The Family Mirror: Why Self-Improvement Creates Systemic Change in Business Families

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 Holly Simmons, Principal Managing Partner at Golden Lasso Consulting. Holly is a Family Enterprise Advisor who specializes in leadership coaching, facilitation, and training for growth-minded family businesses. With a strategic approach, Holly helps family enterprises align values and purpose across business and family systems. Her tailored strategies integrate leadership development, effective communication, and purposeful role definition to propel her clients toward sustainable growth and family harmony.

My goal is to be the most curious person in today’s conversation with Holly Simmons, where we explore her journey from understanding individual values to building thriving family enterprises. We’ll discover how Holly’s unique approach helps family businesses navigate the complex interplay between personal boundaries and collective purpose. Holly will share practical wisdom on creating lasting legacies that span generations while maintaining healthy relationships along the way.

Now let’s dive in!

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

Holly: I’d love that. Thanks, Cory.

Cory: Imagine you’re delivering a 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?

Holly: Thank you so much, Cory. Such a great question. The first thing I would want to say is that I believe that what underpins life are relationships. We have relationships with so many things, and the ones that are most important to us are the relationship that we have with ourself, with our family and friends, with our coworkers, our community, the environment that we’re in, and and for some, their spiritual relationship that they have with the world and with their their spiritual teacher.

Part of that relationship is knowing how that will shape who we are in our life and what makes it important. And so there are three things that I have found to help me throughout my journey that I hope will help the listeners. The three things are do hard things, be generous, and notice the good. Each of these is interdependent on one another, and they provide us an opportunity to deepen relationships in each of those areas. So if it’s okay with you, I’ll share a little story about each of those.

The story I’m going to share is a personal one, and it is back in 2007 when my son was born. My son was born with a rare disease. And at the time, as a mom, before he was born, I was thinking that I was pretty pretty confident and didn’t need help from others. And when he was born, At the time, my daughter was 19 years old and it was a real shock for our family. And I realized that I couldn’t do this alone. And yet in that moment of overwhelm, I didn’t even know how to ask for help because I hadn’t practiced asking for help. I was pretty independent, I thought I could do everything myself. And yet I needed the help of others. And so I had to do the hard thing of figuring out how to involve others so that we as a family could navigate this very challenging situation for our family. And what I discovered is that people craved providing support and help, especially those closest to us, and that being generous was an opportunity for those people to step into. Helping and providing something that they could give and being generous isn’t about just the amount of time or giving financial support. It could be as easy as sending a text and saying, “thinking of you.” You know, that’s being generous.

And then the last piece is “notice the good.” When we are in times of struggle, and as we think about how we can often focus on the things that aren’t going right and that are really hard, when we take those moments that are good, it helps balance out our perspective. It helps us see that there’s more to life and the situation than we, maybe on the surface, are paying attention to. So it’s not about ignoring the things that are hard or that are negative, but it’s actually creating a more balanced view and picture so that we can make informed choices and feel more centered in ourselves.

Now these three things. This is one story that incorporates all three things, but these three things show up time and again throughout our life in relationship with others. I don’t know if we’ll get into it, but there’s also a paradox between these things. And I’ll say that specifically, let’s say, do hard things and be generous. Sometimes we think about being generous as giving of ourselves, and we have to sacrifice our own needs. But as I said, our relationship is about with ourselves, with others, and with our community and environment. So doing hard things is knowing our own boundaries and communicating our boundaries while also being generous. So in these three things, there’s complexity of the paradox that exists between each of them. And yet if we’re able to manage those paradoxes, our relationships will flourish.

Cory: Absolutely! When you talk about communicating boundaries, I think about that practice asking for help and also communicating boundaries. There’s so much in that. How do you see people within the relationships with themselves and others, practicing this well and developing those muscles?

Holly: It’s such a great question, because it isn’t easy, and it can sometimes feel like a bit of a tug of a war between those two things. What I have found is it’s a bit of an evolution for people. If you think about it as a spectrum, some people may be really clear on the boundaries, and then are maybe less on their ability to serve others, whereas some people are very much in that service place and then have difficulty expressing their boundaries. So it’s on both sides of that. So if we look at the side of the giving and, having that challenge of expressing boundaries, what I have found with people is it’s first about the reflection, the self reflection of knowing where you are on that spectrum and then knowing what your boundaries are.

