When Partners Get Stuck, Look for the Gray

What happens when three business partners cannot agree on what comes next? 

That was the spot Jimmy Taylor found himself in at Novotus. The company had grown for more than a decade, competitors were getting bought by giants the size of IBM, and the three owners could not align on whether to take on a partner, take on investment, or chart a path to retirement. The tension did not stay contained to one decision. It crept into everything. In this episode, Jimmy and Elizabeth trace how that stuck feeling spreads, what it took to break it, and why the partners walked away as friends. 

From there the conversation opens up into the bigger pattern Elizabeth has seen across thirty years of this work. The dilemmas that keep owners frozen are usually imagined futures, not present-day facts. The mindsets that trap them often sound like loyalty. And the exercise that changes everything is simpler, and more uncomfortable, than most people expect: actually writing down what you want. 

Key takeaways: 

• Why a stuck partnership turns every ordinary decision into a source of conflict 

• The difference between the functional side of a transition (tax, legal, closing) and the alignment work that actually frees people 

• How the objectives matrix surfaces what each person truly wants, often for the first time 

• Why most dilemmas live in an imagined future, and how looking for the gray opens real choices 

• The mindset traps that keep owners in place: the business cannot run without me, nobody can do what I do 

• Statistics and stories as the two things that genuinely shift an owner’s thinking 

Chapters in this episode:

01:00 — Welcome and Jimmy’s background
03:18 — Inside the Novotus story
05:30 — What “stuck” actually looked like
06:44 — Why alignment matters more than the closing details
08:34 — The stakes: 32 million family enterprises
09:16 — Defining a dilemma, and the passion behind the work
11:46 — The framework that has not changed in 15 years
14:13 — Elizabeth’s own transition story
17:32 — The relief of a clear path forward
18:47 — What keeps owners stuck: mindset
21:57 — The weight owners carry for other people
24:10 — Dilemmas and the gray in the middle
27:03 — Reflection and close

Connect with Jimmy Taylor: 
https://www.linkedin.com/in/jimmy-taylor-sphr-25b230/ 

Connect with Elizabeth Ledoux and the Transition Strategists:
Website: https://transitionstrategists.com/
Facebook: https://www.facebook.com/thetransitionstrategists
Elizabeth on LinkedIn: https://www.linkedin.com/in/elizabethledoux/
Transition Strategists on LinkedIn: https://www.linkedin.com/company/transitionstrategists/
Transition Strategists on YouTube: https://www.youtube.com/@transitionstrategists

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When Partners Get Stuck, Look for the Gray Transcript

Elizabeth Ledoux:
Hi everyone and welcome back to the Business Transition Roadmap. I am Elizabeth Ledoux and I’m the founder and owner of the Transition Strategist. I’ve been doing transition strategy work for over 30 years and today I am thrilled to have Jimmy Taylor with us. ⁓ He is just a long time entrepreneur.

He’s got an absolutely incredible background and I’ve had the opportunity to work with him many times over the years. ⁓ He’s just wonderful to be with. So his background, I’ll tell you right now, he ⁓ serves as executive director of the Dallas Human Resource Management Association. That’s a mouthful. It’s a nonprofit organization who trains and equips human resource professionals.

So he’s the executive director there. He also said he was a longtime entrepreneur. He previously was a founding partner of a company called Novotus, which was a Texas-based recruiting process outsourcing provider. And ⁓ back in that time, it was named the number one mid-market RPO and HRO. And he…

recently decided to come back to be ⁓ working with me and with our firm. He is a transition guide with the transition strategists. And again, I am so excited to have him back working with us. So today what we’re going to do is we are going to walk through the Novotus story, which I think you will find fascinating. And then we’re going to talk a little bit about his passion behind doing the work that he’s doing today.

So Jimmy, thank you so much for being here.

Jimmy Taylor:
Thanks for having me, Elizabeth. It’s great to be with you. We have been friends and occasionally coworkers for quite a number of years, so it’s an honor to join you on this podcast. I’m looking forward to the morning.

Elizabeth Ledoux:
Thank you. Well, let’s just dive right in. And why don’t we start with some of your background and experience and walk through your Novotus story.

