
50/50 Accelerator Podcast · 2025-08-06 · 27 min
Brad Henderson draws on 45 years of business experience, including roles in family-owned enterprises during critical transitions, to discuss how family businesses can build sustainable enterprise value beyond the founder. The core challenge he identifies is the gap between founder mindset and rising-generation readiness: founders often believe what made them successful will continue working, while the next generation needs to develop both owner and leader mentalities rather than remaining followers. Henderson emphasizes the importance of documenting processes and procedures - illustrated through a system integrator he helped transform using a "Lego blocks" framework that ultimately became a named asset in a $100 million acquisition by a major Canadian telco. He stresses that effective transitions typically require 3-5 years of consistent effort, a hired hand who can speak truth to power, and crucially, ensuring the rising generation reports to the external advisor rather than their parent. Without these structural safeguards, family dinner conversations often undermine workplace progress, and founders may inadvertently sabotage the transition by overruling their successor's decisions.
Brad Henderson found it took approximately four years, which aligns with Josh Patrick's typical 3-5 year range. This timeline assumes consistent, deliberate effort with a skilled advisor guiding both the founder and successor through the transition.
The largest obstacle is shifting the rising generation from an employee mentality to an owner mentality, combined with developing leadership thinking - many heirs remain psychological followers under a dominant parent's influence regardless of their formal title.
A hired hand can deliver difficult feedback that parents cannot, because family dynamics and childhood history prevent the same messages from being received well; however, this requires the advisor to have explicit authority and the parent to refrain from overruling decisions at family dinners.
By documenting their proprietary solutions into formal processes - represented visually as Lego blocks that could be combined for different client needs - the company transformed from an opaque trust-based model to a replicable intellectual property asset that the telecommunications buyer specifically named in the acquisition.
Founders should support small experiments with controlled failures rather than large projects, allowing the next generation to learn through iteration; what got the founder to their current level will not get them to the next level, and that requires different approaches.
Computed from the transcript - who did the talking, and the words that came up most.
Podcast Summary Unlock the secrets to successfully transitioning family-owned businesses with insights from Brad Henderson of the Consistency Edge Leadership Coaching Program. Discover strategies to shift from serving family needs to enhancing enterprise value, ensuring these businesses are sale-ready even without imminent plans to sell. Brad shares a compelling success story of transformation, leading to a profitable exit and expanded opportunities for employees. Learn how structured processes and systemized approaches not only improve operations but also boost enterprise value, ensuring a consistent customer experience. Join us as we delve into effective succession planning strategies with Brad, emphasizing the art of "controlled fault" to minimize project risks. Explore the pitfalls of assuming skill transferability across business areas and the importance of flexibility and recognizing systemic failures. Brad highlights the importance of mindset transformation for the next generation, shifting from employee to owner and leader, with the aid of an intermediary to manage family dynamics and foster honest conversations.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Since 1974, I've read a book a week searching for what it takes to achieve business success. After thousands of books, hundreds of client success stories, and decades of hard won business wisdom, here's what I know for sure. Working yourself to death isn't a badge of honor. It's a failure of strategy. So thanks for joining us today. Hi, I'm Josh Patrick and this is the 5050 accelerator where we explore how real business owners are cutting their hours by 50% while, uh, growing their profits by 50%. No consultant BS here, no theoretical frameworks, just proven strategies from people who have actually done it. Because here's the truth. If you're still working 65 or more hours a week putting out fires and missing family dinners, it is what it is. But that's not how it has to stay. So let's get started.
Speaker B: Hey, how are you today? This is Josh Patrick and you're at the 5050 accelerator podcast. And my guest today is Brad Henderson. And during our pre interview we had a fascinating conversation. Oh, Brad is from, uh, the Consistency Edge leadership coaching program which he runs. I always forget to tell people what these folks actually do in their real life, but we had this really interesting conversation about family business transition. And Brad is in a really unique position that he's been a hired hand in a couple of family businesses where they were going through generational transition. So we're going to start there. Uh, so I'm going to bring Brad in and we'll start. Hey Brad, how are you today?
Speaker C: Awesome, Josh, thank you very much for having me.
