The Courage to Continue: Why Emotional Readiness Shapes Enterprise Legacy

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 Krista Rabidoux, Partner at Andersen in Canada. With more than 24 years of experience in U.S.–Canada cross-border tax planning, Krista supports families and businesses with their tax compliance and planning needs on both sides of the border. She’s also a Family Enterprise Advisor, bringing a thoughtful, coaching-based approach to her work with family enterprises. Krista currently serves on the boards of Family Enterprise Canada and the Alberta Enterprise Group, and is Past Chair of the American Chamber of Commerce in Canada West—roles that give her a broad perspective on the challenges and opportunities her clients face.

My goal is to be the most curious person in today’s conversation with Krista Rabidoux, where we explore how lived experience, adaptability, and insight converge in her work with family enterprises. We’ll discuss how Krista helps families move from feeling stuck to seeing possibility, guiding them through transitions with clarity, courage, and care. From navigating emotional complexity to preparing the next generation for real-world ownership, Krista brings a grounded yet visionary approach to building resilience, shared leadership, and lasting legacy.

Now let’s dive in!

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

Krista: Yeah. Thanks for having me. 

Cory: Imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Krista: I think a lot of people, we make assumptions based on where we come from, from who we see we are today. If I’m thinking about when I’m motivating others to do their best and be themselves, there are probably three keywords that come to mind when I’m thinking about my story of the past and it’s adaptability, perseverance, and always assuming the best of others.

When I started my life, my first six years, I lived with my aunt for a while, my dad for a while, and my mother for a while, until I finally settled with my mom at six years old. I hopped around for the first formative years, if you will. And I think because of that, I really learned that adaptability. Different environments, different structure, different people. And there were probably points in my life where it caused me a lot of angst and trauma, I guess, if you will, if you want to put it that way. 

However, once I matured, and through a lot of talk therapy and hypnotherapy, I realized it actually taught me an extensive skill of adaptability, to be able to see things, adapt quickly, and overcome obstacles. And I think that throughout life, we can all either take that mentality of, poor me, I had to deal with, or we can go, what can I learn from this, and how is it my superpower, and where have I brought it to life?

So if I were to say, you know, adaptability, what happened in your past is the formative years, and perseverance. I didn’t grow up in the best. I grew up in low-income housing. I grew up in a world of “be on guard,” I guess, if you will.  And that’s where my perseverance comes in. I was a teenage pregnant young lady, got pregnant in high school, had my first child, and I say to this day that my first child was my saving grace, and forced me to go, what am I doing with my life and who do I want to be with my life? 

Again, just that, going back to my core of adaptability, I then had to persevere and say, okay, am I going to be this person who has been in this path, or am I going to go, no, I’m going to persevere, change this up a bit, and and look at something different. And change is hard for people because it takes a lot of perseverance to have a significant change, decide to do a u-turn, and and go the other direction and go, don’t know what’s there, but we’ll overcome it.

And I think that that’s a core thing that really just, you know, persevere. Think through it. Think about what is, and then goes to my third. What is the best? The best of the people, the best of the situation. What is that outcome? What is possible? And focus on that, you know, kinda like your north star. I’m assuming the best thing’s going to happen, and that’s my north star.

Some people call it manifestation, some people call it plannings, your process mapping out, you can do it however you want, but it’s there’s my north star. I’m going to assume the best of the people and of the situation that it’s going to end how it’s going to end, and persevere through that. And here I am today, you know, I was a high school dropout. I got pregnant, and now I’ve persevered through many tribulations and learnings in life. And I think it’s just adapt, persevere, and assume the best is going to happen. Because if you’re not doing that, it’s hard to look forward.

Cory: Absolutely! So, when when you talk about adaptability and your upbringing, Dan Martell in in his book, Buy Back Your Time, he talks about entrepreneurs, and how that strength of being an entrepreneur, and he prefaces it with not every entrepreneur needs to have an unstable upbringing, but how that instability, you know, you spoke about being on guard and not really knowing where you’re going to be next. How has that helped you in your career, and with the families and individuals that you work with?

