How to Deal with the Emotional Turmoil Selling Your Business Actually Creates with Jonathan Bennett
In this episode of the Experience Leadership podcast, host Marc Haine interviews leadership and executive coach Jonathan Bennett to explore the emotional and practical complexities of exiting a small or mid‑sized business. The conversation begins with a stark statistic that 58 % of small‑business owners lack a succession plan, setting the stage for a deep dive into why exit planning is both a financial and psychological imperative. Bennett explains the various forms of mergers and acquisitions (M&A) that affect smaller firms—owner retirement, management buyouts, employee buyouts, and strategic mergers—highlighting how each path carries unique risks and timelines. They discuss the emotional weight of letting go of a business that founders often view as an extension of their identity, and how this can trigger existential questions about purpose and self‑worth. Practical challenges are also examined: the need for a long runway, the importance of being able to step away from the business for three months without disruption, and the pitfalls of last‑minute planning. Employee reactions to news of a sale or merger are described as a spectrum from shock and disengagement to excitement about new opportunities, underscoring the necessity of transparent change‑management communication. Bennett advocates for structured support mechanisms—coaching, advisory boards, and succession‑planning conversations with staff—to surface hidden risks, prepare for due diligence, and maintain cultural continuity. They also touch on alternative exit structures such as employee ownership and vendor‑take‑back financing. Throughout, the hosts stress actionable best practices: write a concrete exit plan, treat it as a project with milestones, develop SOPs, build a board of advisors, and involve employees early where possible. The episode concludes with Bennett urging entrepreneurs to seek external support to avoid isolation and stress, and provides his contact information for listeners seeking guidance.
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Imagine this. You've spent years building your company from the ground up, nurturing a dedicated team, and creating a brand that stands out in your marketplace. But now the time has come to consider a significant change— an exit strategy. How do you ensure that everything you've built remains intact? How do you prepare your team for the inevitable upheaval? And most importantly, how do you navigate your own emotional journey through this turbulent process? And that's what we're talking about today on Experience Leadership.
Welcome to Experience Leadership, a podcast that challenges small business owners and entrepreneurs just like you to dare to be the exception. Join our host, customer experience expert Marc Haine, as he uncovers relevant and timely content to help you script and direct your business and teams to create jaw-dropping experiences your customers and staff deserve. Here is the host of Experience Leadership, author of Lights! Camera! Action!, customer experience expert Marc Haine. Welcome to this episode.
I am your host, customer and employee experience I'm your host and strategist Marc Haine. And I am so glad that you're here with us today. My guest for this episode is the Leadership and Executive Coach Jonathan Bennett. And today, we're going to highlight the emotional and practical challenges of exiting from one's business, whether that be through the mergers or acquisitions or through retirement. I have one simple request. If there is somebody in your circle who could benefit from the insights that we're sharing today, please do them the favor and pass along a link to this episode. You know, when I was an economic development officer, I was shocked to learn how unprepared most business owners were for exiting their businesses. According to one statistic, 58% of small business owners have no succession plan. Now, you might be thinking, well, I'll get to it when I'm ready to retire or when I'm ready to sell. But this is so much bigger than just the financial oversight. This process, whether you know it or not, has deep emotional consequences, not just for you, but your team of dedicated employees as well. And that brings us to our Question of the Day. So have you thought about how a merger or acquisition will impact not just your bottom line but the morale and loyalty of your team. And ultimately, the legacy of everything that you have built. Again, I'd love for you to share your experiences. I encourage you to share this episode on your favorite social media platform. #ExperienceLeadership and put your comments down. I'd love for you to be part of this conversation. As I mentioned today, my guest is Jonathan Bennett. He is a leadership and executive coach and a trusted advisor to many, many businesses. He is the founder of a management consulting firm that grew into a B Corp and serves hundreds of organizations. He's an experienced, successful management buyout, and he now runs a coaching practice to help businesses do the same thing as well as to thrive in their businesses. He's an advocate for social justice and has a progressive approach to leadership. Jonathan, welcome to the show. It is so nice to have you.
It's great to be here, Marc. Looking forward to our conversation.
Yeah. Before we get too deep into today's conversation, could you give us a little bit more clarity about how you serve your clients and who are they?