Oftentimes, we aren’t even clear about what our own boundaries are. So how on earth are we able to express them? To others, if we don’t even know what they are and how they show up is that somebody has stepped over a boundary and then we’re annoyed or frustrated. But in fact, we didn’t even know there was a boundary there. So the first step is really doing the work of understanding our own boundary and having the realization that if you feel frustrated, offended, or in a place where a boundary has been crossed, isn’t that interesting? There must be something there that I can identify as a boundary. And then how do I then move into communicating that boundary?

Cory: Right! You mentioned not knowing that that boundary exists until it’s crossed. Are there other ways to identify those boundaries, maybe proactively and really understand one’s own values as it relates to that?

Holly: And that’s the key word, the values. Starting to understand our own values, what matters to us, is a great exercise that we can do to help us be proactive on our boundaries, as well as observing others, observing the relationship dynamics, and seeing what we can see causes friction in us, even if it’s not a boundary crossed by us, but upsets us, or we find that that’s “I don’t agree with that.” That is a signal that there’s a boundary. But starting with your own values, understanding not only the value, but the meaning you create around that word.

So let’s say you have a value of respect. Respect is a value. A lot of people have that. However, words create worlds. And so how you would define respect might be different and nuanced in comparison to how I define it. And so the meaning I create around that world, that word respect, actually signals then the boundaries that I have that might be slightly different than yours, because the meaning you create around the word respect is different than mine. And so when you think someone is being disrespectful, for them, because their definition of respect is different, they may not see it that way. So the work of understanding not only your values, but the meaning you put around that value is critical.

Cory: I love that! And, you know, as we think more about that that relationship with ourself, and really understanding ourselves and what’s important, how does that show up when it comes to that relationship with family and friends, thinking about that family system and how the individual relates?

Holly: When we think about the family system, sometimes the system itself can overshadow the individual. When we have done the work with families and actually got to know individuals first and what they bring, their talents, their skills, their treasures that they bring into the family system, it allows the system to expand. And so doing that individual work, understanding an individual family member’s values, their vision for their life, what makes them tick, what are their strengths, what are the areas that they need to manage because it’s a weakness for them, and then bringing that into the family picture, allows for the family to leverage all of those skills and all of those talents and gifts instead of the family trying to correct things that are deemed not fitting. And so there’s a celebration versus a desire to try to conform.

Cory: And how does that relate to your topic or theme around notice the good things? I think there’s something there Holly so can you expand on that.

Holly: Yeah so, when we think about families, there’s this old saying of familiarity breeds contempt. When we are with people that we know well, they tend to get our least amount of attention. We’re maybe a little less generous. We’re noticing all the things that they’re doing that we may not enjoy or create friction for us because we’re with them a lot, and we feel we know our family really well. And so this idea of noticing the good in a family, it allows a family to start to see each other differently in a unique way, like you’re seeing a person for the first time, and it balances out our view of how they fit into the family, what they add as an additive positive, and allows for not an excuse for things that are maybe poor behavior, but allows us to see a broader picture of an individual in that family setting.

Cory: Right! And so, families listening to us today, when you talked about “do the hard things,” I think about some of the habits that have been formed. That familiarity that you talk about is not only in the people around us, but some of those habits and the way that we treat each other. Where can some of that hard stuff start, that maybe doesn’t seem like we’re about to throw everything up in the air and create chaos?

Holly: Yes, and we don’t want to do that. We definitely do not want to create chaos in family. I think about it as “everyday, a little up.” It’s these micro shifts that we do that over time accumulate, that steer the ship in the direction that we want. We’re aiming for our true north. So what can we do daily? And so the doing the hard things, think of them as base hits. The hard things are typically the things right in front of us. It might be putting down our phones when our spouse is talking to us, or our kids come and and want to have a conversation with us, or they mention they have this little inkling of, they mentioned something that happened at school, and we have to be aware and be generous with our attention in that moment, and do the hard thing of setting aside our own priority so that we can be fully present with them in that moment.

And so these “doing hard things” are often related to your point about the habits that we are now unconscious of within our interactions with others. It’s stepping back, up, and out, and observing ourselves without judgment as to what are these habits that may no longer be serving us, saving me in our family, and then do the hard work of going down a dirt road until new habit is formulated. Do the hard work of moving into a new habit formation.