Jimmy Taylor:
Sure. Well, as you mentioned, I was an entrepreneur for most of my adult life. like a lot of entrepreneurs, probably got started because I couldn’t find a real job. I ⁓ started my own company. I’ve actually had three different companies. Two of them, we had successful exits. One of them was a colossal collapse and failure. no matter where the entrepreneur is on the entrepreneurial fly,

Elizabeth Ledoux:
You

Jimmy Taylor:
I can relate. I’ve been there and done that. So, and it is one of the reasons I’m so passionate about both my work with human resource professionals and my work with entrepreneurs and helping them successfully transition because in a lot of ways, there’s a lot of similarities and they’re one and the same in terms of helping people prepare for, decide and change through an ongoing process. So I have a passion like you do for entrepreneurs, particularly family-owned companies.

You and I both recognize that such a vast majority of people in the country work for a family-owned business. And it’s just important to the backbone of our culture and our economy that those companies not only thrive, but they successfully transition into new ownership and a lot of times, next generation. I do enjoy that work. In terms of the Nevada story,

honestly, one of the reasons I’m so passionate about the work you do is because you helped us through our transition when we were totally stuck. We had done a startup, we’d been in business for about, I guess about 14 years, had had some great success. But most of our competitors that we were going up against on a daily basis had been purchased by much larger organizations. I’m talking organizations the size of IBM and similar.

And so we were faced with a real dilemma in terms of how we were going to continue to grow and finance our growth in the space that we ran. We three owners, two of us were minority partners, one was majority shareholder, and we were completely stuck in terms of what we were going to do, the direction we were going to take. And for any partner…

Elizabeth Ledoux:
was the stuck part? just kind of how were you stuck?

Jimmy Taylor:
Yeah, we were not in agreement or alignment on what was going to come next in terms of our growth. Were we going to take on a partner? Were we going to take on a huge investment and manage through that? How would we eventually transition the company when we all wanted to retire? And when entrepreneurs are stuck, particularly in partnerships, whether they’re family-owned or just other partnerships,

everything in the business becomes stressful. It’s not just a stressor on that particular point, but every decision can become a source of conflict and tension within the organization. So when I say we were completely stuck, we found ourselves having difficulty aligning on anything. And had we not had the benefit of your process, I’m not sure how it would have gone, but I can tell you the outcome was incredibly successful.

And today the three partners are, we’re all great friends. We no longer work together, but we’re great friends. And I think a lot of that is because we managed with your help and your process through the transition successfully.

Elizabeth Ledoux:
So great. Well, I’m glad we were able to do that for you and that your relationships are intact because, you know the function of a transition is important, such as tax, legal, exchange of money, all of those different things, the closing, those are all functional items. But if you can’t get to a point where you can agree,

on what you want. That tension usually just not only tears up the relationships between the partners, but it also tears up the company. The company suffers so much when that’s happening.

Jimmy Taylor:
That is so true. ⁓ It can literally take a company to its knees. And you and I have seen that where the transition or the pending transition just froze everything in place. And so there’s lots of great advisors who can help with the legal and the tax and all of the details of the transaction. But what’s few and far between and what makes your work so unique is the fact that

when you work through the why and the when and the details that you take companies through, it allows people to move past ⁓ the attorney speak and the CPA speak and the tax speak into what’s really important in terms of their objectives with their company, with the future of the company, the future of their employees, and with their life, their next journey.

At least for me, I had not seen another process that dealt with that the way you do, which is why I think you’ve had such success. And given the number of family-owned businesses, and I looked this up because I hadn’t looked at these stats in a while, there are 32 million plus family enterprises in the country. So you got a lot of work ahead of you.

Elizabeth Ledoux:
my gosh.

I guess so. did not know that statistic has gone up significantly since the last time I looked at that. Thanks for bringing that forward. That’s a lot. That’s a lot. So as you walk through, ⁓ you and I worked together in the past and then you went to do some other HR kind of work because you have an incredible background in people and human resources. Coming back into the transition strategies,

Let’s talk a little bit about your passion behind being a transition strategist guide.

Jimmy Taylor:
Yeah, thank you. I think it’s because I’ve been there. I’ve been there and I know the pressure that they’re under. ⁓ It’s a lonely feeling when you’re not sure what the next step is. And so when entrepreneurs are stuck and when they’re struggling and when they’re, you know, conflicted either with potential successors who are in the business already or maybe family members who may be potential successors, that’s a hard place. You describe it well. It’s a dilemma.