Krista: I think not always knowing where you’re going to land, but having the history to go, I’ve always landed on my feet. It’s not without its tribulations as I said. Even with the families or the clients I work with, sometimes I think they feel like there’s no way out of this. They feel trapped, whether it’s in a tax situation, whether it’s in a transition situation, whether it’s in a planning situation, and and the hardest part when you’re working within that and facilitating is to help them identify they’re not trapped and feel as though there is actually the north star. It is possible. You will get there.

It’s probably going to hurt, whether it’s physically or emotionally, depends on what it is. Think about somebody doing physio after an accident who has to learn how to walk. It’s going to hurt. There’s going to be pain. In some of these, it’s emotional pain. It’s psychological pain, but it’s still going to hurt. And that’s okay because from our hurt, we learn. And we go, oops, don’t do that again. And that you have to learn. You have to take those moments and go, okay, don’t you do that again. And that’s how we learn. Do you think even toddlers as we learn to walk, how many times we fall on our bum? Don’t do that again. Hold on to something. That’s smarter.

So I think it’s, when working with people, it’s just helping them get to that point that you’re not in a cage. There’s boundless pathways you can take here, and you’re not in a cage. You have to identify what path it is that you want to walk down.

Cory: Thinking about some of those situations that you’ve seen families or individuals in those systems that you are lucky enough to be a part of, where have you seen people where they feel like that cage is just so small?

Krista: I think it’s when you feel as though a mountain is so insurmountable. I’ve trained to climb a one kilometer mountain, but that mountain’s 10 kilometers. I don’t know if I can do it. It’s going to take training, and it’s going to take time.

I think about situations where someone thought it was just so insurmountable, it took a number of years. But now they look back and go, okay, I get it now. I see where this was. I couldn’t see it because they were stuck in their cage at the moment. You think about anybody such as myself who, when I first started my therapy journey for my past, I was like, I’m stuck. This is who I am. And it’s, well, no. This is who I’m going to become with who I am. And I think with the families that I’ve worked with when they get to that stage. When you see that light bulb go, it’s like, yay! Because all of a sudden they’re feeling there is a possible possibility here, but like I said, it hurts. Yes, it’s painful.

Cory: For that experience and that learning to happen, do people have to get to that position, or do you find that there are ways that you can help them understand from a position of strength, of success? I think about risk management, how important it is to plan for great outcomes as we do strategic planning, but we still need that risk management in place. So how have you found that you can still have that attitude of thinking about the best outcome, but still being prudent, when it comes to leading the enterprise?

Krista: There’s always the differential between optimistic and realistic. You can’t be so optimist with the north star that so optimistic that you don’t mitigate for what might turn left. And I think, you know, you have a death in the family unexpectedly. You’re halfway through and all of a sudden, one of the players is gone. That’s a big risk mitigator that you have to go, what happens if, this happens during our process and our planning, and we’re already thinking one thing, and then all of a sudden, you’re turning around because you have to basically start at ground zero and restart the conversations. 

In our business, my business, we restart the conversation every year because every year the economy changes, every year eco-political stuff changes, every year people change. And there’s so many things outside of the control as an entrepreneur that you have to go, okay, let’s revisit this. Are we still on the right track? Has anything changed that we need to adapt ourselves to? Going back to the adaptability because the climate’s changed.

Right now, we’re in a crazy world with tariffs and yadda yadda that we don’t know. We actually don’t know which way to go. So we’re in constant risk mitigation because you have to be adapting almost weekly right now to what might happen. And when you’re working within the family enterprise group, there’s a lot of dynamics that can happen. You can go to a family function, and there’d be an argument, and then you’re back starting at a certain point because people got hurt. There’s more emotions involved. And so, like I said, that adaptability and that perseverance. The North Star is there, but it can’t be without ensuring you have proper governance for when something comes up. You have the tools to be able to turn down the lane that you hope you don’t have to go down, but it’s there for you if you need it. It’s like the back alley. You have a water main break in your front driveway. You’re going to have to use the back alley. It’s adapting right?

Cory: If we were right now talking to a family, maybe it’s the parents who are saying, I really want to teach some of these skills to our next gen. We’ve got them coming through the ranks, we’ve protected them from a lot of the issues that we face and the decisions that we’ve had to make to get to where we are. How can that family help bring those learning outcomes in a way that allows the enterprise to continue to thrive and be safe, but also with and without it being just a simulation, actually being real world?