Cory: Right! And thinking about families where there’s a certain level of help, and generosity is in its form, whatever it looks like in the family. But maybe there’s a member who’s saying, I really want to reach out to that person and give them help. And so thinking about maybe one of your family members in 2007 where they didn’t know how. And maybe you weren’t aware enough or didn’t have the skills to ask for help. How do you think a family member could approach somebody in a respectful way and something that might actually have a positive interaction, and look generous rather than judgmental?

Holly: And that’s that’s the key. The judgmental piece. Because sometimes we believe we know the help that people need, and we get frustrated when they don’t accept the help that we believe needs to take. So being generous is a mindset in a sense that we want to be open to give in a way that the person needs, versus in a way that we believe they need to take. How do you step into that, especially when we may feel fear around not doing the right thing and being afraid of stepping on someone’s toes, or saying the wrong thing and that person getting upset with us? And this even is within family business context, where we may see a rising generation where we’re seeing that they’re struggling, let’s say, in a certain element of their leadership role. And as the matriarch or patriarch, we want to help them and be generous in giving them guidance, and yet we feel like they’re not willing to accept it. So how do we approach this?

I think the first thing is to acknowledge the desire to provide support, and that we don’t know the best way to do it. And this is acknowledging to the person, so I really want to support you. I’m thinking of you. I see that there’s opportunity here, but I don’t know how best to support you. When you’re ready, let’s talk about it. And then they may not take you up on that because they’re so overwhelmed that even thinking about how someone else can help them isn’t going to resonate. So at that point, it’s actually stepping in and working alongside the person. So how can you meet them where they are and go and say, so what are you up to? Ask questions and be curious, and step into this place of being beside, versus the person who knows. Take ourselves back to a moment when we may have been in a similar experience. Even if we haven’t experienced the same thing as another person, and technically, everyone has their own experience, so we can’t really have the same experience. But the emotion of an experience can be something we’ve all felt. Whether it’s grief, insecurity, or feeling overwhelmed, we can channel that emotion. So put ourselves in that place and walk beside the individual so that the generosity feels supportive rather than instructive.

Cory: That’s fantastic! And thinking about that, we all have our own experiences, there comes a time where often we see somebody who’s tried to relate to how somebody’s feeling or or where they’re at. And it was a bit of a swing and a miss. It was like, you’re trying to relate something that happened to you, but it feels like it was nowhere near what I’m feeling right now. And so, is there anything that you would say from that perspective where somebody could be a little bit more aware of how they’re communicating that?

Holly: That’s so great! The communication piece, it’s that mismatch in the conversation. We’ve missed the ball that’s thrown to us by someone. They’ve thrown us a ball of needing some understanding. And what we’ve been taught in society is that how we show understanding is to share a similar story about ourselves to show that I get you, and that can land flat. It can get missed. So I think we can recover from that in the moment and actually acknowledge that and say, I sense that the story I just shared with you didn’t really land. It’s about that vulnerability and that transparency in those moments.

And then the other piece of it is that walking beside somebody, it’s slightly different than putting yourself in another person’s shoes. And I say that because when we try to put ourselves in somebody else’s shoes, we think about the stories that are like the story we’re hearing. But when we walk beside somebody in empathy, we actually feel a connection to somebody and are curious about their experience. And so we move to a place of curiosity to understand their lived experience versus relating it to us. So the focus goes from being about me to being about this other person who’s sharing something personal and is looking to be understood. And really, it’s through just asking some questions and being curious about what you’re hearing.

Cory:  I love that, that’s fantastic! I love the journey that we’re on. We started talking about the relationship with ourselves, and then talking a little bit more about family and friends, continuing on and thinking about this in the constant context of community. Maybe those who aren’t as close to us, and some of the skills that we need to be able to go beyond. I’m thinking about it in the sense of it could be employees within our business. It could be advisers in which we work with. It could be community members who we support from a charitable perspective. How do some of these skills that we talked about help in those contexts and those relationships?

Holly: Yes, and it might work from the notice of good, be generous, do hard things. Think about these things as we think about our community, it’s thinking about our role in a community and the purpose we have beyond ourselves, beyond our immediate family, and the impact we can have within a community. And that impact can be as simple as when you’re out in the community or at your local grocery store, and you look the cashier in the eye and say, how are you today? You know, you’ve made this connection with somebody in your community, which is very simple and yet can have a powerful effect on a person’s well-being in that moment. You’re showing your community that you care.

