Who You’re Becoming: How Strategy, Leadership, and Legacy Start Within

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 Keita Demming, Partner at The Covenant Group. Keita is an award-winning author, educator, and coach whose work focuses on transforming organizations into idea-driven, people-centered spaces. His book, Strategy to Action, offers a practical path to closing the gap between what we envision and what we actually do, both in business and in life. As a trusted advisor in design, strategy, and innovation, he brings a belief that by learning from others, we can make our own path forward a little clearer.

My goal is to be the most curious person in today’s conversation with Keita, as we explore what it means to become the kind of person who can carry the future you’re building. We talk about strategy not as a fixed plan, but as something shaped by the questions we ask, the relationships we build, and the way we reflect in real time. From curating your inner circle to facing conflict with clarity, Keita shares how leadership and legacy are shaped by the quality of our conversations with ourselves, with others, and within the systems we seek to influence.

Now, let’s dive in!

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

Keita: Looking forward to the conversation.

Cory: Keita, 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?

Keita: I think the advice that I would give is to ask a better question. So I’ve really come to appreciate the value of a good question. So if I could speak to my younger self, I would really get them to zone in on what’s a guiding question that you need to set as your frame in this moment. And I’ll give you an example.

So currently, the frame question that I’m using a lot is, who are you becoming while you’re building what you’re building? And it kind of comes from this idea, of sometimes, in a very difficult situation, there’s a question that I find to be very powerful, which is, who do I need to be in this moment, or what does this moment demand of me? And I find that to be a really powerful pause when I’m navigating the world, especially as unpredictable as it is as of late, if that makes sense.

Cory: Absolutely. And so tell me, Keita, the “who are you becoming,” what does that question mean to you as you ask that to yourself?

Keita: I do get a coach, really high-performing financial advisers, people in this space. And I think if you’re not getting better and you’re not focusing on personal development, you’re kind of stalling. So if I’m building this thing, I’m building this business, I’m building this community, whatever I’m building, hopefully, in that process, you are changing and you’re evolving. And I think some intentionality around who I need to be or who am I becoming as that process moves along, I think that’s a good thing. But because we get so busy and we get focused on the product, we don’t necessarily then bring the question back to us and say, okay, what skills am I missing? What skills will I need if I want to go down this path?

There are lots of examples where I have a client whose biggest challenge was that he was very conflict-avoidant. And what I did with him was I kind of did some rough numbers, and said, hey. He was so conflict-avoidant that he would pay his vendor’s bills when they made a mistake because he’d rather pay that than confront the person. So we did some rough numbers, and it turned out it was about 12% of his revenue. His expenses were I could attribute to him avoiding conflict. I could directly draw that line. So for him, the person that he needed to become was somebody who was okay with having those hard conversations. Not somebody who’s going to go and fight with everybody, but somebody who is just more comfortable saying, hey, I need to go and have a hard conversation with somebody. And what he realized was that most times, it was okay if he had a hard conversation. And it was more we made up fear of what might happen that was preventing him from having this hard conversation. It’s really turned around his business. So sync things like that.

Cory: And in that pursuit, or that builds, where does that focus come into play?

Keita: Can you, in that pursuit of that, but what say that? Ask that again.

Cory: So your question is, who are you becoming while you’re building? And so that I focus on myself and who I am, and how I’m showing up versus there’s a pursuit here. We’re building something. There’s a goal. There’s a strategy. And s,o where do you see that fit into the equation? And as you mentioned, a lot of people are focused on the goal and not on themselves.

Keita: So maybe I’ll answer in a different way. And even I’m guilty of this. So when I wrote my book Strategy to Action, it really centers around four moves. What’s your desired future? So I get people to lay out, hey, this is where I want to be five, ten, fifteen years from now. What do you need to prioritize? That’s move number two. It prioritizes these three things, no more than three. How do I create alignment in the short term with where I want to be moving forward? And then resource allocation, which is really the essence of strategy. How do you allocate resources? What am I saying? That’s the essence of strategy. Building out those four quadrants is what helps people.