Sure. I serve founders and CEOs right across North America, primarily small and mid-sized businesses, but also some nonprofit and public sector leaders as well. I kind of think of the work I do as like work therapy. I spend a lot of time with folks digging in and talking about the kinds of things that they sort of feel like they can't talk about with anybody else. So sometimes it's very practical, very business orientated. Other times it's emotional. Other times it's very future orientated. So that's a bit of an overview.
Wonderful. Now, I mentioned the word mergers and acquisitions, and to some small business owners, they might just shut down and say, Oh my goodness, I'm not Rogers. I'm not Bell Mobility. Could we talk a little bit about what mergers and acquisitions is? And can you describe it from the context of small business?
Yeah, sure. So I think you're right. We have this general societal idea of what M&A is, a merger and acquisition. And we hear about takeovers and buyouts and big things that only happen on the news. But there are, of course, hundreds of thousands of small businesses every year that transition owners. And that's what happens with small and mid-sized businesses all the time. And it can look like lots of different things. It can look like a founder eventually retiring and just kind of winding up. It can look like another company coming along and purchasing the first company. It can look like 2 companies that have synergies coming together and creating a whole new third company. It may also look like the existing management team buying out the owner. So there's— and I didn't mention, it could also be the employees buying out the owner. So lots of different ways of thinking about mergers and acquisitions.
So just so the audience knows, you yourself have been through this whole process of a management buyout yourself. Could you tell us a little bit about that?
Yeah, I'd be happy to share. So, I built a company over the course of 10 years, and it was a really exciting, emotionally up and down journey, just like every entrepreneur's story, I'm sure. And I got to the point where I was sensing a couple of things were happening. The first was I was starting to lose my joy and focus for the work itself. The second was we had built and scaled enough that I was no longer really in the business too much. I was mostly working on the business. And so, I had something that I could step away from. And thirdly, I had an amazing young leader coming up who had come up through the ranks and was now kind of second in charge. And I had this very strong realization that if I didn't get out of her way, she would leave.
Mm-hmm.
And I realized she was my plan. And so I could wait and miss the train, or I could decide to work with her early and build a succession plan so she had enough runway and I had enough transition time to execute what ultimately was a very successful transition. She is the CEO and owner today, and it's 2 years later, growing and doing amazing things. So, you know, in the rearview mirror, it all looks quite simple and slick. But I'd like to say I planned it long ahead of time. Not so much. And so, my lessons learned is you really can't sort of start early enough.
They say that the best time to plant a tree was yesterday. The second best time to plant a tree is today. And so, you know, and this is something that I'm constantly getting. When I was in economic development, I'd be talking to these aging entrepreneurs and business owners. And it's like, what's your succession plan? Oh, I'll worry about it. I'm going to retire in about 5 years. So, I'll think about it then. And it's like, oh, there are dangers to that, to waiting till last minute. Could you talk a little bit about kind of the runway that's required to succeed from one's business?
Yeah, it's much longer than you think. And also, it may happen when you least expect it.
How so?
The first— yeah, well, I mean, the first I'll just sort of deal with. It's like, you can have plans in your head, But if your folks around you aren't participating in the plans, i.e., your key staff, maybe the potential people that will buy your business, maybe you've got a competitor across town or across the province or across the country who, in your mind, you'd be perfect for them to just swoop in and buy. But it won't be that simple, obviously. And you're going to need to do a lot of due diligence and all that sort of stuff. And it can take much longer. And there are many, many factors, macroeconomic factors, to say the least, financing, you name it. The second part is people think that they've got lots of runway and then an offer comes out of nowhere. Interest comes out of nowhere. Your business hasn't been evaluated maybe ever. You don't know whether you even want to sell. You don't know how it may impact the folks that you really care about that have helped you build this business. And so, to not be ready at all, to just put it off for later and not have those component parts always kind of in front of you and always be thinking about them, is to risk the scenario where somebody swoops in with an offer that may or may not be a good one and you really don't have a lot of kind of like plan in place or even attention to all of the things that you'll need to be thinking about.
Which could also mean a lost opportunity as a whole and the boat sails and it's done.
Absolutely. Yeah, absolutely.
So, at the beginning of the show, I started about talking about these emotional challenges. What are some common emotional challenges that leaders face when considering whether or not they're going to sell or merge or whatever?