We think of dilemmas as being difficult, hard decisions, but as you so well state, a dilemma is really just an option where you have no good options. There are no good choices. There are only hard decisions. None of them are perfect. And trying to find a path forward through the dilemma, the best possible path for the entrepreneur and the successors and the enterprise itself is just crucial. So.

That’s why I think I’m so passionate about what you do because I think that ⁓ it’s much needed and there’s just not a lot of other solutions in the marketplace today that I’ve seen that work effectively. I don’t know what your success rate is over the 30 years you’ve done this, but I know it’s very high.

Elizabeth Ledoux:
Yeah.

It’s very high. It’s over 90%. It’s close to, I’m sure it’s over 95%. But of the businesses that we’ve worked with over the years have successfully transitioned. And when I say successfully transitioned, one, they’re still in business, right? Still in business, still cranking along because we all know business is not easy. And yeah, that stewardship of the business is in another generation’s hands. So that’s great.

And Jimmy, you keep saying the work that you do like me, and maybe it’s transition strategist, but it’s the work that we do together. Because yeah, it’s fun to be a part of a community that where we have multiple guides and we not only help our clients, but we also learn from each other so that we can continue to provide more and more value.

Being a transition guide is a practice, just like you practice law or you’re practicing CPA. Being a transition guide literally is a practice because laws and everything are changing all the time. And people, every single family is different and every single business is different. It’s amazing.

Jimmy Taylor:
Yeah, yeah, I agree. They are all different, which makes what we do more of an art than a science for sure. So speaking of statistics, because you just talked about transition strategists in the 95 plus percent, ⁓ only 30 percent of family-owned enterprises successfully transition into Generation 2 and only about 12 percent successfully transition into Generation 3.

95%. I’m not great at math, but I think 95 % is lot better than 30%.

Elizabeth Ledoux:
⁓ I think so. I think so. It’s a, ⁓ you know, the framework that we have and you walked through the framework. How many years ago was that when you did that, Jimmy?

Jimmy Taylor:
Oh, good question. I think that was probably about 15 or 16 years ago now.

Elizabeth Ledoux:
Yeah, so that framework really materially hasn’t changed. It is a proven framework. And I call it a framework instead of a process because it’s a framework, you know, my engineer and me, right? It’s a framework where you can put a lot of information into it. And the framework can take various families.

various businesses, various situations. And this framework allows the participant, what we would call an evolve member, it allows that business owner and successors to look at the business and to look at the situation and to see what I think of as puzzle pieces and understand what puzzle pieces you clearly see, what puzzle pieces you are not really sure of.

and maybe some puzzle pieces that are missing that you haven’t even thought of already, or they just might be missing because you don’t know, you haven’t asked the question, you haven’t provided the invitation, you haven’t opened the door yet, and you might be afraid to open that door too. So ⁓ yeah, this framework, really hasn’t changed over the years. ⁓

But the process of how we deliver it has, because it’s all virtual now and it’s easy for families to quote unquote get together whenever they want to to do the work. So it’s exciting.

Jimmy Taylor:
That part has changed. when I think about that framework, and there’s so many different pieces and tools that you have built as part of that framework that are important. for us, when I think about our journey, and I talked about us being stuck, I can still remember the afternoon. We got out the office. was just the three of us. We got a private location away from the office so we wouldn’t be disturbed. And we worked through the objectives and compared.

each of our objectives with our potential options. And that was the light bulb moment. The light bulb went off, it became really clear what the transition path was. And so I think that’s what’s interesting about the framework is lots of pieces, lots of tools, lots of things that you’re going to do through that transition process. And you don’t necessarily know which one is going to unlock what’s stuck for your organization. But combined, when you look at the framework overall, it just moves people.

to great outcomes.

Elizabeth Ledoux:
Thanks. Yeah, it made me think, Jimmy, and I think most people know that I’m in transition of the transition strategist. And so I’m beginning that. Started it five years ago when I did not have a successor in mind. So just for our listeners, you don’t have to know who’s going to take over to start using this framework to understand what you want. A couple of years later, found my successor.

who now is in the process of buying in, which I’m excited about. But I remember going through the process and that it’s called the objectives matrix. That objectives matrix is so key to what your words unlocking because I thought since I built it and I did it all the time, I thought that I knew what my objectives were and I also thought I knew what my husband’s were. I did.

when we took the time, because people don’t take the time to write down and think about not only what do they want for themselves and their family members, you know, and their spouses, but also what do they want for others, for some of their employees, for some of their partners, for the business itself, and you know, maybe a legacy that they want to leave, and whether or not that’s actually possible, because usually if you put your mind to it, it is. And I thought I knew.

what he wanted. And we had some of the best conversations I think we’ve ever had ⁓ over that. And then again, later, just in my example, I had my objectives, I knew what my husband wanted. And then two, almost two and a half years later, I pulled that back out when Andrea walked through the door, then she and I, she did hers and I shared mine with her and she shared hers with me. And that it’s just a foundation.

