Episode 30

Scaling Without Chaos: Strategies for the Entrepreneur to CEO Transition

In the dynamic world of business growth, the transition from entrepreneur to CEO is often fraught with challenges that can either propel a company forward or lead to burnout. This episode sheds light on the pivotal strategies that help business owners navigate rapid growth, avoid common pitfalls, and build sustainable success. The conversation uncovers the importance of strategic planning, effective delegation, and the mindset shifts required to lead with clarity and purpose.

Key insights from this discussion:

  • The Entrepreneur’s Growth Struggle – Why many business owners feel stuck working long hours and the critical mindset shift needed to break free.
  • Hiring vs. Outsourcing – When to hire in-house and when outsourcing might be the smarter, more cost-effective solution.
  • Decision-Making Strategies – A simple three-question framework to make better business decisions quickly and effectively.
  • Strategic Planning for Scaling – How a clear roadmap can prevent overwhelm, improve efficiency, and prioritize the right tasks at the right time.
  • Transitioning from Entrepreneur to CEO – The mental and operational shifts required to successfully lead a growing business.

About the Guest: 

Lynne Roe is the President of LSR Consultants, a certified professional coach, group facilitator, and change-maker, Lynne helps independent businesses owners develop a foundation of leadership that serves as a catalyst for growth. Applying knowledge and skills acquired over decades of working with small and large companies, non-profits, and family businesses, she guides clients in building businesses that are profitable, sustainable, and valuable – with a focus on strategic planning, sound decision-making, and leveraging their strengths and those of their teams.


Lynne has grown two successful businesses; designed, conducted, and managed market research for major corporations; and developed and led non-profit programs and organizations from the ground up. She has worked with hundreds of individuals and stakeholders over the years, pulling together diverse teams to work towards a common goal. Lynne is also a certified facilitator and coach for The Alternative Board of Northern New Jersey, an organization dedicated to helping business owners and executives excel in their fields through peer advisory, mentoring, and leadership training.


Lynne’s Website: lsrconsultants.com

Free Resource: Lynn’s Entrepreneur to CEO Assessment


About the Host:

Your host, Maartje van Krieken, brings a wealth of experience from the front lines of business turmoil. With a background in crisis management, managing transformation and complex collaboration, she has successfully guided numerous organizations through their most challenging times. Her unique perspective and practical approach make her the go to First Responder in the arena of business turmoil and crisis.

Podcast Homepage: https://www.thebusinessemergencyroom.com/

https://www.thechaosgamesconsulting.com/

https://www.linkedin.com/in/maartje/


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Transcript
Speaker:

Maartje van Krieken: Hey, thank you for tuning in again today. I'm glad you're here, and today is another somewhat special episode to us to hear, because we're recording live from podapalooza. Podapalooza is an event that happens a few times a year, which is a podcasters event, by and for podcasters, their guests and aspiring podcasters, and a big element of the day is that there is a, yeah, I think you could call it speed dating. So podcast and podcast guests are matched up in terms of fit and do a serial recording of episodes short and sweet. And Lynne and I here were matched up, and I'm really happy that she's here on the business emergency room, because Lynne does similar work as I do, but not the same. Lynn works with entrepreneurs and small business owners to develop a strong foundation to lead their business. She guides business owners in developing Strategic Action Plans and sound decision making that leads to dynamic business growth. So yeah, decision making. You all know that that's one of my favorite topics. And strategic direction and action plans are equally very important. And what's interesting, I think, Lynne is, in the space where you are, is that you probably see a disproportionate amount of businesses that go through their first major growth spurt, and I was comparing it to teenagers, when we just briefly talked right, how you suddenly a business gets to the same place as a teenager does, where suddenly the growth is in inches per couple of months and no longer per year, and which is typically also where some of the chaos and the emergencies First start to happen. So I'm really glad you're near. Welcome.

Lynne Roe:

Thank you so much for having me today.

Lynne Roe:

Maartje van Krieken: Yes. So tell us. Can you give us a story about some of the clients that you work with and the chaos they end up in, and how you, how you help them get out of there?