My biggest realization in working with my clients has been that the world will tell you to chase the dream, and I tell you to chase the dream of a desired future and frame that out, write that out in detail. And I think it’s a worthy pursuit. Today, I would answer that. I would tell you to chase a better question. Dreams are there. They make sense. They can be quite nebulous, but the questions that we hold orient where we head. So if you break down the road question, it starts with the word quest. So what journey am I going on as I think about it? And I actually think strategy is about asking a better question.

So one of the things that I work with my clients on is, instead of having a vision or mission statement, what’s the question we’re trying to solve as a company? So what’s our guiding question we are asking ourselves? Because in answering this, we become the best in class, if that makes sense. And a lot of this comes from, let’s call it, recognizing that the world is nonlinear. It’s complex. It’s ever-emerging, ever-evolving, and we see that every day, even more so in today’s world. But because we come from a long tradition of scientific management where we try to reduce things, and we think about things as machines, and that’s what a lot of the management literature says, is that you want to build a machine, and organizations are like machines. I believe organizations are like conversations. And if we change a conversation in the organization, we transform the organization. And I think the best conversational tool we have is a short, powerful question, and that’s where a lot of it is coming from. Does that better help to frame what I said initially? Is that a better way of positioning it?

Cory: Absolutely. Now that quest, Keita, that each organization is on, when you’re thinking about this short question that’s being formed, where, and how often is that being adjusted? Is this a guiding question that if we can get it right, it doesn’t matter the environment we’re in that that question still allows us to be best in class, or do we need to be looking at that question constantly to say, is this still our question?

Keita: So I think it’s a bit of both and, but in general, you don’t want the question to be changing too often. It’s kind of like you don’t change your mission statement very often. And if you do, then maybe you’re a startup that’s constantly pivoting. I don’t know. And there could be really good reasons to shift your mission very often. But what I’m talking about is a framing question. I’m trying to think of a company that I can work with where I could share the question without getting myself into trouble.

So for example, you think about a company like Patagonia. Patagonia had this essential question, which is how do we create athletic wear and have a light footprint on the planet? That was essentially a guiding question. And they kept asking that question over and over. Companies with a strong purpose-driven focus tend to be very good at having this framing question that informs everything they do. The reason I like it is because I’m about to do X. Does X answer this question that we think is the essence of our company? And it’s a really easy thing for us to share with colleagues, for everybody to have in mind those kinds of guiding principles, if that makes sense. For some reason, I’m really struggling because the examples that are coming to mind are of clients who would not want me to share them publicly. This is why I’m struggling. So I’m just going to make one up.

So let’s say you think of somebody who’s trying to make environmentally-friendly washing pods. I’m just making this up. Their framing question would be something around how do we create a product that is minimal in the environment, but for our clients, it’s giving them the best washing experience that they possibly can. The reason that question becomes important is that in their research and development, that’s what’s guiding them. In their sales, that’s what is guiding them. In their packaging, that’s what’s guiding them. So these guiding questions end up being a very easy tool we could use that everybody in the organization can have, if that makes sense.

I’ll use financial advisers. If we are a retirement company, I’ll make up a retirement company. My company is called RetireWell. Right now, I’m helping people retire. The guiding question in my company should be, when we engage with our clients, are we setting them up in the best way possible so that on the day they retire, they retire exactly how they’ve always dreamed? Did we do that today? And one rule could be if somebody breaks that rule, that’s like strike one. You get three strikes like that, and then you have to find someone else to work. That makes the HR very easy. So we made it really clear that this is our guiding question. This is the thing that we’re constantly doing. We decide to implement a CRM. We start with our guiding question. How does this CRM help our clients retire the way they’ve always dreamed? Because that ends up being the thing that informs us.

Let me try and say this a different way. I say strategy is a practice. There are people out in the world who define it as a pattern. They define strategies, all kinds of things. I think it’s about behavior change. It’s about the conversations we have. So for me, if you have a strategy and it’s not embodied by your people, what are you doing? It has to be lived. Your strategy must be a lived thing. And that might sound esoteric or hippy-dippy. But I really believe that when it comes to strategy, you have to think about it as a practice, something we intentionally do on a regular basis that helps us achieve some kind of outcome. And I think that’s a piece that is often missing from folks, if that makes sense.