Yeah. I mean, it's your baby. This is something that where there was nothing, you created something, and now there is a thing. It becomes part of most founders' identities in separating themselves from their business. They, you know, invented the name of the business, the brand of the business, all of the relationships, you know, how it's grown and scaled over time. They've got their hands in everything. And suddenly to think about that not being there anymore is a very emotional journey to go on. It can bring up all kinds of existential kind of questions. Who am I? What is my purpose if I sell this business? Sure, maybe a payout and money might be great and I might be able to retire or move on and buy my next business. But who will I be after that? And will I miss it? And will I miss, you know, all of the things that I've attended to and grown? So all of these questions really go to the heart of what I think of as the legal and accounting Part of it, figuring out, you know, your EBITDA and what the business is worth and all of this stuff, tallying up your inventory or, you know, sales that you've got in the can and trying to figure out a valuation. That's just, in some ways, that's the easy part. The hard part is choosing to let go. It's choosing to give it to somebody else. It's choosing to walk away. Many deals that happen have the original founder or CEO ask to stay around for a period of time. That period of time is also its own special emotional journey. So all of these pieces are quite complex. And when I talk to other founders that have exited a couple of years later, hardly ever they talk about the money. Mostly what they talk about is the emotional connection and the journey they went on. of letting go, of reinventing themselves, of rebuilding themselves, of seeing somebody do something different, better, worse, doesn't really matter, than they would've done themselves. That is actually pretty hard.
Yeah. It's interesting because, you know, as you were saying that, I was going through in my head when we took over a restaurant from a previous owner and we had asked the owner to stay on board for 6 months as we made the transition to understand all the systems and all the methods that were in place. But very quickly, we recognized some weaknesses and start— we started to make and instigate some changes on the get-go. So, this would've been within 2 months of taking over with him still on board. And my goodness, it was like we might as well have been putting thumbscrews to the poor guy because we were driving him absolutely crazy because this was not the way that he ran his business, right? And so, we had—
Oh, boy.
This huge conflict with him. Because we weren't going to wait the 6 months to make changes. We needed to make changes for profitability's sake and for customer service's sake immediately so we could get out of the hole that we were in transitioning a business.
Absolutely.
And so, we saw those emotions. But then, there's the other part of it when I talk to people who want to retire. Is the fear of what the new owner is going to do a very real thing?
Oh, it's a huge thing. And I mean, later on, probably the most common dynamic we haven't talked about, which is many businesses are family businesses. So, we've got one generation taking over from the previous generation. The transition is rarely clean.
Even if it is family, right?
Oh, especially if it's family. Like, rarely is it a clean break. You know, we've got mom or dad still hanging around, sitting on the board, coming into the office or the shop a couple of days a week. Whatever's going on, it can be exceedingly difficult. And that is fraught with a lot of, we'll just call it intergenerational psychology to shorthand it. And so, for all these reasons, it's really, really hard. In the same way, you can kind of liken it to when you take over a team in a corporation and the previous manager did things in a certain way. And now, you're being asked to manage this team and you'll see some good things and some bad things and some and things you want to change, and you are going about it in a kind of careful way. You're managing change. You're managing people's expectations. You're giving them a taste of the new things. If things are really rotten, you're doing a turnaround. If things are humming and great, you kind of don't want to break anything. All of those things, you can kind of take that idea and translate it across to what happens when you're either selling your business or you're purchasing a business. A part of it is just simply a change management exercise.
Yeah.
And there's a lot of psychology wrapped around that.
So, what are the typical reactions from employees when they hear about a potential sale or potential merger? Are you seeing happening when it comes down to owners making this decision?
