Building Sales Team Values with Chad Estis

Success in sales is gained not just by yourself and the position you have achieved. More importantly, it is impacted by how you influence the people around you, which calls for the right sales team values. Join us as Lance Tyson goes one-on-one with Chad Estis, Executive VP of Business Operations with the Dallas Cowboys and Legends Global Sales. They discuss several topics ranging from how selfishness could destroy any dream team, the importance of career development, and how selling would look in the future. This is a fast-paced 30-minutes episode you do not want to miss.

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Building Sales Team Values With Chad Estis

I’m here having a riff session with an old friend of mine and business partner, Chad Estis, with the Dallas Cowboys. He is gracious enough to spend a little time with me. What we are doing in this show is talking to sales leaders about their approach and their outlook on things in this day and age. Chad is going to talk. I’m going to ask him a lot of questions. He has one of the best stories I know. Not only is he somebody I do business with, but I also consider him a coach. Welcome, Chad.

Thanks, Lance. I’m looking forward to spending some time with you in a new format. Let’s jump in.

For people that don’t know you who might be outside of pro sports or maybe some people don’t know your story, give us a few minutes on your rise coming through sales and to what you’re doing now.

The quick story is I was upwards to my junior year of college. I had no idea what I wanted to do post-college career-wise. I had always loved and played sports. I was fortunate and lucky enough to be at Ohio University and got exposed to the fact that they have a Master’s in Sports Administration, which I didn’t know what that was and what that meant. As soon as I gathered a little more info about that and realized, “There’s a whole business career in sports that I was unaware of at that time,” then I got pretty focused on trying to get into that program. That’s how it started for me.

One of the first things they told me was, “If you want to get into the program, go get an internship that’s going to have to put on your resume.” I was able to use a family relationship to get an internship at the Cleveland Cavaliers. That was my first exposure to the inside of a business of sports. I did that for the summer. I liked it and got a chance to ask a lot of people in the organization what they did and how they did it. I watched, learned and that set me off.

People told me to go into sales. That wasn’t something I probably would have come up with on my own. I didn’t consider myself a salesperson. They said, “That’s how you should start.” My first job was an entry-level sales job at the Cleveland Cavaliers. I got committed to it, worked pretty hard at it and made some different moves. I went up to the Detroit Pistons and worked there.

I got an opportunity to get into sales leadership and then went down to the Tampa Bay Lightning and back to the Cavs. I had a long stint where you and I met. I worked there for eight years. It has been many years now that the Cowboys opportunity came up. Legends became a part of my responsibility as well. That’s a bit of the quick career history.

Between you and I, you use some real specific language. What did you suck at in your first sales job?

Honestly, I remember it well and it’s an easy question for me to answer. This was pre-computer and the internet. This was in the mid-’90s and I was at the Cavs and in one day, they set you up. They had me sit next to another rep and listen. They handed me a computer printout stack that if you’re bored, you could peel the sides off. I had a ruler, highlighter, phone and script. The expectation was around 100 calls a day. I was extremely uncomfortable. I lacked confidence. I didn’t feel like I was good at it. I wasn’t having much success. I didn’t like it. There was nothing about it to report to you that was positive on the early sides of that.

How many times were you ready to quit in the first couple of months?

The problem with the quitting idea was that it was difficult for that to enter into the mind because I invested a lot to get there. I had done an internship and then I had a Master’s Degree. I had told everybody in my circle I was going to work in sports. You create that own pressure. What are you going to do? In two months, “I didn’t like it and I quit.” That wasn’t part of my DNA.

You had enough out there. It’s like how we always talk, “Are you the chicken or the piggy?” The piggy commits his life for the breakfast. The chicken just contributes to you.

ASO 1 | Sales Team Values
Sales Team Values: If you could spend a little time learning how to sell early in your career no matter what you end up doing, that is a great skill set.

It would have been a bad look for me to walk away from that. I would have been letting some people down. I had that good pressure on me in a good way to stick with it. My parents doubted me at that time. Unfortunately, I had to move back into my house. I was making $16,000 a year with no benefits. That put me right back into the home in Aurora. None of it was good. Personally and professionally, it wasn’t good. You go from college back into your twin bed in the house. All of it was rough.