Cory: It does. And so thinking of that behavior on an individual level, where do you see people showing up their best in that moment? That was kind of the second part of what I heard you say, is that who are you becoming, and that they’re actually asking themselves in that moment, who am I showing up to be? And so when you’re seeing people or speaking to our listeners, maybe a rising gen member here who’s thinking, okay, I’m reflecting on the way that I showed up in that moment or the way that I need to show up in this moment. What does that look like as a thought pattern and behavior?

Keita: As a thought pattern and behavior, I think just adopting the frame that we build the future through the conversations we have. Just that framework, I think, alone changes your behavior. Now you’re having those conversations at three levels.

Level number one is the conversation with yourself, the conversation with your inner circle, and any conversation you’re having with the sector or system within which you’re working. Most of my work is on conversation with yourself. I’m coaching a client and helping them really understand how their emotions are either hindering or helping them achieve their desired future, their goals, objectives, those kinds of things.

Some of my work is now team-building stuff for your inner circle. They put people closest to you. Your family, your best, your business partner, that’s your inner circle. You don’t let people into that circle. The reason that’s important is that, especially in immigrant communities, and I’ve had this happen to me, you tell them a big dream that you have. And what happens is, because that scares them, they tell you it’s not a good idea. So you have to curate your inner circle in a way that helps you achieve your wildest dreams and be willing to go after it. Because if you play safe, which is what often happens, I think you will never live up to your full potential.

So it’s really important to first have a healthy conversation with yourself, and that takes a lot of work, inner work. You need to curate your inner circle to put people who believe in you. After you figure out how to believe in yourself, you don’t have to have people in the inner circle who believe you. You have to know when to ignore people. And then you have to go into this sector system that you’re working in and execute relentlessly. And a lot of people really struggle with that piece. It’s the unspoken side of strategy where it comes down to who’s contributing to the conversation, who’s not. Which conversation puts us in a better shape to have our desired future? Which conversations are worth having, not having? Because for me, the conversation is the action, and a lot of us do not see the world like that. And I understand that that’s a very different way of just framing things, but I’ve come to really double down and believe that we create or build a future through the conversations we have.

Cory: Now that hard work that needs to be done on that self side of things, maybe a couple practices for somebody or who are saying, okay, I need to start here. Do you have one where it’s like, if you’re doing this as a practice, you’re probably in embodying that self side well?

Keita: That’s a very good question. I think the best way to answer your question is that one of the questions that I quite like, or one of the things I’d like to tell people ,is that talk to yourself the way your best friend will talk to you. Because for a lot of us, the way we talk to ourselves is horrible. If somebody talked to us like that, we wouldn’t be friends with them anymore. The way we talk to ourselves is quite detrimental to our own self-confidence and our own belief systems. So I think starting with your self-talk and becoming your own biggest fan might sound easy and trite, or like I’m making light of a situation, but you have to start with the way you talk to yourself. You have to start by talking to yourself in a way that builds you up.

Now, there’s something that I think is often missed, and is how I landed on this notion or idea, is that I do a lot of strategy planning with people. So people hire me to walk them through the strategy quadrant, and we will put them on a quarterly basis or whatever. The thing that I’ve realized is that for most people, they think that strategy is about logic. It’s about data, logic, frameworks, and those things definitely play into building out your strategy. But the things that determine if a strategy is going to be successful at any level are always things like egos, relationships, and emotions. And in our world, for some reason, we have taken emotions out of the conversation. So we can even have a conversation about how our emotions, egos, and relationships play in the decisions we’re about to make here. Because they do play a big role. But for a lot of us, we lean towards the data, and we pretend as if the emotions are not helping to curve or influence what’s happening here. And I think that that’s a big piece for me that I think is often overlooked as people build out their companies, go after their big dreams. Does that make sense?

Cory: It does. And I think it goes back to talking about companies being machines.

Keita: Right.

Cory: The people being machines that we don’t have emotions. That notion is foolish to think that we’re not more than just an inch deep of depth. There’s a lot to a human being there.

