Leadership Lessons from Major Dick Winters (Band of Brothers)

Leadership Lessons from Major Dick Winters (Band of Brothers)

This is a book report of sorts, not a review so much as a collection of thoughts from a book I just finished reading entitled Conversations with Major Dick Winters: Life Lessons from the Commander of Band of Brothers by Col.(ret.) Cole C. Kingseed. Kingseed helped write Winters’ memoirs called Beyond Band of Brothers.

Major Winters and Col. Kingseed became friends in the final years of the former’s life. Kingseed recollected and recorded conversations with Maj. Winters about leadership, courage, friendship,and character, among many other topics. The conversational style of the text makes it a comfortable, if somewhat artificial, read. No disrespect to Col. Kingseed or Maj. Winters on that effort, the ease of the read more the counters the slight artificiality.

A couple of passages really stood out regarding leadership and the qualities that help create strong leaders. Winters’ said,

“Self-discipline keeps you doing your job. Without it, you lose your pride and you forget the importance of self-respect in the eyes of your fellow men. Pride keeps you going on. This is what I feared I would lose — the loss of the will to measure up to my men.” pp. 75-76.

As small business owner myself, outside of client imposed deadlines, my entire work is the result of self-discipline. Some days, I admit, I have more than other days. I believe all small business owners must have more self-discipline than the average person to remain focused on the current task as well as the future.

Later in the text, Winters enumerated ten principles of success that he felt were his legacy:

  1. Character
  2. Competence
  3. Courage
  4. Leadership by example
  5. Physical fitness
  6. Succession readiness, which Winters described as “delegate responsibility to your subordinates and let them do their job.”
  7. Humility and self-reflection
  8. Ability to make calm, rational decisions under pressure
  9. Anticipate problems before they occur
  10. “Hang Tough!” was Winters’ standard sign off, to which he added, “Never, ever, give up.”


Small business owners, particularly those with a very small staff of one or two employees, rarely think of themselves as leaders. But I believe every owner is a leader. It takes courage to step out on one’s own and that is leadership by example.

This book tells more about Major Winters the man than it does about Major Winters the ware hero. I strongly recommend the book. I may have to buy the book rather than simply check it out from the public library….Amanzon Wish List it shall be.