Kickstarting Your Business Transition with Andrea Carpenter

Episode Description:

In this episode, host Elizabeth Ledoux is joined by Andrea Carpenter, the Director of Programming at The Transition Strategists. Tap or click the play button below to listen to: Kickstarting Your Business Transition with Andrea Carpenter.

In this episode, Elizabeth and Andrea discuss their new Big Six Program, which helps business owners think about their business transition and plan for the future. They explore the six critical questions that every owner must answer when considering a business transition:

WHY? —Why do you want to transition your business?

WHAT? — What do you have and want to transition?

WHO? — Who will succeed you in ownership?

WHEN? — When will the transition begin and end?

HOW? — How will the transfer be structured?

HOW MUCH? — How much do you need for your ownership interest?

They also discuss proven tools that deliver successful results for owners, families, and businesses going through a business transition.

Learn more about the Big 6 Program featured in this episode: 

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Connect with Elizabeth Ledoux and the Transition Strategists:
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Get Elizabeth Ledoux and Laura Chiesman latest book, “It’s A Journey: The MUST-HAVE Roadmap to Successful Succession Planning”: 

This episode was produced by Story On Media & Marketing:


Kickstarting Your Business Transition with Andrea Carpenter Transcript

Elizabeth Ledoux: So there are many wins. And when you go through a transition, it truly is a transition. A lot of people think of selling a business quote, unquote, selling a business, that’s an exit, when you actually transact and 100% done out, but along the way, that’s why we like the roadmap concept and the transition concept, we’ve, you’re on this journey. And so you know, you give up accounting, and then you give up something else. And pretty soon you’re able to give up your CEO role, or you’re in then you only are the big decision maker with maybe your successor. So there’s another one there. And then ultimately, along the way, there’s the transaction. And the transaction could be all at one time, it could be at the end of the road for you, where you just say, Hey, I’m out, and I’m gonna sell 100%. But it also could be transactions along the way. Welcome to the business transition roadmap. My name is Elizabeth Ledoux. And through my years, I have seen how communities thrive. When business succession and transition are done. Well, me and my team at the transition strategists have been helping business owners develop and implement transition strategies for over 30 years. And on this show, we want to help you by giving you the roadmap to a healthy business transition. Let’s get started. Hi, everyone, and welcome back to the business transition roadmap. I am thrilled today to be here with Andrea carpenter. She is a fabulous, fabulous person. And we are so lucky to have her she and I met through but an interesting meander. And I, when I met her, she just hit me as being a very special person. She and I over quite a few months chatted and she ended up coming in and working with me in our development of some of our new programs for the transition strategists. So I’m just thrilled to have her here. Today, we’re going to talk a little bit about one of her brain ideas, which is a program called the Big Six. And we’re going to just dive into that so that you can learn more, and hopefully get inspired to think about your direction. Think about your transition direction where you’re headed. Even if you’re 10 years away five years away, it’s just so important to know where you’re headed. So Andrea, welcome. And can you tell us a little bit about yourself?

Andrea Carpenter: Sure, thank you. So glad to be here, my first podcast experience, and I’m hoping to see more of you in the future. This is really exciting. When I first met Elizabeth, I rolled out with my work at the intersection of and I saw Elizabeth eyes get a little bit wider. Really I find my best work happens at the intersection of design strategy, facilitation and connection. So when we we look at what people need, and we can design a strategic experience to really sort of level up and take people to the next level, and do it in a way that’s about the human connection. It’s about the way that we come together. And we we leverage our strengths, we leverage the strengths of those around us in these group experiences. It’s really cool. It’s really exciting. And so when Elizabeth sort of softball to me that we could build some programs together, I was like, yes, let’s try to build some programs. So really excited to be here and ready to talk about the first one that we’re experimenting with.

Elizabeth Ledoux: Thank you. Thanks. So let’s just dive right in. And we’ll just talk a little bit about the big six program. How did you come up with the idea? And tell us a little bit about it?