Speaker B: My pleasure. So tell me a little bit about, you know, when you were working with other businesses. I mean, when you were a hired hand, what was that like?
Speaker C: So, uh, I'll start by saying that, you know, over the 40 something years that I've been uh, in business, I've worked for companies large and small, um, so work for many enterprise companies and leadership roles, but have also been involved in some of the family, uh, owned and operated businesses that you talked about. And it was a real change for me, uh, when I came to First Family owned business because it had been run really as an enterprise to serve the family that owned the business. And there's nothing wrong with that, it's just what it was. But the patriarch, uh, wanted the business to grow beyond him and his family and he wanted it to be more sustainable and that was the impetus for him bringing me into the business. So that was really my first experience with.
Speaker B: So were you able to get the family to focus on enterprise value besides Family value.
Speaker C: Yes, we, we focused on making the business sales ready and even if there wasn't going to be a capital event, um, it was really the rally cry if you like, to try and change a number of the dynamics that happened within the company. And it was really to try and introduce some more rigor and discipline into the operations. A lot of businesses when they start off you can have a staff meeting in the elevator, uh, because it's so small. But when the organization gets beyond uh, being able to do that, particularly if there's a number of different geographic locations, that's where things start to change significantly and where many older operators find themselves a little bit out of their depth in terms of how to manage that. So when we put a lot of that process and procedure in place, it was a bit foreign not only to the founders but also to the people who had come to work in the organization because they had bought into a uh, more freewheeling organization where things were talked about in the morning and implemented in the afternoon. So that I think the balance was to be able to retain that flexibility because it's definitely one of the strengths of a small or medium sized company. But at the same time start to introduce the processes and procedures that will help to yield that consistent, that consistent result that was looking for and to also appear more valuable to a potential either uh, merger and acquisition party or someone who's actually going to take the business over.
Speaker B: So did they actually end up uh, selling the business or what was the result when you left?
Speaker C: So the result was an exit and we ended up selling a company of about 80 people, about $100 million in revenue to one of Canada's large telecommunications companies. It's a very positive outcome for the family because it provided the generational wealth that they were looking for. It released the generational wealth that was in that business. Um, it was also designed to try and give a pathway to the employees in the business because as a comparatively small organization there were limited opportunities for the employees to grow, uh, and there was no uh, stock of uh, ownership equity vehicle inside of the smaller company. So moving to the larger company they got options uh, in the larger company and that became a, a, uh, a new opportunity for them in addition to the fact that they could grow into different areas, have custom career development plans, have, have a more robust career process.
Speaker B: So um, just a little, you know, aside, my second book is called the Sale Ready Company by the way. So I, I, one of my big beliefs is businesses need to be sale ready even if you have no intention of selling. Absolutely. And if you do that a, your business is much more fun to run, it's probably more profitable and people actually know what they're supposed to do. You know, one of the things I love about systems, I don't like running systems myself because they annoy me, but that's besides the point. I'm a founder, so what can you say? But nice thing about systems is your employees, your team members know what they need to do for excellence and your customers know what to expect on a consistent basis.
Speaker C: Totally.
Speaker B: And without that, neither of those happened. No.
Speaker C: And you have, you know, the old adage, are you working on the business or are you working in the business? And if you're monkeying around with, uh, the business, you're not building a sustainable one which is going to have enterprise value at the end of the day. And so it's being able to package that message up, uh, in a way that is digestible to the families that are running the business so that they understand that you're doing these things for their own good. You're trying to plot their well being as opposed to putting in processes and procedures for some academic reason or purpose.
Speaker B: Yeah, I hate academic purposes because they don't work in business, in my experience.