Yeah, Marc, it's soup to nuts. So, mostly what's happened is that the deal has been happening in some kind of private way, in secret. And there are reasons for that. Going through a due diligence process is never easy. A new owner is going to come in and it's more than just kicking the tires. I mean, they're going to go in and inspect contracts. They're working with their lawyers. There's accountants involved, financing. It's very complex. And so a deal gets structured and a deal gets done, even for a fairly simple business, it feels like it's complex. And you come out of it finally done and you've been in all these kinds of secret meetings. And finally, you can tell the staff. And here's what's happened. You've had a lot of time as the owner to go through a kind of emotional journey. Do I or don't I want to sell? Is this the right buyer? If it is the right buyer, can I get the right price? How am I being treated through this process? Do I think they're going to take my baby, my staff, my brand, and do good with it in the future? Or will I look back in the rearview mirror, maybe richer except unhappy at And so, all of these things are swirling in your brain, but you've had some time with it. Now, you've walked into the lunchroom or you've flicked on the computer and you've jumped onto a big Teams meeting or a Zoom meeting and you've said, guess what, everybody? I have some big news. And you've done the big reveal. And every single one of those people are going to have their own private reaction. Mostly, people kind of power down. There's a kind of like absorption time that happens and they're nodding and they're going, uh-huh, but they can barely let any information in. It's a really big deal and most people have a big reaction to it. It just looks different for everybody else. For some, it'll be super exciting. Maybe you've been taken over by a much bigger organization and maybe now they've finally got the career Advancement opportunities that they didn't have in your smaller company. Maybe the exact reverse is true. Maybe they came from a big, enormous company and they actually chose you as a founder, and they are looking for a smaller, much smaller organization. And maybe they'll be super disappointed that you've let them down and that you've been disloyal by selling, and everything in between.
It's interesting because I feel that there may be some people who may be tuning in thinking when they make the decision, This is a financial decision. It has nothing to do with emotion. What do you say to them? Because it's to your point, they've already gone through the roller coaster and it might be months in the making and they've forgotten how they felt about something. And so, when they're standing up in front of their team, they're like, this is— it has nothing to do with you guys. It's all me.
And I see that exactly what you've described often. What people forget is how long it took them. We have a very short half-life. And then we look at it and we say, what's wrong with you guys? Like I told you on Tuesday and it's already Friday. And like, what's wrong? And like, you had 6 months to process it and work through it. And you want them to get it in 3 days and be fine with it and actually be excited for you because you're getting paid. But P.S., they're not. And they've got a brand new boss and a whole bunch of uncertainty. And you don't know what's going on in their life. Maybe they just got a new mortgage. Maybe they're, I don't know, in a relationship that's dissolving. Maybe their kid has got a thing going on. You have no idea. And so, all of this stuff is happening and in their world, bombs have just gone off. And so, I counsel my clients as a coach that are going through any kind of transition in leadership to just be patient, give people a lot of grace.
Yeah.
And a lot of space. If you're able to bring any of your team in earlier into the conversation and it won't harm the deal, then do that because they can participate in the thinking and they may see things that you can't see all by yourself.
Yeah.
Often that's not possible though, and for good reason. Some of your key employees may actually be kind of assets that are wrapped up in the deal. And so, you know, all of these things are things that you really need to consider as you're going through it. But just to be You know, show up with as much patience and kindness as possible for everybody else that's going through it. You know, after all, you're, you're the one that's walking away and you'll be leaving this, but they're staying behind. And so whatever decision, you've just done it to them. And that's, you know, that comes with a lot of emotional, you know, like reactivity.
I can definitely see that a lot of patience would be needed and a lot of discussions. A lot of— I would imagine that probably the owner's time taken up for the next few months is going to be bringing people into the office to talk about their concerns, their fears, their questions, because they're going to have a ton, especially if it's mergers. I think mergers gets a really tough rap because, you know, if you're the director of marketing and you're merging with a company that already has a director of marketing, what the heck is going to happen to me?
Yeah. Oh, absolutely. Yeah. Kind of 2 things there. The first is Don't make promises that you can't keep.
Right.
So sometimes to keep the peace, what I see exiting founders say, they promised me nothing's going to change. They've got the same culture we do and nothing will change and they're going to look after you. And, you know, that's why I chose them. So those things all maybe have been a part of the negotiations and you may in your heart of hearts believe that. But, if you've watched anything go on before, it will not be identical. The new culture will come and affect the old culture. Then, of course, we get to exactly what you're talking about here, Marc, which is we don't need 2 directors of marketing anymore. So now, suddenly, we're in some kind of competition. We're either having some attrition, finding some efficiencies, and any new shareholders are going to want to drive out some costs and find some efficiencies.
Yeah.