Krista: I think that that’s actually one of the hardest parts, because we’re all individuals and we all lead differently. So let’s say going from first gen to second gen, where you have a solopreneur who is used to making all the decisions, and yet now you have a sibling group who are trying to figure out how to work together, but they’ve been taught to lead by a solopreneur who makes all the decisions. Who now makes those decisions, and how are those decisions now made? It might be that one of the siblings is going to be the sole decision maker. That might be one of the options.

I’m actually a firm believer that most family enterprises can’t do it on their own. Even ones that think that they’ve been successful in their transition on their own, there’s always things that come up that they didn’t think about because they are instilling their way of leading, their way of doing, their way of being into the next generation without the understanding of how are they different generationally, economically, emotionally. There’s just different things that come up within them as a leader. How are they going to adapt, and what do they need to have in place to continue doing that?

Some of my clients I work with, I do leadership development. Some of the next gen don’t really know how to even do, like, the financials. Obviously, as an accountant background, it’s my strongest suit, and so it’s teaching them what everything on a financial statement means, and why is it important, and how do you know if certain things are out of whack and not out of whack?

It’s things as an entrepreneur when you’re a solopreneur, you just know from experience. But generally, next gens aren’t in those conversations, and they should be very early in understanding what’s happening, why certain decisions are being made or not made, and why things are happening. And I would say the earlier you can do that, the better. If they’re in the business, they should be in those meetings. As we talk about in the family enterprise world, we have the different segregations of the business, the shareholders, and the business shareholders and family, owners and family. It’s important if they’re in the business, they’re in all of those business discussions. Because how are they ever going to learn to do something in the future if they’ve never experienced it?

Cory: Absolutely! You made a comment that even if a family feels as though they’ve done it successfully, there’s still something to learn. And so where is that balance between, putting my own imprint on this and not knowing what I don’t know?

Krista:  I think it’s that our egos want to put our imprint on stuff. It’s inherent in all of us. We all have some form of ego that it’s, “I want to have my imprint on this.” However, when you exert too much of your imprint, you’re not leaving room for the next generation to find their own imprint. And as I go back to the adaptability as a founder or the generation that’s passing, we have to say to ourselves, “I like to have this. I like to have everything printed for me.” But does that make sense for tomorrow? And it’s very hard, especially for someone, let’s say, who’s been running the business for sixty years, and it’s successful. It’s hard to say, how do I stop doing that? Because that’s how it’s always been done. It’s very difficult.

Probably the most important thing to do is to listen. Listen to what the next-gen says. Hey, I think we could probably do it this way. Especially if they’ve been in the business a long time. They’ve obviously seen different cycles and seen different things. So it would be difficult if someone wasn’t in the business and they came in all of a sudden to take it over, and they don’t know much about it. That’s a little bit different. But if somebody’s been in the business working, participating, and doing their best to learn the concepts, it’s important for the founder to listen.

Cory: Absolutely! And so we started out with the theme of adaptability. And now we’re talking about adapting to maybe not big risks or jolting external factors, but now we’re talking about how do we do things the best way we can and leaving room for that growth of, you know, paper is now not the most common thing. We’ve, you know, moved a lot of things into digital storage, and so thinking of it really as that continuum, where do you find in some of that leadership development work that you do, maybe the generation that’s used to leading can say, I’m going to give this aspect away. So where do you see some of those where maybe it’s easier, maybe we can practice those habits?

Krista: I think you can do different divisions. You can oversee the finance and start making some of those observations and oversights, and maybe lead the finance meetings. Not necessarily making decisions without the founder, but start overseeing it.  And let’s work together and figure out, I can teach you how I make my decisions versus you making your decisions. Maybe it’s an operational section, right, depending on the business.

If you’re talking about a family business, a farm, you take over. You’re going to become the harvester. I’ll continue with the livestock, but you start managing the projects of all the harvesting and timelines, when you have to do stuff, and how many hands you’re going to need to support and etcetera. I think it’s leveraging the different components of a business, breaking them into pieces, and allowing people to work through those different pieces.

