237: Heather Monahan on Building Confidence Throughout Your Sales Career

Hey, everybody. So what you're about to listen to is a really cool conversation with Heather Moynihan. And she has been somebody who has really charted her own path, but made a lot of mistakes to get there and a lot of learning lessons along the way. So she's a bestselling author. She's a top 40 keynote speaker. She's glass ceiling award. So she's broken a lot of rules out there. And she talks about building confidence. You know, we go through, you know, as a young sales rep, how do you build confidence when you're not the expert? And, you know, how do you think about your goals and stay centered and, you know, listening to your gut and that voice in your head? So I hope you enjoy this. It really got me thinking about a lot of different things here that my career and what I've been through.

And hopefully it'll help some of y'all skip a few steps along the way. All right. Enjoy. What's popping y'all? It's your man, James. Say What Sales Buckley. And this is your weekly Make It Happen Mondays episode with your host, John Barrows. Big shout out to our partners, Sales Loft, Proposify, Gong, Vidyard, Chili Piper, and Salesforce Sales Cloud. Sales Loft, our original sponsor, is the premium cadence platform for all things outbound cadence to drive results. Customizable in every way and with APIs for your additional technology, Sales Loft's value is unrivaled in the sales community. So visit salesloft.com to see it in action for yourself. Ever wonder what happens to your proposals after you send them?

Proposify tracks and measures your proposals in the hands of your prospects in real time. Know what's happening. It really does matter. Check out Proposify.com to learn more about Proposify. How well do your salespeople perform on their sales calls? Gong.io is the leader in conversational intelligence, and the insights that they bring to the table can change the game for your company as you scale. Check out Gong and Gong Labs to follow along with them as they show you what works and what doesn't. Video is fast becoming the standard for all things personalization. There's no better way to create videos, track them, and impact your clients and prospects than with Vidyard. With APIs for Sales Loft, LinkedIn, and more, Vidyard is quite possibly the most easy-to-use video platform out there.

As a long-time user, I can stand by the value that Vidyard delivers to me in my outreach process every single day. Visit vidyard.com to find out more today. Scheduling can be a real nightmare when you have a packed calendar. Chili Piper makes calendar management easy. Your prospects, clients, and internal employees are but two clicks away from a meeting time that works for everyone. Everything you need can be found at chilipiper.com. Schedule better. Salesforce Sales Cloud delivers a streamlined experience for your front lines. More than just a CRM, this super-powered digital Rolodex is customizable, drives actions, manages tasks, and is the engine for all things sales at scaling organizations.

Make no mistake, Salesforce Sales Cloud will be the last CRM that you ever have to buy. Learn more at salesforce.com and dive in. The water is fine. Good afternoon, everybody. This is John Barrows making it up on Monday. Hopefully, you had a fantastic weekend. Mine was actually pretty decent. You know why? Because the weather was nice here in Boston for two straight days in a row, which was amazing this summer. It's been pretty crappy. But anyways, I am looking forward to this conversation today because we have Heather Moynihan on the show right now. She is a top 40 keynote speaker. She's a best-selling author. She's got the Glass Ceiling Award. She's got a whole bunch of accolades. And we are going to talk today about a whole range of things going over confidence and everything else.

Heather, you want to say hi to the audience and give a little background of where you're coming from? Yeah. Thank you for having me, John. And funny enough, as I mentioned to you, I actually grew up in Worcester, Massachusetts. That's where I'm from. Yeah, I'm a Worcester kid. And if that doesn't resonate with people listening, it is not a vacation spot. It is not some fabulous place like I live now. I live in a high-rise on the ocean in Miami Beach. But I started out really poor. I was one of four kids with a single mom. And I started a paper route at age 10, which led me to working at a diner as a busboy, which led me to working at fast food restaurants and then waitressing and bartending.

So essentially, I look back on my younger years is I was building this whole sales platform and sales skill set around customer service, upselling clients, repeat business, raving fans, this whole concept that I didn't know. I look back now and I can connect the dots and see that's what I was developing with my sales skills. At the time, I was just trying to make some money. So I went from there to made the epic fail of I just wanted a paycheck. I wanted money. All I was about was the money because I grew up poor. And so that drove me incredibly. And I remember I was bartending and I was graduating college. And someone said, what are you going to do after you graduate? I said, I don't know. What do you do?

Because you have a really nice car. And of course, he was in sales, right? And so he said, well, Heather, I'm in sales for the Gala Winery. You should totally work there. There's like no women. So I said, okay, done. And there was 3 women and 100 men on our sales team. I joined the sales team right out of college. I became the top salesperson my first year, essentially just outworking everybody. It was one of those organizations that had great training, but everyone was kind of just stuck in their rut in there. This is the way we do it. And don't push beyond it. And I just pushed beyond it. So I ended up getting promoted to the beginning of my second year to brand manager. And then I got sexually harassed.

And so I didn't have a lot of confidence back then. So I just quit and ran away. And I landed in the radio business, which I had no experience in, right? And I was lucky enough to have a great boss who was a wonderful human being took me under his wing. And a year later, I was his top salesperson. My boyfriend cheated on me that I lived with. And I went to work and I was just a train wreck. And he said, what's gotten into you? You're my number one. What happened? And I said, I'm devastated. I don't know how to function. He said, then you know what? It's time for you to make a move. Will you jump on an airplane with me? Don't ask me where we're going and go only for money. I'll make you my partner, my equity partner.

And I said, yes. And I only said yes, because this awful situation had just happened, which ended up being a blessing. Jumped on a plane. He dropped me off in Saginaw, Michigan, which yet again, not a vacation location, not somewhere that anyone's dying to go. But it was a great opportunity. I took a $25 million property and turned it into a $55 million property in under three years, netting our company $30 million. And that put my name on the map in media around revenue generation. And I went to a publicly traded company, which was a bigger, much bigger company. I pitched myself for a job that didn't exist. I was awarded the position, promoted three different times, became chief revenue officer, was named one of the most influential women in radio.

