Podcast #163: Leadership Lessons from Major Dick Winters

Brett McKay: Brett McKay here and welcome to another edition of the The Art of Manliness podcast. If you’ve read Band of Brothers or at least in the miniseries you are probably familiar with the name Major Dick Winters. He was a member of the Band of Brothers, Easy E Company, part of the airborne division that dropped in on Normandy on D-Day, as there at the Battle of the Bulge that captured Hitler’s Eagle’s Nest at the end of the war. All the Band of Brothers, we’ve written about several of them on the site before, all of them had something that set them apart from each other. They all had their unique talents. With Dick Winters the thing that probably set him apart from the other men in his company was his leadership ability. He displayed phenomenal leadership.

Today on the podcast we’re going to talk to someone who had a close friendship with Dick Winters in the latter part of his years, helped Dick write his personal memoirs of his wartime experience after The Band of Brothers series was released. His name is Colonel Kingseed. He is a retired colonel from the Army and he helped write Dick Winters’ memoirs, but after Dick Winters died a few years ago Colonel Kingseed wrote a book, put out a book called Conversations with Major Dick Winters just highlighting some of the conversations that he had with Dick about leadership, about character, about courage, about family, about friendship, about old age and just all these life lessons. This book, actually, was a big source in our article we did a few months ago called, The Way of the Mastic Warrior: Lessons from Dick Winters. I had to get him on to talk about. Great conversation. A lot of practical takeaways on how to be a better man in all aspects of your life, physical fitness, courage, your character, your leadership. Without further ado, Colonel Cole Kingseed and Conversations with Colonel Dick Winters.

Colonel Kingseed: Okay, well Dick Winters was the commander of an A-league airborne company in World War II. That company was Easy Company, second battalion, 506 parachute infantry regimen. Easy Company was the subject of Steven Ambrose’s best-selling book called Band of Brothers, and Band of Brothers later became an HBO miniseries, ten-part miniseries on World War II.

Brett McKay: It’s one of my favorite miniseries. I know a lot of people love that miniseries, that series of movies. Before we get to more about your relationship with Dick Winters, because it’s fantastic. It’s the subject of your book, Conversations with Dick Winters, let’s talk more about his actual involvement, specific actions he took or battles he was a part of as a commander of Easy Company.

Colonel Kingseed: He became the commander of Easy Company on D-Day. The company commander of Easy Company was shot down on a night drop and Dick was the second in command, so he fought on D-Day. A week later, staying in Normandy, they fought at the Battle of Carentan and they also participated in another airborne jump in Holland and then, of course, the most significant battle that Dick fought was the Battle of the Bulge where the 100 First Airborne Company was surrounded by several German divisions and at war’s end Dick’s company was responsible for the capture of Hitler’s Eagle’s Nest at Berchtesgaden.

Brett McKay: That’s all documented in the book and you can see that as well in the film, or the series, Band of Brothers. I’m curious. How did you meet Major Winters? Did you know who he was before you met him? How did that happen?

Colonel Kingseed: Very very interesting. Before I retired from the Army in 2001, I was the Chief of Military History at the United States Military Academy at West Point, New York. During that time, it happened to coincide with the 50th Anniversary of World War II. What I used to encourage my officers is to invite these veterans of World War II to talk to the cadets at West Point. I had one of my officers, in 1998, who came to my office and told me that he had invited Major Dick Winters of Band of Brothers to speak to the cadets. I had never heard of Dick Winters at that time. I had read Band of Brothers, but it had been years before, and the name just didn’t register for me. What happened is this officer invited me to join Major Winters for dinner, and it’s the only time I ever pulled rank with one of my other officers and I told him, I said, “I will gladly take that invitation,” but I wanted it to be just the two of us, and that’s really how it began. Our friendship evolved from that initial dinner meeting at the Hotel Thayer, right there at the United States Military Academy at West Point.

Brett McKay: We’ll talk more about this friendship because it’s one of the beautiful parts of the book, Conversations with Dick Winters, but that initial meeting lead to you helping him write his own memoirs of the war after the Band of Brothers book came out.