Speaker C: But just a quick little note, uh, the company in question, the company we were talking about was a system integrator. So it integrated, uh, sophisticated, uh, computer systems and its customers were medium and large organizations, so enterprise organizations. And the reason why these people were, uh, successful is because they were able to attract technology people who wanted to be involved in the most complicated integrated processes in the marketplace. And so they were able to attract better talent than other companies. But what they didn't do is they didn't write these things down. So their processes, their solutions, if you like, were very much of, you know, trust us, we've done it before, we can do it again. Uh, we'll help support you. And that's a very difficult, uh, business model to be able to sell, if you like, to a potential person who's going to acquire your company. So we just very simply took what it was that they were doing, documented it into system processes and procedures. And we actually used Lego blocks as a visual to be able to say our solutions are like individual Lego blocks. And we're our specialty is being able to put those Lego blocks together in a way that best suits your requirements for the business. And even it was unbelievable because when we sold the company to this large telco, a named part of the acquisition was the intellectual property that was this Lego blocks and the documentation that went behind it. So to, to be able to demonstrate to the, to the um, the founders that this was something that was comparatively simple, maybe even considered a perfunctory exercise, added significant value to the uh, eventual sale of the company, uh, was the ultimate ahuva moment for them in terms of how it all came to be.
Speaker B: You also worked for a private enterprise where um, there was a rising generation that was getting ready to take over the business. Can you talk a little bit about what the challenges might have been there?
Speaker C: Yeah, the challenge is when the next generation is not necessarily cut from the same cloth as the founder, uh, and the founder, uh, either the matriarch or patriarch might um, have grand designs that the business stay in the family for generations. Uh, but it's really a question of whether the matriarch patriarch is going to be able to let go of the reins and whether the scion if you like, um, is going to be coachable, uh, in that monk line and not feel um, overly privileged and feel that just because their last name is the same as the founder's last name, potentially the same name as the company, that they are uh, uh, magically endowed with all of the same capabilities to be able to take over the business. And typically the founder, and I know you know this because you've, you've been in the same situation. The founder, what got them to where they are right now is not what's going to get them to the next um, stage. And so if all they're doing is following what the founder did for the last 10, 20 or more years, they're not going to necessarily be able to grow. And there's a multi part dance to that because if the founder feels well what got us here is going to get us to the place next and if they silent feels either that's right or they feel that something else needs to be done but they're being pulled uh, in the opposite direction by the way they're parent, then that is where you get a lot of challenges.
Speaker B: Yeah, that's one of the big, one of the big deals I find is that and I tell the elder generation that look at your rising generation is going to do things different, just get over it because that's what's going to happen. They're going to do things differently.
Speaker A: Some will be better, some might be
Speaker B: a little bit worse. If we have them do small experiments, we're likely not to hurt ourselves very much.
Speaker C: A controlled fault is I think what we call.
Speaker B: Well the truth is in business Most of the things you try don't work. And ah, where my issue is, is when you go on a major, um, major, major project and put all this energy into something, you're not going to give up till way past you should have given up. Well, if you're doing small pieces, you break that great big thing down to lots of small chunks and you do one chunk at a time. If it doesn't work, it doesn't hurt. No.
Speaker C: So it's an excellent point, Josh. And I'll bring up another aspect of it and that is the, for lack of a better term, the Midas touch. So the company who started off, uh, and they're building widgets and then all of a sudden they decide, well, we were very good at building widgets, so we must be able to be very good at building something else. And they take that same business model, they superimpose it on, uh, potentially either an acquisition or a startup or uh, some combination, uh, and they're shocked that their skills and capabilities don't translate or don't transport into this new business. Uh, and to your point, um, they keep chasing that same opportunity, not recognizing that there's been a systemic failure, um, in the approach to that.
Speaker B: Yeah, absolutely. So what did you do to get the rising generation ready to take over the family business?
Speaker C: I think the most important thing was to try and help them to understand and doing it in a very diplomatic and respectful way, um, that they needed to, to under. They needed to understand that they needed a lot, they needed to learn a lot, uh, and being able to have uh, that conversation, you have to build a relationship. You know, people are not going to take what you say until you've got some level of rapport. So you, a big part of the job is building rapport early on in the process, not trying to force it. And once you've got that rapport, being able to bridge it and to say, okay, well look, here are the things that you need to develop in order to become that leader and to recognize the things that the matriarch patriarch, uh, may have done well, uh, and should be replicated, and the things that they may have not done well, that should not be replicated. So it's a journey. It's not a one and done medium. It's a long.
Speaker B: How many years did it take you to get the rising generation to be ready to take over the business?
