From Boss to CEO: The Mindset Shift That Changes Everything

by Amanda Kaufman

When we talk about leadership in the entrepreneurial space, most of the time we’re talking about what to do—not who to be. But if you want to grow a team, scale your business, or lead a community that’s aligned and activated… you’ve got to go deeper than your to-do list.

In a recent episode of The Amanda Kaufman Show, I had the absolute pleasure of sitting down with the incredible Lynne Roe—leadership coach, speaker, and author of Leadership in Action: Inspiration for Intentional Leadership. And let me tell you… she dropped some serious wisdom that every business owner needs to hear.

Because here’s the truth:
👉 Your business can only grow as much as YOU do.
And that means shifting out of “boss mode” and into your identity as a CEO.

Leadership Is About Who You’re Being—Not Just What You’re Doing

I asked Lynne early in the conversation what separates the leaders who are truly leading from those who are just kind of going through the motions. Her answer hit me right in the gut:

“Leadership is about who you are being, not what you are doing necessarily. You have to be the inspiration and the example.”

Let’s sit with that for a second.

Anyone can make a checklist. Anyone can assign tasks. But being a leader—a real one—means your actions are aligned with your identity, not just your intention.

Lynne explained it beautifully: Being a leader means doing what you said you would do, when you said you would do it, in the way you said you would do it. It’s about integrity. It’s about conviction. And it’s about being someone your team (or your clients, or your audience) can count on.

That’s not something you check off a list. That’s who you become.

The 3-Part Leadership Framework Every Business Owner Needs

One of my favorite takeaways from this episode was Lynne’s three-part leadership model—and it’s something every entrepreneur needs to hear.

According to Lynne, if you want to grow your business, you must learn to lead in three distinct ways:

1️⃣ Lead the Business

This is where vision comes into play. Leading the business means building a strategic plan, implementing systems and processes, and guiding the ship with purpose. So many entrepreneurs get stuck in the business, doing task after task—but real growth comes from rising above and leading it from a higher level.

2️⃣ Lead the Team

Whether you have contractors, employees, or collaborators, how you lead people matters. Leadership here is not about barking orders—it’s about enrolling others in the vision. It’s about listening, giving space, building trust, and calling people into their best. A true leader brings others along for the ride.

3️⃣ Lead Yourself

And here’s the one that too often gets overlooked. Leading yourself means stepping into the identity of the person your future business needs. Not the version of you that’s overwhelmed or playing small—but the version that leads with clarity, courage, and character.

You can’t scale your business without also scaling yourself.

From Terrible Boss to Intentional CEO

One of the most powerful moments in our conversation came when Lynne got real and shared a story from earlier in her career.

She admitted that she used to be, in her words, a “terrible boss.” Like many of us, she thought leadership meant giving orders and expecting people to fall in line. Until one day, a team member brought her exactly what she had asked for… and she didn’t recognize it. She questioned it, criticized it, and only later realized that she had misunderstood—and mishandled—the moment.

That experience became a turning point for her.
Because leadership isn’t about control. It’s about connection.

That story reminded me (and probably every listener!) that leadership is a process. None of us arrive fully formed. We evolve, and if we’re willing, we get better.

Stop Doing It All Yourself

Another big topic we covered was the “I’ll just do it myself” trap that so many entrepreneurs fall into. I see it all the time in the coaching world—brilliant, capable people who end up burnt out because they haven’t learned how to lead a team effectively.

Lynne said it best:

“If you want your team to stop coming to you with every question, stop answering every question.”

Instead, teach them how to think. Ask them to bring you solutions, not problems. Create a culture where people own their roles, instead of depending on you for every next step.

That’s how you stop being a bottleneck—and start being a true CEO.

Your Leadership Defines Your Legacy

What struck me most in this conversation was the reminder that leadership isn’t just a business skill—it’s a life skill. It affects how we parent, how we partner, how we show up in our communities.

And it starts with who you choose to be—every single day.

Lynne’s message isn’t just for high-level executives or big team leaders. It’s for anyone who wants to lead with more purpose, more clarity, and more courage. Whether you’re just getting started or scaling your operations, this mindset shift from boss to CEO is absolutely transformational.