Colonel Kingseed: Well, no. You know what? I don’t think Dick was even thinking about doing his memoirs at the time. What really got Dick thinking about writing his memoirs … Now, remember, we’re talking about 1998. What really kind of encouraged him to do that is when the miniseries came out, Spielberg and Hanks, when that miniseries aired, and that was in September of 2001, I think it was as a result of that. The miniseries focused on Easy Company, the company that Dick commanded in World War II. Dick then decided that he wanted to share his memories as the leader of an A-league company. Dick didn’t even contemplate writing his memoirs until Thanksgiving of 2003.

Brett McKay: Let’s talk a bit about … One of the things that set Dick Winters apart from other soldiers and all the men who fought in World War II are fantastic, the Band of Brothers amazing, but he was set apart as he had just displayed incredible leadership ability. When did Winters begin, and this is something I always forget, too, when you read about Dick Winters, you watch the show on TV, is that these were young guys. He was 26 years old at the time, but he was displaying just phenomenal leadership, something you’d expect from a 30-year-old, a 40-year-old, who’s a seasoned veteran. When did Major Winters start displaying his leadership ability? Was it at training camp or was it something he nurtured along the way?

Colonel Kingseed: It’s very interesting Brett. You mentioned 26 years old. He was 26 years old at D-Day, but when he joined the Army he was just 23, the Dick Winters that you see in the Band of Brothers miniseries, the seasoned Dick Winters. He often reflected upon a couple of things in his youth when he was in elementary school and all of that, but I really think that Dick’s really refinement of leadership really came when he became a member of Easy Company and by this time he was a second lieutenant, so he was a commissioned officer. That’s the one. We’re talking about 1942, right when he joined this airborne unit. I think it was the mantle of command that provided Dick Winters the courage to succeed and to be a leader.

Brett McKay: I thought it was interesting, he mentioned this in several points throughout the book in your conversations with him, he pushed himself really hard during airborne training, the physical training aspect. The reason he said he did that, he said that physical fitness was an important part of leadership. Why did he think physical fitness was an important aspect of being a good leader?

Colonel Kingseed: Part of it was, remember the unit to which he was a part, Easy Company which is an airborne company. Airborne paratroopers have to have the ability to fight and to think on their own because they’re often very isolated. What Dick would end up saying is simply this, “Easy Company, airborne training made me. It brought out the very best of me.” He wanted to be part of the best. He knew that men’s lives were going to be based on the decisions that he made. He was a great athlete, very physically fit. What he ended up saying, “In times of crisis a leader has got to be mentally tough,” and he says, “Mentally tough has its foundation on physical toughness,” and that’s why in his quiet time he was a very reflective leader, but it allowed him, when he was running, that gave him time for the personal reflection. He knew that he needed that when the time would come for combat.

Brett McKay: Actually, your books inspired a post that we did called The Way of the Monastic Warrior, Taking Lessons from Dick Winters on Leadership. Before we get there, let’s talk about how did Major Winters define leadership? Did he think it was something that was innate in men or was it just a matter of being put in the position and you rose to the challenge or did he have a systematic way of developing it in himself and the men that he lead?

Colonel Kingseed: Dick always told me this. He said, “Leadership itself is very difficult to define.” He often quoted General Eisenhower. Eisenhower said this, “The one quality that can be developed by studious reflection and practice is the leadership of men.” Dick had a tough time defining leadership other than that. It was very easy for him to define a leader. He said that a leader is a person who has not only the ability but the willingness to achieve exceptional results through people, and that’s really kind of how he focused on leadership. Are leaders born or made? I think Dick would argue that he was given certain innate qualities, but the leader that Dick Winters became really was really based, as Eisenhower said, “It was an evolving process based on the studious reflection and practice.”

Brett McKay: One thing I was interested in that you highlight in both books was the daily practices and habits that he continued even in the midst of battle to, I guess, instill self discipline in himself to be a great leader. Can you talk about some of those habits and daily practices that he kept going? Even during The Battle of the Bulge he was doing these things to maintain his ability to lead.

