The Quiet Fix: Why Better Family Communication Starts Before the Meeting Begins

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 Shauna Trainor, Principal at A&O Partners LLP. Shauna supports enterprising families in articulating ownership vision, enhancing communication, and implementing governance strategies that align with their long-term objectives. With a structured yet adaptable approach, she blends systems thinking and solution-focused frameworks to guide families through transitions and the nuances of wealth and relationships. Shauna brings a deep commitment to collaboration, learning, and clarity, believing that when families work well together, they not only sustain legacy but also enrich the communities around them.

My goal is to be the most curious person in today’s conversation with Shauna. We’ll talk about how families can begin to notice what’s not being said, and why readiness, more than urgency, can shape whether progress takes hold. Shauna helps us consider what it means to approach complexity without rushing to fix it, how complaints might carry important questions, and why setting even the simplest meeting norms can shift how families show up together.

Now, let’s dive in!

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

Shauna: Let’s do it.

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?

Shauna: Well, I have to start by noting the Steve Jobs quote from the video that you had shared of his commencement speech, which is, of course, very hard to top. But I do love that, you can’t connect the dots looking forward. You can only connect them looking backwards. And this idea that you need to really trust the process of life and the experiences that will shape our paths that we take. And, you know, I think this question is actually a very unique offering you give to all those who join this conversation, because it’s quite deep, to look back and think about what it is that I’d really want to say? And actually very hard to make it concise, as he did in his commencement speech.

One of the books that I like is this book called Life Is in the Transitions. Just living with that idea that if I were giving a commencement speech, I would really want to be encouraging those students to take time to reflect on their accomplishments to date, to take time to really reflect on the relationships that have impacted them in their lives to date, and to really get curious about the questions that linger for them. And probably, moving from there, it’s that learning is actually just beginning at that moment in time.

Sometimes we might think, if we took ourselves back to being 22, 23 years old, it’s like, woah, all I’ve been doing is being immersed in education, year after year of learning. And is this really at the end of graduation? It’s not actually a break from that. It’s like a whole new opportunity to go after what you really want to learn about. Whether you’re diving deeper into maybe exactly your next step, and so you’re diving deeper into that path, or you have no idea where you’re going, and that is also a huge opportunity. And for students, they’ve been spending so much time directed to where they need to learn and not necessarily having the space and time to even really learn more about themselves.

Cory: Amazing! I love that because I’m thinking about how much of life we can be in somebody else’s plan, like, somebody else’s curriculum for education, as you talk about. And having that opportunity to now go from that directed to having space. And that can seem very powerful, but it can also probably break a lot of anxiety for people who have lived in this space where they knew what was next. They didn’t really have the choice, and now the choices are endless.

And so speaking to somebody, and maybe they’re not 23. Maybe you’re speaking to somebody who’s maybe later in life, and they’ve realized, wow, I now have this choice. Something’s changed. How would you speak to them in that?

Shauna: It’s actually a very good question, because even in my own work, when I look back, somebody says, how did you stumble upon working with families? In the beginning, I probably stumble on clarifying that to someone else, whereas now I can actually see the through line. As I started to actually tell my story, I realized, wait a second, there are these dots that have brought me here. There is consistency to where my interests lie, and why I see families as so valuable and at the heart of our communities as tremendous agents of change. 

And so I think, where somebody is experiencing uncertainty, or even might feel lost in some way, it is grounding them in what they do already know, the questions they have already answered for themselves, and uncovering what the big question that remains for you. Because I think we often underestimate the wisdom that lies within. And I certainly see that in working with families, where it’s trusting that they actually hold the key questions that they need to address. They hold a lot of the knowledge that will support them moving forward. And it’s just uncovering that. That is a big part of the work and individual work as well.

Cory: You made comment of the reflection on accomplishments, but you also made comment about the relationships. So let’s dive a little deeper into that one. Where does that play into the work that you do?

Shauna: There’s probably two pieces there, at least with how I see it. I think a lot of our culture, Western culture, is very individualist in nature, and supports this idea of going at it alone, or one person is really the leader. And I think it’s really important that we continue. I think that model is, by many, challenged, and that we continue to do that for young people, especially because nobody gets to where they are alone. And it’s so important that we encourage people to ask for help, get support they need, and look out to their networks.

So that’s sort of on a general sense, but in the work with families, that is going against the grain in that same individualist versus looking at the interdependence and the collective nature of the work that really, they need one another, and they’re to to both challenge each other and also support, to really kind of realize where they want to go to achieve their desired objectives.

