In this episode of the Courage to Leap & Lead podcast, host CB Bowman interviews leadership coach and author Lisa Earle McLeod. The conversation centers on how entrepreneurs and executive coaches can move past a fear of selling by grounding their work in a clear, purpose‑driven sales narrative. Lisa walks listeners through three key reflective questions—how their offering makes a difference, how it is distinct, and what they love about their work—to craft a compelling story that shifts the sales conversation from persuasion to helpful problem‑solving. She stresses the importance of positioning oneself as a helper rather than a closer, and of demonstrating genuine care for the client’s challenges. The dialogue then moves to pricing, where Lisa explains why many coaches undercharge, especially women, and argues that fees should reflect the financial impact a coach can have on a client’s organization (e.g., retention costs, revenue loss). She advises targeting high‑value decision‑makers and articulating the monetary implications of business problems. Marketing is addressed next: rather than generic self‑promotion, coaches should showcase thought leadership through articles, videos, and LinkedIn posts that convey a distinct point of view. Throughout, Lisa ties each strategy back to courage—acknowledging personal struggle, embracing vulnerability, and acting despite fear. The episode ends with mutual appreciation and a call to listeners to seek out courageous mentors like Lisa.
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You've got courage to leap, courage to lead. Be brave and be bold. Whoa, let it roar. Welcome to the Courage to Leap and Lead podcast, where each of our guests share the stories of courage that helped them become powerful leaders. Before we start today's show, please remember to visit courage-consulting.com. Where you can find all the episodes and other excellent resources, all at courage-consulting.com. Now, here's your host, Leadership Courage Coach CB Bowman.
Hello everybody. This is CB with Courage to Leap and Lead podcast. Actually, we do live streaming also on LinkedIn. And today I'm talking to the brilliant Lisa McLeod, who has written— I mean, the first part you have to listen to to hear her story, which is like, take your heart and squeeze it. And then the second part is continuing the first part, but she's talking about how people like me who have a fear of selling, and you have a business, you're a solopreneur. How do you get past that fear of selling, especially when you've taken 20 million sales training classes and they are not successful? So if you didn't see it, watch the first part because Lisa actually— she didn't tell me she was going to do this— took me through an exercise that makes me feel so much better about selling. So now I'm going to talk about, uh, some more about noble And how do you sell as an entrepreneur? So, Lisa, for people like me who have this fear of selling and they really believe in their cause, what's the first step they should do to get beyond that fear of making the call?
The first step— you said 2 things: fear of selling but believe in the cause. That second thing is what you've got to ground yourself in. So I work with, um, a number of entrepreneurs as, as a coach, and one of the things that's always helpful is to define with specificity how what you're selling, you're offering, your coaching, your ice cream shop, your whatever, how does it make a difference? And there's a couple questions that you want to answer. How does it make a difference? Number one. Second question is, how do you do it differently than anyone else? And the third question is, on your best day, what do you love about your job? And so the reason that you want to answer those questions is that is your sales narrative. And the reason people hate selling Is because they think they're trying to convince people to do something that people don't want to do. And so to that, I say 2 things. One, don't give yourself that much credit. People are smart. They don't do things they don't want to do. I mean, really, they're not going to make an impulse buy.
So don't, don't over-index on how persuasive you can be. So that's point one. Get that out of the way.
But the second point is, All our research tells us what our own lived experience validates. They can tell if you are there to help them or there to close them. And all you have to do is decide that you're there to help them and they will feel the difference. And so will you. Because if I was here to close you on your own workshops, let's say I would say, CB, these workshops are really valuable. Oh, a lot of people have found them great. You know, I'm doing them because I'm doing them with the book launch. I've got this great special, blah, blah, blah, blah. You're going to feel that. But if I come to you and say, you know, I've been doing workshops on how to be courageous after a failure, and I'd be curious, what role do failure and courage play in your organization? That conversation is no longer about me. It's about you. But it's about you in my area of expertise. And so I don't need to push that on you. I need to have a conversation with you. And I think one of the things that I hear from entrepreneurs is, I don't want to be one of those icky salespeople. Well, good, because it doesn't work.