I’m always telling salespeople all the time, “If you look at the trajectories of very successful people, most either come out of high finance or they could bring something to the table like a sale.” You worked your way up. With that said, what were you good at? The second question is, what was difficult about managing you when you were in sales?

Sales is a great teacher of life. It’s got a little bit of everything.

At the earliest stages, I was good at nothing. I’m being honest with you about that. What I became decent at was my work ethic. When I had no skill, the one thing I knew I could do was work. Honestly, that was a page out of my athletic book. I worked hard to be a college basketball player and had some success and I thought, “I know I can do that.” I was like, “I’ll outwork everybody.” I was a grinder.

You know a little bit of this story. My brother was two years ahead of me out of school. He was in a sales role and he said, “You need to start self-educating and reading these books. There’s a material out there that you can teach yourself how to sell to be a good salesperson.” I started to do that. Self-education became something that I valued greatly back then.

The first time I started reading about what you teach, the skill of selling, it became a different mindset. I started worrying a little less about what people were saying on the other end of the phone. My anxiety dropped, my feelings of failure. If I wasn’t making sales lessons, I started to treat it as more of a game. Some of that stuff mentally and emotionally was helpful to me.

ASO 1 | Sales Team Values
Sales Team Values: Even when you’re just trying to convince your boss about something, what you are doing is also a form of selling to some degree.

To your second question about what was I like to manage, I was hard on myself. The failure element of sales in that environment was hard for me. I was probably to my manager more of like, “Why can’t I be better?” I was frustrated and I probably projected that. I would assume my manager also saw me as a hard worker on the positive side. I was pretty much willing to do whatever anybody asked me to do. I volunteered for the extra stuff. I was trying to make an impression in a variety of different ways.

I’m sure my manager would have liked me to produce more, quite simply. I had two managers at that time. I had good relationships with both and carried those for a long time. I look at that stage of my life and view it as I get through it. It was more of how I felt. It’s probably part of why I have made a commitment to try and help people when they are in that stage of life because it was the stage that was rather difficult for me.

It doesn’t sound like you were the top guy. It sounded like you worked hard. You probably had glimpses of genius. I never heard you say once like, “I was the number 1 or number 2 guy.” You probably made your way up and down the list a little bit, correct?

It’s interesting you bring up the list because the list was up on the board. I was a high middle of the packer. I couldn’t find my way to 1, 2 or 3. It’s probably hanging in around 4 or 5. It’s like, “Just good enough.” Back then, there was an expectation of top of the board for sure. With those early learnings, I logged a lot of that stuff in the memory bank because when I got into leadership and particularly as I evolved more and when I got to the Cowboys, we hired 36 salespeople. We had a top ten and we celebrated it, but there was no shame in being 25th. The difference between the 25th and 8th could be a day or two in the office of picking up the phone.

I tried to get away from the emphasis of top of the board. I found myself promoting a fair amount of people with years in a leadership position that wasn’t necessarily top of the board but displayed the skills and qualities of good teamwork and leadership. It’s not about being number one. I have seen some people being number one that quite honestly, at some point, didn’t even belong to be in the office because of the way they acted and handled themselves. Being top of the board was overly emphasized to me to the point of discomfort. I tried to make a note that’s not how I was going to operate when I had a chance to run it.

Success means too many things to too many different people. Only you can define your own success.

Let’s flip this over then. As you started to move your way through your career, you started getting some more sales leadership. How did sales prepare you to be a sales leader? What did it not do to prepare you to be a leader?

My belief now and I have been selling my whole career. Sales is a great teacher of life. It’s got a little bit of everything. One thing is at the very heart of it, if you can develop the skill of selling, there’s a place for you in the world. It’s a little bit of that security and comfort that no matter what happens and thinking of it in this weird time, you can think about that a little bit. I feel like if my career didn’t work out how I had hoped or expected, I’d be able to sell something somewhere to somebody. It’s a baseline that gave me a little comfort.

ASO 1 | Sales Team Values
Sales Team Values: Your days, success, and income are defined by your own actions to a large degree. But at the same time, you need people who are good teammates.