And then from a charitable perspective, it’s getting involved in those areas and community organizations that you’re passionate about where you can make a difference, and that you can feel like you’re giving back to something that’s bigger than yourself. And you’re part of creating something that is adding value to your community, you’re one of the many people, and you get to share in that collective, uplifting of that community, either of organization or the community as a whole, and the value that brings to you as an individual. And so that’s that generosity piece. It’s stepping into a service mindset. And that can be hard because sometimes we have to prioritize and make sacrifices to do that hard work for the long term return, which may not be seen in your lifetime. You may have done some seeding of work in an organization or in your community that comes to fruition in the next generation. That’s hard because we’re so conditioned to have instant gratification. And so the instant gratification comes from that feeling in the moment of doing good, of contributing. And the hard thing is keeping focused on that long-term vision.

Cory: Right! And so going back to the word purpose. We talked about values, beliefs, and behaviors, but going to purpose in the relationships that we have, how can someone really become true to that purpose? When we talked about boundaries, we said sometimes we don’t even know they exist. And so from a purpose perspective, we are living to a purpose, but sometimes people just haven’t identified that. Any insights on really identifying that purpose for oneself and then for the family?

Holly: So this work is reflective work. I think the first step is actually giving yourself space and time to do this work. And I’m not talking hours. I’m talking five minutes in the morning with your cup of coffee, that quiet time, just thinking about “what is my purpose?” And just keep asking that question over and over again, and allow the intuition to rise within you and jot a few things down. And then over time, that purpose starts to meld together. Think of it like a seed that’s planted in the ground. The seed isn’t, or the acorn is not an oak tree. If you cut open an acorn and looked in it, you wouldn’t see an oak tree. But if you plant that acorn in the ground, it calls out oak tree, and it draws towards it all of the things it needs in that moment to grow roots and sprout.

And so this idea of purpose is very similar. We have to keep calling it towards ourselves, and the things that are important will be drawn to us. And then it will be formulated for us. And think of purpose as something that is, in the distance as our true north in the sense of it’s out there in the future. It’s out there in the distance. It pulls us towards it, but we never quite reach it. It’s like finding the end of the rainbow, where it allows us to strive and achieve and work towards something that is so big that it brings us great joy and great satisfaction, and yet we know there’s always more that can be done to get there.

Cory: Right! And so, talking about the words, you mentioned this as reflective work, and I think about your story about chasing the rainbow in that you’ll never actually get to the rainbow. But in reflection, how do we use the past to help us identify that true north?

Holly: Great question! Our past gives us information on our habit patterns, our belief systems, and opportunities for improvements, like things that worked? Great, I want to repeat that! So stories of our past provide a framework of learning that we can utilize and take forward into the future. It allows us to experiment. Think of past experiences as experiments, and we created a hypothesis at the time. We had a thought. We acted on it, and something happened. So our experiences from the past that are examined provide us with information that we can leverage for the future. Whether it’s the generational history of our families, of a family business, of our ancestors who came to the country and started with nothing. There’s stories here that provide us seeds of wisdom that can help us draw a picture of that purpose, as well as the map of how to move towards that purpose.

Cory: Right! And in your experiences, can you share a story of a group that has done this well?

Holly: There’s a wonderful family who I had the privilege of working with where three generations, the third generation is working in the business today, and the second generation is leading at a high level of the organization. The third generation did a deep dive into their grandparents’ path to starting the business, and that deep dive allowed them to see their relatives or grandparents very differently, and renewed this respect and this desire to harvest or to mine the wisdom of their grandparents. And then that helped them see that their role and purpose within the organization was way bigger than being the leader of the company, and way bigger than growing the business to being a certain size. It was about this legacy, it was about holding on and paying homage to their grandparents, making their grandparents see the value that they see, and the respect that they have for their grandparents.

Cory: Wow! And so taking that story of those before us in finding what is that purpose and that north star. Once that’s been done, what’s some of the byproducts we see happen because of this?

Holly: Well, I think we know that family businesses in general are very long term thinkers. And so this having clarity around this purpose allows for that to continue and gives us a reason behind why we might be putting off a decision or why we’re making certain decisions that on the outside might seem counterintuitive. But because we have this very clear north star that we’re moving towards, we can clearly articulate why we’re making certain decisions that may seem counterintuitive. The other part of that is it also allows us to create vision, because a vision is something that moves us forward towards that purpose.

