Lee McCroskey, speaker, trainer and coach, Southwestern Speakers and the John Maxwell Team

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Lee McCroskey has been an inspiration for decades of Southwestern Advantage participants, including myself and many of our fellow interviewees. His presentations on personality types, how to overcome adversity, and his overall storytelling prowess are well-renowned.

Some of Lee’s stories I had heard before – often from being in the audience of one of his inspirational or educational speeches  – but many of his insights were brand new to me. I hope you’re similarly energized by this powerful interview.

You can read Lee’s full biography here


Jamie:  Lee, looking at your career in sales and leadership coaching, training, and public speaking, what have you found most fulfilling thus far?

Lee: Everybody is different, Jamie. But most of the time, my fulfilment comes from an internal sense that I have, at least for a moment, made a difference in someone else’s life. If I have made a tiny impact, if I say one thing that helps somebody pass a hurdle or get unstuck, it has been a good day.

Now hopefully, if I give a talk, I have a little bit more impact than a tiny thought, but I also understand that people think seven times faster than I can speak. So, my goal is to keep their eyes open. Some people can listen or sleep with their eyes open and hear me talk! I try to interrupt their train of thought occasionally.


Jamie: You mentioned helping to get people unstuck in their career. What do you think are the main causes of people getting stuck?

Lee: I think people get stuck because they get at cross purposes with either their own mission, goals or with their corporate mission–or just internally. You could get stuck by doing the same thing over and over and ultimately feeling like, “I am not getting anywhere in my career. I am stuck.”

I am a firm believer in NLP. A popular version of NLP is Tony Robbins.

NLP is really keen on selecting the words you use to describe your situation. People describe their lives as, “It is so crazy. My life is crazy.” I mean you know, when you say that word, ‘crazy’, it paints an image in your mind, and it typically reinforces what you do not want. No one wants insanity in their life, but they are describing their life as insanity.

So, I say, “Pick a different word.” Say, “My life is different right now.”  That does not have the same sting as “crazy.” I am not saying that a single mom who has to home-school their kids suddenly, and is trying to hold down a job, and has a husband who is trying to work at home for the first time; that is a little crazy. I’m not suggesting people deny reality.

But you can choose a different description for what you are experiencing. I think that makes a big difference. But people get stuck with the words they choose and think and use.

There was a really cool website, which I think is now defunct. It was called When you went there, you would enter the site, and it would say, “What are you stuck about? Is it work, career, or home?” You clicked on one of the options, and it would take you to the home section, and you would dig down and figure out exactly what you are stuck about. It would give you articles, options, new thoughts, and affirmations. I thought it was a really cool site. I do not know what happened to it, but I like to help people get unstuck.

That is what I did at Southwestern. Whenever I had conferences with salespeople, I would sit down with young, new salespeople and just say, “What is going on?” and they would start complaining or grumbling. They would start with very general thoughts, like, “My life sucks.” Okay, that is another way of saying, “I am really stuck.” I would try to shift that down to a specific bit of clarity. They would say, “Oh I hate x,” or they would say a huge statement like, “I hate sales. I just hate it. I cannot get through to prospects, and they do not listen to me,” and I would say, “Okay, slow down. So, what exactly about sales do you hate? We would eventually get to: “So what you hate is the fact that you are ineffective at it?” Then we’d talk about specific solutions.

I am just trying to find a little nugget of what is really tripping them up rather than these blanket statements. Like, “The world is crashing down on me.” That’s too generalized to deal with.


Jamie: Do you think salespeople get stuck more than other people?

Lee: No. Everybody gets stuck. I will give you an example. My wife is the Director of Medicine for Vanderbilt and their walk-in clinics. She has a big job. Everyone has to go to Vanderbilt for testing now. Thousands of people were coming down, and they were not set up for the crush; they were not organized. She was losing her mind. I was literally bringing her food, and she was not eating much. She was on the phone calling doctors, scheduling nurses, and going in testing patients – there were lots of people to organize.