If you understand what you’re trying to achieve and how you’re going to help everybody live their best life, successors coming in live their best life, transitioners leaving live their best life, whether it’s leaving quickly or leaving over 10 or 15 years, or maybe even at death, that’s okay too. ⁓ When you understand that, it’s more clear, isn’t it? And it sounds like that was your experience.

Jimmy Taylor:
Right.

It is, it’s more clear and what a great stress reliever to have a clear path forward because every entrepreneur, particularly as they approach the later stages of their career, this is their baby that’s been their life that they’ve built. so, you know, the stress and the concern, worry, fear, whatever you’re going to call it, that they feel over trying to figure out that transition on top of running their business on a day-to-day basis.

can be just overwhelming. So the freedom that that brings and you know, as you well know, every transition is not perfect. Things come up, economies change, business conditions change, adjustments have to be made, but it’s lot easier to adjust a path that you’re on to a slightly different path than to create that path from scratch.

Elizabeth Ledoux:
Absolutely. So what do you think, you know, in your opinion, when you think about business owners, what do you think keeps people from engaging in figuring out that next path for their business as they think about transitioning? They may not even be thinking about it at all, but what do you think stands in the way?

Jimmy Taylor:
⁓ I think it’s probably what stands in the way for most of us in business overall is usually just a mindset. Their mindset is ⁓ either the business can’t afford to run without me or I can never find somebody that could do what I do. Or, you know, my attorney said this is the way I should do it and I’m not happy with that. It’s just a mindset, a picture they’ve built of a box that they think that they’re in. And I think that’s one of the great things about having.

someone to partner with to talk through those transitions, it allows you to change your mindset. It allows, you know, there’s two things that change us in life, statistics and stories, right? And understanding stats about your business is one thing, but when you hear stories about other entrepreneurs, other family businesses who’ve successfully transitioned, it starts to be a great encouragement. It starts to unlock that potential that maybe there’s a future that I really haven’t even thought through and imagined yet that’s possible.

So I think, but I think that’s where they say stuck and just, just in the mindsets we all have within ourselves and about our businesses.

Elizabeth Ledoux:
Yeah, that’s really an interesting, yeah, really interesting conversation because

And do spin up some really interesting stories as entrepreneurs about how hard it’s going to be or how difficult or impossible that’s even worse. Impossible, like, and nobody would want this business, that kind of thinking. ⁓ Yeah, that can really, really, really get us stuck.

So how do you, when you talk to people who are entrepreneurs, how do you start to get them to work through those mindsets?

Jimmy Taylor:
I think first of all, just a lot of questions. mean, one of the things I learned from you is just, you got to dive deep and understand not just the business and the business environment that they operate in, but the life that they’re living. What’s their family like? What’s their extended family like? What’s in their mind, something they want to be part of their journey ahead? So I think getting to know the organization is the key to starting to really have meaningful dialogue about what any transition would look like.

And I think that’s the reason so many of them stay stuck. And I’ve talked about this over the years, but so often they spend a lot of time with their CPAs and their attorneys trying to figure out their transition. And that is an essential part, but they start that process too early and they become constrained by maybe a tax belief that they have based on a conversation with their CPA or something their attorney said about a transition.

⁓ So I think that’s one of the keys is just stepping back a minute, getting the full picture of who they are and how they operate, and then getting them to really take the time to look at what’s their future look like in an ideal state. I think that’s a key.

Elizabeth Ledoux:
Yeah, that’s interesting. And sometimes they’re not thinking about that future state. You know, what came to mind too is I think one of the things that keeps owners stuck many times is, is believing that if they move forward, they’re going to either let somebody down or somebody is going to be upset. And it’s a relationship that’s important to them. ⁓ Because I think owners take such a big

I’m thinking of a person walking around with bricks on top of them, you know, and they’re carrying the load. And I think owners get so used to carrying the load that they may be tired of carrying it, but they continue to do it for others.

