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The Art Of Confidence Building With Emily Jaenson [Episode 150]

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How will you change your selling approach once you gain more confidence?

If you’re like many of us, you may be inadvertently delaying your goals in order to feel more confident about reaching them. In this episode, Doug C. Brown speaks with Emily Jaenson, confidence expert and one of the first female general managers of a AAA baseball team. Doug and Emily discuss their journeys of overcoming shyness and lack of confidence, strategies for expanding confidence in selling, why finding your why is key to success, and much more.


In this episode you will learn:


Episode’s guest – Emily Jaenson

CEO Sales Strategies | Emily Jaenson | Confidence Building

Emily Jaenson is praised as a next-level motivator and inspiring leader who lives by her motto, “Be so good they won’t forget you!” Her TEDx talk, “Six Tips for Building Your Confidence,” amassed an impressive 3 million views within a year. Renowned Fortune 500 companies, sports organizations, and national conferences frequently call upon Emily to speak and consult on creating more confident and goal-driven employees. As a pioneer in the sports industry, she made history as the first female General Manager of a Triple-A baseball team in nearly two decades. Emily’s highly-ranked podcast, “Leadership is Female,” features interviews with female executives, aiming to guide the future generation of female leadership.

Emily is giving away a copy of her book, “Let’s Go! A Guide to Increasing Your Confidence”. Follow Emily at: @EmilyJaeson and send her a message saying “I heard you on CEO Sales Strategies and I want a copy of your book!”

Visit her website: https://www.emilyjaenson.com/


The Art Of Confidence Building With Emily Jaenson

I have Emily Jaenson who is a high authority on confidence. I thought it would be amazing to bring her on here because she has such a great story from somebody who has risen in a male-dominated industry. She was a general manager of a triple-A baseball team. She worked for the Chicago Bulls before. She went on and continued to go on. 

She sold corporate sponsorships on very high levels. She is a well-sought-out person by Fortune 500 companies, sports organizations, and national conferences. She teaches people, employees of companies, individuals, CEOs, and business owners how to experience less fear and anxiety and increase motivation that all wraps into confidence, to be their authentic selves, and to show up as that person. You might go, “What’s that got to do with business in selling and selling to CEOs?” The answer is everything. 

The more confidence that you possess in a business situation or a personal scenario, the better you are going to be perceived as an expert, and the better you are going to be perceived as somebody who can solve problems, and who can bring forth future opportunities. As a leader, it is critical. In selling to CEOs and business owners and growing businesses, the more you work on your self-confidence, the more you’re going to grow, the more the organization is going to grow, and the easier things get. Even if that sounds a little counterintuitive or a little bit woo-woo, it works. Without further ado, let’s speak to Emily right now. 


Emily, welcome to the show. Thanks so much for being here.

My pleasure. Thanks for having me.

I hear you’re out speaking for a lot of well-known companies. Is that the case?

Yeah, It’s been so much fun. The message is about confidence and how to increase your confidence. There’s a myth that’s been around forever that you’re either born with it or you’re not. It is a myth. I’m here to help corporate leaders grow their confidence so that they can achieve big goals in the workplace and life, and also empower their employees to do the same. 

Mental Game

I’m so grateful you’re here because I always tell people confidence is sexy in selling. In sales, especially when we’re selling to the high end, the mental game is the majority of the play. The greatest sales closer in the world who lacks confidence isn’t going to close well. 

No, because people would doubt their capabilities. They shy away from difficult tasks in those domains. If you’re thinking about sales and you encounter a rebuttal or a negative reaction to what you’re selling rather than going into it, overcoming those objections, trying to find a solution that benefits all parties, you’re saying, “Hands up. This task is too formidable in nature. There are adverse consequences of this failure. This is about me and my deficiencies. I’m out.” 

You need to have somebody who has the confidence to make it through difficult situations. Those people they commit and they set higher goals for themselves. They realize that if they fail, it’s probably due to insufficient effort rather than aptitude, which is a completely different mindset when it comes to success. 