Lynne Roe:

Yeah. So it's, it's so common with business owners who are growing growing rapidly, but they've been entrepreneurs for so long, because they get to the point where they are doing everything and they're working so hard and they're just treading water. They can't get any further. They can't grow anymore because they just don't have any more time in their own day. So one of my clients came to me, and she said, I'm working every weekend. I'm working every day. I work every evening. I'm working even on Thanksgiving. I just really want to have Thanksgiving dinner with my family, and this is fairly common for a lot of entrepreneurs. So we talked, and she was so afraid to hire anybody, because she said, I don't have time to train them. They won't do it as well as I do and and I'm not even sure I can pay them right. I'm not even sure that I can afford them. And after some multiple conversations, I finally convinced her to hire one person and it she was after that, it was perfect. She said, Oh my gosh. I was able to go to Thanksgiving. I was able to go to Christmas and New Year's with my family, and very rapidly, she doubled her business because she now had multiplied her time by hiring someone, she multiplied the time that she had in the business, and that meant that she didn't have to work quite so many hours. She stopped working weekends, she stopped working holidays, and everything got done. And it got done well. And so that's the kind of thing that is hard, very hard for new business or business owners as they're growing to think about how I decide, am I ready to hire this first person or not?

Lynne Roe:

Maartje van Krieken: Yeah, unfortunately, the that doesn't seem to get any easier, right? Because most of my clients also are in quite hot water by the time they stick up their hand and say, Okay, actually, I do need some help and and it's hard because we're all hard working and capable people and our own drive and passion, yeah, is large, and we can do everything, anything, right? It's not about capability. Yes, I know you can do anything, but you cannot do everything. And if you try to do everything, you become, yeah, ineffective. And there are also truly people who can do some of the stuff that you do quicker or better or at a lower price?

Lynne Roe:

Yes, absolutely, absolutely. And the other thing that often happens with businesses, small businesses, as they're growing and growing rapidly, is something will come up and they'll say, Okay, we need to do this thing. And Susie is available, so let's give that job to her, even if she's not the right person to do it, even if you know it doesn't even make sense that it be, but she was available, and it becomes her job forever. And so I often find that as I'm working with businesses that are a little bit bigger, we have to actually restructure their org chart, essentially, so that who's. Reporting to whom or what position is reporting to what, and what that position is responsible for, so that it makes sense. And when we do that, it becomes so much more efficient, just because everybody knows who's who to go to for this thing, and it's something they actually do well.

Lynne Roe:

Maartje van Krieken: yeah, yeah. And in larger businesses, unfortunately, you sometimes see the other side of the coin, right? That in upheaval, there is work that needs doing and on paper, or in the hierarchy, there is this one person with whom it should sit right, but that person, at the moment, doesn't have the capacity right, for whatever reason. They also have five other projects, or they're going to personal stuff, and then the it seems so hard to then maybe give it to the second best person, because if you have a large organization, there is a second best person, yes, give it to the second best person and acknowledge that in that situation, you're likely going to get more output that way than holding on to where Things should go. Right, right, yeah, right. Which leads me to my next question, because you work with businesses that just start to enter that territory where there is staff and a growing base of staff, when, yeah, resourcing with the wrong people, or resourcing too slow or too late, or building up that base when you don't have that experience is a is a challenge, right? Which can is by role. So what are some of the the big things to think of or to spend some time on thinking through when you start really growing a personnel base in your business?

Lynne Roe:

Yeah, so this really is part of your strategic plan. It's when you're doing your strategic planning for growing your business. It should include, how are we going to develop our team? What capabilities do we not have? What capabilities do we need to grow within or look for without? Another thing that I think often people, business owners, they're thinking, Okay, I gotta hire someone to do this. But sometimes it's much better to outsource something because you're outsourcing it to someone for whom that's their expertise. And even though it will cost you something, it often costs you less because they know what they're doing. They can do it faster and better often than you can, and you don't have to spend the time to train someone. You don't have to spend the time to pay someone while they're learning. You just have someone who can do it. So sometimes that's a better solution, especially for these small businesses.

Lynne Roe:

Maartje van Krieken: yeah, and I think also if you're growing. So I work with regularly with startups that are going through their next leap, then the growth starts to happen at all fronts, right? Initially it's a few extra bodies, but then it becomes departments, and if you have to do a bit in parallel, right? So if you're going into proof of concept and actually building stuff and putting it out in the market, then suddenly you have eight or nine departments in your organization, instead of one and less people with integrated heads, or, like, with multiple hats on. Yeah, and you need to probably spend your time shaping up the team in your core function, right? So if you're manufacturing something, then you need to build up your manufacturing team and your quality control people, and maybe also your sourcing is very key, and so you want to do that yourself, your finance and your HR function. You want some capability and control in house, but the transactional stuff that's probably not best use of your time, right to start there exactly because, yeah, that that is not what's going to drive the biggest value in your business right now.