And in 2017, and three weeks later, I was fired. And I took that opportunity to reinvent myself as a bestselling author, a podcast host, top 40 keynote speaker in 2020. And now I've got a new book coming up. I mean, holy shit. So many questions. Let me back up. Why were you fired from being top of your game as a CRO, if you don't mind me asking? I mean, we all can have opinions, right? So I'll share my opinion and I'll share what I was told. So in the meeting, I was told that I had a new CEO take over the company. And she said, I no longer have a need for a chief revenue officer. Therefore, I have no spot for you. We no longer need you. That was what I was told. My opinion is that I had been working in a toxic environment for a couple of years.

And here's the thing. Companies don't always start out toxic. When I first got there, it wasn't, right? But over time, power was shifting hands. I didn't see it or I didn't pay attention to it. And I certainly turned a blind eye to all the toxic stuff that was going on. I didn't want to see it, right? I liked my job. I was making great money. I built this huge team. And so I accept a lot of responsibility that I was trying not to see what was happening in front of me. And ultimately, power changed hands. And the minute that it did, this woman who had always been my arch nemesis ended up becoming my boss. And in that instance, she wanted to get rid of me because when you are a threat, you will always be someone's target.

How do you recognize this? I mean, you said something interesting that I tell kids all the time. It's like one of the things that I didn't do early in my career enough of, and I wish I did, was pay attention, right? Like not just do my job and just try to do it well. But I mean, you think of all the nuances that happen in startups and growth, and there's so many learning lessons there, but we're so blind to it because we're just like, we need the job, we want the job, we like the job, whatever. But, you know, simple things like when your VP of sales or something like that rolls out a new comp plan and people don't like it, right? Most people internally, holy shit, that sucks for me and whatever.

But if you take a step back and realize, like, wait a minute, how did they roll that out? Why did they roll that out? What was the reaction? How could they have done it better? So therefore, in five years, 10 years, if I'm ever in that position, I can do it better, right? How do you pay attention when you're in it? Like, are there some things that you've learned for yourself that say, hey, I need to take a step back here and realize what's happening around me as opposed to to me? Yeah, I mean, that's such a great question. And it's that old adage that you can't work on your business if you're in it. And that's a really powerful thing to remember. You can't work on your big picture of your life and your career and where you're going if you're always in that grind.

And I definitely made that mistake for a really long time. I had a mentor say to me years ago, hey, pick your head up, kid. All you're doing is grinding for the number. You're grinding for the month, for the quarter, for the annual number, for the budget, for the bonus, for the whatever. He said, but start picking your head up and thinking big picture for your life. What do you want? And so what I've learned to do is pump the brakes. And I still do this today, right? Every day, I have a plan. Every month, I have a plan. Every quarter of a plan, annually, I have a plan. And those shift and change and evolve as I come up with new ideas, trends change, technology changes. And that's normal for everyone.

But I know that every month, I'm pumping the brakes to pick my head up out of my day-to-day to say, what could I be missing right now? What's happening around me? What competitors could I be looking at to learn something from? Because when you get really busy and you're in that grind, we often forget to do it. So schedule it in your monthly plan. Schedule it on your calendar. Today's the day I'm picking my head up. I'm going to take a half an hour. I'm going to look outside of my industry, which is so incredibly powerful, to get great ideas and see what's actually happening and how your skill set could apply to a lot of different things. I love that. And I think, you know, reps ask me that all the time.

It's like, hey, John, you know, I'm not happy with my job right now. I'm thinking of making a career switch. And I always take a step back and say, all right, well, what's the five-year plan? Like, I think five years is a decent benchmark to look out to. I think anything more than that, there's too many changes. But it's a nice benchmark from a lifestyle standpoint. I say, forget about your job. Forget about how much money. In five years, where do you want to be in your life? You know what I mean? Do you want to be traveling? Do you want to be an executive? Do you want to be like, what do you want? Like, what kind of house and, you know, significant other, all that stuff. And then back into what it's going to take to help you get there.

Because if you don't have something to go for, if you don't have a kind of a bigger picture, what to go for, then it's very just in the moment. I'm going to go from this shitty job to this shitty job. But if this shitty job is helping me get to there, I can handle it. So, A, for you, how far do you tend to look out? You just mapped out daily, monthly, quarterly, yearly. Do you look a little bit further out for a big picture goal? Two, we'll get to is, when did you start looking? Was it when you got that advice? And have you honed in on your why? They're all kind of three of the same questions. But let's start with, first of all, how far do you look out? That's changed drastically. And I'll tell you, it's because of the coronavirus, right?

I don't believe right now you can look out five years. I really don't. And you and I were talking about this, you know, before we were starting to feel good about business, where things were going, what's happening. And we're seeing a moment here where we may be, you know, backing up a bit. So, to me, that has changed the way I think. I used to be the girl that said, I'm looking 10 to 15 to 20 years out, and I will be CEO of a massive company. And here's how much money I'm going to make. And I'm going to be on the cover of this magazine for Fortune. I had this clear vision. And I'm not saying that's bad. I still believe in having a vision for your future. But I was so married to that that was a linear path, and it was happening in corporate America.

Here's what I want people to know. You can have the vision, and you can have the goals in mind. And it's important to have those things, to feel proud of who you are, to build momentum, and to have something to chase down. But you also, and this is what was hard for me, have to provide the flexibility for yourself to say, it may not go the way you think it's going to. And when it comes off the rails... It probably won't. It probably won't, right? But for me, for a long time, it had gone. Once I got into that big company, I just kept getting promoted and kept seeing, oh, yeah, I know the next one. I know the next one. I'm going to win this award. And it kept happening. Sometimes that can work against you because I became so just focused that that next thing was happening, too.

And when it didn't, when you have that clarity and certainty, which is not real. By the way, there is no certainty in business. None. Zero. So much is out of your control. And like the idea of a new CEO coming over, a hostile takeover in business, a bankruptcy, a technology change that wipes out your industry, or a coronavirus. Coronavirus, yeah. These things happen, right? So I wasn't thinking that way when I was younger. I do think that way now. And that's why I don't want to allow myself to get leveled the way I did mentally, emotionally when I got taken out. Instead, I want to find certainty within me. And that means always being open to, wait a minute, where else could my skill sets apply?