Through that difficulty, through that pressure, through that time of stress, you saw how doctors, nurses, and administrators reacted. Their true nature was revealed. Some people are cool, calm, and collected. Others, including some of the test providers, were flipping out and some refused to even come to work – which is shocking. Pressure and stress reveal our inner workings. There were lots of people in the medical field who did not know the answers and did not know how to react; I would say they got stuck mentally.

We go on dog walks every day, my wife Deb and I. We walk and talk. It is her chance to vent about being an administrator and what she is dealing with. It helps her get unstuck. These are brilliant people, doctors and nurses who are between 35 to 50 years old who are intellectual giants and emotional midgets.

You never get past that, whatever field you are in, so it’s not like salespeople have the corner on the market in being stuck. Everybody has problems.


Jamie: You have trained and coached thousands of salespeople. Based on your experience, what kind of people would you recommend go into sales?

Lee: I have seen all kinds. I selected a guy for one of my sales teams from a small agricultural school in Kansas in the U.S. He was an accountancy person, and he is like the poster child for accountancy; I mean pretty nerdy. He had a huge cowboy belt buckle, and he could not look me in the eye when I met him. When I shook his hand, it was kind of like ‘pft!”– weak. He did not have a lot of confidence. In the DISC profile, he would be a high C. Conscientious, detail-oriented, and a perfect accountant. So, you might think at first, “This guy could never deal with people.”

But the fact is he wanted to learn about people. He was very diligent. He was very persistent. He was very systematic. His learning curve was very steep, and it took him a long time to get it. He studied the script.

He learned the material and went to prospect after prospect. He had a slow start. Once he locked on to the system, he outsold everybody. He worked with me for seven years. As a university student, he saved over $100,000 and travelled the world. He certainly changed. He can now look you in the eye, shake your hand, and is very confident. Ultimately, he had a lot of drive that you could not see.

Most of the people that I knew who were super-expressive, outgoing, slap-you-on-the-back, easy to talk to, good with people– sometimes things came too easily to them, and during the first couple weeks of sales, they quit because they were not used to difficulty.


Jamie: Are you aware of any personality tests that determine sales aptitude?

Lee: I do a rudimentary test. I teach a sales course, and one of the books that I have used is from an old friend of mine named Dr David Lill, who was a professor at Belmont University here in Nashville. In his book, he has some remarkably simple aptitude tests, but I do not have one in particular that I send people online.

I would much rather have them know their DISC profile or discover their Enneagram so that they get how they are wired, and then how other people around them are wired. They can start to appreciate differences.

My big problem when I first started was, I thought everyone in the world saw the world through my glasses. Everyone is like me, and this is how I need to sell because I sell like this, and I like to be sold this way so I think everybody should. Well, the fact is that at least 75% of the world did not see the world the way I did. 

I think if you have an appreciation for how other people’s mental framework– then you can adapt to their buying style. If you are flexible, you can adapt to their style, which is really important.

Selling people the way they want to be sold is just mission-critical.


Jamie: What happens if you do not do that? 

Lee: Normally, people end up selling to people who are like them. For example, my friend, Roger, who I just mentioned; he’s a logical and analytical person. He would tend to present with his voice as flat and monotonous, and he provided way too much detail for someone that was at the opposite end of the personality spectrum—someone who was more people-oriented. In that case, Roger would simply sell to the 20 – 25% of people he ran into who are just like him. He appreciated finding someone who was slow-paced, monotone, not too-out-of-the-box and gave lots and lots of detail. People like people who are like them. I always say, “likes like likes.”


Jamie: Do you currently teach sales at college/university?

Lee: I teach a sales course, a management course, a communication course, a literature course on CS Lewis, and a leadership course.


Jamie:  Do you think that is a sign that sales is being taken more seriously as a profession and scales skills are being taken more seriously?