Andrea Carpenter: Yeah, so I am second generation, I watched my dad build a successful company, and ultimately exit that. And man the turmoil that I felt him going through an even if you take a step back, when you’re at a moment of transition, or you’re thinking about transition or something that’s going to change in the future. There’s so much internal, oh, what do I do what’s right? Is it in alignment with my values? How’s it gonna affect my family? There are so many questions, so many different things that we think about as we come up to these moments of transition. And I saw my dad navigate this, and he came out on the other side really well. But when you think about is there some type of structure or is there some type of community that you can lean on to help you navigate or move through a transition? And so that’s kind of where this all rooted From how do we bring people together to really lay a foundation, give them somewhere to start, I don’t think it’s too soon to start thinking about what you want to do in the future. There’s obviously, we have to live in the moment. But a lot of us are planners, maybe we’re a little bit type A, we want to think about the next step, to make sure that, hey, maybe it’s gonna take three years or four years to actually execute that or to make sure that this piece is in place so that it can happen in the way that I want. Or maybe there’s a key relationship or something that I haven’t quite considered yet. And so to look at all these factors early on, in the journey was kind of the origination of the idea around the program. And then when you mentioned the big six questions that you use in your business, I was like, that’s the program, you can just take people through answering these questions, and I’m sure we’ll talk a little bit about exactly what those questions are. Absolutely.

Elizabeth Ledoux: So when I developed the intellectual property, right, and I developed this program called the transition roadmap. One of the things that was that I learned, because this is all based on my experience over the last 30 plus years, one of the things that I learned is that most business owners don’t know where they’re headed. When it comes to transition. They’re, they’re very focused on building and they’re very focused on growing their companies. And they, even though they may not believe it, they actually have mastered, how they’re doing that, you know, they’re, they’re actually really good at it, because the business is still in business. And it’s still running. And, you know, people are being paid, and it’s all functioning. So they’re actually masters at how to run the business and grow it the way that they’re doing it. But they haven’t figured out where they’re headed as far as transition. So what we did is put together this concept called the transition compass, so it can give you a direction without you having a specific destination. And then from that, the idea of not always starting with the how and how much, and people have heard that before. But most people when they think about transitioning their business, they go, Oh, well, how am I going to do it? And how much is am I going to get? Or how much is it going to cost for somebody to come in. And that’s a great place to start. But there are too many choices there. And it doesn’t really get your why. So the compass was there to help get a direction that met your needs that fit for you. So anyway, that’s where the compass starts. And the big six, those are the big six questions that get answered. So Andrea, tell us a little bit, you can walk through the big six for us.

Andrea Carpenter: Yeah, definitely. So maybe start with the first one, which is maybe my favorite. And we’re going to spend a lot of time in the program. And that is the why. Why do you want to transition your business? And and as you think about your next adventure, and what comes after? What’s the why behind that? Maybe you could tell us a little bit more about about the wireless.

Elizabeth Ledoux: Yeah, so the why the why is interesting, because many owners haven’t had the opportunity to think not only about their why, but also about how they want the business to serve others. So most people think of why and it’s like, okay, well, why do I want to do this are wise a little bit different, are why what you do in the program as you go through and you envision what you want your life to be like, and what’s important to you in your life as you go forward. So one of my favorites for an individual was to surf when the surf was up. And so if you can imagine a business owner sitting there going, Man, I’m sitting in my office, and the surf is up, and I want to go, but he can’t, because why he’s got the business and he doesn’t ever know when the surface is going to be up and when he’s going to have to, you know, when he’s going to be in a meeting or whatever. So they you walk through and you really dig kind of deep and play with the idea of what is life look like for me, when I’m happy. I’m doing what I love and it could be partially that you’re selling the business. It’s not maybe that you’ve sold completely, but maybe you’re not doing some of the stuff that you are doing today. So what does it look like for you in your life? What does it look like for your spouse? What does it look like for you as a couple? Family? All of that that is very personal to you and your best friends you know, how are you helping them? But then also what’s it look like for partner Your successors for the business are your employees, because you’re used to taking care of them. So this is like a compilation of all of these different items, objectives is what we call them. And that forms your complete why your whole why.