Wait a minute, what else could I do? What service could I offer my existing client base? How could I change and evolve? How can I innovate and constantly challenge yourself to ask those questions instead of having that linear only path? And I think that agility and adaptability are some of the best traits you can have, especially if Corona taught us anything. It's agility and adaptability, right? Like you got to be able to pivot. But that balance of the goal versus, okay, I'm going to go where this leads me, you know what I mean? Different mindsets on that, too. But I think you're right. COVID has kind of forced us all to think a little bit more short term with our, okay, what's in front of me?

What can I do with this? And how can I take it to the next level? But be open to options here. The centering point, though, I'm guessing for it might not be, but when did you solidify on your why, on your values? And was there a moment in your career where it was like, I know you've had Gary Vee on your podcast, right? I went to Gary Vee's 4D session, you know, and it was a perfect timing for me because, you know, you get in, you get to talk to all, and then Gary comes in at the end and does a little Q&A with you. And they brought us through the why exercise. And I had always had, because of Think and Grow Rich, I had always had my core values and what was really good, you know, my why, I thought.

But it solidified it for me, and it helped me make decisions. Where in your career, was that a point in your career? And has it been clarified for you? Yeah, yet again, that's something that's fluid. My values have changed over time. When I became a mother, things changed massively for me, right? So there are life events, or someone's lost a parent or a spouse. I mean, there are life events that truly will shift your values, and that's okay. This has been my experience, right? It's a growth experience. This journey is an interesting one, and this human condition is wild. I never thought about it that way when I was younger, right? But it's, you're always evolving and learning and making mistakes and hopefully getting better throughout it all.

So when I was younger, I didn't really think about a why. The why was a paycheck, and like, Heather, just don't be poor. You know, that was my inner dialogue I had with myself was don't have to struggle. So then one day, that same mentor I mentioned earlier that said to me, pick your head up, start looking at what you want in life, not just about your paycheck, and then maybe you'll find more interesting and better ways to make even more money if you follow that. And I thought, well, that sounds crazy, but I love the guy. So I said, all right, I'll do your dumb little exercise, but I think it's ridiculous. And as I sat and thought, I started challenge... I was on planes all the time traveling for work.

I would take that time instead of working on spreadsheets to start saying, think about what you really want for your life. And as I did that, I started noticing something. This is really important. When you start observing your life outside of you, instead of in the moment, right? But take a step back and look at your life. What are you spending most of your time doing? What are the things you actually like doing? What are the things you wish you could do? When I ran through that exercise, I noticed I wasn't home very much. I love my son and I want to be a role model of someone who's successful and builds businesses and companies. Yes, but I also want to have fun time to do fun things with him and not just be the one that's always gone working.

But one of the reasons I was gone from him a lot was I was working on a charity too. And then I noticed, wait a minute, I'm working on a charity because I'm not fulfilled in my day-to-day job. If I was in a job that was purposeful for me, I wouldn't have to be gone doing charity work all the time. I'd feel good enough and fulfilled enough. That's when I noticed this is my breakdown. I need to merge my business opportunity with a give back. I need to not just make rich people richer, which is what I was doing in my old job, making shareholders wealthier than they already were. That wasn't meaningful to me. So I thought, okay, I like what I do during the day, but I'm not bringing any purpose, meaning, or goodness back to the world.

I'm not making the world a better place. How can I find a way to make that happen? And that took me down a journey that's led me to where I am today, but I didn't figure it out. It took years to figure it out. It took really getting fired to say, I'm willing to let go of what I've always done to try to figure out something new. And it was certainly a process that took a really long time. It's funny, like, I think there's, we all kind of have this idea of what career should look like. And I kind of was on a similar path where it's like, okay, next, next, next. And same thing happened. I had to get fired to wake up, right? And I have two very clear moments in my life. One is when I got fired from this company that bought it, like Staples bought us and then fired me.

And I was like, oh my God. And then the other is a personal when I was engaged, you know, seven years coming out of college, I was engaged. And I'm like, I knew it wasn't right, but like, that's what you're supposed to do. You're supposed to get married after seven years and you're supposed to buy a house. Then you're supposed to have a kid, right? And she, thank God, broke it up with me. And I was devastated, but it was the best thing that could ever happen to me. Wait, but I want to make a point to everyone, John, right now. You just remind me of something, and it's so true in my life too. Oftentimes the behavior we're exhibiting at work is the same one we're exhibiting in our personal relationship.

So notice what John just said. He was in a situation where it took somebody else, pushing him out of something that he probably should have seen. It wasn't the right fit anymore at work and simultaneously in his personal life. Yep. That's, that's a hundred percent. And they, and they're, they're too, they couldn't be more clear because both of them I knew was wrong. I knew I felt it in my core that it wasn't right, but I was fighting. I would, cause I was going to win. I was going to make this work. I was going to do this. Right. And in nowhere in my entire mindset, did I think I would ever get fired. I'm taught, I'm the best rep out there. I'm always the top guy and blah, blah, blah. And like, fucking, you can't fire me.

Like you out of your mind. And when the hammer came, I was like, go, let's go back to self-worth. Right. I mean that we tie a lot of our self-worth into our job and, and we're about to do a webinar actually shit tomorrow on how do you get out of a negative tailspin? And one of the, and we're going to talk about the causes and then what to do about it. But can you talk a little bit about how, how you, you search for purpose, right? You were, you were saying your side hustle was, you know, because you weren't having purpose in your main job. So how do you, I guess what process, because a lot of people just think they're uncomfortable in a certain job. I don't like my job, but they don't look internally.

And you talk a lot about your villain, right? Uh, the book that you have coming up, you had an external villain that, that helped you understand that you actually had some internal villains that you had to deal with. So how do you suggest people look at their current situation with where they are and asking themselves, am I just going through the motions because I'm, you know, I'm supposed to, or I'm unfulfilled, but it's more me than the job. You know what I mean? Like there's so many pieces where I think people are just sitting scared to do anything right now because they, they don't know if it's them. They don't know if it's the job and they're, they're putting blame in other areas. What's a way to look internally here to figure out what's really going on.