And so, what does that mean for you? It can be very unsettling if you're the director of marketing, you're only in there for 6 months, and the other guy at the other company has a lot more seniority than you and a lot more experience. You're like, well, this isn't going to work for me. So, what do you do? You just dust off your LinkedIn and get going, right? But that can be a real problem for companies that are trying to do the work of it is that they've got half the people that are checked out and busy trying to look after themselves. as they're trying to go through some kind of merger. I mean, we haven't even talked about the other stuff like we're integrating systems, we're integrating processes. One is maybe eating the other or maybe we're creating some third new thing. So, there's brand and all kinds of new things that have to be kind of created, co-created between these 2 cultures. I'll tell you a funny story. I was on the senior team of a hospital And it was forced merged into a single hospital with another hospital across town. And so, these 2 cultures couldn't have been more different. One was a civic hospital, one was a Catholic hospital, and the government decided now they were to be brought together. And the old joke was it was like 2 buildings that were smashed together and tied up with a Tim Hortons. Like, that was the only thing that was like keeping them together was this Tim's. And I think that, you know, it's not a bad metaphor for a lot of mergers that happen. Distinct cultures that are asked to come together, either one will win out or, you know, some new brand new third thing needs to get created. And, you know, the advice to anybody leading that kind of work is just to be as intentional, as transparent as you can about it. It won't just sort itself out. Like, this is a leadership moment and you have to really lean into it and be, you know, quite, you know, like focused building these things out because people just won't go along. Yeah.
Yeah. And, you know, and it's also in the best interest to, for the companies acquiring you, if it is a merger or if it's a sale, you know, a, it's in their best interest to be able to appease as much of the uncertainty themselves as it is for you who's selling the company to appease that uncertainty. Before we get into some solutions, could we talk a little bit about what are some of the long-term consequences for a business that doesn't address the emotional needs of its employees during this transition? Like, what happens if they just decide, you know what, this is a bookkeeping thing, we got the CFOs working on this thing, and it's all about money? What are the long-term consequences to them, to the business itself?
Yeah, I mean, they can be many. Obviously, it depends on the sector. But your example before, your restaurant example, is a pretty common one. There's a lot of loyalty that exists with existing staff to the current founder. And if that founder's being asked through the transition, you know, if they're the old things, like if they staple their foot to the floor in order for them to get the rest of the payout at the end. And of course, this is done for good reason. We want the relationships to be appropriately transitioned. We want an act of good faith in the person to show all the systems and train the new owners in how the business works. So, you know, nothing wrong with it. But potential for harm during that period is great.
Yeah.
And the wrong personality types can do a lot of sabotage on the way out the door, and it can be really quite hurtful and harmful. And sometimes those transitions are a bit lumpy and they don't always work well. I'd say the other long-term problems is that a lot of value is locked up in a workplace culture, and it's pretty intangible and it's probably off-book. And so, Why are sales slumping? And, you know, as a management consultant, I've gone in and dug into things and you realize it's because the relationships of the people that are no longer there that were thought to be the brand's relationships were actually an individual's relationships and they walked and those suppliers, those vendors, those clients walked with them because the loyalty wasn't to the company, it was to that human. And in a small business context, 2, 3, 4 people can make all the difference. And so what can look like bang-up financials are actually resting in really small pockets of the business, and it doesn't take much to unwind that. So if you're a seller and you want to keep the thing whole and you want it to thrive, it's in your best interest to explain that to the acquiring person and that you have to look after these 3 folks because a lot rides on their relationships. And over time, let's do the right thing and sort of decentralize and disperse those relationships so they're a little deeper and we're a little less vulnerable in those spots. So, there are a few other things that come off the top of my head to me.
Yeah. And it's also the same thing if it's the owner themselves who have the relationship, right? That can be probably the most damaging is If when the owner steps out, the new owners step in and all the clients start thinking, well, let's do RFPs for our whole service base and see what happens.
Yeah.
Yeah. I'd like to jump into some strategies that owners can consider as they make the transition, and we'll get to that right after this.
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I am speaking with leadership and executive coach Jonathan Bennett. And we're talking about this idea of owners moving on, exiting their businesses, and all the kerfuffle that goes along for the ride. So, we talked earlier on about that owners and operators have to start thinking early on about how they're going to exit their business. In fact, I talked to one consultant who said he himself exited his business. And he thought that the best time his businesses ran was when he was planning to do the transition. Because all of a sudden he put standard operating procedures into place. He started, he started setting up the business that it didn't need him in it. And because of that, it ended up valuing a lot higher. Is this a typical practice? Is this something that you would recommend that businesses do from the get-go?