Chapters List

00:00 Introduction to Leadership and Business Growth

03:19 The Essence of Being a Leader

05:47 The Importance of Self-Awareness in Leadership

08:30 Transformative Leadership: Learning from Mistakes

11:11 Building Trust and Relationships in Leadership

14:04 Creating a Culture of Empowerment

16:49 The Role of Leadership in Team Development

19:34 Conclusion and Resources for Aspiring Leaders

Full Transcript

Lynne Roe (00:00)

a leader really has to have a vision for where they're going and where they're taking the people with them, too. leadership is about who you are being, not what you are doing necessarily. So you have to be the inspiration and example for whoever you're leading.

Amanda Kaufman (00:03)

Hmm.

Well, hello and welcome back to the Amanda Kaufman show. I'm so excited to have my friend Lynn Rowe here on the show. She 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. She takes business owners from entrepreneur to CEO of a successful and profitable business. Sounds good.

know, Lynn is the author of Leadership in Action, Inspiration for Intentional Leadership. And it's a book designed to help leaders of all types improve their leadership skills a little bit every week. Amazing. Well, Lynn, welcome to the show.

Lynne Roe (01:22)

Thank you so much for having me today. I'm happy to be here.

Amanda Kaufman (01:24)

I am so

excited to have you. In my programs, I am often speaking about marketing and sales and all of that kind of thing. And I've noticed in 2025, the topic du jour has been leadership. So I would love your general philosophy in leadership. Like what makes a leader?

Lynne Roe (01:45)

So anyone can be a leader at any level. But when you're a business owner, and I think that's most of our audience here are people who are business owners, you really have to lead your business in three different ways. You have to lead the business itself, and that's with a strategic plan, it's with deciding where the business is going, it's deciding what processes and procedures we need to put into place. So that's one way you have to lead.

You also have to lead your team, so you have to be that kind of a leader as well. And you have to lead yourself. You have to lead yourself to become the person that the bigger business that you're trying to grow into needs. Not the person you are now, but your business is only going to grow as much as you grow. So you have to be this three-part leader.

Amanda Kaufman (02:29)

I love that perspective. I think that that's a really awesome framework. You know, when people start really examining leadership, you mentioned like everybody, know, anybody can be a leader. What do you think distinguishes the most leaderly leaders? Like what sets them apart from someone who says, yeah, I'm a leader and they're maybe approaching it a bit casually versus someone who's decided that they're gonna go pro with it. What would you say is the biggest difference?

Lynne Roe (02:55)

I think it's two things. One is a leader really has to have a vision for where they're going and where they're taking the people with them, too. And the second thing is, leadership is about who you are being, not what you are doing necessarily. So you have to be the inspiration and you also have to be the example for whoever you're leading.

Amanda Kaufman (03:01)

Hmm.

Okay, so I hear as a coach that whole idea of like, do, have, where you need to be something and then you can do something so then you can have it. You just said, you know, who you're being, not what you're doing. Can you break this down for us a little bit? Like, what does it really mean to be something? And how is that different than somebody who's just automatically doing something? What's that distinction, do you think?

Lynne Roe (03:45)

Yeah. So being is doing what you say you're going to do when you said you were going to do it in the way you said you were going to get it done. I mean, I know that sounds like doing, but it becomes who you are if you're doing it right. You're someone that people can count on. That's one way of being. Another way of being is understanding yourself.

as well as understanding other people. So it's reflective as well as being out in front and being the example for others to be reflective as well as being out in front.

Amanda Kaufman (04:10)

Mm-hmm.

I think I was listening to Alex Hermosy. I listen to a lot of Alex Hermosy. And he really challenged that our tendency as business owners to say like be, like be the thing. Because, and he said exactly what you said, which is, well, what are we doing if we're being that? And so, you know, put another way, thinking about this on another level, it seems like you're saying that,

A true leader has integrated the things that they do or the choices that they make all the way down to the level of identity that they can't see themselves doing anything other than what they are doing or making the decisions according to that character compass, if you will, versus someone who is maybe not convinced.