The first thing is to know this, and this is fact. I'm certain there is one voice and opinion that counts and is right in your life. And it is your own. You have to start tuning out these other people. I had to tune out my own family. You know, people who want well for you, right, John, they're, they're looking out for you. They love you. They're, they're your champion, but they're talking from their own limitations, their experience. They are not you. I have had countless people try to talk me into going back to corporate America, countless people that I know want good for me and countless people that I know don't. Right. But all say to me, this is what you should do. And it takes a moment to say to yourself, what I need to do is tune into my own voice and hear what my own thoughts are.

And for me, journaling has been super powerful. It was one place that I felt I could go that I didn't have to say what other people wanted me to say, or look the way they wanted me to look or make the decisions they wanted me to make. You know, people pleasers have that problem. And for a long time, I was a people pleaser. I wanted people to be excited for me and, you know, cheering me on on the sidelines. But what I decided was I can either lead a life that other people wanted me to do. And then if it didn't work out, I was going to be pissed at them, or I can lead a life that I chose for myself. And if it didn't work out, then I can go back to the drawing board and not be pissed at anyone else, but just say, okay, now let's try, you know, how can we fix this or salvage this or do something different?

And journaling for me was really that process to start owning my voice. The one time you start saying, wow, I noticed something here. Like this is something I didn't realize I was thinking. And the more you journal, the louder your internal voice gets. And then when you act on it, you amplify that internal, my internal voice now is so freaking loud. I couldn't quiet it if I wanted to, but back then it wasn't, it was, it was tiny, tiny. And I had to like, how do I turn this thing up? How do I put the gas on it? And the best way is to work quietly on your own, to hear what that voice is and start taking action steps against, and to further that. If your voice is saying, you really need to start applying for another job.

You're not happy here. Start sending out resumes. And as you do, that voice is going to start turning up. And as you start saying to people in your circle, Hey, if you know anything in this industry, I'm looking to expand. I'm looking to make a move. The more you start taking small action steps towards that goal that your internal voice is telling you to pursue, the louder and stronger you become. So, so how do you, so this is interesting from a management standpoint too. So how do you know though, at a younger age that that internal voice is real? And I know it's real in general. Like I know it's real in general, but you might not have enough experience to realize where you are. And I'm going to use a very specific example here.

So Morgan Ingram on my team. Okay. This kid is a absolute rocket ship. Okay. Like I even told him when I brought him on, he was my first hire from a trainer standpoint. And I said, Hey Morgan, come work for me for three years, bleed for me. I'll show you how to run a business at the end of three years. We'll figure out whether we still want to do this together. And if it's as great, if not, I wish you all the luck in the world. Right now I'm 45, Morgan's 27, something like that. I've been there, done it. I've made a whole shitload of mistakes to get to where I want. I understand where Morgan wants to go. And part of me going back to limiting mentalities here is I'm worried that I'm putting my limitations on him for his growth.

Right. But then there's the other side of me that says, yeah, but you know what I mean? Like if he, you know what I mean? The risk and like, I know the landscape and all these other things. So like, how do you, um, let's talk to, let's talk two angles on this one. You're a younger rep and you're just frustrated because you might not be, you might not be able to see the bigger picture and you just, for some reason, this job isn't right, but it might not be because it's not the right job. It's might because you don't have the right experience or something like that. How do you know that that's a real thing that that internal voice is real versus it's telling you the wrong things and you should keep powering through that or even, or even it should you look at it that way?

Well, here's the thing. Like we said, I truly believe in listening to your own voice. And if you're listening to your own voice and you're confused, that's because your voice is too small. You haven't amplified it enough because I don't care about experience, John. I don't care. That to me means nothing. I've had people my whole career when I was in my early twenties say, you can't go run a $25 million company at 23. And you know what? Maybe they couldn't and maybe I couldn't, but I wasn't going to know if I didn't get on that plane and get dropped off and figure it out. And I figured it out. And if I can figure out how to net 30 million in under three years, when I was 23 years old, this kid can figure out if that's the right job for him or not.

And it does take risks and it does take saying, you know what? I'm going to make the leap and I'm scared to death to do it, but I got a bet on me. And I will tell you the biggest risk in life is not taking it. You don't ever want to be that person on your deathbed looking back saying, I had that book that I wanted to write and it was just too scary. I couldn't do it. So, you know, unfortunately that message will never move on. You want to be the person that said, I ripped it and ran with it at 23 and it was okay. But after that, I wrote 10 or 15 more and they came out amazing. Right? So that to me is, that's what inspires me and drives me is that I know, look in your own career at 23, 25, 28, whatever.

And know this, your experience is your life experience, your personality, your creativity, your vision. No one owns that. You own that. You are going to see opportunity through a very different lens and there is massive value and start appreciating yourself for who you are, how different you are and how you see things differently. And you're going to see opportunity differently that nobody else has seen and be able to create and innovate. And that is what life is about is showing up as that unique version of you taking chances and seeing what happens. And if you are in a situation where you're saying, I don't know if I'm in the right job, my inner voice isn't helping me enough, then ask your boss.

I would have a direct conversation. So many people think others know and they assume things are good. Ask for a meeting, get it on your calendar, sit down face-to-face, never through email or through the phone, sit face-to-face with someone and ask open-ended questions. I'd love some feedback on what you're seeing from the job that I'm doing. Do you see me as a good fit in this role any longer? What are your thoughts about me moving forward? What do you see as a unique value proposition in me? I'm trying to identify that. I need your help and ask other people for help. I love it. All right, y'all. Confidence is an important characteristic when we are hunting for success. Heather's perspective comes from taking the hits that she took to earn the success that she attained.

Paying attention and realizing what's happening around us can help drive us to better decisions in the future. Big picture. What do you want, right? This is some really masterful thinking here. Send me your experiences and your thoughts on this topic. We're on the hunt for the best guests that matter most to you, our audience. So send me your stories, recommendations for people that you think should come on the show to talk with John, and your why. Send me direct email at james at jbarrows.com and share with me today. We'll get you hooked up. We love shouting out our people on the show. So today, we're tipping our hat to Tyler Uden of DocuSign. Tyler took filling the funnel and felt prepared for the job for the first time in a long time.