I separate the two. I see purpose as being different than vision, that vision is, let’s say, a three year rolling thing, and we get to the vision and we’re able to achieve some element of that vision, and then we have to cast the next vision. Because as we climb one mountain, the next mountain range becomes visible. And so that vision piece is actually drawn from and falls out of the purpose piece, which then leads into our strategies as a business of how we’re going to make that vision a reality, which then rolls up into tactics of what we’re going to prioritize this year. So you can see how that purpose piece, which is also included with the values that we have as a family, trickles down into creating tangible, actionable things, but they’re tied together.

Cory: Right! And so in the theme of doing hard things, thinking about what these actions can be today, I want to go back to your comment about thinking long term, the impact of something that we’re doing today that maybe we don’t get that instant gratification. Maybe we’re laying that foundation so that our grandchildren can look back, that gen five can look back and say, wow, look what gen three did in their work. And so what are some of those frameworks that you see, or actions that are being taken where the family is like, why are we doing this? We really don’t feel like this is instant gratification. This isn’t the tactic or strategy of the business that’s going to make us lots of money right now, or we’re going to see the fruits of our labor from this today.

Holly: Yeah! right on. So this idea of purpose and doing hard things, how do we move to that, and how do we do hard things on a daily basis? And especially in the face of that instant gratification piece. I think it has a lot to do with doing the daily things that are related to who we are, and who we want to be in our character. And so by understanding where our purpose is and defining where we want to go, what our values are, well, in that I know the kind of person I need to be to achieve that. And those pieces, I get to choose every day in how I show up, in the interactions I have with the people in my life, and the things that are even unseen, the actions I take that nobody notices. I know, but they may not actually come to fruition for a month or three months. But I do believe, and I have to trust, that if every day I make the right little moves, that I’ll be moving in that direction towards my purpose, and I have to trust it because I know in my heart that I am being the kind of person I want to be.

Cory: Right, I love that! And it makes me think of if we’re all in the family acting that way, it really does create a culture, and allows people to see that maybe without it even being written on the wall or presented in writing, because we’re living that day to day as you mentioned.

Holly: Yes. I think the paradox here is that we can have a tendency to focus on how other people are doing in living up to the character that we think that they should have. And the fingers are all pointing everywhere else, or we’re holding up mirrors to other people without turning it on ourselves. And there is so much work we have to do here in ourselves. There’s really not a whole lot of time to be focusing on other people. And so there’s humility in knowing that we all have work and opportunity. I know what kind of person I want to be. And does every decision I make every day match that? No, because I’m human, I know that I could do better. Sometimes my energy is lower, and sometimes I’m not feeling great. And sometimes life circumstances are that my hundred percent that was a year ago is different than my hundred percent today.

And so we have to remember as family members to keep that mirror and that focal point on ourselves, because as soon as we start looking outward at others and judging other people, we end up actually missing the opportunity to do the work on ourselves. When we do the work on ourselves, other people notice it, and can then want to strive to be better themselves.

Cory: Love that! What a great place for us to transition as we near the end of our conversation. Holly, there’s a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Holly: Yes, I think so.

Cory: Alright, let’s do it. What is one key strategy that you believe is most essential for building a successful family enterprise?

Holly: Wow, I mean, this is a big question. So, you know, definitely don’t make it easy for me. I would say that one strategy, and it’s a really simple one, is having awareness around how your family and your business operates. So stepping into that experience like it’s the first time, like you’re a visitor to that system, or you’re sitting on the balcony, and observe without judgment, so that you can start to see it with fresh eyes and be able to notice what’s working really well, and where there’s opportunities to build in on those relationships and do some hard work of, habit adjustment, maybe being generous and noticing the good. So it’s that the strategy is taking time to notice, observe without judgment, and see where there’s opportunities.

Cory: Fantastic! The opportunity that we have as consultants to be that observer, it doesn’t necessarily require somebody else to come in and observe. I think that there’s so much that the family members can do, and those business leaders to also be observers, daily.

Holly: Absolutely! It’s a co-creation, actually. We can utilize our advisers as ways to hold up the mirror for us because we can be too close to something, and then take that observation, sit with it and see where it’s true for us and where it might not be true because we’re closer to it. And so it’s a co-creation with others that makes it very powerful.

