, or becomes a member of the Chamber of Commerce, or somewhere else that contributes to the overall business ecosystem, because this just isn’t about that one business. If people are elevated in their performance and their confidence, then they could do great things for the community.

Cory: Fantastic! James, any closing comments before we wrap up?

James: No, I just really like to thank you for the opportunity. It’s great to spend time with both of you and talk about these important things, and it’s exciting. So I look forward to the future.

Cory: And, Barb, any closing remarks?

Barb No. I mean, this is a great topic. It’s something that I like to sing from the rooftop, because I see so many families that aren’t ready, and it’s kind of a shame. But the one thing I would also like to say too is that, quite often, to be successful, the founder also needs a bit of a support network, because it’s hard to let go. And it can be a really tough emotional ride for them, making them feel like maybe they’re irrelevant, lost their sense of purpose. And so, you can’t ignore that part of the equation, and making sure that they have sort of a coach, a peer group, or whatever, to help them along the journey that they’re going to be going.

Cory: Yes, great point! We’re both developing down and developing up, and role of involvement matters and, helping people into that uncharted territory, including the founder bar. So that’s great. Now thank you both. I really appreciate you sharing your expertise, spending your hour with us, giving back to the community. And thank you everyone who joined us today for our first Legacy Builders Live.

As we hope this discussion demonstrated, some of the most important family enterprise conversations benefit from more than one perspective.

Throughout this discussion, Barb and James approached succession planning through different lenses: governance, executive search, leadership development, and strategy. Yet their message was remarkably consistent.

Succession is not an event. It’s a process. The strongest transitions begin long before they’re needed. Leadership readiness should be assessed through evidence, not assumptions.

And successful families create the structures, conversations, and development pathways that prepare both future leaders and current leaders for what’s next.

I’d like to thank Barb Schimnowsky and James Grieve for sharing their experience, insights, and practical wisdom with us today. 

One of the reasons we created Legacy Builders was to bring together forward-thinking leaders and trusted frameworks that help families and their advisors gain the clarity and confidence to lead with purpose today and for generations to come. Today’s conversation was a great example of that mission in action.

If this discussion sparked ideas or questions for your family, business, board, or clients, you’ll find both Barb and James’ contact information in the show notes.

Thank you for joining us for another episode of Legacy Builders. Take care, and keep building a legacy that lasts.

Disclaimer:

This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at CI Assante Wealth Management Ltd. This is not an official program of CI Assante Wealth Management Ltd, and the statements and opinions expressed during this podcast are not necessarily those of CI Assante Wealth Management Ltd. 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.