Lynne Roe:

Yep, and you need to be focused on your core capabilities. So and that's that's also something that as the entrepreneur, you also have to start to change your way of thinking as you're growing. You have to move you have to shift your brain from entrepreneur, where I'm in charge of most everything, to CEO. And it's a very different way of thinking. And when you become CEO, it's no longer, how do I do this? It's now, who can do this for me, or who should do this for me? And then the other thing is that you need to have a lot of focus on is this the right thing for us to be doing right now, so make sense of that as well.

Lynne Roe:

Maartje van Krieken: Yeah, prioritization and filtering and yeah, because if you had a small scale and it's just you, you go down some rabbit holes, you're also the only decision maker, right? So you go down a rabbit hole, and it's not useful. You probably haven't wasted that much time or effort. But if that cultural going down rabbit holes persists, how do you control how far people go? How do you make those decisions? Right? So can you talk a little bit about decision making in that, yeah, that step change growth that you see?

Lynne Roe:

Well, absolutely. It really. Starts with knowing where you're going with your business. You know, if you and I always like to talk to my entrepreneurs about where, what is the lifestyle they want to be living? Because when you're building a business, you want that business to support your life. You don't want your life to be there here just to support the business. So what's the lifestyle you want to be living? And then design the business so that you can live that lifestyle. What that really means is you are coming up with very realistic goals for yourself and for the organization, and that's really where it starts. If you don't know where you're going, if you're not really clear about what you're trying to build, it's so easy to go down the rabbit holes, but once you have clarity, once you are really sure about the direction you're headed. Yes, it's never a straight line. It's never a straight line, right? But you don't end up going off on tangents as far, and you don't end up wasting as much time and money on things that don't take you to where you you want to be in the end. So having that, having it very clear about the direction you're headed, helps you make those decisions much more quickly and also with greater clarity and to get where you want to go. Yeah.

Lynne Roe:

Maartje van Krieken: Yeah, a clear goal and clear, unambiguous objectives work like a filter, right? They really help you build that focus, because it's much easier for everybody to see what's relevant and what isn't Yes, yeah. So in the businesses that you go in to help with their strategic planning, what is some of the the pitfalls that have have derailed them around. So what did they before not have strategic plans, or that has strategic plans in place, but then what happened that that needed work?

Lynne Roe:

So honestly, it's very rare that I run into a small business owner who actually has spent time creating a strategic plan. I they really don't have them for the most part. And so all of a sudden, when we start to build one, they they get this tremendous clarity, oh, this is how, this is what I want to do. And there's also a lot of freedom in it, because once you, when you're an entrepreneur, you're thinking, I need to do this, and I need to do this, and I want to make this happen. I want to make that happen. But when you put it all onto a strategic plan, then you said you your plan will tell you we're doing this piece first, and when that's done, we're going to do the next piece. When that's done, we're going to do the next piece. So it's you don't have to worry about that thing that's going to happen six months from now. Yes, it's on paper. Yes, we know we're going to do it, but we have to get these other pieces in place first, and you save a lot of time and money by doing things in the right order. I can't tell you how often I run into people who who have, let's say, built a course that they want to put out there, right? But they have no back end for how am I going to sell the course? What am I going to do with these people afterwards? They just put the course up there, and there's, there's no reason, no reason coming back of, how do I get money out of that right? So getting things and putting them in the right order makes a huge difference, and it's also freeing knowing this is the order we're going to follow.

Lynne Roe:

Maartje van Krieken: Yeah, having a hierarchy in your decision making, or an order in time which decisions need making first and where are some of these decision interdependent is also really helpful, particularly if more parties need to be involved in decision making, right? And I hear you say, the conversation with the with the business owners, is enlightening and important. Equally, if you have a bigger team, even if you have a strategy in place where you did a strategy at higher level, if you do a strategy jointly with a team, to me, most value comes out of the conversation, because there's just as much what is your strategy as what isn't. And actually writing down the things that are out of scope and are not you and can help also reduce the unnecessary workload. Equally, if you have a strategy, it's worth to have the good conversation sessions where people can ask the questions, because there might be more little fine tuning that needs to happen in the communication to really get it unambiguous. You might not realize that somebody looking at it with a very different reference frame still has a huge potential to interpret things very differently, and deploy that in the work that they do for you, right? So