Speaker C: Oh, I would say it was probably, it was probably four years.
Speaker B: Yeah, my average is three to five years is what I, I find. Uh, and the biggest challenge I See, I, I'm curious if you see the same thing was, is having the rising generation change their mindset from an employee's mindset to an owner's mindset. Ah, I don't care what you do. That unless you actually work, at least has been my experience. Unless you work really hard on changing that, uh, mindset, there's a good chance that, uh, the transition is going to fail.
Speaker C: I think. I absolutely agree. And I also think that they need to start to think of themselves as leaders.
Speaker B: Yes.
Speaker C: In many cases, if you're working for a very strong personality, a family member, you've almost been relegated to a follower. Uh, it might be a fast follower. You might have a follower with an opinion, uh, and an ability to say something, but you're still a follower and not a leader. Uh, the leap, the journey, the migration to that leadership mentality, in addition to the owner mentality, uh, is an important step. And it's something that can be taught, it's something that can be learned if that person is opener and, um, wanting to see that journey for themselves.
Speaker B: That's been my experience. Also, uh, this is where the value of somebody like you comes in, is that I believe rising generations should never report to their parents. And that's where the hired hand comes in, is that the rising generation reports to the hired hand. Hired hand can say things to the rising generation, the younger generation, that the parent can't say because it won't be received well because of family dynamics when they were growing up.
Speaker C: And it's. That's easy to say, and it intellectually might be the case for a lot of people. Uh, but when you go to the family dinner on Sunday night and the one that's missing from that table is the higher hand, that's where the challenge begins to break down. Because those conversations on one morning are all about, well, this is what we talked about last night. And so you have to be able to. To not, um, not control it, not contain it, but to steer it, uh, in the right direction.
Speaker B: My belief is the hired hand needs to have the ability of speaking truth to power. In other words, you have to be able to go to the right, to the senior generation, and say, stop having these conversations. They're not helpful. Yep. And you don't want to say it that way because that, like, will get you fired. But essentially that's what you want to be saying.
Speaker C: I always, uh, I always remember Jack Welsh's line, which is that I'd rather be fired for something I did than something I didn't do. Yeah, and so I've always, I've always pushed, uh, maybe sometimes to my detriment, a little harder than otherwise might be the case for the exact reason that you just mentioned, and that is that it may not be what they wanted to hear, but it's what they needed to hear.
Speaker B: Well, my experience also, especially if the elder generation is a founding, founding generation, they're fine for you getting right in their face and saying stuff that other people think you should never say. In fact, they love it because nobody ever tells them what tells them the truth because, you know, they're so used to shooting down other people that if they can't shoot you down, they kind of go back for a second. M. This is interesting.
Speaker C: Yeah, totally. And it gets back to that building of rapport because.
Speaker B: Absolutely.
Speaker C: Unless you built that rapport and what I've seen in other situations where colleagues of mine have gone in and taken perhaps a little too strong a hand, uh, and not spend the time building the rapport is that they become out of good, uh, graces with, and sometimes the founders are not great employee managers and particularly if they brought on somebody at a very high level. So then the relationship becomes very dysfunctional. Talk, um, they talk only when necessary, um, talking why each other as opposed to, to each other. And, and that's where things start to break down. And either it break, it gets to a point where somebody, either the hired gun leaves or the, the uh, family decides that they need to part ways. And of course hired guns are used to um, employment agreements and severance packages and, and those kinds of, those kinds of perks. Whereas you know, more family owned businesses are like if you're leaving, go, good luck to you. But you know, uh, there's no exit package here. So that can be another source of tension and frustration.
Speaker B: You negotiate that up front would be my recommendations totally.
Speaker C: But doesn't mean to say that it isn't uh, a more challenging situation.
Speaker B: No, it can be. And those are typically the family transitions that fail. And there's an awful lot of them that fail.
Speaker C: And I think it comes back to the, it comes back to that point about your experience in three to five years, mine saying four years. Um, you have to approach it as a long term venture, um, and you have to approach it with something that has consistency because if it's on one day and off the next day, um, it isn't going to stick. And the employees are used to a certain regime and if that regime keeps moving back from where it used to be to what it's what it wants to be in the future and it isn't kind of moving in one direction or the other. They're going to be very reticent to get onto the new program and that's going to be another speed bump in the whole problem.