And his connection to JB sales helped keep his head up during the tougher times over the last 18 months. And the tools and techniques that he's learned to leverage have kept him moving in the right direction. Forward. Great job, Tyler. We got your back. Let's throw it back to JB and Heather. Let's switch to the other side as a manager or let's talk parent because I'm curious on this for you too, right? You have kids, right? I have a 14-year-old. 14-year-old. So my daughter's 9 or 10. Shit. And, you know, I struggle with this too. It's like how much guidance do you give them based on your experience versus how much do you just let them go and figure it out, right? And I think that's the same with a manager, right?

Managers who give a shit. It's like, hey, I've been there, done that. So here's my advice to you to make sure that you get to the next point in your career and we're aligned and all that other stuff versus, all right, here's some structure, kid. Go figure it. You know what I mean? Like, go do you. Where do you fall on that nurture from experience as a parent? Let's talk parent first. I'm very curious on your thought process on how much you let your kid just go versus how much guidance do you give them? Okay, so I'll give you a great story on this. And I'm a big fan and believer that stories sell, facts tell. So if you want to engage your audience, definitely lead with a powerful story. So I am a single mother.

I work a ton. And I've always enveloped my son in the business side of my life. When we're having dinner, I'm always talking about, here's what I'm up against right now. Here's what went wrong. You know, this thing fell apart. But that's okay. Here's what we learned. You know, here's what we're working on next. So he's always saying, oh my gosh, where are we at? How many views are your TED Talk, mom? He's really invested in my success because he's been along for the learning lessons that I'm having. He's learning as well, right? So that's why it's important, I believe, as a parent to show that I'm not perfect. I make mistakes all the time because that's going to let our kids know, oh, I don't have to be perfect either.

My mom always saying that her feet stink and she's still a good person. You know, like, just because someone called me fat at school today doesn't mean I'm a bad guy. It just means that they saw me differently, right? So to me, I really like to show all, I like to cheer when I succeed and I want him to high-five me. And I like to say, oh, today's a tough day. Let's talk about, you know, why it kind of stunk for me and share that there's a lot of mistakes. So that's sort of how I've parented him along the way. Obviously, kids are away at school the majority of the time with the exception of coronavirus. And so they're doing their own thing, having their own autonomy. I am not... One thing I always think to myself, and I say this to your audience, is like, think to your...

Who do you like as your best manager ever? For me, I didn't like micromanagers. I didn't like people that doubted me. I didn't like control freaks. I felt most confident in myself when people would teach me and when I asked for help, help me and work with me. But then would say, hey, you know, I believe in you. I believe you can do it. I want to see what you come up with. Like, go get this done and come back and let me know. If you need help along the way, raise your hand. I'm here. You know, I wanted more of that supportive but not micromanaging. And so I really tried to raise my son that way. And so you cannot be prepared for what's going to happen, people. And, you know, you just... You wish the best.

But I was confronted with one of these situations where my son did not do well in virtual school, as many kids didn't. And he had to make up credits. And the only way the school would let him do it, he goes to school in Miami, was to go to a sleepaway camp in New Hampshire by himself for four weeks in the rain in New Hampshire in a tent. Okay? Holy shit. That seems a little harsh. It's one of those things that, hey, I sat down with him. I said, you're responsible for your grades, as you know. He accepted responsibility. Yeah, I didn't pay attention. I hated it, whatever. I have empathy for that. But it's also, these were your choices. So here's your choice. You can repeat a grade or you can go to this not desirable location for a month, which is...

I've only ever been away from him a week in my life. I said, which I understand is going to be challenging. It's your choice. And really, he's 14 again. So allowing him to have decision-making versus being dictated to is powerful because that helped him get on the plane. And that helped him stay at the camp. And that helped him on the days he would call and say, oh, mom, this is horrible. It's freezing. I'm sick. I don't like this. And one of the things we always say in our house is we can do hard things. And, you know, anyways, he ends up breaking his arm, John, at camp. And it was a disaster. And he was in the emergency room and was some stranger. And it was... But here's what's so interesting.

And I had Jesse Itzler on my podcast. And he taught me this lesson in that podcast is that we coddle kids too much. And he's right. And I do as well. He said, the real growth occurs in these super challenging moments. Wouldn't you rather have your kid go through really challenging moments at different times during various years of their life versus being thrown out of the nest as an 18-year-old child and then confronted with a real challenge and saying, I don't know what to do. So I never forgot that story that he taught me and that example he taught me. So I knew I went to the worst case scenario that he broke his arm and I was heartbroken and I had to get on a plane and get there. But when I got there, I saw a young man, he had grown so much in just a few days from breaking the arm to being scared, to understanding he was safe, to understanding the knowledge around it.

Okay. It's going to heal. It's four to six weeks. Okay. To understanding, I can teach myself to write with the other hand. And I thought he was going to ask to come home. And he said, Mom, I'm already halfway done with this thing. I'm not giving up now. We can do hard things. And I'm going tomorrow to pick him up from the end of camp. And he got great grades. He taught himself to write with his other hand and he won writer of the week at the camp. So I'm so freaking proud. That's super. Congrats to him. So that's awesome. You're going to pick him up this week, you said? I'm going tomorrow. That's awesome. That's fantastic. So, you know, and I think a lot of those, you know, that kind of comes to that, like, you got to let them fail type of stuff.

But hopefully with a support structure to let them know it's okay. And I think, you know, I translate that to management, too. It's like try different things. Realize that I encourage that. But I think the transparency factor is the big one that most people fall down on is, like, having open and honest conversations from both directions. From a management standpoint of how, I mean, it always blows me away when, you know, a performance review is a shock. You know what I mean? Like, if you're a rep right now and you walk into a performance review and what you're getting feedback on is a shock to you, then shame on your manager. You know what I mean? Because they should be working with you on that the entire time.

It shouldn't be this event where I tell you you suck. It should be like, all right, well, there's some challenges. And by the time it's a performance review, like, yeah, we know these are issues and we're working on them here. So how do you, I think, as a, you know, if we were to look at it from a management standpoint, what are some of the things that you would put in place to, first of all, encourage that level of transparency? You know what I mean? With your reps coming to you or your team coming to you and having that conversation. And then I want to transition to this confidence factor here. But what are some things as a leader that you do to foster openness, transparency, outside of leading by example?