It’s got so much too. It’s got the ups and downs. It’s got the thrill of victory and defeat. You need to do your best when you’re working around a team and you’re collaborating on selling. It’s got strategy and relationships. It’s fun. I would almost say to anybody if you early in your career could spend a little time learning how to sell on selling. No matter what you end up doing, it’s a great skillset.

How did selling prepare you for leadership? What I heard you say was like, “No matter what I’ve done, I still had to sell.”

It prepares you for life to a degree. Even when you’re not directly selling, you’re trying to convince your boss around an idea or you’re trying to convince them that someone should get promoted. When are you not selling to some degree, is the way I look at it.

If you have never met Chad, if you do any looking him up and looking at the number of people, I always gauge somebody with how many careers they have started and Chad has promoted so many careers. You’re always known, especially in sports and entertainment, for building some of the best sales cultures you could ever find and the loyalty that creates.

I’m going to ask this question this way. When you look at a sales team, sometimes it’s hard to define the words to determine your value system. What is it about a salesperson’s behavior that grinds you? An observation is something you have to keep reminding somebody of or you observed the behavior and it pisses you off. What is that one thing? A lot of times, that is where your value system starts. It’s something that bothers you with their behavior.

It’s selfishness.

Define it.

The interesting thing is you do need to be a little bit selfish to be a good salesperson. When you’re solely selling every day, you’re working on behalf of yourself. Your day and often your success and income are defined by your own actions to a large degree. At the same time, to have the right culture of an office, you need people that are good teammates.

What I want is that aggressive, hard-charging sales rep that wants to be the leader on the board but, at the same time, would stop and make a sale for the person next to him when they receive no credit and not worry if anybody knows about it because they want to help their teammate. It’s someone who is willing to celebrate the success of those around them even if they are in a slump.

It’s someone who, when you rally around in the morning getting ready for the day and you have someone to share a sales success story, has good body language because they are generally happy for that person even though you’re not talking about them. That gets displayed every day in a whole lot of ways. It’s someone who is generally positive even when things aren’t all going their way or things aren’t in the office maybe all the time the way they want them. They are not the first person to gather, three people to go to lunch and have a session.

Success will come to you if you just put your head down at all costs. You will get there eventually.

I have seen it manifest in a whole lot of ways. That to me, probably more and more as I go. A good salesperson that’s overly selfish has no place with me. I’ve addressed that with people over the years in a whole variety of different ways and seen different versions of it. A lot of salespeople want to become the next leader. It’s not everybody but a lot of them do. That’s a quick way in my eyes to take yourself out of the running for that.

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Don’t Fire Them, Fire Them Up: Motivate Yourself and Your Team

With your definition of selfishness and I definitely concur, it probably takes a lot of communication to your teams of how you define that because there are a lot of angles there where you throw at that. You said like, “You display this. You’re doing this. You’re not doing this.” It sounds like you need to be in tune with your people to say, “This is my expectation.” Talk to me about what your sales leadership style is now. You and I have talked a lot over the years about this and how your leadership style has evolved. In the beginning, it was this. Where is it now?

The way to talk to the team about not being selfish is to do it in the positive form, which is how to be a great teammate. If you’re a great teammate, then you’re not going to display selfish characteristics. I don’t talk about, “Don’t be selfish.” It’s more about, “Let’s talk about what our office would look like if everybody is being a great teammate.” We do talk about that.

As far as my style and evolution over time, it’s constantly evolving. Some of it is with the times. There are times where I have been more old school. Things shift in the world and you have to adapt to that. There were some core principles of what I would like an office to look like from a cultural standpoint. It all starts with career development. That’s the first thing I think about. That’s the first thing we talk to people about when we interview them.

We try and interview people and find people that are interested in that. We like a career to be a motivation, particularly for young salespeople. If they are interested in career advancement and we are interested in creating an environment that helps them evolve in that way, then you have what I call an unwritten agreement right out of the gate. We are here to help you evolve your career. For that, we are going to ask you to do things a certain way and lay out the expectations.

I have found if they generally believe you are there to help them, you laid out the expectations and have hired a good career-driven person, you have got a nice little arrangement there that doesn’t need to be cleaned up that often. You can put them around other people that are living the same thing. What stands out like a sore thumb is the selfish prick that no one wants in the office anyways. It’s not that hard. Being committed to developing people’s careers doesn’t exist everywhere. That exists at Dallas Cowboys and within Legends. That’s a core philosophy and principle that we go by.