I’ve seen it over and over as you have described. The thing is that as we climb the ladder of going higher and higher in the sales process, i.e. I want to sell to CEOs of major corporations or business owners of major companies, I have found that they will test your confidence to see if one can handle the situation that usually presents itself within. It may be the CEO directly or it might be a consensus by the CEOs to have people on their team that are going to test your confidence. They will test that right up front. If you don’t pass that first hurdle, the game is over. How about you? 

You have to know your stuff. I’ve been on both sides of the table, either buying or selling. When I’m buying, I’m testing. Do you know your products? I’ll ask questions. If I get too general answers, I lack confidence in this product or in the person or their ability to deliver. Knowing your stuff and knowing your product is essential because confidence is also linked to competence. The more that you are informed and the more knowledge that you possess, the more confident you are to endeavor in difficult situations. 

I was talking to the CEO of a company. It’s a $100 million company now and he built it in four years. He does it with a commission-only sales team and their leadership and sales meetings completely focus on building up the confidence within their sales team. When I asked him why, he said what you said. He said, “When you build confidence amongst your people, my salespeople aren’t even the best salespeople but they’re confident because they exude confidence in that process.” 

One of the reasons I was so excited to have you here is because a lot of people push this thing a little bit to the side. It doesn’t feel comfortable sometimes for them. I’m the guy saying, “This is what we need to embrace,” because when you embrace this and you have employees who embrace this, we have less fear and less anxiety. We have increased motivation and greater resilience within the organization.

Confident Vs. Authentic Self

For all of us who own businesses, it’s never gone straight up. We all know that. It’s up and down, but it will also improve relationships internally and externally. When somebody is confident, do they tend to be their authentic self? Do they alter that process as well when they become more confident? I’ve always wondered about this. I thought I’d ask an expert.

First, I want to acknowledge the CEO that you spoke about. Imagine if all of us were running sales meetings focused on building confidence rather than reporting on your leads list. We’ve all been in on those sales teams where it’s like, “These people are at this percentage. I had meetings this week with these people.” You spend an hour telling everybody what you’re doing. Imagine if you spent that hour building your sales acumen. I have to shout that out first before I answer your question. 

Focus on building competence and confidence rather than simply reporting on your leads list. Click To Tweet

Is practicing your confidence being your authentic self? This comes up a lot because people know that cute term “fake it till you make it.” While I see a place for that, it’s not necessarily what I teach. I talked about the behaviors that you can start now to increase your confidence. What these behaviors will do is they will put you in the situation. They will put you in the arena to use your skill sets in an uncomfortable way to survive. 

The result is that you’ve grown your comfort zone a little bit further. You’ve grown your personality. You’ve grown your confidence to know that, “I was afraid of this situation. I was thinking worst-case scenario, but then, I got in the arena. I did the thing. I had the conversation. I got uncomfortable. I made it through and now I am in a better position to get into those situations in the future and be successful.” 

That’s so important. When you were speaking, I wrote down this little note for myself because there were a couple of things. One of them was I remember early on in my life, I was an introverted shy guy. I remember there was a school dance coming up. Karen Fitzgerald was the prettiest girl in the school. When you’d look at Karen, you’d say, “She’s pretty. I’d love to get the know her.” Most of the guys didn’t have the confidence to go up and talk to her. I was one of those guys.

I was friends with this girl named Mary Ellen. Mary comes up to me one day and she goes, “Why didn’t you ask Karen to the school dance?” I’m like, “I don’t think Karen would go out with me.” She’s like, “Are you stupid? She’s talking about you all the time.” I said, “I don’t know.” She said, “Doug, man up.” That’s what she told me. I’m in sixth grade and she’s telling me this. I said, “Okay, I’ll go ask her.” She goes, “You can’t.” I said, “What do you mean?” She said, “JP asked her to the dance.” She said yes because nobody was asking her. Therefore, she took the first one that said yes, not that JP was a bad guy.

I liken this to what happens in sales scenarios when people don’t have the confidence to ask for the sale, or in life in general when people lack that inner strength to ask for what they truly want and they miss out. The crazy part of that whole story, and the reason I told that and I’d love your feedback on this, is later on my brother asked her out and they went out for a long time. 