Keita: So I think the other piece around this is a conversation around power, and that power is often being negotiated. So people in companies would play games, and we’re striving for power, trying to be on top, and get more of what we want. And that is happening, but very little of the literature talks about that. So if I’m doing a strategy, most people think, what would success look like here for me? We would have a strategy plan we’re all confident in and believe in, and we can execute on. That’s what success is initially when somebody comes to work with me. By the time they finish working with me, success is strategies and lived practice of having hard conversations faster. We now have a culture where we can move to the hard conversations faster. And that’s what a successful strategy is to me.

Because what happens is we then have these beautiful plans that usually sit on a desk somewhere, and everybody’s going along together. Everybody’s focused on, I need to do this thing for me, and I’ll get my bonus. But really, the thing that will make this entire company go to the next level is this hard conversation I need to have where the cofounder is disengaged, and he’s really become a waiter on this company, and we need to figure out a way to buy him out, because he’s now the biggest liability in the organization. Who’s willing to have that conversation? Nobody. Especially, like, the co-founder might be living in past lives. He used to be so amazing. And then the people who are working on them were like, this guy’s an idiot. It’s a disaster. I am unfortunately using a real-life example, but things like that, if our strategy is successful, we now have a culture or practice of moving towards those hard conversations faster, if that makes sense.

Cory: It does. And, Keita, I want to go and talk about that inner circle. So moving a little bit beyond self, I want to clarify, does the inner circle include people, and your words were around people who will cheer us, I think is what I heard, challenge us, and really be our best cheerleaders. And so I’m thinking about this in a personal context, but then I’m also thinking about surrounding ourselves in a leadership team. Is the leadership team part of our inner circle, or are these curated people, from a personal perspective?

Keita: So the answer to that is always depends, and I’m not copping out on that. It just depends. So for example, if you have the capacity to choose your leadership team and it’s your company, I hope that everybody you choose in their leadership team is what I call a wolf, somebody who you could rely on. Like, we work with wolves. We don’t hire sheep. The biggest reason people work with me is because I have them realize, hey, the three people I hired, they’re not wolves, and I need to, like, replace them or change that out.

But here’s the general thing I want you to understand about your inner circle. Nobody influences you more than you. We could all agree on that. But then the people around you then have more influence than you. So your wife, your partner, your best friend, your business partner, etcetera. That becomes the inner circle. Now there’s a social side to things where there are people who you socialize with, and they have nothing to do with your career ladder. They’re not on that train. But the work that I do is about how we become intentional about where we want to be five, ten, fifteen years from now. And a big part of how we realize our desired future is being very intentional about the relationships that we have in our lives. I have friends who, the only purpose they serve in my life is entertainment. There’s no deep conversation with them.  I have other friends who I could talk about what fatherhood is like and what. And I have an intentional group around those people that do that. And then I have an intentional group of people who help me advance my career in some way.

If you’re not intentional about who’s in your inner circle, you are not serious about where you want to be five, ten, fifteen years from now. You need to curate that group. And the number one thing you’re looking for is red flags. And there are yellow flags and red flags. So there are things where people will make a mistake, and that’s a yellow flag when you let them slide. There are some mistakes that people make that you should label as a red flag. And as soon as you see a red flag, that person is no longer part of your inner circle, trusted circle. They are now out. It takes a lot of work for somebody who’s been kicked out of your inner circle to get back in the inner circle. Now they don’t have to know, or they shouldn’t know that they’re in the inner circle. There’s no need to do that. I really believe you have to intentionally curate your network if you want to be serious about achieving a desired future and going beyond what you thought was possible.

So one of the frameworks we use is that people often think too small, too short, and too solo. And I should start with too short. So what we try to do is we try to get people to think on a longer timeline. Most people overestimate what they can do in the short term, and underestimate what they can do in the long term. So I want you to start to think on a five, ten, fifteen year timeline. Like, what can we do? Where will we be ten years from now? So that’s one. I want you to start to think bigger. Most people, if we think too small, our dreams are safe. The risks we want to take are safe. Like, there’s some risks that I thought of as risk, and I realized that those weren’t risks at all. Because if it goes south, my life doesn’t really change. But if I’m truly taking a risk and I do this particular thing, my life will be very different. This is a risk. Most of us, at least those people who kind of listen to this podcast, what we call risks, on a scale of one to 10, that’s something that’s high risk. Most of us are not doing anything that’s high-risk. We’re playing it safe.