Cory: And so having families made up of individuals, and that one end of the spectrum, we’re individualistic, other end, our identity is in the collective. When you say that families have the answer, they have the questions. Where do those come from?

Shauna: I think where relationships matter, so do conversations. And so I think they typically emerge through conversations together. I mean, sometimes I think there are questions that have been lingering in families that they want addressed, or there are complaints within a system that need to be turned into requests. So, you know, that’s reframing a question.

But I do think it’s in the listening and talking with each other that the biggest questions do emerge, and giving everybody time for reflection. All too often, we’re living busy lives, struggling to slow down, and can be passing each other by. And so it’s not until you slow down and connect that you can do that digging deeper and figure out what the questions are.

Cory: So, thinking of those complaints that are sitting there in the system, what do those sound like? Like, if a family is listening right now and they’re thinking, you know, what sort of complaints are there in our system here? And what do you see on the surface?

Shauna: Two quick ones come out for me, which is blame or shame. They sound like somebody’s being blamed for something, or they sound like somebody’s hurt and feeling shamed by something. If it’s just like, what are we listening for when on the surface, and how can we use what we hear to then kind of go after what’s underneath? And I think it’s also very important what that looks like, because if we hear blame or shame and we go into defense or judgment, then we’re not going anywhere, whereas if we can get curious, be patient and build our empathy in a system, then we we may just be unstoppable, because we’re willing to embrace the the vulnerability and go after what’s really going on.

Cory: Absolutely! And so you made a comment of the busy lives we live. And so this blame and shame it sits there, and maybe we tolerate it for a month, a year, a decade. How do we get that reframing? You talked about the complaints to request. So where did those go? How do we get there?

Shauna: With great courage. I think that without the courage to bring something forward, it might never come out. And that is sort of a sad thing for any relationship that you don’t bring forward, even if you don’t have the tools to necessarily change something from a complaint to a request. That a complaint is not brought forward or that requests aren’t is a sort of loss to any relationship. 

And, yeah, doesn’t recognize the strength we have to manage and tolerate those complaints and requests, if that makes sense. Like, we all have the courage to bring stuff up, and then I certainly believe that we all have the courage and capacity to take that feedback. It’s not easy. But I think, where there is love in that relationship, there’s certainly an opportunity to work through it.

Cory: Thinking about “we’ve tolerated this, we’ve grown accustomed to this, this is how our relationships are, this is how our system seems to be thriving.” And so we’re speaking to a family who doesn’t see this as a problem. Maybe there’s somebody who’s saying, I see that on the surface. Maybe there’s more, and they’re becoming curious. What would this mean to the family if they really dove deep into it?

Shauna: Well, I certainly think you don’t necessarily want to raise a problem a family doesn’t yet see. There is a “readiness for change” element to all this. And so timing matters. I think that the timing is important, and there might be somebody who sees something more. I mean, this is not unusual. You have, you know, one family member who thinks they see all the cracks, and they want to go after them.

And I think that patience is really important when working with families, because we want to be careful that we don’t actually turn any cracks into caverns. We want to mend the cracks, not widen them, or go after them in such a way that it feels like we’re going after drama, so to speak. I think it’s really important that there’s an intention, or a clear intention, as to why you’re going after a certain issue.

You can at least sort of see a potential path through, rather than going after something, because one or a few select family members really see that as the main problem. I think our role is to help family members step back and see the big picture, see even how they might be contributing to the problem. Because if they’re so eager for some change, that could be where the opportunity lies. Those who are most, or at least appear to be most, interested in the system, there’s a great opportunity for them to be role models. And how do we do things differently, to your point? Can things really change, or is this how our system is meant to operate?

I think just as individuals and in our families, we can just be in patterns that we imagine, like, no, we cannot really be like this other family over here. That’s way too far of a stretch for us. You don’t have to be like any other family. You will be your own, but it is important to tap into that potential and possibility.

Cory: And so, thinking about education. So we’re talking about education and structure. And so bringing that to families and their journey that they’re on as a collective, you made mention of comparing to another family. And I’ve had many guests talk about the power of peers, getting together with other families, and using their wisdom and their journey as an opportunity to say, where do we want to go? How do you see that balance of I want to be more, or our journey is our journey? And so how do families balance that looking out to others versus looking into themselves of where they’re going?