Colonel Kingseed: What he would end up doing, prior to D-Day he would always get up in the morning. He was staying away from the men, very similar to what you discussed in that excellent article. He lived away, so I know we’ll talk about this. He lived a life apart from his men. Both in the morning and in the evening he would always take a 2-to-3-mile run whenever possible. During the war what he would end up doing, he would still get up in the morning. The very first thing he would do, he would always shave. Most of the times infantry men in war don’t shave. For Dick it was also part of that self discipline that he thought was absolutely required. He would still end up doing his push-ups, his sit-ups and whenever possible he would go on a run or a walk just to maintain his physical fitness.

Brett McKay: That’s amazing that he even did that during battle. Let’s talk a bit about the solitude aspect. I mean, the picture you pain in the book, Conversations with Dick Winters is that he didn’t have too many close friends during the war and not too many after the war until later in life, but that seems like it was a part of his plan or strategy to be an effective leader. How did his solitude or keeping apart from the group help him maintain his ability to be an effective leader.

Colonel Kingseed: He felt the loneliness was all part of his giving him time to personally reflect. What Dick told me many times, I think that maybe this is what kind of brought us together, we used to chuckle about this. He said, “I like to count my close friends on one hand.” Here’s the other thing that was so relevant. He goes, “I don’t want anyone to know me.” The reason he felt that way, he said if he had personal relationships that would cloud his judgement when times were tough. He didn’t want to end up doing it. He wanted his mind to be focused on the job at hand. He said, “If I develop too many friends or personal friends even outside the unit, that would cloud his judgement,” and he wanted to stay focused. He clearly understood that the lives of those paratroopers were based on decisions that he was going to make.

Brett McKay: This isn’t to say that he was really ice cold and aloof. He displayed great leadership. He balanced it with a bit of warmth, but with distance, I guess, would be the best way to describe it.

Colonel Kingseed: Yes. You know what, Brett, that’s exactly right. In the book on his memoirs, Beyond Band of Brothers, he gives you a wonderful balance prior to D-Day. He’s writing to a platonic friend, and we can talk about that later on if you desire. He says, “I want you to picture it is the spring in England.” This is a couple of months prior to D-Day and Easy Company is out on maneuvers in the English countryside. It is wet. He said, “It’s always raining in England in the spring. I want you to picture a paratrooper in a fox hole, cold and wet, and he looks to the east and he sees a figure approaching him.” Now Dick writes. He kind of says, “It’s me because I’m the only officer out that early in the morning. I go down on one knee and I ask the solider how he’s doing, and the paratrooper is shivering and he takes a picture of his girlfriend from his helmet and he says to Lieutenant Winters at this time,” this is prior to D-Day, “I want you to promise me that I will get a chance to see my girlfriend again.” Dick can’t do that but what he does do is he tells him, “I will do everything within my power to ensure that you get a chance to see her.”

The secret of Dick Winters’ leadership, the loneliness, is simply this Brett, Dick began the war as an enlisted solider and he never forgot where he came from. Dick used to refer to himself as a half breed. That was his words, an officer, yes, but an enlisted paratrooper at heart, and that balance is really what propelled him through the war.

Brett McKay: One thing Major Winters listed as an important aspect of becoming a good leader is the development of character. Can you tell us a little bit about the character of Major Winters?

Colonel Kingseed: You know what, Brett? He was a very complicated man. He was very difficult to know. Once he allowed you into his inner circle you could discern the essence of Dick Winters. He thought that character was really the very foundation of leadership. Character revolves around doing the right thing all the time. Character implies really daily choices and right over wrong. I would say this. When Dick would talk about character, because he always talked about character in war. He said, “War doesn’t alter character. War merely brings out the best that an individual has to offer.” The Dick Winters that I knew in the very latter stages of his life, that was the same Dick Winters that the public knew who watched Band of Brothers. It never changes. As I said, Dick was cognizant of his role as a result of the publicity of Band of Brothers, and his character never changed. He said, “War brings out sometimes the best and the worst in men.” Dick Winters brought out the very best.