And you know what I'm thinking about somebody who's just like doing leadership, doing it very task oriented. I'm from a corporate background, so I have quite a bit of experience there, but it's also an entrepreneurship. It's like everywhere. But I notice like people that are going through the motions, so to speak, maybe don't have the level of understanding or conviction is the word that's coming to my mind. Conviction in like, why are you doing?

Lynne Roe (05:17)

Yeah, it is everywhere.

you

Amanda Kaufman (05:33)

the task. Like what's the what's the real why behind it? Would you would you agree with that?

Lynne Roe (05:38)

Yeah, I like that word conviction because it is deeper down. It's not just, I'm doing this. It's a, I believe in what I'm doing.

Amanda Kaufman (05:47)

Mm-hmm. Yeah, I believe in what I'm doing. So when you see somebody who's really stepping into that next level of leadership, like what are maybe some of the changes in their behavior that you notice? Like what are some of the things that are demonstrative of that character trait, that that admirable leaderly set of character traits? What would you say is a bit of a difference?

Lynne Roe (06:13)

think one thing you can observe is that the people around them are listening more closely, are paying attention more closely, are interested in what the leader has to say, but

Also, the leader is very interested in what the rest of the people around them have to say. So not just dictating this is the way it will be done, but listening to understand what the other people's perspective is and then incorporating that into whatever final decisions that they make.

Amanda Kaufman (06:44)

Hmm. Yeah, I think we've all had that boss or that family member who was exerting power, you know, and saying this this shall be the way that it is because I said so and we've all probably experienced that frustration of not being heard understood and you know, Do you find that when you're working with people that that they have a fear that they could turn into that or that that that could? They could become

Lynne Roe (07:00)

Yes.

Amanda Kaufman (07:12)

their memory of somebody who is maybe inappropriately exerting power and maybe that might lead them to their own hesitancy and leadership. Have you ever seen that?

Lynne Roe (07:21)

Usually the people who are concerned about that are not the biggest problems. I mean, because they're self-aware enough that they can pay attention to how they're interacting with people. It's the people who aren't paying attention to that that become a bigger problem.

Amanda Kaufman (07:28)

Interesting.

Okay, say way more about that. It sounds like there may be a little hint at your mission in here somewhere. So talk to me about the terrible leader that probably does need the leadership training. Why don't they get it? Why are they not understanding this?

Lynne Roe (07:45)

you

Hmm, that's a good question and I think it happened. It's different for different people, but, and I was one of them. I was one of those people originally. I was, in the beginning, yes, I was a terrible boss. I had no idea what I was doing. I thought that being a boss was you just tell people what to do. And of course that doesn't work, right? You alienate people, don't get them.

Amanda Kaufman (08:06)

You were a terrible boss?

Right.

Lynne Roe (08:24)

to understand where you're headed at all. just get, they're just afraid to even deal with you sometimes. So you need to change and think about the other person, but also think about, you know, this is where we're headed and as the leader, I don't want to be making all the decisions. I need your input to help us make the best decisions. Because it's not always, yeah.

Amanda Kaufman (08:30)

Mm.

I love that enrollment is such, yes,

enrollment is such an important, not just a strategy, but I would say pretty fundamentally, if you're have characterful leadership, then enrollment of people around you is super important. Well, I didn't know you were gonna fess up to like the firsthand knowledge, know, the mess becomes the message, am I right?

Lynne Roe (08:53)

Yes.

I don't really talk so much about the mess becoming the message, but it takes some thinking. If you're one of those people who's walking in saying, I'm just going to tell everybody what to do and it'll be great, you have to take a step back and say, did I like the person who just told me what to do when they were my boss?

What did I like that they did do, right? You need to be aware of what you are doing and pay attention to what you want to do, how you want to be seen and how you want to be interacted with.

Amanda Kaufman (09:29)

There it is, yeah.

So you obviously didn't

stay a horrible boss. You turn into a transformative leader to the extent that you wrote the book. You literally love leadership this much. So I'm just so curious. What was that catalyzing moment or that aha moment for you? And also I'm curious, where do you see it in others that they realize, I have the responsibility, but haven't dialed in the role yet?

Lynne Roe (09:52)

I do, yeah.