Not only did I lack the confidence, I backed off and never followed up on it, which is another sales mistake. When people are willing to step up and ask because they have the confidence, what I heard is it brings greater things to them all across the board personally and professionally. Did I get that right? That’s what I heard you say. 

Yeah. You have to step up to the plate and take your swing. There are a lot of reasons why we don’t do this. I was once too shy to order pizza in high school. I couldn’t even dial a phone number, which today maybe we would call a cold call, but in this case, I was calling a pizza place to get a pizza. There was not going to be an objection. It was like, “What do you want?” 

Attitude Shift

I realized that the person I wanted to become did not align with my current attitude. To get there, I needed to change my attitude. To change your attitude, you have to change the way that you behave. If Emily wants the pizza, you have to make the phone call. In my first job, I had what I thought was a dream job. I was selling season and group tickets for the Chicago Bulls. I grew up in Chicago. I am a huge Bulls fan who wanted to work in sports and I got my chance. My dream job was also a living nightmare because I had to make 80 or more cold calls every day from my cubicle. 

While I was in the environment, I had yearned to work in sports, but the actual activity of the job was a nightmare. I knew and started to understand the landscape of that business. To be an executive, I needed to learn how to sell. Executives drive revenue or know how to drive revenue for their companies. This is where you started, at the bottom, making these calls. I had to get outside my comfort zone one call at a time and sell those tickets to build that skillset.

There are a lot of different factors that play into getting there and being able to do something that makes you sweaty, and very uncomfortable. Getting into that situation, some people run away and hide, but you have to ask yourself what is it that you want and why you want that thing. Why do you want that thing? For me, it wasn’t about showing up every day to this job that I thought I should love and making cold calls. I only thought one day ahead in front of me. If not, I probably would have quit and moved home with my parents and then started over again. I don’t know.

What I thought about was that end game. My why was, “I’m 21 years old. You’re not going to get to the top right away unless you start your own thing and hit it big.” If you’re working inside a company, you have to prove yourself first and that often starts at the bottom until you become a star. I wanted to get to the top but to get there, you have to go through the process. The process was 80 calls a day. Understanding my why and the end result that I wanted helped push me to do the thing that I didn’t want to do.

CEO Sales Strategies | Emily Jaenson | Confidence Building
Confidence Building: If you are working inside a company, you often have to prove yourself first to get to the top. You have to go through the process.


You blew my mind with what you said because here you are, a 21-year-old young lady who gets this dream job with the Chicago Bulls but lacks confidence. You had enough confidence to get yourself in through the door. I have to bring this up because weren’t you the first female general manager of a minor league baseball team? 

Yeah. At the triple-A level, I was the first female GM in twenty years. For those who know baseball, you have Major League Baseball, right underneath that is Triple-A. We’re like the B-team for those Major League clubs. On my team, we had 200 transactions a year. Our guys are moving up, moving down. To make a long story short, I worked my tail off selling to drive revenue and understanding how the business of sports works to earn that general manager role. 

That girl who was once too shy to order a pizza was greeting the visiting team, visiting that manager in the clubhouse, and my female face was popping up for the first time in the last twenty years. Every single other ball club in the country saw a man. It was another level of confidence that I had to achieve to not only get that role but succeed inside that role. 

Career Journey

I have to ask the obvious question. Firstly, there’s a gal, her name is Sophia Jurksztowicz who’s a sportscaster for the Boston Bruins and she’s breaking through in a male-dominated industry. You did the same thing. By the way, Sophia is one of my heroes. I adore her. I’ve never met her but she exudes confidence. It’s amazing how from a 21-year-old who was like, “I don’t know if I can make a call to get a pizza,” to getting to the Bulls, to being a general manager of a Minor League baseball team, to selling huge corporate sponsorships, and now getting on stages with Walmart and big corporations. I think other people are interested in this like, “I’m the genesis.” How did it go? How did you get there? 

It all starts with the why. Why do I want to do this thing? Where do I want to go? What is my destination? I had big dreams but I lacked the confidence to get there. I kept that dream in mind. What I needed to do was practice the behaviors that would lead to my attitude change. Knowing that I had these goals in the end, I needed to start behaving like that person. We’ll use the baseball example. Not just in baseball in general. You play a million games. You’re playing every single day. 