Lee: Yes, absolutely. There are universities here in the States that now offer a degree in entrepreneurship and sales, which you would never have seen years ago. Some universities feel, “We are still academic. We would never have that as a degree.” But I think you are seeing sales taught with business school, at least here in the U.S. There is a book that came out that I love and it is one of my required readings – To Sell is Human, by Daniel Pink.

He cites the fact that one out of every nine professionals in the U.S. is in sales, and that eight of nine say that 40% of their time at work, no matter what they do, is in what he calls “non-sales selling.”

My wife is down in the kitchen right now. She is organizing positions and schedules for people to go into all these clinics. She has to persuade them to work at a particular time. She has to influence them. When she met patients, she was selling them on, “Here is why you should quit smoking,” or “Here is why you have to cut back on sugar.” Everybody is in sales. When I get into a classroom, for most of the students, their initial reaction is like, “Oh no, I am not in sales. I would never do that.” I tell them, “Well, my job is to convince you that you will be in sales, whether or not it is your profession.” I have heard people say, “Well, I am going into law. I do not need to know how to sell.” I think, “You are an idiot. Your ability to influence is everything in your career trajectory.”


Jamie: What extracurricular or outside of the workplace activities would you recommend to an aspiring salesperson?

Lee: This goes back a little bit to how you are wired. For example, I know my daughters are a little bit more reflective and task-oriented than I am. My daughter is in Chicago. She works with a non-profit organization.

She needs to recharge. Her extracurricular activity is to be alone, get quiet, and read because she has been around people enough. She has poured out into them, and she needs to refill her cup. Other people, they need to go out to a networking event because they just get excited and enthusiastic being around other business professionals. They need to go connect and get wired that way.

I think it is different for different people. I tried to always lead a balanced lifestyle if you look at a pie chart of life; I have tried to have all the spokes in that wheel. I tried to have balance. I had my career at Southwestern for 36 years, but I never let it become a detriment to my family.

I just took my family with me on business trips rather than saying, “Sorry, I have to be gone the next six weekends, text me pics of your tournament.” I would say, “Hey. Luke, you get to come on this trip.” I did not miss their games. I took the kids with me. When they were in sports, I always tried to be involved. For me, the spiritual side of things is super important. I take time every day to get centred, read my Bible, and pray for people. I swim with the U.S. Masters swim team. Just a minutes before our little chat here, I got out of the swimming pool.

I try to do things in physical, social, emotional, and spiritual balance. I read a ton. I watch lectures because balance is on the top of my list of priorities in life. I think everybody is going to pick a different set of activities to recharge. I won’t say, “Oh, salespeople, here is what you need to do.” I think you should study your craft and read about it and learn more.

You’ve never arrived in selling. You should never think, “Well, I have maxed out. I am done. I am at the pinnacle. Nothing more to learn here!”

I have a wall of business books, and I just cannot sit and read those all day long. They start to sound the same.


Jamie: You weave in stories about people all the time when you are talking. How do you go about being good at that and how important is it to a sales pitch?

Lee: It is important. This gets back to speaking in front of groups, but it correlates well with sales. If you can make a point to tell a story, people remember that. That’s what I’m constantly doing, whether I am in a classroom or in front of a group. I want to make a point and tell a story. They will remember the story. They will not remember statistics that I just spewed out from Daniel Pink’s book, about one in nine, 40% of their day, blah blah blah.

If you can tell a story, “Let me tell you about what my wife is dealing with.” Then people go, “Oh, I can picture that.” Especially if the person you are trying to reach out to is relationship-oriented. Then they will appreciate this story aspect. If I am calling on somebody who is, again, like my friend Roger, a detailed person does not really care as much about stories; he might not respond to testimonials of what other people said about the product. If they just want the data, then I’m going to give him the data.

Discovering who you are dealing with, what their needs are, and then orienting your presentation and delivery around their style is key. I think that is what I have to figure out first – who am I dealing with.