I go back to my last thing. Just assume people are doing their best, instead of people are out there to sabotage. If you make those assumptions that it’s going to work out, it’s going to do this, there’s going to be bumps, there’s going to be bruises. But like I said, you had to fall on your bum a few times before you learned how to walk. And protecting someone too much can also be a detriment to their learning. 

Cory: Hmmm! Let’s go a little bit deeper into that one.

Krista: Yeah! If you never let someone fall, where are the lessons? You always hear the “do as I say, not as I do,” which is completely opposite. Everybody does as they see, not hear, the actions we learn. And if we’re not allowed to fail and fall, where’s our self-lesson? How have we learned anything in this? How have we gotten that bruise so that we go, oops, don’t do that again?

And so it’s scary, especially for people who are transitioning, to say, what if my business fails? That’s gonna hurt the family. It’s scary. You have enough oversight that that’s not gonna happen, or you have enough advisers that you trust that are supporting the family as a team. And you know we talk about that a lot in the enterprise world. As a team supporting that family to make sure you’ve got enough checks and balances, that there’s going to be things that it’s not going to fail, but it’ll be caught before it fails. But you have to let the failure happen. At least micro failures.

Cory: And what does enough oversight look like? What is that balance of enough but not too much?

Krista: I’m a proponent that if you have strong people who have been in the business for a long time, oversight means participating in the weekly meetings. How are things going? Give me updates, give feedback, give stuff like that. Participating in the financial discussions to make sure things are looking as they are. What it doesn’t mean to me is walking down the hall to the receptionist and saying, hey, you should be answering the phone one ring faster. So it’s getting out of those details that you’re used to being involved in for every component of the business and letting it go. It’s still important to have oversight. I actually do believe it’s very important to have oversight throughout a transition because there are things, especially for a next generation who hasn’t learned how to be an owner. They’ve learned how to maybe be a team lead. They’ve maybe learned how to run a department, or they’ve learned how to run a sales. But until you’re an actual owner, it’s a very different mentality than a team leader.

Cory: Very different skill set.

Krista: Very different skill set as well, exactly.  So, letting go enough so that they can get the experience of what it means to be an owner. You don’t collect your AR. Guess what? Your salary is not coming. It’s those types of things of this is what it actually means to be an owner. When your livelihood is your business, and if it fails, your paycheck stops.

Cory: And so when we think about the different components of a business, it makes me think about wearing different hats. And you mentioned the three circles, but there are many more. So when we get that leader to really think about what all the different components and roles are in my business, how have you found that some of the development and coaching work that you’ve done helps to enlighten them and think about where I am making this decision from?

Krista: I mean it’s different for the next gens than it is for the ones that are transitioning out. I would say the ones that are transitioning out, you really need to understand where their blocks are, as to why they’re afraid to pass it on. Yeah, a lot of times it comes from a place of fear. I mean, I’m not a psychologist or a therapist, but a lot of the time it comes down to where is this actually coming from? Because most of the time, it’s not actually the enterprise itself. There’s a lot more to the story of why a transition is successful or unsuccessful. And as I said, it comes back to their original story, similar to mine. Like, what made me who I am today? What is your story? What made you who you are today? And maybe that’s why some of these blocks exist.

There’s always that fine balance as a coach going to help those people explore, okay, maybe I’m doing this because this happened in my past. And if that’s the case, how do I let go of that to allow things to happen in the future? And like I said, I’m not a therapist or a psychologist. I don’t profess to do that, but helping people to explore their own blockages is what I probably would work with mostly, as the people just release some of that. Because it is our own blockages that get in our way.

Cory: Let’s focus on that story for a moment. Where have you seen the power of story help in those transitions?

Krista: When I’m working with different enterprises, one of the stories is that the next generation has taken over successfully. There were no problems, no disputes. They had decided how things were going to work. But there was some embedded historical stuff that had happened within the next gen, living out someone else’s story, I guess. And, it didn’t work. But there were no exploratory transition discussions that happened throughout the transition to say, well, who are you trying to be with this business? And that happens a lot. It happens a lot where it’s, I’ll run my mom’s business, and it’ll be fine. And I’ll run it like my mom ran it. So it’s I’m just thinking about myself, and it doesn’t always work because we’re all different humans. We all have different visions. We all have different values. We all have a different core belief system. We might have a unified family one, but we have our individual ones. And so when it doesn’t work, I think, is when you don’t go through that full process of really doing the exploration of what I am trying to achieve in the future? What’s my vision or our vision, as a sibling group? What do we want to be?