Lynne Roe:

I wanted to add to that, that very often people will say, Okay, well, I just need to make a quick decision on this. And I always say, even with the quick decisions, it really helps to spend 30 seconds or a minute to ask yourself, you know what? What's the outcome I'm looking for from doing this thing? And what could get in my way? What are the obstacles I have to watch out for, and what is most important for me to get right? Those three questions can really help you evaluate something very quickly. I mean, obviously the bigger things you'd need to have more long term conversations with. And with more people. But even your short decisions, you shouldn't just say, Okay, we're going to do this. You need to think about it a little bit.

Lynne Roe:

Maartje van Krieken: Yeah, yeah. So I worked in oil and gas for a long time, and the drillers had do did these exercises, which they call drill the well on paper. I was used to things like that, for my skippering, for my sailing experience, to kind of work through the scenario. But the idea of a drill, the well on paper is that if you drill some of these wells, they cost a quarter of a billion dollars, right? And you're putting an asset on site that's going to do the drilling for you, that works by the minute or the second, that is very expensive. And so if you have delays because you didn't manage some of the interfaces, where you don't have the pieces on site, or you run into a scenario that you really hadn't expected, or you don't have access to the right people at the right time to make decisions, then, yeah, that's another million down the drain for another day of the ship. And it's really just an exercise with people sitting around the table, all the disciplines present and say, Okay, from the day we mobilize on site, or even the prep work. These are all the steps and who that needs to be involved, and what then happens, and what happened next,

Lynne Roe:

and what could get in our way? What could be, what could problems might we encounter that we can think about now and plan for?

Lynne Roe:

Maartje van Krieken: Yeah, and taking, I think, that trick, to take the thinking out of your head and put it on paper, on a whiteboard, on the back of an envelope, whatever works for you, right? Because it's not about the document. I'm not necessarily interested that you can show me the envelope you did it on. Yeah? If you take it out of your head and put it on paper or and or talk somebody else through it, right? There is always something else you find, yeah.

Lynne Roe:

And when you do that, you also can get the different perspectives from the other people involved, right? If you're going to take the time to figure it out, get their perspective. And there's always things that you didn't think about because you don't think the same way that they do.

Lynne Roe:

Maartje van Krieken: Yeah, very true. Well, Lynne, we only have a short time together, but there is a you touched on some very relevant thing, I think, for the listeners. So if they listen to you and they're like, I want more of Lynn, or I want to work with Lynn, where do they go? What do they do?

Lynne Roe:

Sothey can go to my website, which it is LSRconsultants.com, LSR stands for Leadership Strategy Results. So that's my website, and I would like to offer your listeners a free assessment. It's my entrepreneur to CEO assessment, and when they take this, it really helps clarify what kinds of things do I need to put in place as I'm building my business, from being an entrepreneur to being a much bigger business where I'm the CEO, and they can find that at Lynnesfreegift.com. So that's L, Y, N, N, E, S, Lynnesfreegift.com.

Lynne Roe:

Maartje van Krieken: Wow, that sounds fabulous. I'm gonna go and assess myself. We will put also these links in the show notes. So wherever you are listening, if you go back in when you're not driving in a safe place, you can find these links. It was too hard to capture in here. Lynn ver, thank you very much for being on my Colusa episode with today. I'm glad I met you, and I'm glad you shared some of your experience working, yeah, in a similar space, but in a different size, yeah, but the different size organizations, by the sounds of it, so, yeah, glad you were here. Do you have much for having me? Yeah, if you have a closing wisdom, a chaos theory for our list, there's something that helps you in chaos.

Lynne Roe:

It's really answering those three questions and getting clear about, you know what? What is it that that I want? What's the outcome I want? What are the problems that could get in the way, and what's most important for me to get right? I can use that with a very big problem, and it's a much longer conversation, or a very little problem, and we do that real quickly, in 30 seconds, and you always make a better decision if you think that through.

Lynne Roe:

Maartje van Krieken: Fabulous. I love a simple, anchoring, thought provoking checklist. So thank you for that. Lynn, thank you for tuning in today. I hope to hear or see you all here at the next episode. Thanks, Lynne, and bye for now.