The guys would leave one city and take the first flight out in the morning and then be playing in our city that night. They have a travel day. Their clubbies got all the equipment. They played the night before. They were up till midnight. They were up at 4:00, they got on the plane, and they flew to us. They got to the stadium. They’re unpacking. They’re tired. One of the million pieces of my job was greeting the team when they arrived. They have to know where they are and who to call upon should they need help. The manager wants to meet with the leadership.

No one on my staff is going to substitute for me shaking the hand. The difference was that the 29 other GMS are dudes. That’s all that they’ve seen for twenty years. I was often mistaken for the player’s wife. “Do you do marketing?” I do but I oversee the whole department. “Are you running the team store?” I am, but I oversee the whole business line. That’s what people thought when they saw me because of stereotypes. They exist and you acknowledge them and you work to break those barriers. 

The visiting team arrives and I have to go and say hello. It sounds pretty simple like, “I’m just going say hi. It’s not a big deal,” but it was because I often didn’t know at least in my first year who I was going to encounter on the other side of that door and what they were going to say to catch me on my heels when you’re walking into their space. What I would do is I would have the clubby call me and say, “This team is in town. The manager and the other coaches are in their locker room. Everyone is dressed.” 

I grabbed my business cards for my desk. I would walk across the stadium, head downstairs to the clubhouse, I would open the door, and hang a left right away into their space. Managers usually sit at their desks and their head pops up looking at me like, “Who is this person?” I have my business card in my hand. I would go straight to him and hand him the business card, “I’m Emily. I’m the GM. How was your trip?” You would see the recognition happen of like, “She’s the general manager. I get it. She should be here. We should be talking.” 

Things would roll, but because of that clumsy introduction in my first season, I went to use some tactics to get in the arena. I didn’t want to potentially have something said to me that I would not enjoy or put me on my heels. I would use the countdown. I was an athlete my whole life. Before I push through that locker room door, I’m saying, “3, 2, 1 go.” As an athlete, you’re used to working by the clock. It gets to a certain time, a certain number, tip-off happens, and you go for it. 

I’d go through that door. Momentum would keep me going straight to that desk and make the introduction and things would roll. For me who lacks confidence or anybody who lacks confidence, getting into uncomfortable situations is not fun. You’d rather avoid it. In this case, I would ask myself, “Who am I? Who do I want to be?” The answer was I wanted to be a GM who people knew was competent, who could get the job done, who they could go to if there were any issues. To be her, I need to start with a simple introduction. 

I had to say hello. Those were the steps that it took to get to that situation and you could apply that scenario to a lot of different circumstances in your life, to a networking event you don’t want to be at that makes you nervous, to a job interview, to a first meeting, and to a first date. There are so many applications for how to enter into the arena. If you’re thinking about boxing, you step in between those ropes, or baseball, you’re getting up for the plate. How do you get yourself there and get yourself in that environment where you can rely on your skillsets to get you through it, but you have to get there first? When you lack confidence, it’s hard to even start. 

In order to get to an environment where you can rely on your skill sets, you first have to build your confidence. Click To Tweet

There’s so much for me to unpack there. I appreciate that. I can only imagine what it felt like being a person in your position or I’ll say a woman in your position, especially. It’s uncanny. I was watching this thing on television of a girl who wanted to break in to play baseball, even on the high school level or the middle school level, she was the first one in the state of Texas, and the pitchers were throwing bean balls at her head, trying to sway her to get her out of that whole process. 

I can only imagine some of the things that you went through, but I heard a formula and I want to bring it back. Here’s what I got, know what you want, know why you want it, get truthful about what the reality is of that particular knowing what you want to do, knowing why you want it, and knowing why you want to go there. Taking steps each day, pointing our noses in the direction we know, and taking one step a day every single day, then challenging ourselves on a small level of challenge to prove to ourselves that that was scary but not so scary.