Brett McKay: Yeah. You mentioned some actions there that I think reflected his character in spades. Even like after the war he went to the IRS to pay back taxes while he was gone. He didn’t have to do that, but he said he wanted to do it anyways.

Colonel Kingseed: In fact, when he went there the post master said, “You do not have to end up doing this.” He says, “Yes I do have to do it because I have an obligation to pay the taxes.” That tells me a lot about Dick Winters’ character. As I said, it revolved around doing the right thing all the time, not just when someone’s looking at you.

Brett McKay: What lessons can men today take from Major Winters on developing a solid character like he had?

Colonel Kingseed: I think his greatest legacy is to be true to yourself, never compromise your integrity and if you can look at yourself in the mirror at the end of the day and say you’ve done a good job, everything else will be okay.

Brett McKay: Here’s another aspect of his character that I thought was interesting because oftentimes we think of soldiers out at war. They carouse. They sort of let loose. They let go of their morals. It’s battles. What happens in war stays in war, but while he was preparing for the invasion of Normandy rather than going out on the town with all the men in his unit to paint the town red, Winters preferred to stay home and have quiet evenings with this English family with which he was lodging. I thought it was interesting, too, you talk about in the book that in the original Band of Brothers miniseries they had him swearing and sort of being like a typical soldier. What did Dick Winters do in response when he first saw that or heard about the amount of swearing that was happening in the movie?

Colonel Kingseed: Well, Tom Hanks had called him, and Dick Winters and Tom Hanks were very dear friends through that. After the production had been finished as far as filming, before it was viewed by the public, Tom Hanks called Dick Winters and he says, “What do you think about it?” Dick responded and said, “I don’t like it Tom. The man you have portraying me, Damon Lewis, is cursing and swearing and is very profane, and you know that I’m not like that, and I don’t want some young boy or girl to watch that and think that’s the type of character that I am.” Dick then followed up and says, “I want you to change it.” To his credit, Tom Hanks called the studio in London and said, “Dick’s displeased with it and I want that to be changed.” Dick said, “That’s what it is.” That’s what I’m talking about. His character never changes. Even with all the publicity and everything he was always true to himself. He wanted to make sure that he was setting the proper example. I think that’s part of his great legacy.

Brett McKay: Just wanting to be an example all the time.

Colonel Kingseed: All the time. That’s what I’m saying. It’s that character implies daily choices of right over wrong.

Brett McKay: We talked a little bit about this, touched on it a bit, but I want to go a little bit more into detail because he talks about it at length in the book. That is, one of the hardest thing about being a leader whether you’re in the military or in a business is keeping morale up amongst those you lead. It’s doubly difficult during battle, but Major Winters was able to do this. How was he able to keep morale up even during the Battle of the Bulge when it was freezing cold, constant shelling? What did he do to keep morale up amongst his troops?

Colonel Kingseed: Again, it goes back to being true to himself. Dick Winters, one of the reasons why he became such an effective leader and that even during the Battle of the Bulge, the individual paratroopers in Easy Company would always say long after the war, the best leader they ever met was Captain or Major Dick Winters, whatever he happened to be. The thing is simply this, Dick Winters lead through example rather than by rank or by fear. He always lead by example.

What Dick would end up doing, during the Battle of the Bulge, and Stephen Ambrose who wrote Band of Brothers said this, “Three or four days under artillery bombardment is hell. A week is worse than hell.” What Dick would end up doing, he said, “Know your soldiers so well that you can detect when they are about ready to crack under pressure. Then you have to pull them off the line. You need to understand what are the symptoms when a soldier has had enough.” I asked Dick about this. The first time I asked Dick about that I said, “You know what? Gosh darn it. Why didn’t you crack under pressure.” The very first time, before I knew him too well he said, “I’m Pennsylvania Dutch. I don’t break.” Well, okay. There were a lot of soldiers that did break.