Shauna: I love this question because I think, at least what I’m hearing is, there’s often this, we’d love to hear from other families. We want to know the best practices of other families. What is the language that they’ve used in their family employment policy? And it is absolutely wonderful to learn from others, to capture what they’ve learned from going through their experiences, their process, or establishing policies and structures for themselves. And it is critically important that each family then says, would this be a good fit for us?

Actually, we love this book A Captivating Story of Family, Endurance and Love by Enterprising Families. Each chapter is the best practice a consultant gave them, and that they did the opposite. So, a best practice they were told was not to give spouses shares, but to keep them within the family. And based on their stories and their experience, they decided to create a structure that did allow for spouses to participate as partners, as co-parents. They thought that was the way to do it best for themselves. And that doesn’t mean that since they did something different, now we should adopt that best practice. 

They looked critically at options and suggestions and asked, will this work well for us? And, wow, what an amazing question to ask, before implementing and getting just very clear on what is our intention in implementing this structure, practice, or policy. And that does involve slowing down and getting really at the heart of what you’re trying to achieve.

Cory: And so, thinking about those biases we have or others who we interact with have, how do you see families use that critical thought to be able to say, is this right for us?

Shauna: I see them just actually thinking through the unintended consequences of what they might be implementing, and sort of thinking through doing some scenario planning around how will this really unfold, and inviting people they trust to also help them in that process. Whether that is a peer network that they have. “Hey, we are thinking of doing this for our family. 

Do you have any experience with this?” What questions would come up for you or their trusted advisers, depending on, or using the critical thinking skills of others, not just the family. I think the family is a very good start. And then I think to the point of where you have your own set patterns, thinking, and narratives that inform what you think might work best. The more people you can invite into that conversation to get at questions, consequences, and opportunities, the better.

Cory: I love that! So, consequences and opportunities. Sometimes we can get caught in chasing a rabbit down a hole. And sometimes it’s, this is way too much. I really don’t see where we’re going here, and why are we spending that time? There could be somebody who’s a bit critical of the process, or we also then could look at it and say, there’s so many opportunities here, and look what this can bring. And so how do we filter that? What’s going to have the highest impact on our family, or where are we going to have the best return on our efforts here by focusing on this? You talked about the family employment policy, the ownership policy. There are many different aspects. And, ideally, we’re growing that as the family has the need, rather than trying to anticipate everything that might come our way. But how do we know this is the right time?

Shauna: That’s a very good question, because I think sometimes in our work, where we start off with a discovery process and then we say, okay, there is a long list of elements to go after here. And I think there’s certainly an element of starting with the end in mind. So getting clear on a purpose, a vision, and the values of the family is very important. And I think, in doing a lot of consulting with businesses and entrepreneurs before that, that is, I would say, almost always where we would start in consulting with a business in my previous work.

Interestingly, I find in starting with families, sometimes it’s very hard to do that work first. And it’s, to your point, kind of finding when somebody’s ready. I mean, I don’t know this. This is sort of just an intuition that sometimes I believe that work as much as it’s so valuable and important, and it almost feels so daunting at the beginning for families. How could we possibly do that? Especially where there are communication issues. How are we going to come up with our vision when we’re struggling around a table? And so there’s a big piece of where there are small and big wins that a family can experience, depending on where they lie at the start. Are people frustrated with the system? 

Are people fatigued in the system? Or are people really excited and ready to go? Those variables really make a difference in what you can accomplish at the start. Because sometimes it’s building skills and capacities is where you’ll get the most value.

And to your point, you’ll see that return on effort. We’ve been practicing coming together as a shareholder group or as a family, and look at us. It’s not easy. It’s tough work. But we’re seeing different people, different groupings show up. And sometimes it’s just timing. You don’t do a family employment policy until people are saying somebody’s coming into the system. And it’s like, well, we did mention that that would be a really important policy for you. And it may be some families go after things early on, and some might not see the immediate relevance of something until it is relevant for them. It’s not right or wrong. It’s just I think that there are often so many things going on that you need to balance, what can we achieve? What kind of time can we set aside for this? And what will be most relevant for us?

Cory: You made mention about societal norms. I’m thinking about how you mentioned vision, mission, and values. And oftentimes, in management consulting, we’re in a group, in a boardroom with these executives, and there are norms. There are things, how we act, our behaviors. Now we’re talking to enterprising families here. There’s a boardroom or two in the mix, but now we’re bringing a family together who maybe don’t have that experience or knowledge of those norms. 