Cory: They’re not life-changing.

Keita: No. We’re playing it safe. Like, I have a big life decision that we have coming up right now, and it’s positive. And I’m agonizing about it. I’m like, you know what? This is a champion problem.

 A champion problem isn’t a problem I need to solve. But in the grand scheme of things, it’s not a crisis, not a risk, but it changes my life dramatically. And I think we need to understand that. You want your inner circle to be the people who push you to think bigger, be better every single day. And those people who are not in that mindset, they’re not part of the inner circle. There are people who will be in the inner circle for a reason, a seasonal lifetime, and that’s okay. And that’s perfectly fine. And I think sometimes we feel guilty about saying, okay, this person is not in my inner circle.

Recently, there was somebody I was becoming good friends with. I really liked the person. It was great, and then a red flag happened. That person’s cut out. We have a lot of mutual friends. I see them at social parties, but that’s not the guy I’m going to confide in anymore, because I lost trust in him. But I think there’s a lot of value in being ruthless about how you make those decisions, but merciful in how you execute those kinds of decisions. So I really believe in curating a network.

And then when you go into your third circle, which is the sector or system you’re working in, I think, again, you need intentionality with that as well. There are certain people in that, you and I both spend a lot of time in financial services. No knock on financial services, but there are people in financial services who are out for them. They’re not interested in the best interest of the client. I want nothing to do with those people. I do not associate myself with them. I don’t want to be on their podcast. I don’t want to be in their blog. I want nothing to do with them. The people I want to be around are the people who are absolutely laser-focused on what is in the best interest of my client.

So when I go into that third circle, which is the sector or system you’re working in, you have to curate your network. People who are part of your network, you have to filter them. If you go back to that commencement piece question, I think, pick your friends like you pick your fruit. That’s an Erykah Badu song. I don’t know if you know who Erykah Badu is. Erykah Badu is an amazing soul musician from the nineties, and she has this line that she says, you pick your friends like you pick your fruit. I almost sang on your podcast there for a second. I refrain. I don’t have a singing voice. But the point is it’s how do we be intentional about our relationships? Because the only relationships that are sustainable are win-win relationships. If a relationship is lopsided, it can’t be sustainable.

Cory: Right. And so thinking of that analogy, the blemish versus the bruise, like, I’m thinking about the yellow flags versus the red. Where does that cross the line? And I’m thinking values-infringement when I think red flag. What more sits there?

Keita: So I have a six-year-old. And I was getting tired of being, like, stop hitting, dude, like, all of this stuff. And I know from the work that I do, a positive reinforcement works better than negative. Right. So I’m like, Keita, you’re doing a lot of negative reinforcement, what is happening?

So we’ve stopped that, and we’ve started to say, hey, what are your standards you want to hold yourself up to today? And he says his standards, etcetera. And I’m like, okay, is hitting part of your standards? And it’s not one of my standards, but if that’s your standard, go for it. You have to live with the consequences of that. He’s like, no. Now the conversation is about, hey, did you hold your standards today? No, Dad. I held my standards for most of the day, I didn’t hold my standards because I was so angry or so upset or whatever. And then I went back to my standards.

So I think the lesson in that for me, I’ve found this to be quite a powerful exercise with my son. And then, of course, it’s now bled into other areas of my life because his jujitsu teacher now talks to him about standards. His teacher now talks about standards. I talk to him about standards. So at the end of the day, when he’s 16, 17, I hope that he’s like, okay, this person does not meet my standards. This activity does not meet my standards. Therefore, I’m not engaging with it. And then it becomes an internal choice for him. But the first step, because I learned this from him, is he went to basketball, and the two kids would do each other on the basketball. They weren’t passing 10. And he was like, you’re not passing me. I’m not passing you. And I pulled him in his eyes. I looked. If those kids don’t meet your standards, if your standard is to pass the ball to whoever’s best positioned, you keep that standard. Just because they’ve dropped their standard doesn’t mean you drop your standard. You keep your standard. And he’s like, but, dad, I didn’t set standards before I came with a basketball court. I’m like, okay, now we’re going to. So he taught me to have a conversation with him about what the standards are. Let’s set the standards.