Later on when I got to know him a little bit better he said, “You have to understand that the Battle of the Bulge, my command post was only 75 yards from the front line. You might not think that 75 yards is much distance, but it’s a tremendous amount of difference because you don’t have the individual observation from the enemy to where you are, so you need to then have to get up, get around, talk to the soldiers, just to convince them that things are going to be all right.” He said, a lot of times he demonstrates courage. He said, “Listen. Everybody is fearful in war.” He says, “Courage is not the absence of fear, but rather the willingness to rise above fear and to do the things that you know need to be accomplished, and that’s what he was doing.” He had the command presence and his willingness to share the hardships with the men, and that’s what inspired him.

Brett McKay: He lead from the front.

Colonel Kingseed: Always he lead from the front.

Brett McKay: Let’s go back to the friendship. I can understand why keeping a distance from his soldiers would help him be an effective leader, but you mentioned his platonic pen-pal. This was a gal that he met before going over to Europe and they were writing each other letters. The way you describe it, it seems like she wanted a bit more than just friendship, but Dick always, again, kept her at a distance for some reason. Why did he do that, even with personal relationships.

Colonel Kingseed: You know what? It’s very interesting. Her name, by the way, was Getta Almond. Dick and another one of the officers had met Getta and one of her friends really right around late 1941. The friendship evolved. It wasn’t a physical relationship at that time.

When Dick deploys to England and certainly in the last year of the war from the Battle of the Bulge to Berchtesgaden she definitely wants more of the relationship. Dick would tell me, he says, “I know you want me to say those three little words, but I don’t feel it.” He goes, “My family, my focus are the soldiers of Easy Company,” and he didn’t want to have any distractions. I read those letters, and I told Dick Winters, I said, “Dick I have to tell you, I’m reading your responses to this. I would dump you in a heartbeat on that.” He goes, “But you have to understand. My focus had to be on the welfare of my troops and I did not want to have any personal distractions that would take me away from what I knew had to be done.” Your article is excellent in the way the monastic war, you end up saying Dick had the ability to leap behind the maddening crowd, develop himself completely and to fight and lead in whatever kinds of battles he finds himself. They may not be in combat. That might be personal battles as well. Again, he had like a razor-like focus on what needed to be done.

Brett McKay: Yeah. He had a mission objective at any moment in life.

Colonel Kingseed: He understood that the decisions that he made would affect the lives of those soldiers. Commander has always been something, Brett … There’s a difference between a leader and a commander. You can become a leader based on the rank that you wear or anything else, the position that you hold, but the commander in war has to make individual decisions that affect the lives of individual soldiers. When I think about Dick Winters I don’t think of him as Dick Winters, the leader. I see him as Dick Winters, the commander who’s willing to go ahead and make those critical decisions that affect the lives of individual soldiers.

Brett McKay: He didn’t have too many friends during the war, not too many immediately after the war, but you were able to develop this really close friendship and bond with him. Can you tell us a little bit how that friendship developed and what it meant to you?

Colonel Kingseed: First of all, it evolved from the very beginning. Even from the military stance, I still remember him when he came out of the elevator at the Hotel Thayer for the initial dinner when he walked over there. I wore my uniform. Most times I would not do that for a social engagement on that, but there was some mutual respect because we both had worn the uniform. That respect and this evolving friendship transcended generations, and I think more sometimes after a couple generations it will transcend nationalities as well. I always said this, “From the military sense we were unequal in military rank, but we formed a perfect friendship because the friendship was based on trust and admiration. It was friendship free of competition or seeking advantage.” Having said that, it took five years before Dick felt comfortable enough to ask me to help him with his memoirs.

I guess the last thing that I would end up saying, Stephen Ambrose says this when he’s describing the relationship between Lewis and Clark, in Undaunted Courage, he said this, “The last friendship a man makes is often the best one.” I may not have been Dick Winters’ best friend. I don’t think I was. I think that honor goes to a man by the name of Bob Hoffman, but I do know this, that I was the last friendship that he made, and I think that’s the thing that really kind of … It was obviously based on a mutual respect with really common values.