You know what I mean? I think that that's the first and foremost part here. But is there anything else you specifically do to really foster those, that dialogue, if you will? So what you just reminded me of in corporate America is this BS line that so many empty suit managers have, which is open door policy. And it just means, hey, come into me anytime, any problem, I'm your guy, you know, no problem. I can't stand that. I saw so many managers, and I'm sure everyone listening knows these kind of people, right? So, again, you have to be willing to fall on the sword. Here's a great example. One of my first few years at a publicly traded company as a leader, I got arrested for DUI. And I remember, oh, God, this is going to be all over the news, like this is a smaller town, you know?

And I decided to call a company meeting and to let everybody know what happened. And I'll tell you, I got a really positive response from that. A couple people said, would you come with me to clients because they're going to hear about it and they're going to want it. And I said, sure, let's do it. It sucked, right? There was not one minute of that I enjoyed, but falling on that sword and just owning responsibility for my mistakes, for my bad decisions, really brought me so much closer to people. And, you know, that's one of the nice things back when we're all together in real life, because we would do, you know, happy hour events or Christmas parties or holiday parties, whatever. When you get to spend time with people outside of work and hear about their real life and bond a little bit and create a little bit of trust, you know, really, that's where everything stems from.

Because so often people in corporate America are conditioned to think, I have to be perfect. I can't make a mistake. And they're conditioned that way because the company really wants them that way. They say open door policy, no problem. But when the minute somebody doesn't hit a mark, they're fired, right? So the actions will always dictate the behavior. If you're a leader and you're saying, hmm, no one comes to talk to me about problems, I'm the last one to find out. The problem is you and or the culture of the company you're working for, which sometimes it is, it starts above you and you don't even realize that you're falling in line and following suit. So I would say if that's the case and it starts above you, find another job, go to a different company.

There are plenty of great companies out there that lead with transparency and let people make mistakes. Sarah Blakely has a, every Friday, she has an oops meeting at Spanx where everyone has to raise their hand and say where they effed up that week. Here's where I blew it. And then they cheer each other on. That is putting into motion what other people are preaching. Like, how can you actually be part of that and more than leave, but make that the habit, make that the routine, make that the reward. I used to run contests when people would get stuck in sales and I would say, all right, that's it. We're running a month-long contest and it was be the no contest. And what that meant was the person each week that would come back with the most signatures that say, I don't want this.

And they'd sign their name would win the contest. Well, guess what, John, that would be the top biller for the month too, because they made more pitches. They made more ask. They asked more people to sign. They had the courage to go face to face. So it's sort of reverse engineering that instead of being so afraid I'm going to get a no, let's trick ourselves into saying the more no's I get, the more yeses I'm going to get. So let's lean into the no. I love that. Yeah. We, I used to celebrate. We used to do call blitzes and yeah, whatever team one, whatever, but I'd have a, I had a train wreck medallion and whoever had the biggest train wreck on the call got to wear the medallion. And it was a fun thing.

It wasn't like, Oh, you know, you suck. It was like, that was hysterical. Tell that story. Oh, you just called somebody who died. That's awesome. You know, how'd you deal with that one? Those types of things. And it just fostered this. It's okay to fuck up. You know what I mean? And to your point, I don't understand why more people don't understand like the ownership of it. Right. I mean, there's example after example, after example in, in all aspects of society, when somebody fucks up and they own it, how we're a pretty forgiving people. You know what I mean? Yeah, but ego gets in the way for some people, ego and insecurity. Yeah. And that, and that's why it's just like, screw it. Like, yeah, this is, but I, you know, I use the baseball steroids as a perfect example, right?

Barry Bonds, for instance, the reason everybody hates Barry Bonds is because he never admitted that he did steroids when it was so blatantly obvious that he was doing steroids. Whereas there was other players who just stood up and like, yeah, everybody else was doing like picture. There was a couple of pitchers who like stood up of like, yeah, I did steroids. I was facing Jose Canseco who was juiced up beyond his wildest belief, smashing 500 yard bank. Like, what do you want me to do? And everybody who did that, everybody still loves them. You know what I mean? Like, oh, whatever. They did steroids, but good for them. Right. Whereas the Barry Bonds, the Jose's, all those people that didn't admit it, people hate.

And it's just like, just own it, right? I don't know. Let's talk about that. But I think it's a good transition to confidence because I think you have to have confidence to own stuff like that. So let's talk about building confidence as a, as a younger kid, if you will, in business. First and foremost, do you believe in fake it till you make it? I did when I needed that. And what, and let me tell you what I mean by that. When I was younger, I had to fake it till I make it. And I learned from Beyonce, Beyonce Knowles, one of the biggest singers in the world, that she, she essentially gets on stage and she channels this inner Sasha Fierce. Another person, she shows up as another person on stage because she doesn't feel strong enough or confident enough as Beyonce to take the stage in the most powerful version of herself.

I see that as fake it till you make it. I used to do that. So when I would go into a meeting and I was the youngest woman or I was the only woman or whatever reason I thought that it made me in, you know, not the same level of everybody else. I would think of the most powerful person that I would say, if I could be anyone right now, who would I be? And I would walk in like that person, like Beyonce channeling her inner Sasha Fierce. And I knew it was okay because she did it. And I started doing it and it got me to walk into the room, right? It got me to raise the hand. And the more you do that, right? It still wasn't the most powerful Heather Monaghan, but I was still showing up. And that, to me, that was the key.

Those were the baby steps I had to take. Now, you know, cut to years later, when I go to take a massive stage, I don't channel anybody anymore. I channel my inner beast, Heather Monaghan, and I have all of these tips and tricks I use to, like, get myself so strong to walk into it. I don't need to anymore. So the answer, in my opinion, is fake it till you make it so you don't have to. And that's because, you know, Gary V, you know, I follow a lot of what he says and he's just like, no, fuck that. Don't fake it till you make it. And I'm like, in some ways you kind of have to when you really have nothing to go on, right? And I got this one saying that confidence overcomes most shortcomings except for an ego, right?

If you have an ego, screw you, like, whatever. That's gross. But if you have confidence, you can kind of get by on a lot of stuff. You just can't, like, pretend that you know answers that you don't. Like, you have to go, I'll figure that out. I'll go learn that, right? Give me 24 hours to get you an answer. That's what I used to always say to people. And that's, I think, you know, a good example is, again, another member of my team, younger woman. You know, she's right out of school. And I think business acumen is one of the, like, I think sales is an uneducated profession in general. But we're finally getting to the point where sales is somewhat educated. But what most kids miss in sales is business acumen.