Cory: I love that! Just thinking about that sibling partnership, and now it’s not one person’s vision. And just because that sibling group is running the business, might not be, you know, mom and dad might still own a part of the business. So, how are you balancing what was versus what?

Krista: Meeting the shareholders’ needs versus also making money for yourself. I’ve had that conversation a lot, that you know, siblings in the group’s not going to run their business into the ground because they now need to make 10 times as much because they have to pay a lot more people. It’s not one or two mom and dad anymore. There’s a whole group of people who have to be paid with these profits now. They’re going to try and make it bigger.

Cory: Right! So thinking about that vision, how have you seen families really lean into that and say, we need to grow because there are many more mouths that are reliant on this?

Krista: I mean, right now, in this stage and age, there’s a lot of fear, because nobody really knows what’s happening today. There’s a lot of fear about what’s happening in the world, what’s happening economically. And because of that fear, it’s unfortunately leading a lot of conversations and driving decisions. The mindset of scarcity versus abundance is making it challenging right now, because it’s hard to be hopeful.

As I said, “yeah, the north star is there. I’m going to get to it, having patience that it might take three years instead of one year”. It might take five years because of what’s happening. But I think there’s an importance of really slowing down. Slowing down entrepreneurs, we love to get stuff done fast. We love to push through, but it’s slowing down. I actually think that’s the thing that’s important.

Cory: Yeah, that’s slow down to speed up.

Krista: Slow down to speed up, yup.

Cory: And so when we think about that fear, I think there’s a healthy amount of fear to know, let’s not be reckless here. I also think about the other end of the spectrum that it’s just so scary. Let’s be done. And so, a lot of these businesses are massive employers. They add a tremendous amount to our GDP. How do we ensure that we’re actually making this environment something that the family can say, we’re still going to do this and do it well, and there will be a future where we exist and can prosper, and have that abundance?

Krista: You know, it’s interesting. I’m thinking of the Rich Dad Poor Dad book, and in that book, it talks about there’s a few things you shouldn’t cheap out on, your accountant, your lawyer, and your financial adviser. I’ve actually added the fourth one now, and that’s your family adviser. Because in this world of transition that we’re exploring right now, with a lot of baby boomers leaving the workforce.

There’s one or two ways this is going to end. The big companies are buying out everybody, and it becomes a large corporation world, whether it’s through private enterprise, whether it’s through a conglomerate, whatever it is. The other way is you spend the time and step back and go, okay, we’re going to have to do this transition. Let’s start it now because it does take time. And I don’t know that I’ve seen one less than five years ago. It’s going to hurt, and there’s going to be pain. But at the end of the day, if it’s part of your family values that it’s important to keep this business in the family, that’s the fourth category you don’t cheap out on, because there’s nothing more powerful than having those facilitated conversations.

As much as we think we can facilitate our own conversations, I think about my own business with my partners. Our conversations without a facilitator are much different than those with a facilitator, because we have our own emotions that come to the table. So it’s very hard for us to self-facilitate with our own emotions. And so having those advisers, whoever it is, but someone who’s truly well-versed in helping conversations move things forward, there’s really nothing more important in this day and age than conversing.

I think the biggest roadblock to the future is a lack of communication. Doctor Thomas Dean, I heard him speak a few months ago, and he said this phrase, and it’s going to stick with me forever. And he said silence kills wealth. And it’s true. Yeah. If you don’t talk about it, it’s the destroyer of wealth. And you can’t talk on your own. As much as we’d like to think we’re good, we can talk about this, there are certain things that people don’t like talking about. Money is one of them. Power is another. Well, what do you think is talked about in those rooms? Money and power.

Cory: Right! Absolutely. And so that next generation leader that’s listening to us right now, who’s thinking, there’s so much that’s going unsaid right now in our family. Where can they begin?