That's great. You don't want to be one of those because no one likes them. So don't even worry about that.
And if, if you've ever seen someone care passionately about a charity.
Yes.
They're not leaving till they get a donation.
Yeah, true.
And so, and but you feel it. It's because they care so much.
Yes. Yes.
And so if you care passionately about your cause, you, you don't— you're not going to have problems closing.
Okay. But Lisa, you just said something interesting. Step 2, how do you do it differently? If you are selling a workshop, a workshop is a workshop. Uh, a, a presentation, a keynote speaker is a keynote speaker.
No, no. What's different about you? So I'll ask you this and how you do it differently. Why did you want to write this book?
I wanted to write this book because most of my life I felt like I didn't have the courage to lead. I didn't understand what that meant. And when I started— I'm going to start a whole story. When I opened the Association of Corporate Executive Coaches, I knew that I needed one thing first. I needed somebody or some group of people to hold me accountable. Because once that happened, I knew I couldn't disappoint them. Mm-hmm.
What you've tapped into there is if it's just about me, if it's just about the individual, and things get hard at a certain point, I'm going to tap out. We all have different set points.
Yeah.
But if I know that other people are counting on me, think about the times in your life when you're at your best. It is when you know it matters to other people. And that's the story that you have to create in sales. What I'm doing matters. I can't tap out or wimp out on this. It matters. And when you say, how do you do it differently? A workshop is not just a workshop. I want the workshop from the woman who felt like she didn't have the courage and she learned it. I don't want the workshop from the kid, the courage workshop from the kid that was jumping off the top of the building when he was 3 and then climbed Everest when he was 18.
I don't relate to that guy.
I want the workshop on how to develop my courage from someone who's been through this journey. That, that's how you do it differently. You've lived it, you've experienced it, you care deeply. A workshop is not just a workshop. We've all been to bad workshops.
Oh yeah.
Yeah.
And I could go to a workshop on science by the smartest scientist in the world. It's probably not going to land with me because I'm not that interested. Because I don't need it.
Well, I mean, Lisa, all I could say is you're worth every cent that you charge.
You know, let's, let's talk about that because this is one of the things that I've struggled with. I'll tell you, is, is charging what you're worth. And I'm over it now, mostly. But the people that struggle with charging what they're worth are the people that care the most, because those are the people— so the people that women struggle more to charge what they're worth, people who care a lot struggle to charge what they're worth, because it somehow feels ignoble to charge for the thing that you want to give people. But you don't do anybody any favors by undercharging. Every time I've undercharged, I found myself undervalued.
And I—
if I kept my rates low, I would be hired by John and Jane sales rep. and maybe I'd make them a little bit better. But as I've been able to, through my thought leadership and through my books and through courage, um, charge more, now I get hired by the CEOs of giant companies and I'm affecting more people.
Lisa, what do you think about Executive coaches who, A, you sort of answered this just now, don't charge enough, but B, don't market themselves so that it's all about word of mouth, which we know is about as great as a lead balloon, especially during times of Pandemics.
It—
so I'll go a couple thoughts. Let's go to the marketing. A lot of people are uncomfortable with, quote, marketing themselves because again, they're looking at the people doing it badly.
Oh, this is not something that the best coaches should be doing. It should just be known.
The best coaches market themselves through their thought leadership. So the best way to market yourself, and I'm coaching a young coach now through Marshall's group, and he's a go-getter. He's great. But I said, we need to write some articles. We, the royal we, you're going to write them. I'm going to critique them. Uh, to write some articles that showcase your thought leadership, because that's the way you market yourself is not— I mean, we've all seen those coaches that send out these newsletters that go, oh, I'm a coach. I'm a coach.
Hire me.