Now, I’ve gained some additional confidence. I keep my nose pointed in that direction and I keep walking there. At 21 years old, I made it into the Chicago Bulls. A little later on, I made it into general manager. Bigger things keep coming because we have built incremental progress on this process over a period of time. Did I miss anything in the formula? Did I get it correct?

Doing The Hard Work

It was such a good summary. I like how you broke it down and acknowledged the steps. We are in this area where we want instant gratification. You want it to happen tomorrow, but attitude change happens gradually over time with these small building blocks, surviving these small situations, and thriving through these small situations.

Another great analogy is using marathon training. Most people cannot get up off their couches and run a marathon tomorrow. If you want to run a marathon, you could subscribe to a training plan. Six months later after training four days a week and staying committed, you can cross that finish line without dying. It’s small steps each and every day that lead to greater change over time and choosing to get in rather than get out. Even today, I can catch myself wanting to get out rather than get in. Networking events are something that I wish I loved, but I don’t. I love to meet new people. I’m an extrovert but I don’t enjoy networking events. 

I do enjoy them when I get in them and I get into a meaningful conversation and expand my network. Knowing the end result like, “Attending this is not my favorite thing,” but the end result is like, “I’m going to hand out three business cards, meet three great people, expand my network, that’s going to be fun.” That end result is going to be enjoyable. Going through that door and getting a process started, might be a little bit painful for me, but I know my end goal and I know that it’s going to help me further my progress towards an even larger goal. 

I listened to Arnold Schwarzenegger’s Pump Up Podcast. I don’t know if you’ve ever listened to that.

Yeah, it’s so good.

It’s awesome. He was talking about goals one day. He was saying the big challenge with goals is that people are trying to accomplish too much too quickly. He was talking about a person who never lifted weights in his life and was intimidated, because it was Arnold. I mean, he’s this big massive dude and this guy is just starting out. He was like, start with an empty bar and do three reps a day. Two days from now, try four reps, and then five reps, and so on and so on, and then add 2.5 pounds onto the bar on each side, and see if you can do four reps. 

He went through this whole process, and a few months later, he’s now pressing 40 pounds or 45 pounds on each side. It’s scary when you go into a gym and you’re going around, especially going to the gym where Arnold works out where all the guys are huge. I’m 5’8” on my best day walking in. It could be a little intimidating. Going back to your formulas, what do you want? Why do you want it? Alan Weiss has been an inspiration in my life. I don’t know if you know him. He’s written 66 books on consulting.

Alan once said one time, “If you get 1% better a day, in 70 days, you’re twice as good.” I wonder what it would be if I took that 1% out over a year. I did the math and it was 37 times better over a year if we got 1% better a day. Let’s say that’s too big for some people and we just got 0.1% better each day. We’d still be four times better than we were at the end of the year. That’s what I’m hearing, your formula is to know what you want, to get clear and truthful, and to know why you want it because the why is going to be the motivation that continues to keep us going through. 

Finding Out Your Why

If our why is not big enough, then we tend to go, “It’s too hard.” Know where you want to go and take these small steps because if we take too big of a bite into that process, then it’s going to feel bad. We’re going to feel like it’s not working. To also recognize that this takes time but it doesn’t take as much time like you said, four months, you’re running a marathon. I love the formula. You’re coming out with a book if I remember correctly. What’s the title?

Let’s Go! A Guide to Increasing Your Confidence. I don’t know about you or your audience. Everyone is screaming “Let’s go” today. I feel so funny about that because I’m like “Let’s go” to my kids, “Let’s go” to my business, “Let’s go” to this book. It’s this rally cry to you like, “Let’s go,” a guide to increasing your confidence. You can do it and it is this one step at a time, and no surprise, the first chapter is about finding your why. That is the basis for this whole thing. There is no goal that you can achieve if you don’t know why you want to achieve it. 

One hack I want to share with people is if you’re having trouble finding your motivation, ask yourself If you’re making it too much about you. We tend to be pretty good at letting ourselves down. We’re pretty self-deprecating about a lot of things, the way we look. I made that mistake. You talk to yourself in a way that you would never talk to another person. It’s so terrible and there’s a whole other chapter on self-talk in the book and how we can combat those horrible patterns that we’ve started. In finding your why, if you’re having trouble sticking to it, think beyond yourself. 