Like, just learning business and being able to be in the conversation. So how do you, would you suggest that, and let's be specific, a younger woman in a male-dominated sport, if you will, of sales and business, how would you suggest they start building their business acumen without faking it totally? You know what I mean, without misrepresenting themselves, I guess. Okay, first of all, a great question is going to not only get other people to unload information and teach you, but it's going to show that you're interested in someone else. One of the most powerful things you can do in any meeting or in any conversation or any interface is to truly listen to someone else. Not to look at your phone, not to take, you know, writings about, like, what you want to do after your meeting, but actually sit and listen and feel with your heart and your mind.

It actually elicits dopamine in the other person's brain, and they begin to like you, they want to care for you, they want to help you. So use that Jedi mind trick. Shut everything else out and ask a great question. John, what are your thoughts on that? I'm so interested to hear what you have to say with your expertise, right? Allow them to empty their glass, repeat back some of the things they said. You made an excellent point about that. I appreciate you sharing that, right? Really show interest. Any one of us can do that. You don't have to be the smartest person in the room. You didn't have to go to Harvard, okay? So I would start there. Always defer to curiosity and true questions that you have.

The other thing that I would suggest that I know helped me a lot, while all of my other friends were out, you know, going out to party or do whatever they did when I was really young, I would read business books. So at night and on the weekends, I would read good to great. I would read anything Jack Welch wrote. Like I was always immersed in having free time meant I need to study and study not like for a test, but study for life. And there is value there. I promise you. The other thing is current events. The more you can read, I still get the paper Wall Street Journal to my house every day. I always want to read the headlines. If something looks super interesting, I'm going to jump into that article quick.

I don't just do it to educate myself, but I do it for during the day. If I'm on the phone with someone from, you know, Merrill Lynch, and I see that there was a big business shift in the banking industry, I want to bring up, oh my gosh, how did that impact you? I was just reading about it this morning. That's all I have to say. And immediately they put me on a pedestal of, wow, that woman is so sharp. You know, she really knows what's happening. And all I'm doing is reading headlines and a little bit of information so that I can ask better questions. I mean, it's funny. I have a story around this where it was my wake up call where I walked in and it was, I was selling IT services. And I went in with my engineer and I was like 25 years old and I'm supposed to be the rapport guy.

I'm supposed to be the relationship guy. And my engineer is supposed to be the engineer, you know, quiet and just smart. Right. And my engineer walked in and, and on the CEO's bookshelf was, uh, um, Freakonomics. So the book Freakonomics, right. And it had just come out and right out of the gate, my, my CTO, you know, we were 25, whatever. Uh, he says to the CEO is always like, Freakonomics, have you read that yet? And the CEO was like, oh, absolutely. And they started talking about the book in detail and you could legit feel the rapport being built between them. And I'm sitting there on the sideline being like, yeah, Freakonomics, that's a, that's a funny name for a book. You know what I mean?

Like I felt like a moron and literally that day I was like, I got to start reading books that CEOs read. I got to start reading like good to great built to last, you know, winning by Jack Welsh, who's my all time business idol. You know, I've worked for him for two months and it was one of the best experiences, but I had the background of learning from him what he wrote down. You know what I mean? And, and, and you don't even have to read to your point, you don't even have to read the whole book. Like I, I signed up for, um, get abstract, which was a five page summary of every business book there is out there with all the key takeaways. And I would do the exact same thing. I'd be like, oh, you've read good to great.

Oh, really interesting. Oh, the whole thing about like Jack Welsh versus in GE versus Lee Iacocca and Chrysler. Like, what do you think about that? And then just let them unload about all their knowledge on it. And I come across looking as the smart kid, but I really am not because I just asked the right question. And I think you, you nailed questioning skills to me is, is one of the biggest ways you can engage. Yeah. And so another tool is Blinkist. That's another great tool. And I do that for podcast guests. If they've, you know, written some big book and I don't have time to get into it, I go in there. So definitely look at some of those tools. But another thing I do, if I have a big meeting with someone, I'm going to Google them.

You need to Google people. I take out Google alerts on Gary Vee. That's how I got Gary on, you know, my show. I found out he was building a wine company. I have wine experience. I understand the industry. So I contacted his partner and, you know, I offered free services to them, which led me to, you know, speak with Gary. So take out Google alerts on people, research them online, see who's in your connection circle with them. Call those people ahead of time. Tell me about Jim. What is he like? What are his kids like? Where do they go to school? And find a connection point. It doesn't just have to be around business acumen. Oftentimes, some of the biggest connection points I've come up with have been finding out where someone's kid went to college because I went to a college nearby.

And just, I mean, and that's the personal thing that I think a lot of people miss out on, right? I mean, there's that rapport building factor of knowledge, right? Business acumen. But then there's just being a person, you know what I mean? And talking about kids and talking about experiences. And that's what so many people relate to, which is why going back to like the journey and like sharing and those type of things. It's like people are so much more interested in the journey than they are the result. And so tell the journey. And I'm curious for your podcast. Let's kind of end on this note. Like, A, why did you start your podcast? And what's your favorite thing about your podcast for you personally?

Like, what has it given you? I started it because I Googled, how do you write a book? And I figured out how to write a book. Then I Googled, how do you sell books? And one of the ways was to go on podcasts. So I sort of just started pitching myself as a guest, right? I'd put myself in the shoes of the podcast host and talk about how I could add value to them and to their listeners. You know, because I'm trying to sell every exchange as someone's being sold, either me or them. And so I started landing on podcast shows. I ended up on the Lady Gang. The show went number 20 on Apple Podcasts on the episode I was on. So I took that screenshot and I thought, something's here. I don't know what it is, but something tells me I should have my own show if this show did that well.