So that’s a very long way of answering your question, that I think you have to set your standards. And when people violate them, they’re out. End of conversation. If it’s a small violation, an accidental thing, those kinds of things, that’s fine. Life happens, and people make mistakes. But when it’s an infringement, I’m sorry. It makes a very quick filtering tool. And one thing I would say is, I use this a lot in my coaching. If you have on rose-colored glasses, you cannot see red flags. They look gray. So in order for you to see red flags, you have to take off your rose-colored glasses. That is an internal conversation. That is a conversation with yourself. So it always comes back to that personal development piece. What are my blind spots? Which is why I believe, study groups, coaching, all those kinds of things are so valuable, because other people help you see your blind spots. It’s by definition you cannot see it. The mirrors can’t help you see it. It’s by definition you can’t see your blind spots. And that’s an inner conversation. Those are the kind of things that I think are important for people to understand.

Cory: Amazing. Keita, I want to go back to that. You didn’t pass to me, so I won’t pass to you. And I think that it is so brilliant in other parts of life. And I’m thinking about somebody I want in my inner circle, but maybe I’m not showing up to be in their inner circle. And it rightfully, maybe it’s not always reciprocal, but I want to just toss that around for a second, of what conversation can I have with myself to ensure that I’m showing up to be in somebody else’s? And not only eligible, but somebody says, I really want that person to be in my inner circle as well.

Keita: I think that I think this is such a tricky question. The short answer is I think you have to ask yourself, who do I need to be at this moment? What is this moment demanding of me? I think that’s where you have to start. But because we are human beings with emotions, we have status, desires, if I find myself in a situation where I want that person to be in my inner circle, and for some reason, they’re not stepping in, usually, there’s a signal to me around why do I want that person to be in my inner circle. There’s some sort of distortion that’s happening in that, and we have seen this person.

Cory: And that’s exactly where I was going with this.

Keita: So I think that’s a tricky question. So let’s think about human behavior. Here are some things we know about human behavior. We are predictably irrational. That’s the title of a book, but it’s also true. We are predictably irrational. We think we’re rational. And we do more rationalizing than actually doing logical kinds of thinking. But yet, most of us, our brains are fathers, which I really believe is, with thinking frameworks, you should use simple rules, principles, and guidelines to help you make decisions. So it comes back down to taking standards at different levels, but it comes down to principles. What are the principles I’m going to live my life by? What are the standards I’m going to hold myself up to? It doesn’t matter what other people do. I’m going to hold myself up to these standards.

So let’s go back to my son passing the ball. The thing that I told him on the sideline, it doesn’t matter that they’re not passing to you. It really does not matter. He’s six. This is a tough lesson for a six-year-old. But that is why I love sports. I said to him, it doesn’t matter that he’s not passing. What matters is that you don’t break your standards. If you pass any person who is in the best position, you pass the person. So in business, I’m going to refer you to the best person that I know for the job. So I do that. That person has never referred me to business. Does not matter. Because my standard is I want to make sure that whoever I’m talking to gets the best possible service for me. Once we start to go into this tit-for-tat game thing, and I think this is really important, my undergrad is I did a lot of software development stuff, and one of the things we used to do is we used to code within game theory. Tit-for-tat is you scratch my back, I scratch yours. It works really well in the positive. It does not work in the negative. Like, think about gangs. You shoot my friend, I shoot your friend, and it just spirals into war. And there’s a really interesting analysis of tit-for-tat, which goes back to curating your network. It’s that it’s tit-for-two-tat, I think is what they call it, which is okay.

So I’ll tell a very long story, unfortunately. Sorry, listeners. I tell long stories. Richard Dawkins has this book. The Selfish Gene is what the book is called. I don’t recommend reading it. It’s a very difficult book to read, but there’s a story there I think is worth telling. There are two tribes of birds, and the birds are infested by a parasite. The parasite sits on the forehead of the bird. And the only way for them to get that parasite off is for another bird to pick it off. And in this tribe, there are suckers and cheats. A sucker always takes the parasite off. A cheat never returns the favor. In a colony where there are more cheats than suckers, the entire colony dies. In a colony where there are lots of suckers and few cheats, you grow a lot of cheats to the point where the colony eventually dies, because the cheats end up thriving. What eventually happens is that you end up having a grudger, which is a third type of bird that comes in. And that grudger remembers the last interaction. So he will be a cheat to a cheat and a sucker to a sucker. Or she will be a cheat to a cheat and a sucker to a sucker. That’s a tit-for-tat strategy. You scratch my back, I scratch yours.