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

Holly: I would say one of the biggest challenges I see is holding on to old belief systems about who people are, and then making decisions based on that information. A lot of it shows up as a lack of transparency, communication challenges, feeling frustrated or non-trusting within the system. And that stems from this idea of holding the past as being true today, and proving our belief systems right by only seeing the things that actually align with what we already believe. And so I believe one of the biggest challenges is our attachment to the past and our own belief systems.

Cory: And is there a strategy or maybe one place that you find people can start to overcome this?

Holly: I would say that it’s often in the point where you’re feeling most stuck or the most friction. Like, you’re just so frustrated or feeling like you can’t make a move out of that place, this is the perfect opportunity to do some work in that area and uncover what those belief systems are. And, okay, I have a bias as a coach that that’s the kind of work we do as a coach, to help dive into what are those belief systems, what might be a new belief system you can experiment with, and see what happens. So that’s where working with a coach can really help.

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

Holly: I would say the first is a willingness to learn so that they see opportunity in taking experiences and constantly learning, and then applying that learning to what’s next. Strong vision, ability to not only picture the future, but also articulate that and paint that picture for those who are looking to be inspired and brought along on the journey, helping provide that immersive experience of what that future can be like so that it creates momentum. Great leaders have that ability. And lastly, I would say they have this ability to have humility. They’re aware of what they’re strong at, and they’re also able to see where they have gaps. At the same time, see how other people can help support them in those gaps. So there’s that humility of being able to say, okay, here are my gaps, and I’m going to trust another person, whether it’s another family member, or other advisers, or senior executives, to help in that area because I know I don’t know it all. And I’d say those are the three key areas.

Cory: Awesome, love that! And before we conclude our discussion, I’d like to highlight where our listeners can engage in more of the conversations you’re having, as well as some of the conversations or resources that you’re engaged with. Could you kindly provide us with where our guests could find those?

Holly: Sure! I think you’re going to share my contact information. My website is golden-lasso.com, you can find me there and on LinkedIn. And then other resources that I find really helpful, there’s a great book called Conversational Intelligence. It’s a fabulous book that talks about the science behind conversation, and allows us to understand how to build trust with people, going from distrust to trust, and how we can use regulation and co-regulation to create those environments for candid and sometimes difficult conversations. And then the other, maybe a little different content that I listen to regularly, is a podcast called The Knowledge Project. And it is a fabulous podcast with really interesting leaders from all different types of organizations who have gone before and have learned so much, and they share that learning. And so there’s always wisdom I find in that podcast, especially because of the variety of people presenting.

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

Holly: No, Cory. I think we really dove into a couple of important areas that I think was a very philosophical conversation. But overall, I think all of that underpins the work I do in helping families with their communication and succession planning.

Cory: Fantastic! Well, thank you, Holly. I appreciate you sharing your time with us, your expertise, telling the stories and experiences that you have with some of the families you work with. Your insights have been incredibly valuable to me myself, and I know that our listeners will also find some amazing pieces where they can get started, or wherever they are on their journey. So thank you.

Holly: Thank you, Cory.

As we wrap up this episode, we invite you to reflect on Holly’s powerful insights about boundaries, self-reflection, and the importance of daily intentional actions within family enterprises.

Whether you are part of a family enterprise or provide consulting to family businesses, Holly’s emphasis on noticing the good, embracing generosity, and doing the hard things provides valuable guidance for creating lasting legacies and healthier family systems.

Throughout our discussion, we explored the journey toward purposeful family enterprise leadership. We delved into Holly’s philosophy of “walking beside” others rather than instructing them – those moments of genuine curiosity that strengthen relationships. We examined how understanding individual values creates stronger collective systems, particularly when family members focus on improving themselves rather than critiquing others. These insights offer a practical framework for transforming daily micro-decisions into long-term vision, ultimately fostering resilience, authentic communication, and a legacy that honours both individual contributions and shared heritage.

For those seeking expert guidance on family enterprise communication, leadership coaching, and strategic alignment in family businesses, Holly Simmons at Golden Lasso Consulting, is ready to assist. We’ve included Holly’s contact information, along with links to her website and additional resources, in the show notes to support you on your journey.

Disclaimer: 

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