So I went to the CEO of Podcast One and I asked for a meeting to thank him for putting me on the Lady Gang. And so he saw me. I sat down and in 10 minutes, he offered me my own show. That was always my ultimate goal. But again, you want to lead with, you want to create rapport, you want to be grateful to people, you want to make things about them and then see where it takes you. You never know. If you didn't offer me a show, there was no skin off my back. It's fine, right? But I ended up... I launched the show in 2019. And I'll tell you that it's so funny. Whenever you do anything, you need to be unique and different, right? And there's millions of podcasts out there. So people will say niche down to a certain audience, target an audience no one's speaking to, you know, find a white space.

But for me, you know, and this was from working with some of the experts at Podcast One. They said, why don't instead of just doing an interview, why don't you also do a part of just your personal journey because you are vulnerable and willing to do that about where you're failing, where you're struggling. So the audience can relate that they're not alone. So we started that and it's morphed into... I do one episode a week, which is just a straight interview so that we can learn things and business tactics and whatnot. And the other one is really about my behind the scenes, what's really happening in an entrepreneur's day to day, which is a lot of times awful, sucky. Sometimes it's my son breaking his arm.

Sometimes it's me struggling with forgiveness and, you know, releasing people from, you know, difficult situations in my life and really just, you know, what can you learn? And then I do a bit in my show where I respond to the questions people send in to me to try to provide, you know, real value to them and their issues. Very cool. Yeah, I found that the podcast for me was basically how I learn, you know what I mean? And going back to curiosity, I don't learn by reading books. I don't learn by going to classes. I learn by talking to people who are smarter than me. And, you know, just being genuinely curious about their background and their insights and those type of things. And, you know, hopefully I can obviously learn some stuff along the way in the audience as a proxy, right?

So let's finish with this, which is your book, right? So Overcoming Your Villains. You tell a very powerful story on your TED Talk about how, you know, and you kind of alluded to it here where, you know, you faced a villain and it was this woman and she, you know, had it out for you and you got fired. But how that helped you identify your internal villains. So do you want to talk a little bit about the book and what it's all about here to give us a glimpse of, because it's coming out in what, November? It's coming out in November, but I'm going to share a great reason why people should pre-order it today. So the book, Overcoming Your Villains, is a powerful and proven three-step process to overcome any adversity in your life or business.

It's repeatable. It works every time. It works all the time. And you've got to freaking put it in place because it's helped me immensely. And really writing this book was my first chance to articulate and lay out the system and process, not only for myself so that I can remember, okay, these are the three things I have to do. And I use it all the time. I use it when my son broke his arm, right? Anytime I go into a panic moment, I'm confronted with a challenge. I constantly look at my three-step process, beliefs, actions, and knowledge, which is broken down as three sections in the book so that anyone can take on any adversity they face. But one of the things that I learned through the adversity I faced in corporate America was I wasn't getting to the root of the real challenges in my life, or you call it villains, whatever you want to call it.

But the real challenges in my life originated inside of me. However, as long as I was in a toxic environment, as long as I was not in the right job, not in the right company, surrounded by people who want me to fail, I was constantly fixated on those issues around me, not how did I actually end up here. And my book really takes you through the process of, okay, yes, we need to fire the villains. Yes, we need to get out of the negative workspace, negative people, toxic work environment. If you're a painter, no, you cannot be going to an accounting job every day. We've got to find time for you to paint and do things that help you be your creative, real, true self. Let's tap into that inner voice.

Let's work on getting rid of all those villains and negativity around you. And once you clear that out, you can start dealing with that real biggest villain you've ever had, which may be the story that you're telling yourself in your head that you're not good enough or the label that you're still falling under from when you were a kid and your sibling had a better label and you weren't as good. Or, you know, there's so many different, you know, some people just run negative tapes in their head of why they can't and constantly come up with reasons why other people can do it and they can't. So to me, it's just, it's a powerful process. It works. And I truly believe that this book is going to help so many people.

And I'm so excited. So as with anything, if I'm asking people to do something, I'm asking people right now to pre-order the book. Now I need to give them a reason. I need to give them more value than I'm asking for. So the book is on sale on Amazon right now for $24.99. And when you buy that and upload your order number to my website, OvercomeYourVillains.com, you immediately get my $500 bonus bundle, which includes my $299 confidence video course, my 30-day accountability email program to achieve your goals, my Overcome Your Villains workbook to get started on going for it now, the first chapter of the book before anybody else can get it and more. So I put together a lot of value so people can get to work on becoming their best selves, overcoming their challenges now, and then get the book when it comes out November 9th.

Love it. Absolutely love it. So givers gain, right? Always lead. And that sounds like a fantastic package of information from people who are out there trying to figure out what their next step in their journey is going to be and if they're stuck, right? Like, you know, if they feel stuck right now, this sounds like a great process to go through to start to identify some of those things and do something about it. So Heather, thank you so much for coming on. It's been an absolute pleasure talking. Did we miss anything? Or is there anything else that you wanted to get out to the audience that we probably, I mean, we probably talk about a ton of shit, but is there anything that you wanted to leave the audience with here?

Yeah, the only thing I'd leave everybody with is that in any moment, you're either creating confidence in yourself or you're chipping away at it. And when you decide to see every action that you take through that really simple lens, it makes making a decision a lot easier. Perfect. Awesome. Well, thank you, Heather, so much. And look, everybody, hopefully you enjoyed this conversation as much as I did. Please go out there and pre-order Heather's book. I mean, $24.95 for $500 worth of value that'll probably change your life if this whole conversation resonated with you. To me, it seems like a pretty good deal. So look, everybody, like I always say at the end of my podcast here, go out there and make somebody smile.

Because even if you had a shitty day, if you make somebody smile, you know you had a good day and the world needs a lot more of that. So thank you all very much for listening. Thank you, Heather, for being on. And let's go out there and make it happen. All right, y'all, that's a wrap. As always, we encourage you to become a JBSales member and gain access to the JBSales team. Our training, our courses, tips, webinars, and replays are all available for you at ondemand.jbarrows.com. Follow us on Instagram for daily sales techniques and tactics at JBSalesTraining, all one word, and we'll catch up with you on the gram. Have a great week, everybody. Get out there and serve those clients. Catch up with those prospects.

Be sure that you are asking the right questions, doing the right things, and serving people to the best of your ability. Get out there and make somebody smile today. It'll make your day and theirs. We'll see you next week when we bring you another stellar guest to help you sell better. Make it happen, everybody.