Krista: Well, I’m a big fan of coaches, advisors, and facilitators. What I’m not a big fan of is coaches, advisors, facilitators working with one person and hearing their story, because they will be the advocate for that person, not understanding what other dynamics are happening. And so if you’re out there and you’re going, okay. I’m trying to take over, but I’m struggling, being in a room, those conversations, they suck. They hurt because you’re family. As much as you’d like to think, we can segregate it; it’s hard. Having a group of advisers, one who is willing to work together, is absolutely key to having advisers that want to work together, are willing to sit in the room with you together and talk through stuff, each bringing their own unique skill set, is very important.

Depending on the size of the enterprise, I actually don’t think there’s a minimum to even having, you know, quarterly advisor meetings. And everybody sits in the room. What’s our strategy? What are we trying to achieve? Being really thoughtful and purposeful about creating the future. And is the next generation leading that saying, I think this is what we need to do? That’s important. That shows your first step in leadership. It’s your first step, saying we actually need to do this because we’re not moving. And making your business case as to why it makes sense. What would happen if you don’t? For the next generation, I think that’s the main thing. Don’t go get your own adviser and have them tell you the story you want to hear to sell, because they’re not going to hear the full story. They’re going to miss a piece, and it will go nowhere.

Cory: I love that! So, really, that next generation should be in those adviser meetings, and those advisers need to be talking to each other, which is maybe led by the family, or maybe led by the advisers. But if the advisers are doing it, the family’s probably going to start doing it. And if the family’s doing it and advisers aren’t, let’s hold our advisors accountable to upping their game.

Krista: I agree. Yes, and it’s hard. I mean, even as advisors, we have egos. So it’s like, what if they say something I don’t agree with? Well, that’s okay. Maybe I’m going to learn something.

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

Krista: Sure!

Cory: What is one key strategy you believe is most essential for building a successful family enterprise?

Krista: I think the most important strategy is developing a communication guide guideline. How are we going to communicate? When are we communicating? What are we going to communicate? It is the most essential thing in a transition: communication and over-communication. It’s going both ways. Next gen up to founder, founder down to next gen, or if you’re going from next second gen to third gen, over-communicate.

I learned this phrase: if you don’t think you need to say it, it probably means you need to say it. Because, well, I just said silence kills or destroys wealth. It will destroy the wealth, the silence. There’s one thing that I would say is pretty fantastic, and it was, I was talking with a colleague about the public boardroom, public businesses. And the thing that I most admire about a family enterprise is that most people are honest in that room. Again, it hurts. It sucks. But you’re getting the real deal. And that strategy of communication is going to, in the long run, help move forward. It’s it is.

Cory: I love the communication guidelines, and actually documenting that, and worrying when and how. And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Krista: I would say there are two. The first one is just, like I said, the leadership development, changing the next gen’s mentality for maybe being an employee team lead to an owner. There are a lot of challenges with that. The second would be capital. If they’re trying to buy their parents out, trying to allow the parents to exit with their money. It’s fairly difficult right now to generate that capital in the economy that we’re working in today.

And so there are two components on how you plan for that so that the parents can exit, slowly be redeemed out. What does that look like? How does that look? Every business, if you’re an entrepreneur, myself included, has personal guarantees. How does the next gen do that to get the parents out? There’s actually a lot of mechanics that have to go into it, not just the soft stuff of communication. There are a lot of economic and business things that need to happen with the bank, with the lawyers, with everything. So just that’s part of the communication, but it’s where are they going to come up with that capital? How are they going to come up with that capital?

Cory: Yes, and so important to have that strategy early. And that importance of having a healthy business that can sustain the next generation, also sustain the cost of buying out mom and dad.

Krista:  That’s right, exactly.

Cory: Fantastic! And in your experience, what are the top three key qualities that successful family enterprise leaders possess?

Krista: I think the top three qualities I would say that they possess are one, I would call it faithfulness. As families stick together, I find family enterprises, the employees are treated the same way. Just that sense of community within a family enterprise and the leader that they try to instill is very prevalent in a lot of family enterprises.

The other quality is, I think, a lot of them are very emotionally intelligent as well. They’ve learned how to be adaptable. They’ve learned how to change, observe, and move, which has allowed them to create a high level of emotional intelligence. How it comes out varies by leader, but I think that, you know, it is a key skill that a lot of leaders in family enterprises have.