Oh, for sure. I mean, the classic of working, you know, on the business, not in the business, is a kind of like foundational idea. And especially around sales. I mean, If you're trying to sell your business, any evaluator is going to look at your business and ask a pretty straight-up question of themselves, like, what happens when I extract the founder? How much of the revenue, how much of the EBITDA is connected to this one individual? And so if we remove them and the new person doesn't have the depth of experience or can't step into or doesn't want to be a kind of operating owner, then that business really doesn't have a lot of, you know, it just doesn't have a lot of value.
Right, right. You're buying it for equipment and land. And so it's because it's interesting. I talked with a lady who's now, she just told me that she's got an offer on her business, which is great, but she owns a print shop. She's heavily hands-on. She cut back her staff during COVID and So she's really, between her and a part-time employee, are the ones running this print shop. And it's like, you know, as soon as you can, you have to find somebody to run your business. Because when you try to sell it, if you don't have a manager in place that somebody can come in and start leading this manager, then it's, it's going to have no value except for the equipment that you have.
Yeah, 100%. Like, if, if you can't take a holiday, if you can't go away for 3 months and have everything be fine, then you haven't solved this problem yet.
Oh, that's a great benchmark. That is an absolute great—
You should be able to stand up and leave for 3 months, give everybody, you know, their marching orders, and you should be able to come back and the thing should be humming. Uh, and if you can't do that, then you haven't, you haven't done enough yet. Uh, too much of it is still resting on you.
This is the point I want you to tell people how they can get a hold of you, because if anything resonates during this This show, this is the point at which people might turn around and go, oh my goodness, I'm going to need somebody like Jonathan to help me. How can they get in touch with you?
Yeah. So I'm super active on LinkedIn. So come find me on LinkedIn. My website is clearlythen.com. And I love to spend time with new folks, especially business owners. Spend an hour. Let's have a chat. See if I'm the sort of person that could help you out. By the end of the hour, you'll either know if I'm a good fit for you or not.
Perfect. Thank you for sharing that. What are some of the best practices then for involving employees in the planning stages of mergers and acquisitions? As you mentioned, sometimes a lot of the deal has to be backroom just to alleviate uncertainty and for people to do due diligence. How can people kind of bring their staff into the fray?
Yeah, I think that doing succession planning work broadly with your staff is really important. I did. I had lots of future-oriented kinds of conversations with them in a pretty structured way. And I fed back to the whole staff what I'd learned and what the themes were, what kind of leader they might want next, just in the abstract, what they were concerned about. And that gave me a lot of upstream information to be able to work with as I started my conversation with the person that ultimately bought my firm from me, who was an employee. And, you know, I would just say it feels like the only option if you're a small business is for another small business to come along and buy you. And that's not true. You have some folks around you. They're employees and/or they're your management team. And you might know a lot about them and you might assume, well, they don't have any money. They can't buy my company. But there's lots of different ways of financing an exit. And if you've got an employee base who really know your company well, maybe they can get financing for it. Maybe you can do a kind of vendor take-back where you'll get paid for a long period of time and have a long tail, and they'll continue to run this business without you, and you're not involved, but you'll get paid out, kind of like a mortgage. So there are lots and lots of options, and there's some new legislation that's helping employee ownership, like collective employee ownership in Canada, and that exists in other parts of the world as well, that are opening up just more avenues for owners to be able to kind of extricate themselves from their business without having to go through a kind of traditional sale of a business to private equity or to another business across town or across the province.
Wonderful. Are there any particular frameworks that have proven effective, especially on the emotional aspects of the transition? Are there any frameworks that have been proven effective in managing those emotional aspects of making the move of Being able to bridge what needs to happen?
Yeah. I mean, maybe less a framework, Marc, and more just an acknowledgment that everyone is different and everybody's life and moment in life is different. And so, you need to get some support for what you need. That might be a coach. That might be maybe even an advisory board. So you might have a paid group of 2 or 3 or 4 very experienced directors who you just pay a fee to sit as your board of directors. They have no fiduciary oversight. They just come to 4 meetings a year and you have to show up, explain your business to smart people who are going to ask you hard questions and push you for better answers and better performance. And advisory boards are a very excellent tool. If you're at the point of, you know, if you're somebody that's like, in the next 5 to 10, I'd really like to sell my business, getting an advisory board in place is an excellent decision because they'll push you hard. They'll ask all the questions that valuators and future potential purchasers will ask. So you can get all your ducks in a row long before you need to get the bad news that you haven't kind of done it all right when you finally get to the end line and you do want to sell your business. So there's a couple of like a couple of responses that maybe not frameworks per se, but kind of best practices that you can do. Coaches are helpful because we can go in on the business side and help you make business decisions, support you around some trusted advisory type services. Maybe you need marketing support, maybe you need human resources, or your business model needs support. They're things that I help my clients with all the time. An advisory board is kind of even upper level. They go sort of deeper and harder because you've got more minds around the table and it's more formal. It's also a lovely signal how serious a business you are to a potential purchaser that you have really quite an attractive board of advisors around you. That's just an excellent signal.