That creates that loyalty factor and those roots that you need. I don’t even know what to say to people about this time. If you’re reading this years from now, we are in the middle of COVID-19. We have been all bottled up in our houses. I’m in my office at my home and so is Chad. We have not left our houses in 45 days.

As you’re looking to the future of selling, I’m not asking you to have some positive like, “Everything is going to be okay.” I’m thinking back to your career. When you were in the NBA, you lasted through that first lockout that year. You had to come out of that. It was at the end of the ’90s. It will live through that a little bit with 9/11 and then the other stuff. What is your forecast not just in sports but selling in general? How do you think it’s going to change? What do you think it’s going to look like moving forward, if at all?

To your point, whatever how many days we are into this odd experience, I wouldn’t want to predict what may or may not happen with this. You and I talked a bit at the beginning. You think there are going to be some changes. The fact that we are doing this, you could have said, “There would have been value to this months ago potentially, but we weren’t thinking about doing it. Why not?”

I did a Zoom with my family, with my brothers in Minneapolis and my mom and sister in Cleveland in different towns. We had a blast and we drank some wine. We ended up spending two hours doing this and you say, “Why haven’t we ever done that before? We all lived in different places at that time.” Things will be different. There will be a change. To me, the world will always have a place for selling technology and the use of it like this.

Certainly, I’ve spent a lot of time back in the day driving all over Detroit, Tampa and Cleveland to do face-to-face meetings. I sit here and I’m looking at you and thinking, “We could probably get a lot done going through some information about a premium seat doing it this way.” There might be some more of this in the future. It doesn’t mean that skillset would be any less and if not, maybe it even needs to be enhanced more.

You know me pretty well. Through this, I have had my moments and this has been a bit scary. A significant change happened quickly, a lot of business issues to deal with and a lot of concerns over people’s health. At the same time, I remain optimistic. Humans figure stuff out that there are great scientists and people that are going to figure this out. It’s not without casualty. We’ll come out of this and find over time a world in a better place.

I know personally, I’m thinking of, “What are the things that I want to do more of and less of when this is over?” There are some things about this that have been good for me. There are certainly some things that I miss and want to get back to. I’ll go about some things a bit differently as well. There will be a place for good selling. I have no doubt about that. That means there’s a place for me and you in the world. That’s all that means.

We are going to bring this down for landing with three more rapid fires. You got an eight-year-old niece and nephew and they say, “Uncle Chad, how do you define success to an eight-year-old?”

It’s hard to ask an eight-year-old how they would define success, but that’s where my mind goes first. Success is only defined by the individual. I couldn’t define anybody else’s success because success means too many things to too many different people. I start thinking about things like financial, lifestyle, role, responsibility and how you want to go about your day. I used to think success was defined by the title, role and responsibility. You obtain some driven career that you would put your head down and at all costs, you’re going to get there.

My perspective is completely different. I think to each his own on that question. When someone tells me they are driven and they want to be the president of a team, there was a conversation we had about that. If someone says, “No, I want to be a senior account executive because I like what that provides me for this and this,” I totally appreciate and respect that. It’s defined by how the individual defines it.

When you were selling yourself, pick your sales song. What is the song you play? Mine is Onyx’ Slam.

It’s Welcome To The Jungle. The only reason I picked that is because my high school basketball team used to warm up to that and I would get super fired up.

What book do you gift most? If you had to give somebody a book, what are you giving them? It tells us a lot about how your thinking is. You have gifted me a few.

The most impactful book on my career and life, which I read when I was in my twenties, there’s a book called Don’t Fire Them, Fire Them Up by Frank Pacetta. It’s an old book now. There are incredible lessons in that. That started to shape for the first time. If someone said to me, “What do you want to be as a manager or leader?” Prereading Don’t Fire Them, Fire Them Up, I would have said I have no idea and that gave me a lot of ideas. I’m super appreciative of the fact that it was an early book I read.

Chad, I appreciate your time. You’re the man. We are going to get this out to everybody. Thanks for being a great guest.

Thanks, Lance. I enjoyed it. Take care.

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