Can your why be about someone else? We’ll do anything for other people. You’ll do anything for your family. You’ll do anything for your parents. You’ll do anything for your team that you believe in. You’ll do anything for the greater good, depending on what that why is. Pick something bigger than you because if it’s only about you, too many people quit on themselves. How many times can you quit on a greater and larger idea, person, or influence in your life? That would be one of the things I would say. If there’s a goal you keep failing on, first of all, is that goal still relevant? Is it still true and authentic to who you are and where you’re going? If it’s not, you can let that go and redirect.

We’re not on this one-way trajectory. It’s not a direct point from A to B. We all go in these twists and turns, down this non-linear path in our businesses and our lives. Do you have permission to pivot? When you pivot, you have to select your next destination and identify the why, the reason that you’re going there, and who is it for. Choose beyond you if you can’t seem to get going out of the gate. 

Let me address that because I gave up on my goal of Karen Fitzgerald and I found the great gal of my dreams. But sometimes people hold on to that nostalgia of “If I only…” and time keeps going by. Sometimes it’s wiser to know your why and to let it go because we can’t make space for things. Sometimes when our brain and our mind are too crowded with stuff that is not serving. 

A lot of times in my keynotes when I’m in the Q&A, I get questions about, “What if I have not been able to reach my goal?” No fail, every single time I get asked that question. “I’m too afraid to set a new one because I keep failing at the current one.” That’s my question. Does it still serve you? Is that goal still relevant? Is it still true for your North Star? If it’s not, you have permission to let that go. It is not a failure. You’ve learned something in that process that has led your brain to go, “This isn’t right for us anymore. We’re meant to go here,” and set that new course.

I have found that it’s the universe of some sort saying to you or me in this case, “Doug, you are not supposed to do that anyways. You’re not supposed to be doing that and you keep ignoring the whispers that I keep saying to you,” which is the self-talk a lot of times. That’s one of the reasons I think we’re so hard on ourselves because we won’t let go of that self-talk over and over and over again. I remember when my daughters were young.

I think there was a show that Disney put out called Tangled or something or some ice thing or whatever it was. There was a song called Let It Go or something like that. I think that’s a good song for a lot of adults that when we keep running up a barrier, sometimes we can see it through, but sometimes the gift is understanding that that barrier is creating this impedance for a reason because we should be making a shift, versus trying to bowl our way through the barrier. 

That song is from Frozen, called Let It Go. I was pregnant with my first son. It was like nine years ago. I had signed a corporate sponsor for our team and I’ll say it. It was a bad deal. It was not a good deal and it was not aligned. The partner was over their skis and it was one request after another after another from me. It was making me so mad. You signed a deal with someone and it doesn’t work, but you’re under contract and I got to get the end of the season with these folks like, “We can make it.”

I would listen to Let It Go on full blast in my car on my way to work every morning because it was driving me insane. It’s so funny because looking back, I thought, “I signed this bad deal. This is going to reflect poorly on me or the organization.” I was making it about me. It worked out fine in the end. We didn’t renew with this partner. It was no bad term in the end. It was all fine and good. They say that you learn lessons and failure. That’s a difficult thing to understand and receive when you’re in that moment, but looking back, I think that deals a lot when I’m reviewing partnerships and deal terms. 

I learned so much through that failure and I let it go but I’ve kept the lesson. That’s something for us to remember as we’re building our confidence. One bad deal doesn’t mean that you’re a bad salesperson or that you have some type of personal deficiency. It’s just a bad deal and everybody has had one in their lifetime. Use that to learn and to steer your career in the right direction and future. Use that failure as a lesson and guidance. 

CEO Sales Strategies | Emily Jaenson | Confidence Building
Confidence Building: One bad deal doesn’t mean you’re a bad salesperson. Everyone has had one bad deal in their lifetime. Use it to steer your career in the right direction.