How does one get a board of advisors together? Do they go through a coach? Is there a formal process to do this?
Yeah, there's not really an exactly right one way. I guess if you were establishing one, and I've helped companies do this, find a very senior person that's got board experience, private sector board experience. They don't have to have experience exactly in your business per se, like not exactly in your sector, but what they should have is quite a bit of board experience. And you could ask them, Would you be the chair of my board of advisors? And would you attract another 3 or 4 people to sit around the board table with you? And obviously, I want to participate in the choosing. It's my company. And let me let you structure the board because a board manages itself and it exists in a way to support that owner be as successful as they can be. And usually, there's lots of different ways to structure these things. Obviously, startup culture is completely different than, I think, what we're talking about here. There are boards of advisors that wrap around startups and they take equity or phantom shares and all kinds of things around incentive. That's really not what we're talking about. We're talking about how a mature, small to medium-sized business can leverage a board of advisors to get the information, the advice, and the technical expertise they need to grow and stabilize their business and get it ready for sale. So that's sort of— I just wanted to make that distinction. But it's an excellent thing to be on. Also, if you're a senior business person, I sit on a number of boards. It's intellectually very stimulating. It's just really wonderful to help somebody in that way with their business.
And again, you know, this whole— my whole podcast is centered around serving businesses who are in their businesses, but they don't get to see the outside. And so, This is a perfect example of the value this podcast brings because this is something that people don't really consider is to turn around and say, well, you know, my business is doing great. Oh, I should be thinking about succession. This idea of putting a board of advisors together, I'm imagining that one resource you could use is you could probably go to the bank and ask them if they know anybody who would be really good at leading a board. Or you could leverage the Chamber of Commerce and just get to network with them and just find people who are super strong in that avenue and well-respected there as well, right?
Yeah, for sure. And there's also an organization called the Institute for Corporate Directors in Canada, and their website is going to give you a list of lots and lots of experienced directors. You could find one in your city, and you could just start to network and find somebody that's got really quite a lot of board experience and board training. And if they've been in and around doing this work, they'll have the kinds of networks that they can tap to pull in.
Right.
So, like, just to flash forward, What a board of advisors might look like is quarterly meetings with 3 or 4 people for 2 or 3 hours. You've prepared a package of financial and oversight of how your business is doing, its performance, where it's going. This board of advisors would support you to develop a strategic plan, give you their advice. Maybe you've got some folks that— maybe you've got a lawyer, maybe some folks with HR experience, maybe people with direct operational experience. And triangulating all of that experience, they're going to ask you fierce questions, really push you to get the best out of your business and to bring the best out of you as a leader. And it's like having your own personal cheerleading squad who are also harsh skeptics. They really get a lot out of you.
I would probably challenge that as the owner-operator, you should not be scared of that because I don't think that this kind of a board would get together expecting perfection on the get-go. So they're there, they're there to show you where the weaknesses are. Because I do think that as owner-operators, we have a valuation in our minds based on the years that we've invested in this business that really don't translate to financial statements or to a formal valuation.
Oh, it's, it's so true. Yeah, just, just to address that, experienced board members coming around to do advisory board work They expect not at all perfection. They understand. They've been where you've been. They get how hard it is. They've lived this and they're coming with empathy. They're coming with ideas and support. It's a very inclusive, warm, supportive place to be. I had one at my company and it was a gift. They were— they gave, you know, and they were also in between meetings at the end of the phone, If I needed help with something, I would just call them up and I would just say, oh my God, I don't know what to do. Can you help me with this? Or like, my gut says this. What do you think? They were just— because they knew the overall context. So, in between meetings, I could ping with a little question. So, they were terrific. And I know many, many businesses are supported with advisory boards and it's just a great way to go. Yeah.