The colonies that survived are the colonies that have grudges, that are mostly grudges. But they ran that simulation a bunch of times, and they coded in, tit-for-two-tat, which is I will give you a second chance. And the ones where they give you a second chance, those colonies thrived even more because things happen. The first time you meet somebody, whatever happens. And I found that to be really interesting because that was just an algorithm. But what that algorithm said is you can give people one chance, depending on the size of the infraction. But tit-for-two-tat ends up being the best strategy in terms of helping colonies survive.

And I think there’s a lot to learn there in building out your network and ecosystem, to answer your question, that it does not work in the negative. It works in the positive, and that most people would deserve a second chance, which is why I always go back to having hard conversations. Because somebody does something, they infringe you, have the hard conversation, and they probably would never do that again. Because you set that boundary and they understand you are not somebody to be crossed. So it’s those kinds of things that I think, it’s a very tricky question to answer, but that’s my long-winded way of answering that.

Cory: And a beautiful way of answering. And I think of respect in those hard, or those hard conversations is respecting myself enough to say I need to to step up, but also respecting the other person enough to say you deserve a second chance.

Keita: Well, otherwise, it’s passive-aggressiveness, because I don’t like that you did this thing to me, and you are sitting there boiling, pissed off at m,e and I have no idea. And I’m just like, Cory, you and I are cool. I didn’t know that. Like, hey, I stepped on your foot the other day in your white shoes, and I wrecked your white shoes, and you’re pissed off at me. I have no idea. And you told your wife, and now your wife hates me. You’ve told your best friend, your best friend thinks I’m an idiot. And I don’t think it’s integrity. I think the high-integrity thing to do is to have the hard conversation about the thing that you did that bothers me.

Cory: Great. Now, 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?

Keita: Ready for the tough ones? I thought I thought you already gave me so many tough ones, but perfect.

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

Keita: That’s interesting. I’m going to frame it in family enterprise, but I think it’s a successful strategy for families, which is that a family business survives when a dinner table and a board table speak the same language. So I think that’s just a strong thing around families, is that they spend a lot of time understanding that there’s alignment around our goals and objectives, and we invest in a shared language so that it’s not just shared assets. Shared assets is easy to do. Shared language and philosophy and values is hard. And we have to be singing the same song, or else we’re going to lose out on that. So I think when the dinner table is in alignment with the board table, I think that’s when you get really strong family businesses.

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

Keita: It’s emotions. How do we manage our emotions? I think there are lots of people out there who can help them with estate planning and wealth transfer and all of that. But there are very few people who could help them with the unspoken expectations. And it’s about starting really hard conversations early, before you think you need them. Because I think the biggest thing you can have is clarity. Clarity is your secret weapon. So if you have clarity today, you’re unlikely to have conflict tomorrow. So if you can talk about it, then you can transfer it. And it’s not just about your wealth. It’s about transferring the culture of entrepreneurship, of rigor, of whatever that culture is, I think that’s where you want to focus, if that makes sense.

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

Keita: So these are my three that I talk about leadership all the time, so I think these are the three that matter more than anything. It’s humility, and I’ll come back to what I mean by humility. So that’s about, like, the stewardship matters and not status. People who get caught up in a status game, I think they end up going down a very dangerous path. So humility, clarity. I think if you’re able to take the complex things, make them simple, but no simpler, and you help people align around what really matters, and people are clear, I think that’s helpful. And then the courage, the willingness to have those hard conversations, those are the things that I think matter the most when it comes to thriving family businesses, businesses in general. The three things that I always talk about of humility, clarity, and courage.