And maybe some people are frustrated with each other, or, you know, why don’t you understand how to act that way? Or maybe it seems so daunting to enter this room because there are others in the system who have these experiences in a situation that we don’t, I don’t personally have. So how do we balance that as an obstacle?

Shauna: I mean, what comes to mind, which might sound simple, but I think it’s actually very hard for families to hold each other accountable around just setting meeting guidelines. Because it’s true.  It could be a very new formation for a family to be coming together, whether this is current and future shareholders, to hear about the business, plan for the future, and build the structures and policies that they need to do. If somebody is a nurse in their professional environment or a teacher and coming to the table, I mean, I tend to believe that there are people who sort of know enough about how they should show up. It’s just when we fall back into our patterns of our family that certain unwanted behaviors might emerge.

I know that in our experience establishing meeting guidelines, it’s a way for families to say, hey, we said we’d really work at no heckling in this environment. We said we wouldn’t interrupt each other. It’s amazing where a sibling group has grown up with each other, their ability to interrupt, talk over, dismiss. I think it’s really important to not see it as a bad intention. People have the best of intentions. It’s just really getting clear about what are the behaviours that will best support us, and what are the behaviours that have gotten in the way of us being our best? 

And that simple process of the meeting guidelines, I find often we do this with families and they’re like, these are the things that will help us be our best in a meeting, listening, asking questions, starting on time, taking breaks, slowing things down. And then they can come up with the list. And then it’s practicing it that they realize, wait. Yeah. We do have this tendency to interrupt each other.

Cory: It’s, you know, getting comfortable. We’re a couple of hours in and realize, yeah. It’s not Thanksgiving dinner. We’re used to being around a table, and now we need to go back to those guidelines.

Shauna: Exactly. Like, kind of realizing it this is serious work. This does take a lot of time, care, and commitment, from everybody around the table. And, yeah, how can we help families raise the bar? That’s what they’re trying to do. And it’s never them. Humans have a tendency to fall back into old habits.

Cory: Absolutely! And so, thinking of maybe we’re an ownership group, and we’ve been meeting for a little bit now as siblings. And I’ve realized, my kids, they’re getting old enough now that they’re going to be entering in, either to the business, or maybe it’s close to that time where we as siblings became owners. And so now I’m thinking, I need to bring this forward. And so how do we bring that forward? And when do we start?

Shauna: Actually, we were with a family last week who had, just for the afternoon, so maybe a couple hours, brought in a nine and seven-year-old to just sit in the meeting. The nine-year-old participated in a couple of the breakouts, also created some beautiful artwork as part of the meeting. But really, I think it does two things. One, they see it. They say see, my whole family is gathered around here working, listening to different speakers, and there are these two other individuals in the room. I wonder who they are? And there’s also for the other two generations, this is why we’re doing the work. For this next generation who we can actually see coming, getting older. For the eldest generation in the room, they can probably have memories of their children at that age. And so I think this kind of, when and how we can often put a lot of pressure and structure around how to do that right.

And if I take from Brene Brown, there’s a kind of a gift of imperfection here. Just like parenting, you’re not going to necessarily do it perfectly. It might be a little bit messy, and that’s okay. As long as you have good intentions, you’re learning from that messiness, and you begin to develop a plan around how will this work, when will expectations be set in? At what age? If you’re going to be more specific about it, when will a more serious invite come? What expectations will come? How will we give feedback? How will we engage with another family? So how do you think about the role they can play in the meeting?

And I think each family decides. Somebody might fall off their chair if they hear, like, the nine-year-old was in the room. And some people might say, my gosh, why did we set the age of 16? It really depends on the conversations that are happening in the room, and you can pick the timing. Also, you can be careful about any kind of pressure that’s put on any, the youngest in the system, and ensure that the families are at a stage where it can be fun for them, and they can see you kind of in a good place. Like, where the role modeling is there. And so we have some families, the level of conversation that’s happening in the meeting it’s so serious and deep. They wouldn’t be inviting the nine-year-old to those. They’ll think about other places to integrate them.

Cory: Absolutely! Shauna, 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?

Shauna: Ready.

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

Shauna: I think there needs to be an openness and acceptance of feedback and accountability. I think this is an ongoing practice that we all need to work on.

Cory: Love that! I think that acceptance is a lifelong journey.

Shauna: Yes, and challenge. Like, I want to, I need to build acceptance towards you and the differences that exist between us, and I want to help challenge you to be your best at the same time.