Andrea Carpenter: And there’s a really cool tool that you’ve built called the objectives matrix, which we are going to utilize in the program. And it helps you look at okay, is this a one year or a goal I’m kind of continuing is this like three, like short term or way in the future, and it looks at it from those dimensions that you just looked at. So is it for me personally, I really want to make sure I can go serve, or is it me and my partners is really important, or the culture that I built in my business is so critical, it’s really important to me that the person who’s coming up into my business can help continue maintaining the culture that I’ve built with my company. So looking at it from all angles. It’s a, it’s a really cool tool.

Elizabeth Ledoux: Thank you, thank you took a while to build it, it looks really simple. You know, the best tools are simple and easy to use, and they go deep, so good.

Andrea Carpenter: And this is a special tool, and it’s one that we actually we give away for free on our site. So you can go to transition We’ll put a link in the show notes for you. The objectives matrix page, we have a download of this, and you could start filling it out and thinking about what’s important. The reason we’re inviting you into a program, like the big six is the peer learning component of the program. So it’s not just what’s my objectives matrix, but opportunities to share and share it with people who are important to you, and to potentially share it with other business owners in a peer learning style environment will help take it from, hey, the objectives matrix is printed out and sitting on my desk and something I probably need to do. And the program is a place to actually take action and use that tool. So we’re really excited to introduce you to that one. And that is for the y, which is our first big six question. And the next one is what what do you have to transition? So Elizabeth, can you talk a little bit about what we might discuss when we talk about the wet? Sure, so.

Elizabeth Ledoux: So owners look at their businesses, and they see it as a whole. And sometimes, sometimes they see it as this amazing, kind of like castle. And other times they see it as a shack. And I’ve run into more owners, especially small business owners, who believe that their company might not be worth very much or it doesn’t have very many assets are it really you know, isn’t that isn’t that big, isn’t that great? And what we find when people actually take a look at their what they find that their business is actually something pretty special. And, and that it does have value. And it’s my personal belief. This is just my mission in my life, that businesses should be passed on to next generation entrepreneurs, you’ve worked so hard to build this business, even if it is small, you know, a simple auto garage repair shop in a nice town that a lot of people rely on to get their cars fixed. That’s a good business that somebody else could take over somebody else could do. And they could do a really good job at it and keep it going. It could be the greatest opportunity for them of their entire lifetime. So again, it’s kind of not just thinking about you, but looking at this business, and really understanding what do you have? And then how could it be a value to somebody else? So looking at that, and also looking at the components of it. Sometimes you have a building and you have a business, an operating business? And do you you may have them but you may not decide to transition both at the same time. So you want to look at the components of the business as well as what you have in the value of it.

Andrea Carpenter: Yeah, definitely some nuance for each person and every business is different, but there are similarities that you tend to see between businesses of all types and all sizes. I loved what you said there’s no business really too small to think about it, especially when I think about small businesses and how important they are to communities this the more successful your transition is The more that’s helping the community and it’s beyond just yourself. And that kind of ties into the next question. Which is that who Who do you want to succeed? You as owner? Let’s talk about that one a little bit.

Elizabeth Ledoux: Right? So the who is, I think the who is the hardest question for most owners? Do you take a, it’s kind of the big leap, it’s usually your who could be a third party, there’s always that option to go sell to a third party. Yeah, your options are sell to somebody inside sell to a third party that you don’t know, or shut it down. And shutting it down, I think is probably, it’s the least favorable option in a lot of different ways, financially, and also the energy that the business provides to the community. So we usually don’t look at that one. But selling to a third party is an option. And that is terrifying for a lot of owners, because you don’t know who it is. And you don’t know if they’re going to keep the business and the people. And typically, owners are really interested in the people inside of their companies and how they’ve been treated, and will be treated in the future. So as you go forward, the who becomes very important, because it is a risk for you, it’s a hard road to figure out how to get somebody from where they are today to be you and to be able to run the business the way that you do know as much as you know. And it’s also hard to think about even talking to them about it. Because, you know, will they say yes? Will they say no? Will they be able to do it? Will they have the entrepreneurial spirit to do it, your relationship with them is going to change. Because of it. There are just so many pieces. And then if you happen to be thinking of a family member as a who, like a son or a daughter or somebody like that. There’s an added layer of family on there where you really are not wanting to lose that relationship right with your son or daughter. So the who is really a challenge at times.