Jamie: When we met first, you said I had an interesting face. What can you tell about someone from their face? 

Lee: Well, years ago, we hired a guy to come to speak at one of the Great Recruiter seminars for Southwestern. He was an attorney from Texas, and he came in and talked about what he did for a living, besides being a trial lawyer. He described himself as a face-reader, which was intriguing. I thought, “Well, okay, I want to see what this guy does.” He would bring people up on the stage, and without doing anything with body language, he would just look at them and say, “Well, here is what you are like. Here is your style, your personality.” People would go, “Wow! That is amazing. That is true.” He did that from looking at people’s faces.

That may have been why I made that remark to you some years ago. I bought his book, and there were flashcards that I bought and would I practice on people when I was sitting with them on a plane. I would say, “By the way, I am just curious. Are you like this?” and they would go, “Well, yeah.” We would end up having a conversation.

If people want to know more about that, go to the website at There are other sites about face reading. It is an old science. I think it dates back to Socrates. I mean, it is really weird when you first think about it, but essentially, you can get back to the nature and nurture of how you were born and how you develop – the fact is that your personality impacts your face. Certain features indicate the type of person you are dealing with.

You can go there, learn stuff, and practice on people. That is all I did. I feel like most of the time, people are like, “Wow, that is pretty spot on.” You would say one thing like, “Jamie, I look at your eyebrows and think your brain is really active. It has ideas all the time, they just pop in.” If people have to shave or pluck in between their eyebrows like if they have a uni-brow naturally, that is someone who has got so much mental activity going on that they probably have trouble sleeping at night because they are just brimming with thoughts. You can look at the nose, you can look at people’s ears. You can see how their ears are placed on their head in relation to their eyes. It gets very detailed. Eyelashes, shape of the mouth, and the chin, the whole deal.


Jamie: Is public speaking something you would recommend to any salesperson as part of their career?

Lee: Here in the States at least, the fear of public speaking is the number one fear. I think death might be number two, but speaking in front of groups is at the top. I think if you can, you should, for two reasons.

One, if you can get up in front of a group and persuade them or influence them, then, that gives you confidence. Also, a lot of people are doing consultative selling, or group selling now, and if you then go into a company and you have to present or demonstrate to a group of people, including senior leaders, I think it is a good skill to have.


Jamie: How do you develop that skill?

Lee: You just have to do it. That is part of my classes. No matter what class I am teaching. They have to get up in front of the class and do a presentation. Some people go, “Oh great!” and they look forward to it. Others just wet themselves like, “Oh, my gosh!” Our class has only got 12 people, come on. You just have to start doing it, and I think the more you do it, the better you get at it. Certainly, you need to have people that are supportive and give you positive feedback when you are just starting. One other great idea is videotaping yourself giving the talk or presentation—what a great way to get instant feedback!

Personally, I just found that I enjoyed it and got good feedback from people’s faces and folks who were apparently awake and clapping. So, I thought, “I think I am good at this.” Just like anything else, like skiing or snowboarding; you’ve just got to get up. Get up behind the boat or get up there on top of the mountain and try. Oh, and it helps to take lessons.


Jamie:  What would you look for nowadays if you were choosing a potential employer?

Lee: I would look at them in terms of what other people say. It is like before you go to a restaurant, you can go on Yelp and check out the ratings, and reviews.

The company culture has to be a balance between a supportive and competitive culture. You want to push people to be their best and not just sit around hugging people going ‘Kumbaya,’ and we love each other. But you do not want it to be cutthroat, on the other hand; “I am going to work in your sales territory because I feel like it.”

I know one thing, at Southwestern, one of our strengths was that we were really competitive, but the downside of that was that sometimes people didn’t want to share information.  Like, “I have my sales secrets, here are my keys to success, and I do not want to share those with everyone in the group. I want to keep that to myself. Otherwise, they would also do well, and that would somehow take away the success from me.” That was not the best culture for collaboration.