You are the average of the 5 people you hang out with. So, you can make the advisory board the top 4. That's absolutely right. It sounds like a brilliant way for people to do this, especially if they're the owner-operators in small businesses and they don't find that they have a lot of resources. I'd love to talk about some cautionaries and pitfalls that we should be aware of. And we'll get to that right after this.
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We are having a great discussion. I hope that you're getting lots from this. As evidence from our discussion today, you can tell that Jonathan and I are deeply dedicated to supporting business leaders just like you. So, if you're in the midst of planning a leadership retreat, an industry conference, or are looking for amazing content at any of those kinds of events, or you're just needing some expert guidance, we're just a message away. Feel free to reach out for a conversation about your unique challenges or to discuss how we could collaborate to help you achieve your goals. Our contact information is in the show notes. Jonathan, I'm just really tickled by the value you're bringing us today. What advice would you give business owners to avoid the common pitfalls that you're seeing time and time again even when people do get the coaching?
Make a plan. Make a plan, folks. Write it down. Get the plan out of your head and write it down. And it doesn't need to be complex. But it does need to be structured. And it does need to commit to some milestones and some deadlines. So I spend a lot of time in my coaching practice asking or inviting folks I work with to move from fuzzy things that exist out here in their head and stuff they kind of hope or should or would do to converting it into a project. Because everybody knows how to run a project. A project has a purpose statement. It's got a beginning, a middle, and an end. It's got some deliverables. It's got some milestones. We know what a project is. So get out of your head and convert it into a project. And when you do that, when it comes to creating some goals and a plan for your business, it doesn't need to be super complicated. It just needs to address some financial concerns, some people concerns, some product or service concerns, maybe quality to your competition, and just bust that stuff out and write it down and say, here I am today. These are the things that I'm doing. And here's where I would like to be in 3 years. And if I reverse engineer that, what are the things I'm going to have to do in order for the 3 years to look different than it does today? So I think sometimes, you know, you think about strategic planning and it sounds like really complicated and hard. It really doesn't have to be any of those things. It can be just a good, simple project that you can work on with your team and set some goals and, you know, stop just muddling along. And working month to month and get up and outta your head and think about the future of your business and set yourself some goals.
Yeah. Complacency is the biggest disease, isn't it?
Yeah. Yeah.
Jonathan, this has been such a great conversation. Do you have any last words and last thoughts about what we've been talking about today?
Yeah, I think, Marc, this has been great. I've really enjoyed our conversation a lot. I think that owning a business can be lonely. And sometimes there's only so much you can tell your spouse. There's certainly only so much you can tell your staff without freaking them out. And so, you know, who else can you tell? Maybe you've got business partners or investors. You know, there's only certain things you kind of want to worry them about. And so you end up shouldering and keeping this deep inside you. And, you know, it can lead to bad things, a lot of stress, and the outlets for stress can sometimes be a bit self-destructive. So make sure that you've got people around you that can listen to you, that have been where you've been, that can support you on this journey. You are not alone, and it's important to get the support and help you need in order for you to be happy and healthy as an entrepreneur and as a leader.
Thank you so much for that. That's a message I think we need to hear more often in the entrepreneurial space and in the business space. So thank you for sharing that. Could you remind everybody one more time how they can get a Yeah, absolutely.
You can find me on LinkedIn or my website, which is clearlythen.com.
Thank you so much. Again, I want to thank you so much for sharing your passion and your expertise with us. This has been absolutely brilliant. I've loved every minute of it.
Thanks.
Thanks so much. Why don't you let me know if this was of value to you? As always, my offer stands. If you would like 30 minutes of my time to brainstorm your business with you and your team, feel free to book yourself on my online calendars. The link is in the show notes. It's the one that's marked meetwith.marchaine.com. It would be my absolute honor for me to be of service to you. And while you're at it, why don't you go ahead and leave a comment or review about this episode? I'd love to get your feedback. Was this of value to you? What was your biggest takeaway? And of course, if you haven't done so yet, Make sure you're subscribed to this podcast. By subscribing to it, you'll get notification when we give you brand new content each and every week. I am so blessed that you're here. I have a ton of gratitude for you to share in this journey. My name is Marc Haine. I hope you stay safe, stay healthy, and I hope you dare to be the exception. Thanks for joining me today.
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