I do need to make one thing around humility. So when you talk about humility, there must still be room for your truth. So it’s not about shrinking. It’s expanding your awareness. So somebody who is humble to me, they’re quiet because they’re listening for what they don’t know. CS Lewis has this quote where humility isn’t thinking less of yourself. It’s thinking of yourself less. And I think it’s important to make that distinction, because the humility thing is something I think people mistake for meekness, shyness, or whatever. When you pay attention to what you are missing, who’s not listening to me right now, whose voice needs to be heard, that’s what I mean by humility. Are you willing to step back and really lean into stewardship and those kinds of ideas? I don’t want people to confuse humility for making yourselves smaller. It’s about making the mission bigger, bigger than the ego, because that’s where I think a lot of people fall short. That if you can keep it real and keep it honest without people’s egos being bruised. And that’s the key to the hard conversations part. There’s no reason why humility is not a sign of weakness. I think it’s probably one of the strongest things we can do.

Cory: Fantastic. And great frame. I think that it is a very important part that’s overlooked, where people see it from the outside as something that it truly isn’t.

Keita: Like, Brene Brown talks about, I’m not here to be right. I’m here to get it right. And I like to tell people, I’m here to be real. Because there are too many lumpy carpets. I’ve been in too many rooms with lumpy carpets. And I want to make sure we have way less lumpy carpets in the rooms that I’m in. If I’m in a room, I’m going to point out a lumpy carpet. And that’s why people work with me, because they know I’m willing to do that. And as you think about a lumpy carpet, people trip and fall, right?

Cory: And they don’t ever attribute it to the lumpy carpet.

Before we conclude our discussion today, I’d like to highlight where our listeners can engage in more of the conversations that you’re having, as well as any important conversations that, maybe our listeners could be directed to as it relates to maybe what we discussed today.

Keita: So I think if you visit my website right now, I’m about to launch a free course on how to have hard conversations faster. Because I’ve realized after I wrote my book, Strategy to Action, I realized that the thing that was missing from most of my clients is that capacity. Now that we have the strategy, now let’s go have the hard conversations. People didn’t have the skills to have the hard conversations, so I’ve really started to double down and lean into helping people have hard conversations. So a lot of the content that I’m putting out, and a lot of it for free, is going to be around hard conversations, and then stuff around my book, moving from strategy to action, because those are the two things that I find provide people with the biggest leverage in achieving their goals, and I think it matters more than people really understand.

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 maybe we just didn’t get a chance to touch on?

Keita: I think let’s just go back to how we build the world through the conversations that we have. I think if we really focus on having higher quality conversations, we have really high much higher quality results. And to me, it’s as simple as that. It’s as simple as thinking through how do we have better conversations and ask better questions so that we are building those dreams in a way that is realistic and makes sense. So that would be my thing.

Cory: Well, thank you, Keita. I appreciate you taking the time today to share your experiences, expertise. And as much as you apologize for the long stories, I love the long stories. So thank you for those insights. It was incredibly valuable to myself, and I know that our listeners will be just as grateful for your contribution.

Keita: I’ll say one more thing. Thank you for making a space that I felt open enough to do that, because I think one of the things I often say is that we can only move at the speed of trust. And because I trust you, we were able to move at the speed that we were able to work at today. So thank you for your time, and thank you for being so thoughtful in your conversational approach.

Cory: Amazing.

As we wrap up this episode, we invite you to reflect on Keita’s reminder that meaningful leadership begins with self-inquiry, who you’re becoming, how you show up, and what your daily choices say about the future you’re trying to create.

Whether you’re part of a family enterprise or work alongside enterprising families, his perspective offers a different lens, one that centers personal growth, emotional awareness, and intentional leadership as core elements of long-term success.

Throughout our conversation, Keita shared what it means to align leadership and growth with the questions we ask and the conversations we’re willing to have. He offered a framework that starts with self-awareness, deepens through intentional relationships, and takes shape through clear, courageous action. His insights remind us that the way we think, talk, and connect becomes the foundation of everything we build.

For those looking to lead with more intention through better strategy, clearer relationships, or personal growth, Keita Demming offers a grounded and practical approach. We’ve included his contact information, along with links to his book Strategy to Action and his website, where you’ll also find details on an upcoming free course, in the show notes to support your next step.

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