The people who move forward in life and do the best things recognize that fact and they will utilize that as a learning lesson. We can either look at it as a failure or we can say, “I learned from this and I’m going to capitalize on this.” That’s the difference in the interpretation. I wanted to bring something up because you had brought up that you had a bad deal. I will be bold enough on this show to say if you never had a bad deal, you are not selling enough. Walmart knows what their depth rate is. They expect part of the downside. 

If we expect that there’s going to be part of the downside by getting to where we want to go, and we understand that and we build confidence around that, when that failure happens you go, “Thank you. It finally came. Now, I’ve got one thing more to learn and I can continue to go on.” No CEO has ever thrown somebody out a window of a twelve-floor building because they said no to their sale. Nothing’s going to happen to you, folks. Most of the time, what I’ve learned in my life is that self-talk and that being hard on ourselves is on us. We beat ourselves up worse than anybody in the world when we allow ourselves to continue to do that. That will decrease our confidence level. I don’t know if it’s self-love. What would you call it? 

Positive Self-Talk

Your brain believes what you tell it. If you wake up every day and say, “I suck at sales. I’m not good at this job. It’s so hard,” how do you think you’re going to feel every day? When you’re entering into the job, you pick up the phone, you’re going to that meeting, and before you go in you’re saying, “They’re not going to buy.” Are you going to get a good result? No. Your self-talk is critical. I’m not talking about some magic woo-woo wand that’s going to make everything bright and rosy. You walk in saying, “I know this product, I believe that it’s a great fit for this company, I know it can make a difference, I’m prepared, and I’m going to give the best presentation.” 

Ultimately, business isn’t personal. It’s about budgets. Do they have the money to buy what you’re selling? Can they find the money or can they make the money to buy what you’re selling? You might have the greatest product in the world, but if their business is not in a great place, they can’t buy. If it is, you need to bang up a presentation like signed, sealed, delivered. You did it. You have to be your own greatest advocate because you might get lucky and have an amazing boss who’s going to pump you up.

CEO Sales Strategies | Emily Jaenson | Confidence Building
Confidence Building: You need to be your own greatest advocate.


A lot of us don’t have the greatest bosses and leaders in the world. That’s why they’re so much work being done in the leadership space so that we can empower and grow incredible leaders who can foster and grow those underneath them, to create this amazing economy of producers. If your boss isn’t going to pump you up and you’re not going to pump yourself up, how are you ever going to find success? Start with you. Start with your why. Identify your why and tell yourself every single day that you can do it. 

That was profound. What I heard was to be careful of the labels that we put on ourselves that will stick. There’s a difference between saying something like, “I did something stupid and I am stupid.” When we put that label on, be careful, folks, because those labels sometimes have sticky backing and when you keep repeating that over and over again, you create a label and stick that on your forehead. That’s what we as human beings tend to see in the mirror.

I’ll illustrate it this way. I lost my hair when I was young. I was 28 years old and I was like, “My life is over. I’m losing my hair.” As I was losing my hair, my wife came up to me and said, “Why don’t you shave your head?” I’m like, “No. Only weird white guys shave their heads.” She’s like, I think you’ll look good that way. I shave my head. Here’s what happened. I shaved my head and I went to a restaurant. I sat down at a restaurant. I was working on some business stuff. I had a notebook there and three women who were very attractive came over and they looked at me and they were staring at me and I was like, “They’ll think I’m this crazy guy or whatever because I shave my head.” 

One of them puts the hand on my head and starts rubbing it. I said, “What’s going on?” They go, “Sexy.” I said, “What?” They said, “A man who’s willing to do this has high confidence and that’s sexy.” My point is I was apprehensive like you making phone calls when you’re 21 because I was worried about how people were going to perceive me, but the reality is it’s been a trademark ever since. 

Emily’s Book

People remember me because I don’t have hair and no one has ever judged me unfairly that I know of. I put that label on myself, “If I do this, then I have no hair,” a lack of confidence. The reality is it turned out to be one of the best things that ever happened. It’s a learning experience as you were saying before. I wanted to reaffirm that and thank you so much for bringing that forth. Your book is not out yet. How do people get a copy?