Andrea Carpenter: And depending on who your who is that can really impact timelines when you think about when, and that is our next big six question. When are you thinking you might want to transition? I know this comes up a lot. Is it too soon to start thinking about transition? I’m really loving working in my business right now. I don’t know if it’s time to even start thinking about transition yet. Let’s let’s debunk that that win question a little bit.

Elizabeth Ledoux: Yeah, so. So the idea of when they’re, when you go through this program, and you look at your wins, there are many, many wins because we wear different hats, right? So we’ve got the owner hat, you could call it a board hat, but it’s your big decision maker hat. And then you’ve got a job hat, typically, because you’re active in the company. So there are many wins. And when you go through a transition, it truly is a transition. A lot of people think of selling a business quote unquote, selling a business, that’s an exit, when you actually transacted 100%, then out. But along the way, that’s why we liked the roadmap concept and the transition concept we’ve, you’re on this journey. And so you know, you give up accounting, and then you give up something else. And pretty soon you’re able to give up your CEO role, or your and then you only are the big decision maker with maybe your successor. So there’s another one there. And then ultimately along the way, there’s the transaction. And the transaction could be all at one time, it could be at the end of the road for you, where you just say, Hey, I’m out and I’m gonna sell 100%. But it also could be transactions along the way. Could be with family or non family. But it’s great to have another owner involved. And it’s great to have somebody who picks up, you know, picks up that baton with you and walks right beside you to get the business continuing forward. So the many wins, you may have one or more transactions during the time, and then be changing roles and jobs and everything else. So I think of the many wins and it’s cool to have them all lined up. Because they don’t all happen at once. And we’ve even done 15 year visions. You could call them a vision but 15 year roadmaps because we don’t know what how long your journey is going to be.

Andrea Carpenter: And when you think about those many wins, I think ultimately We’ve we’ve come back back around where we’ve started, the many wins really influenced and your who and what exactly you’re transferring and why you’re transferring and what lifestyle is important to you, when you exit the business. All of those are going to drive our last two big six, which is the how, and how much would you touch briefly on but let’s just talk about it one last time in the context of all of those other questions now that we’ve put before it.

Elizabeth Ledoux: Okay, yeah. So once you actually know what you want, and I was actually on a meeting yesterday with an owner, who probably will transition out in the next five to seven years. Once you know what you want, then your how becomes so much more clear. It is so confusing when you don’t know what you want. Because usually what happens is you’re looking at the how and how much and you’re like, Okay, well, how much am I going to get not taking into consideration what the company is going to make? And what extra cashflow EBITA you’re going to be able to have and invest going forward. You’re not taking into account the growth of it. And so the how and how much are kind of, you know, how would I do it today, when with all of this information, you can start to envision what that journey looks like. And you can put together a strategy, not only a financial strategy of you living that life, go back to the why. Well life that you envision, and that your spouse if you’re married, envisions to Because don’t forget, they have dreams as well, that why not do that, too. So how much are you going to need? How are you going to get that money from the company because it’s your primary source of income and revenue? And then how are you going to transition it so that the people that you want to have in this business and the people you want to at least give an opportunity to take over have the opportunity to figure out their lives, they have to come up with money, they have to figure it all out, too. So there are moving parts on both sides of the how and how much and it’s easier and more clear when you know the four w’s.