Speaker B: They may try to sabotage it because they'll go back to the owner, the founder, and say, blah, blah, blah, blah, blah. But, uh, we can't do that. And they overrule you and they, and they learn that they can go around you. And this is even a bigger problem with the rising generation is that I always say, you know, if you're going to have your rising generation run a section, you can't overrule them and you can't get in the way. You have to. They come to you with a problem, you say, that's cool. Have you talked to my son or my daughter? If the answer is no, so we'll go talk to them. And if that doesn't work, then the three of us will talk. Yeah, and that's one of the things I always train rising, you know, the elder generation. That's how you have to answer these questions, otherwise you're usurping the authority. And by the way, the same with me. Totally. So, Brad, I am really sorry, but we are out of time.
Speaker C: Well, you want it?
Speaker B: Yeah. And I know you've written a book on leadership, so tell us a little bit about that and where you can find it and that kind of good stuff.
Speaker C: Sure. Thank you. Um, so with my 45 years of experiences in large companies and small companies, helping smaller companies grow and build infrastructure and sort of, um, ironically helping large companies to strip out the bureaucracy that was getting in their own way and becoming more lean and meaningful, uh, like the smaller organizations I work with. I used my memoir, if you like, as a framework to learn to share all of the lessons that I've learned. The hard fought successes, the humbling setbacks, and to help the next generation of leaders be able to benefit from that. My hope is that everybody will make new mistakes and not make the old ones because there's really no excuse for making the old ones because they're pretty well documented. But if anyone is interested in the book, it's coming out in the next couple of weeks, they can go to my website, which is www.consistency-edge.com. so www.consistency.com sign up for the mailing list and I'll make sure you get that.
Speaker B: Cool. Sounds great. I've got two things I'd like you to do. First is, um, wherever you're listening to this podcast, please give us an honest rating and review. If you love us, give us five stars. If you hate us, give us one star and I'll just cry a little bit. I promise I won't get your your keyboard all wet, but that doesn't happen anyhow. And the second thing is we're always looking for great guests like Brad. So if you own a business and you have a story to tell or you have a challenge that you would like some help with, why don't you send me an email at Ah JPatrick at stage two solution. That's the number two with the solution being singular dot com. Let me know you are interested in being on the show and I'll send you a link and we'll have a conversation to see if you would make a good guess for us. Again, that's jay patrick@stage2 solution.com and you're at the 5050 accelerator podcast. This is Josh Patrick or Brad Henderson. Thanks a lot for stopping by. I hope to see you back here again real soon.
Speaker A: Look, I spent enough mornings thinking and
Speaker B: writing about what it takes for business success.
Speaker A: Here's an important final thought. The old ways work for a reason. But the best legacy isn't just about what you build. It's about building something that outlasts you without burning you out in the process. If you found value in today's podcast, do me a favor, take 30 seconds to, uh, rate and review the show. And yes, I mean honest reviews. I'd rather have the hard truth than empty praise. Your feedback helps other business owners find these conversations. Hey, I'm Josh Patrick and this has been the 5050 accelerator. If you're ready to work less and profit more, make sure you subscribe wherever you get your podcasts. And remember, you've built something incredible. Now let's make sure you're actually around to enjoy it. See you next time. Look, I spent enough mornings thinking and
Speaker B: writing about what it takes for business success.
Speaker A: Here's an important final thought. The old ways work for a reason. But the best legacy isn't just about what you build. It's about building something that outlasts you without burning you out in the process. If you found value in today's podcast, do me a favor, take 30 seconds to rate and review the show. And yes, I mean honest reviews. I'd rather have the hard truth than empty pro ways. Your feedback helps other business owners find these conversations. Hey, I'm Josh Patrick, and this has been the 5050 accelerator. If you're ready to work less and profit more. Make sure you subscribe wherever you get your podcast. And remember, you've built something incredible. Now let's make sure you're actually around to enjoy it. See you next time.
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