Jamie: What is the biggest piece of advice you would give to an aspiring salesperson starting out their sales career?

Lee: Patience. Patience, young one. Patience, grasshopper.

I think I have seen so many people who would do well as entrepreneurs give up because either their ‘why’ was not as strong as it needed to be, or when it got tough they just said, “This is not for me. I am used to things going well for me. This sucks.”

I mean I always thought that working at Southwestern was not good for perfectionists, because there were so many variables in the equation. It is like a multi-variable calculus equation, and you can get a couple of those variables right, and then miss some of them, and not make the sale. Sales is tough, and therefore good for perfectionists, who like to have everything, every jot and tittle just so, to try. It does not work. It is good for them to feel some pain. A lot of those folks, students at University, who if they do not get all firsts are like, “Forget it. I am dropping that class.” Life is just not designed for that constant victory. I think you should practise being patient.

That is what we try to do at Southwestern. The one thing that made the training different than most sales organizations was we trained people emotionally for what was about to happen.

Most organizations, if you join them, they are like, “Here is a binder. It has everything you need. Memorize this. Here is what you say. Go forth. Call me with your statistics.” At Southwestern, we said, “Well, here is how you are going to feel. When this happens, here is how you might react. When this happens, here is what you need to tell yourself mentally.”

We were trying to give them tools of hope so that they would last a few weeks and then we could let them learn the ropes, so to speak.

Patience, I think, is the real key. Especially if you are new, you do not know what you are doing.


Jamie: If you had your career again, what would you do differently?

Lee: I just think it is all valuable. Even the mistakes, even the screw-ups, even the setbacks, and even when I treated people poorly. Even when I did not act properly, it all worked together to help me grow. There is a little passage in the Bible that says, “All things work together for good for those people who love God and are called according to His purpose.” What that means to someone of faith is that everything that happens to you, even the crappy stuff, even the mistakes, even the times you drop the ball or mistreated someone, in the long run, that can work together for good to help you grow.

If I had avoided some of the big blunders, I would not be the person I am. I certainly discovered during my first year in selling that I was pretty good at it. I could influence people quickly. I could get them to like me quickly. But you know what? I think all sales just boils down to thoughts. I had two thoughts. One thought that really helped me when I was really frustrated. I was sitting there, you know, and I did not want to talk to anyone else. I am sitting in the sun looking at the curb wishing I was home. I just thought, “Would my father be acting this way?” That had an instant effect. I got up and started working. That was a useful thought.

I had a thought later in the summer that completely derailed me right at the end. I had calculated how much more money I had made selling compared to what I had in my previous job. I thought, “I have made four times more money.” I was satisfied with my sales, and I just existed for the last couple of weeks. I felt terrible, but I did not know what to do. I could not motivate myself anymore. I’d made a ton of money. That thought derailed me.

I think if you really boil things down to what causes salespeople to win or not, it is what goes on in their mind. How do you control your thinking? I always said there are two categories of thoughts as you are working. There are useful thoughts, and there are useless thoughts.

The useless thoughts, for me, sounded like, “Why am I doing this? Why do people hate me so much or why do people not buy?” The answer I always came up with was bad, like when you ask a crappy question, you get a bad answer- you know, garbage in garbage out.

When I would ask a question like, “Why am I not working hard today?” My brain would always give me an answer. It is probably not true, but it would say, “Because you are lazy and you are not very good at this, and you should probably quit.” 

But useful thoughts were useful thoughts! When I was first learning the trade, someone said, “Five years from now, something about today is going to make me a better person.” I thought, “Wow. There is a purpose behind the calamity.” “Three years from now, I am going to appreciate today because it helped me to be a better husband.” That is a good thought. Or “I am going through this, and it is going to make me a better father to my children who I do not even have yet.” Useful thought. If people can control what they think about, they will win big.

But if I just click my mind on random thoughts, it’s right to Darth Vader, the dark side. Not useful.



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