And then I would say the third top skill that I think they have is consistency. And some people might say, “What consistency? They’re all over the place!” What are you talking about? What I mean by consistency is they’re constantly trying to be better, do better. And however that comes out, whether it’s by growing a business, growing employees, they’re consistently showing up, they’re consistently at the door, putting their foot out, going, which step do I need to take next? 

Those three skills really when you’re looking at leaders within a family enterprise help to build a community, help to build culture, and help to foster an environment of everybody trying their best.

Cory: Right, love that! Bringing it back to they’re actually doing their best. Before we conclude our discussion today, I’d like to highlight, where our listeners can find you, as well as if there’s any materials, things that maybe you’re putting out, or maybe things that you’re reading, listening to, or consuming, that might be helpful relative to our conversation.

Krista: I think, as you can tell, my biggest thing is communication. And so I’m always reading about healthy conversations, conflict conversations, dealing with conflict, because it’s going to happen. It’s inevitable. And there’s a lot of tools out there that we can educate ourselves on. I would say that that’s where I focus a lot, healthy conversations and healthy conflict.

I went myself and got certified in SDI, Strength Deployment Inventory, which is kind of like a personality thing, but it really focuses on what are our strengths are and what our overdone strengths are. So I use that with families to help them understand how they’re communicating with each other, and why there might be conflict when they’re working through stuff.

Through Andersen, which is the firm that I’m a partner of, we really try to just have that trusted advisor mentality.  Everything is customized. We don’t do piecemeal work. It’s absolutely customized to whether it’s our tax clients or our family enterprises that we’re working with, or our other enterprises that we’re helping with leadership development. I think there’s just so much power that comes back when you can create a communication foundation.

Cory: Fantastic! And I wanna make sure that we covered everything today. Is there anything else that maybe we didn’t get a chance to touch on that you’d like to share?

Krista: Being an individual who’s overcome a lot of mountains, I would just, you know, say out there, it hurts. It does. But you’ll get through it. And find your community. I think about Family Enterprise Canada and the community of family enterprises that are there supporting each other as well, not just advisers, but the family component of it. I so strongly believe in this. I joined the board of Family Enterprise Canada because I just want people to realize they’re not alone.

I fear a lot of families think that what they’re going through is not normal, and so they’re hiding and dealing with it in silence, but it’s not the case. All of your families out there are dealing with the same thing in transition, at different levels. Of things that are happening, they’re all going to feel some component of it.

And so being in a room with other families, going, wait a second, I’m actually not alone. I mean, this is maybe not the right analogy, but you think about Alcoholics Anonymous, where you surround yourself with a community of people who are growing and trying to be better. It’s the same type of philosophy. You’re trying to grow. You’re trying to be better. You’re trying to learn how to do this. Learning from peers is important as well.  If you don’t have the funds to pay for adviser help, surround yourself with peers who are going through the same stuff, helping to support, and learning from each other.

Cory: And having that peer-to-peer coaching is massively important. 

Krista: Massively important. Where we are, Calgary, there are communities out there that host sessions for next generations to get together and have communications, and we’re lucky to have that.

Cory: Yes, absolutely! Well, Krista, thank you so much for taking the time to share your experiences, stories, and your expertise with our audience. I learned a lot and got a lot out of our conversation, and I know that our audience will as well. So, thank you.

Krista: Awesome. Thanks, Cory. Appreciate you having me.

As we wrap up this episode, we invite you to reflect on Krista’s perspective that growth often begins with discomfort. Whether facing change or navigating complexity, steady progress comes from pausing, listening, and being willing to adapt.

Whether you are part of a family enterprise or provide consulting to family enterprises, Krista reminds us that effective transitions are built on clarity, shared learning, and the willingness to make space for new voices in decision-making.

Throughout our discussion, we explored the role of emotional awareness, structured support, and collaborative leadership in preparing the next generation for ownership. Krista highlighted how deep listening, clear governance, and purposeful dialogue help families move through uncertainty while staying aligned with their long-term goals. These reflections offer a valuable foundation for those committed to building enduring legacies within their family enterprise.

For families navigating leadership transitions or seeking to strengthen generational collaboration, Krista Rabidoux offers both technical expertise and real-world insight. You’ll find her contact information in the show notes, along with resources to further support you on your legacy-building journey.

Disclaimer: 

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