Me, hire me, blah blah blah blah blah. But the, the more you put out— and you don't have to do an article, you can do a video, you can— I record all— I'm— I record all these doggone videos sitting here right at my desk. So what you're doing is you're putting out your point of view. So that's number one. These coaches that don't market themselves are looking at a couple people that are marketing themselves badly. But you've acquired a point of view that you need to be putting out there in the form of short articles, short posts. Just do it on LinkedIn, make some videos, whatever's easier for you. But the second thing of not charging what they're worth, I want to be really clear on the charging. I could be worth $50,000. But if the person who wants to hire me is an ice cream shop owner who's barely scraping out $25,000 a year, they're not going to hire me. Doesn't mean I'm not worth it. But so one thing you got to get is if you want to charge high fees as an executive coach and have a big impact, you need to be working with leaders who make big money. And who control a lot of money, because it's— there's always going to be a ratio there, and it has nothing to do with how good you are. So a lot of coaches are weird, say, I'm not getting what I'm worth. If you're coaching a low, you know, a mid-level person, you're not going to be paid big fees. In terms of not getting what they're worth when they're at the higher level, a lot of it's because they're not having a good sales conversation.
What do you mean?
So a sales conversation as an executive coach is, you know, like a sales conversation with Marshall is, can you work me in? That's not the way it goes for most of us. For most of us, it's, I'm interviewing 3 coaches, you know, my company's giving me some money for a coach, or the head of HR goes, oh, we got this person who needs a coach. And so the conversation is very much around What kinds of challenges are we trying to solve? And most good coaches will, will get to that. Oh, I've got a communication issue. I've got all these direct reports are against me, but it's the next level. What are the business implications of that? What is that costing you in terms of retention? So you've lost 3 people. Well, let's do some math on that. How much did each one of them make? How much time did it take you to replace them?
Okay.
So we've kind of got a half a million dollar problem here that we need to solve. Let's talk about the effect it's having on customers or what it's like going to that next level of conversation. That's where you feel more confident about what you charge. Because it's got to, if you're working in a business that has a P&L, You know, Marshall is very public about his coaching of Alan Mulally. There are billions of dollars at stake for Alan Mulally. If Alan Mulally gets 1% better, if Alan Mulally can help his people get 5% better— and it's not just about the money because he coached him on the lifestyle and all of that, and Alan's been very forthright about that. But this has to move the needle. If you want to charge what you're worth, you have to be moving the needle in some way on the commercial success of the organization. And it doesn't have to be a direct line. Like, I'm a— I coach the VP of sales, so we move the needle a lot. But it can also be if we can improve retention. By just a little bit. If we can avoid this quiet quitting, what's that costing you? If we, you know, all these things that executive coaching goes into, if we could make you happier to where you're not going home and being such a shit to your family, what's that worth?
Mm-hmm.
You know, I can tell you the cost of a divorce right now. Let's take your net worth, divide it into 3 parts, a third to her, a third to you, and a third to a lawyer. So right there, we got some money on the table.
I mean, but that's where executive coaches wind up undercharging because they haven't, they haven't just taken that conversation into, and it's as simple as asking, what are the financial implications of these problems? Ask the client. They probably know.
I love where you're coming from. However, we must end.
We must end.
We must end.
I hope that this has been helpful to your listeners.
I love talking to you, and I want your book to just crush it.
The feeling is so mutual, and it's what I love about MG100. There's so many of us that we really don't have a chance to really talk, but when you do have a conversation to talk to somebody Even if it's for a podcast, it's worth gold. It really is. So I'm so—
You have such a generous heart.
And I—
this topic of courage, when you ask how do you do it differently, you are the perfect person to do this. You are the perfect person to talk about courage because like I said, I don't want to hear about courage from someone that's never struggled with it or someone that it's been easy for. I want to hear from someone like you that says, I've struggled with this and here's how you do it.
Thank you. Thank you for recognizing that. Thank you, ladies and gentlemen. My hope for you is that you have somebody like Lisa in your life. Somebody who will challenge you to be better. Somebody who walks the talk. I'm getting emotional. And you know, I hate to show emotions on this show. Not really.
You know what, we should all care about our lives and our work enough to get emotional about it.
I agree totally. Look, look Lisa up. Look at her website, read her books, and go to LinkedIn Learning. I know you'll be on that line behind me because I'm leading that line. Ladies and gentlemen, we'll see you next week. Lisa, thank you.