Hmm. I think it still haunts me. It still haunts me. There was one particular time where I'd asked someone to do something and what came back to me didn't look at all like what I was expecting. And I didn't even realize that it was the answer to my question. And so I not so nicely went to the person. said, what is this that you gave me?

Amanda Kaufman (10:21)

Mmm.

Lynne Roe (10:31)

And when he explained to me this was exactly what I'd asked for, it was just in a different format, I thought, uh-oh, I really need to change how I'm interacting with people because clearly I alienated him at that moment.

because he'd worked hard to create what I had asked for. And just because it didn't look exactly the way I had it in my head didn't mean that it wasn't the answer to my question. that was, I think, the one instant that I said I need to make a change in how I'm interacting with people because this is not going to be acceptable in the long run at all. I'm never going to get to where I want to be if I can't interact with people appropriately.

Amanda Kaufman (11:01)

That's so powerful and thanks for sharing that story because I think not only have we been...

Yeah, and I appreciate you sharing that. I appreciate you so much telling us that story because I think all of us have had that experience where we thought we were doing a good job and then we receive pretty harsh criticism from somebody. We've been on that other side, but I think something that it's making me think about is I'm like, whew, when have we done that? Maybe even by accident where we...

Lynne Roe (11:11)

I was pretty young back then.

Amanda Kaufman (11:35)

We got frustrated. You one of the things I see a lot of entrepreneurs do is they get frustrated. They say, I'll do it myself. And they don't realize how disempowering that can be to someone who is literally waiting in the wings, wanting to help, wanting to grow themselves, wanting to progress, wanting to do a good job, wanting the recognition. And when you wrestle it from their hands and say, you know, it's mine, I'm just gonna do it. It locks you into that individual contributor.

role, but it also alienates your possibility of really leading other people to be able to create something great.

Lynne Roe (12:10)

Yeah, it does. the example I just gave you, it took a long time to rebuild the relationship with that person. mean, yes, I had to apologize and eat some humble pie, but I wasn't trusted right away after that, of course. So it took quite a while. And that is what happens a lot with business owners is something, an event like that will happen, but they don't take the time to rebuild the relationships.

Amanda Kaufman (12:25)

and

Lynne Roe (12:36)

And you're absolutely right that it does alienate people and they feel, well, certainly upset because here they were trying to do what you asked them to do and all you did was say, you did a terrible job.

Amanda Kaufman (12:50)

Right, yeah,

getting, I think of it as being like maybe a little lazy with the communication or not taking the time to really think about it. know, leadership, I've learned over the years personally, it can be both at the same time really fast and really slow. So like meaning,

being thoughtful and deliberate about your communication. But if you're just like waiting to get everything right or waiting to have all of the duckies in a row, the duckies are never in a row, right? Like they are all over the place. They're in different quantum dimensions sometimes. those ducks don't line up. So you have to make decisions with speed.

But at the same time like recognize the ramifications of your decisions on on those relationships and on other people. It is challenging, isn't it?

Lynne Roe (13:35)

Business owners

often come to me and they say, my team is always coming to me with this question after a question after a next question after the next question. I never have time to do anything of my own. And I say to them, but that's because you're answering the question. It makes it easy for them to just come to you because you answer the question every time. If you teach them to think the way that they should be thinking,

Amanda Kaufman (13:54)

this is good.

Lynne Roe (14:04)

Bring it to me after you've thought it through. Maybe you've got two recommendations and you need help figuring out which one is the right one. Then bring it to me. But don't just come to me and say, I don't know what to do here. Come to me with your thoughts. Because once they start to think for themselves, that's when you become the leader that doesn't have people coming to you all the time. That's when you've got the team.

that does the work really well without you getting involved all the time. But you have to not allow them to just come to you with every little question.

Amanda Kaufman (14:38)

That's it. That's it. you know, what you're describing as well is like, what's the culture of your team or your community that you're creating? Are you creating a culture of like that learned helplessness of just, just wait and then I'll ask the question or I'll be late and you know, who cares? So can you talk to us a little bit about how you can create those boundaries with people?

in a way that is, well, I'd love to hear your philosophy on it. Like, what do you see leaders needing to practice more in order to be more effective in bringing the best out of their team?