Jimmy Taylor:
Absolutely, they do. And it’s because they care and it’s because they’re well-intentioned. It’s all for all the right reasons. But it’s also, as entrepreneurs, we have this belief that nobody can do it like I can do it. And in reality, sometimes people can do it just as well or even better if we allow them to step in and gain the knowledge and gain the skills and take over responsibilities and authority.

Elizabeth Ledoux:
Well, what’s funny about that to me is that likely that attitude, that mindset, that tenacity, that’s what made them successful in the first place, right? Especially if they’re a founder, I can do it better than anybody else. And I’m gonna show you that I can do that. You build this business and it’s true, but if you keep that mindset as you start to transition,

⁓ You’re going to be in that business forever. Sometimes, the greatest thing you can do is help somebody else take it forward without you. Hopefully, everything continues on and you are extremely proud of that.

Jimmy Taylor:
Yes, because for sure for every one of us as entrepreneurs, there’s going to be a day we step out of our business either willingly or unwillingly, but we’re going to have to leave the business. So planning for it and looking for that transition is pretty key if we want to step out in our own terms.

Elizabeth Ledoux:
Absolutely. So one thing you mentioned earlier was dilemmas. And I thought maybe talking a little bit about those dilemmas because ⁓ when people think about dilemmas, this is what I’ve learned in my 30 plus years of doing this. When people think about their dilemmas, it’s like, and I’ll give you an example. It’s like, well, you know, I’d love to bring my son in. This is real. Love to bring my son in to work with me.

And give him a job but if I do that my daughter will be very upset with me because her husband’s been out of work for 18 months and I won’t give him a job and I don’t have a place for him So what I’m gonna do is not hire my son even though it would be great for the company Great for him great for me a win-win all the way around because it would work ⁓ So the dilemma so in that case ⁓ the fear is that the daughter might be upset

right, if he did something and if he doesn’t do it, then he doesn’t get to work with his son, his son doesn’t get the opportunity and the company doesn’t, you know, thrive because of it. So that’s the dilemma. The interesting thing about when we envision dilemmas is typically they’re not real, right? They’re there. You’re envisioning a future and that future you have choices and the choice you make could

take you one way or the other, but the dilemma you’re usually seeing A or B. If I do this, I get A. If I do this, I get B. And I lose whatever I lose on both sides. And in that one, he walked through, the owner walked through the process, and it ended up the conversations happened. And the son came in, the daughter was not upset, and…

everything worked out. There was this gray between, I can either have to do A or B, there’s all the gray in the middle. So one, a dilemma, usually it’s a future thing that is not true yet. You could be very certain it will happen, but there may be another way through it. And I think that’s the way my mind works. And I think that’s what this Evolve program allows people to discover. Is there a gray?

Is there another little path we’re not thinking about?

Jimmy Taylor:
And actually facilitating those conversations with the family or the partners or whoever needs to be involved rather than allowing a single entrepreneur to continue to do what we all do, which is have that conversation with ourselves within our own mind. Oftentimes, as you mentioned in that example, the problem gets solved by the conversations, but we’re afraid to have the conversation because we’re afraid of what we think the outcome will be or could be.

So the process of facilitating that is just key.

Elizabeth Ledoux:
Yeah.

Yeah, it’s interesting. Well, Jimmy, I always am amazed at how quickly time passes We’ve talked about a lot of good things today and your Novotus was just a great example of how you can get partners aligned on a path where you can do what’s necessary for the company.

in that case, and also maintain the relationships going forward. And I know you were worried about losing those when we were working together on that.

Jimmy Taylor:
Yeah, absolutely. It was a great outcome. Best possible outcome, in fact.

Elizabeth Ledoux:
Yeah, that’s awesome. So Jimmy, ⁓ thanks for being a part of this podcast today and a part of this show. And also thank you for being a guide, a transition guide. You have incredible background and experience and knowledge on all different fronts. Being a business owner yourself and walking through. Yeah, like you said, been there done that. So lots for people to ⁓

lean from you as you help them walk through their transition strategies.

Jimmy Taylor:
I appreciate that. It’s great work. I enjoy it. And thanks for all you do in terms of getting this process ⁓ ingrained in so many companies. It’s a game changer. It’s been a great conversation today. Thank you for having me.

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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.

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