Andrea Carpenter: Yeah. Awesome. So that’s kind of a long, roundabout story of why I find these questions. So exciting, and why I’m excited to build our first big six program launched this program, and really help business owners think through these questions. Again, you do not have to do it alone. And maybe your businesses small, or maybe you’re like I don’t even know when I want to transition. If you’re like I’m going to transition out of my business someday, which all of us will, the decision will be made for us or we get to make the decision. If that’s gonna happen to you someday, then we encourage you to check out the big six program. Again, it’s really about this peer learning community, having an expert team sort of guide you through answering these questions, thinking about the nuances, helping prepare you for conversations with people who are most important to you, and to begin to lay that foundation of a successful transition where you come out on the other end with all of your relationships intact. So that’s the spirit of the big six program. And we were really excited to share with you today about this this opportunity.

Elizabeth Ledoux: Yeah, it’s great. And and, you know, Andrea, just a couple of things. One is that each for each one of those questions, there’s a tool that they would be able to use. And can you talk a little bit about business owners are so busy, and how this program works with a time commitment might be just in general, how it sort of works. And yeah, it’s I will tell you, it is very, very efficient, your time as you as well.

Andrea Carpenter: Definitely, we want to give you all the tools to give you the biggest bang for your buck. And so the program itself will be structured over six weeks. So that allows us about one week per question. So we’ll introduce a tool will have an online learning module or a resource for you to be able to access more information about that tool. So if you can’t make it live, which we encourage you to make it live because of some of the peer learning components. There are recordings there are resources so you can go back look at anything at any point in time or maybe two years from now you’re like oh, I really need to revisit my when my many wins. What’s a tool that I can use to think about that. So these are these are yours? For as long as we’re running this program, you get lifetime access to these materials, which is something we’re really excited to offer, because it sounds like a transition is a one point thing. But it does happen over time. It is not just okay. And now I’m transitioning, and now I’m done. So these are tools that you can take and utilize throughout your journey. Again, the program itself will be six weeks, one hour live call offered per week, and we are going to offer some special bonuses for people that join us as VIPs. Elizabeth will be doing Q and A’s and even opportunities to get an hour one on one session with a transition guide. We’ll all be opportunities, because we want you to feel super supported as you work through these programs. So and then I yeah, I guess the last thing, I’m just so excited about the peer learning component. So as your cohort comes together, and we work through the six weeks, hopefully you’ll get to know other people on the live calls. And you can help them think through because when we help other people think through, or we see how other people are reacting to questions, things might come up for us that we wouldn’t have even remembered if we were working in a vacuum. And this is really a space of confidentiality. We’re not no one in your group is sharing your numbers or sharing your personal things. We’re all going through transitions. And so this is a really safe space to authentically share with other business owners about what you’re thinking and what you’re feeling as you navigate the transition.

Elizabeth Ledoux: Absolutely. That’s terrific. Well, yeah, Andrea, we are at our time, which is amazing how fast time goes these days. And I just would like to thank you, one. Thank you for this thought and concept and idea and for bringing it to us. I think it’s gonna make a big difference for people in just starting to understand what their direction is at a very high level so that they can begin that journey. And I want to thank you for just being here today. And for all the work that you’ve done. So, yeah.

Andrea Carpenter: Appreciate you and really fun. Thanks, Elizabeth.

Elizabeth Ledoux: Thank you for listening to this episode of the business transition roadmap. If you are listening to this and you find yourself wanting to go deeper into these topics and start the process of putting together your transition strategy. I’d love to offer you a free initial strategy session with my team, where we’ll help you to explore the future transition of your business, head over to To schedule a call. Thank you again for listening, and I’ll see you on the next episode of the business transition roadmap.


The Business Transition Roadmap with Elizabeth Ledoux

How do communities thrive? When businesses experience healthy growth and transition. Join CEO of The Transition Strategists, Elizabeth Ledoux as she and her guests identify what makes a successful business transition roadmap. If you know you want to transition or exit your business “one day”, today is the right day to start planning. This show will give you the roadmap.

If you’ve enjoyed this podcast, you can check out other episodes here: Podcasts – The Transition Strategists
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