Lynne Roe (15:20)

You know, one of the things that I think is really effective with leaders is to limit the time that you're going to be available to your team. And I don't mean that you don't want to talk to them, but you know, maybe it's every day from one to three, come to me with any questions you've got. But otherwise, I've got to focus on my own things, which is good for you and good for them because

They can't just come to you every minute.

and ask you a question, which means they have time to think it through before they come in. Obviously, you say, you know, if it's an emergency and it can't wait, then it doesn't wait, right? Come to me. otherwise, we'll meet at this certain time or I'll be available for questions at a certain time. And by limiting it, people think it through and they know they only have a short time to talk to you. So they come to you with some solutions already. So the conversation goes more quickly. And then now you can praise them.

Amanda Kaufman (16:10)

Mm.

Lynne Roe (16:15)

and say thank you so much for coming to me with a couple of solutions. Let's work through them and see which one is the best for us. Or sometimes it's thanks for doing this. You've done an awesome job. I don't need to do anything. We'll do what you say, what you suggest, you know. So this idea of the boss is always available doesn't usually work as well as the boss is available every day, you know, at a certain time. And the rest of the time,

I've got to work, the boss has to work, but also that gives the person who's working on things time for them to focus on what they're doing.

Amanda Kaufman (16:49)

Lynn, you're making me

reflect on my entire career here because I'm seriously like, I'm thinking about this. I'm like, dang, you know, I was a hot mess coming out of college in some ways. College taught me some things, right? I learned how to prioritize. I learned how to study. I was very self sufficient in that regard, but.

adding the dimension of managing relationships. Like in college, I was an individual contributor. It was all about the Amanda Show, getting the grades and getting through the program. And obviously I collaborated with like team and so on, just very naturally doing that. But when I became responsible for client relationships and I became responsible for like showing up in certain standups and doing project planning and everything like this.

I had to stretch into that. And when I did stretch into that and I learned very proactively how to become organized, my life changed. Like I was developed into the kind of person who could create things on her own and communicate really effectively and do all of these things. And what you're making me reflect on is I'm like, hmm, I was blessed to have leaders that gave me the opportunity.

to step into greater and greater levels of responsibility. And that fear that we see in leaders not wanting to delegate, it robs people of that progress and that ability to become the better version of themselves.

Lynne Roe (18:06)

Yes.

Absolutely, and you know, it used to be you took a corporate job and you were in that job for life, but that isn't the way the world is anymore. And now as the business owner, you need to do things so that your team is excited to stay. Because it's...

Amanda Kaufman (18:22)

Hmm.

Even if you're

working with people overseas, even if you're working with like, seriously, the rise of the internet and the rise of choice and the awareness of the personal brands, I could not agree more. Your leadership skills becomes so critical.

Lynne Roe (18:48)

they absolutely do. They absolutely do.

Amanda Kaufman (18:50)

Yeah,

amazing. Well, Lynn, if people wanted to follow you, what is the best way for them to find you?

Lynne Roe (18:57)

The best way to find me is on LinkedIn, Linro, R-O-E, that's how you spell it, R-O-E. That's the best way to reach me. And I do have a free gift if you are interested in becoming a CEO of your business. So I talk about going from entrepreneur to CEO as a small business owner. You need to make that shift if you're going to grow your business.

And if you would like to, I have a free assessment, the entrepreneur to CEO assessment. So if you'd like that gift, can go to my LinkedIn and just send me a DM that says free gift and I will be happy to send it to you.

Amanda Kaufman (19:34)

Amazing. That is so generous, Lynn. Thank you so much for offering that up. All right, dear listener. Hey, don't forget to subscribe if you haven't already because you don't want to miss another episode. And Lynn did a really good job. She really showed up. So if you could take 30 seconds and leave a rating or review for the show, we would be so grateful for that because it helps people to choose our show when they're out for a walk or doing whatever they do when they listen to podcasts. And finally,

If you've got some leaders in your life, some entrepreneurs who would really benefit from hearing this conversation, go ahead and grab the link and send it to them directly. You might just live somebody else's day. Thank you so much for joining me and we will see you in a future episode.