Cory: Right! And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Shauna: Well, I think it’s almost like the flip of this is being clear around expectations, where accountability lies, and ensuring there’s feedback across the system. This kind of openness to what’s going to happen, how things are going to unfold, and what the opportunities are, but also responsibilities that will come along with that. I think that is a lot of the work with families.

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

Shauna: I really believe that humility is important, especially where you’re across a family enterprise. It’s seeing all that others bring to the table, and how it is really a group effort, even where certain people might hold key leadership positions. So humility.

Learning, I think, to do this work as a family requires an incredible amount of learning, of how to manage best in relationships. I think the second is learning. I believe that it is hard work to be an enterprising family, managing the transitions, understanding the policies that will be important, understanding the different personalities across your family, that this is an ongoing journey, it’s not only on the leadership, but it’s on everybody.

And probably, I want to say, love. Because one of the things I feel is seeing that as a verb, and the actions, responsibilities, and accountability that come along with that.

Cory: That’s amazing, I love it! Showing love is such a key quality, and doing that gracefully. So I think that’s fantastic.

Shauna: In particular, when you have a lot of family around, and for the non-family in your system, that looks to them like care, that people matter, that communities matter. That’s love and action.

Cory: And some of the best qualities of family enterprises is that they do care about themselves, but also, as you say, those non-family members. There’s so much care that exists.

Shauna: Absolutely. They’re drivers of our economies. When they do care about their communities, they can have a tremendous impact.

Cory: Yes, the reason that I do the work that I do.

Shauna: Exactly.

Cory: Shauna, before we conclude our discussion today, I’d like to highlight where our listeners can engage in more of the conversations you’re having, as well as some of the materials and items that you’re engaged with. You mentioned a couple of great books that we’ll link in the show notes. But I wanted to make sure that our listeners can find you, as well as anything else that relates to our conversation today.

Shauna: Well, I can be found on LinkedIn, and my home is in Toronto for anybody that’s around here. Actually, I’m reading this book right now, The Wealth Money Can’t Buy. And he has this very nice little chapter on reading. Book accumulation beyond life expectancy. And opens up about their passion for accumulating books, and that this feeling of having books surround them feels like a lot of wisdom wrapping them, which I thought I really like that, because I have a lot of books that surround me at the moment, and maybe, yes, more accumulated than I can possibly consume in my life. But I think that ongoing learning will never hurt you, and will always serve you in life and in work. So that is typically where someone might find me reading somewhere.

Cory: Amazing! And I wanted to make sure that we covered everything today. Is there anything else that we didn’t get a chance to share with our audience that you’d like to touch on?

Shauna: No. I feel like we meandered around, and I listened to a couple of your previous podcasts and realized, where we begin is with this commencement speech. And then you come up with a title for somebody’s podcast. It’s just from the train of thought and I, of the train of the conversation. And now I’m just curious what will have stood out for you.

Cory: I’ve highlighted a few quotes, and we’ll see where it goes. Shauna, I wanted to thank you for taking your time to share all the stories, your expertise. You’re very humble, and there are so many great little nuggets in our conversation today. I learned a lot, and I know that our audience will find some great strategies. There’s one thing for everybody in our conversation today. It’ll be different for each, but thank you so much for contributing and joining me.

Shauna: Thank you, Cory. I appreciate you taking this time to invite different individuals to share their story. It’s a beautiful gift to us, and hopefully to listeners.

As we wrap up this episode, we invite you to reflect on Shauna’s insight into how families begin to notice what’s left unsaid and how creating space for those conversations can open the door to real progress.

Whether you are part of a family enterprise or provide consulting to them, Shauna’s approach reminds us that effective communication doesn’t begin in the moment of tension; it starts much earlier, in how we listen, prepare, and show up for one another.

Throughout our discussion, Shauna offered a generous lens on what it means to communicate with intention inside a family system. She spoke to the value of patience, the importance of timing, and the quiet power of meeting families where they are. From reframing complaints to setting simple meeting norms, Shauna highlighted how everyday habits can either reinforce old patterns or make way for something new. Her perspective challenges the idea that structure has to feel rigid; instead, she showed how structure can support families in finding their rhythm, one step at a time.

If you’re exploring how to strengthen communication within your family or support others in doing the same, Shauna Trainor and the team at A&O Partners offer guidance shaped by experience, curiosity, and care. You’ll find more about her work, along with helpful resources, linked in the show notes.

Disclaimer: 

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