You can go to my website EmilyJaenson.com, and pre-order the book. Shortly here, it will be available for pre-order on Amazon. It will be available on Amazon for purchase later this spring 2024. If you’re tuning in to this after spring 2024, head to Amazon and pick up your copy. Let’s go! A Guide to Increase Your Confidence. It’s a journey. The whole book is a journey. I have so many stories in there that are isolated and might be a little embarrassing but it shows that personal growth. You don’t get to where you are on easy street. Things happen. I’ve got personal stories.

I’ve got a podcast, Leadership is Female. Many of these executive women around the globe have told their stories about when they increased their confidence and when they found their voice, it’s when everything changed, and when they took their spot at the top of their industry. I got some interesting studies in there. If you don’t believe me or you don’t believe them, you could at least believe the data. The good news is it is possible. It’s possible to grow your confidence and become the person that you are dreaming to be. 

The book is not just for women. 

Yeah. I speak to a woman, to a lot of women. I speak to anybody but I’ve been in a lot of rooms that are primarily women with some guys in the back. When I get off the stage. the guys in the back, I can see them walking towards me and they’re like, “I’m so glad I showed up for this one. I came because I thought this would be good for me to talk to my wife or my daughter about, which it is, but I needed to hear that too and I could use that too.” This is for anybody who has a goal, has a dream, and is curious about what they can do to get there. How can you make some personal changes to live the life of your dreams? 

Closing Words

That’s one of the greatest compliments ever when a guy comes up and says something like that. Being a guy, I’m pretty open and I would do something like that, but a lot of men are like, “That was amazing,” and they would not talk about it afterward. The fact that you’re able to internally motivate them through what you’re saying is a big testament to the quality of the information that you’re bringing forth. I want to thank you for being here on the show because I know this was a message that our audience wanted to hear and some of them needed to hear. I appreciate you being here. Any last parting words that you might want to bring forth?

My last parting words is my favorite quote, “Be so good they won’t forget you.”

Be so good that people won’t forget you. Click To Tweet

Emily, thanks for being here. I appreciate it. Thanks for bringing your A-game. 

My pleasure. 

Did you get the formula down? What do you want? Why do you want it? Being brutally truthful about that particular aspect, and then knowing where you want to go and setting a time frame that is not so large that it’s almost impossible to achieve. It doesn’t mean you can’t push yourself through goals but understand that you’re going to have some days that are great and some days that aren’t great. You want to keep your nose pointed in that direction. Keep taking one step a day. In time, you will get there. You may exceed your goal. You may exceed the time frame of the goal, but you will get there if you continue to keep going and if it’s constant and consistent pushback

The universe is saying, “We might need to go in a different direction.” Pay attention to that as well because that feedback gives you the ability to still get your goal and persist. If you keep running your head into a wall and the universe is saying, “Take a step left or take a step right,” and the wall is no longer there, pay attention to the clues. That’s what I’m trying to tell you. I thought Emily did an amazing job laying that out. If you want to know more about her, please go to her website, pick up her book, and you are going to learn a ton of stuff, I promise you. 

Speaking of learning, if you’re interested in being better at what you do in selling, in other words, you might be starting out, you might be good, you might be great, but you want it to take to the next level, we are running out a University for that. We call it the 1% Academy. We’re also helping people identify their true 100% buyers, who are true buyers and your best buyers. 

If you own an organization and you want that to be clarified for your organization, you want your sales teams to have that clarified, or you want to, as an individual who runs a business or a person who has a large sales team, you want your sales team to experience gross this year, not only in their sales skills but in their improved confidence in their selling, then reach out to us at YouMatter@CEOsalesstrategies.com and let us know. If you love this show, I’m going to ask that you please give it a review. I would be forever grateful.

If you know somebody who is an expert in a field that would help people, have them reach out to us. It might even be you, YouMatter@CEOsalesstrategies.com, and we’ll be happy to give them an interview and see if it’s a great fit. Until next time, this is Doug C. Brown saying, go out, sell something, but sell it win-win. Watch your discount structures as I always say because if you discounting you’ve got to sell more to make it up. Make someone happy today. Make yourself happy today. Help them solve a problem. Gain something for the future. Everybody wins. You’ll be wealthier and happier for it. To your success.


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