Dick Winters’ wife Ethel Winters, said this, she asked me about this, she said, “Why do you think that I allow you to come here as often to talk to Dick?” I said, “Ethel, I don’t have the slightest idea,” and she said this, “You’re the only member of Dick’s circle of friends who has never asked him for anything. A lot of people bring books to sign or you want this or all this,” but she goes, “You never have.” I told that to Dick one time and he says, “You know what,” and I told him before he responded, I said, “There’s a lot of things up here in your office that I’d love to possess, your jug boots from D-Day and all this.” I said, “I would never ask for them.” I said, “What’s more, if you offered them I would never take it because I didn’t want to be beholden to him.” You know what he told me? He said this, “You have something else that no one else has.” I just smiled and said, “I know I do,” and that’s his friendship.” That’s really what it was based on.

If you remember in Conversations, I would like to go right there to the very end. The last time I saw Dick was October 2010. He died on January 2, 2011. The last thing I said to him, and I got very close to him, and I said, “Dick, the country was blessed to have had you in its hour of need, and I will always cherish our time together.” The last thing I told him was, “I love you as my brother.” His response, Brett, was simply this, “Don’t ever change that.” Those were the last words Dick Winters ever said to me. I take great pride in that. Someone asked me, they said, “Dick Winters, he’s like your father. It was kind of a father-son relationship.” I said, “No, no, no. It was a fraternal relationship,” and that’s what it was. Dick Winters was my brother.

Brett McKay: Wow. That’s very powerful. Let’s end on this, what do you think, you kind of alluded to it earlier, but what do you think Major Winters’ legacy is today? What’s his lasting legacy besides the things that he did over there in war? What do you think is his big legacy?

Colonel Kingseed: You know what? It wasn’t the war. It wasn’t the war. I asked him. I asked him direct on that. I said, “What is Dick Winters’ legacy to future generations?” I phrased the question in the third person. His answer simply was this, “That’s easy, and I’m going to answer it this way. It’s the same that I have been saying for many years. Hang tough.” That was his favorite saying. He goes, “By that I mean simply do your best everyday whether it’s school, at your job or anywhere else. You don’t have to have all the answers. There’s no way you should expect that from yourself. Just satisfy yourself so that at the end of the day you can look at yourself in the mirror and say, “Today I did my best.” If you do that, you are being honest and everything else will be okay.”

Brett McKay: That’s a great way to end. Hang tough. Colonel Kingseed, that you so much for your time. Thank you for writing the books. It’s been a pleasure.

Colonel Kingseed: The pleasure is mine, Brett. I take great pride in the association with what we call the greatest generation. I call it the GI generation. Their legacy, not just Dick Winters, but that whole generation, speaks to us today in the 21st century.

Brett McKay: I agree. Thank you Colonel Kingseed.

Colonel Kingseed: Thank you, Brett. Take care.

Brett McKay: My guest today was Colonel Cole Kingseed. He’s the author of the book, Conversations with Dick Winters. You can find that on Amazon.com and bookstores everywhere, a fantastic book. Go pick it up. Also, you can find out more about Colonel Kingseed’s work and leadership development. He has a program called, Battlefield Leadership where he and other people take corporations out and leaders out to battle fields in the US, Civil War battlefields and also to Normandy to show these leaders in the business field lessons they can take on leadership from military leaders in these very big battles. We’re talking Normandy. We’re talking Gettysburg, Antietam, Alamo, all sorts of great stuff. Check it out. BattlefieldLeadership.com.

Well, that wraps up another edition of Art of Manliness podcast. For more many tips and advice make sure to check out the Art of Manliness website at artofmanliness.com. If you enjoy the podcast I’d really appreciate it if you’d give us a review on iTunes or Stitcher and help us get more feedback on how to improve the show as well as get the word out about the podcast. Always appreciate your support and until next time this is Brett McKay telling you to stay manly.