3 Leadership Characteristics of My Mentor, Col Dick O’Grady

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By Lee Ellis

What value would you place on your most treasured mentor leader? It could be a parent, teacher, coach, or any adult that made a significant impact. How did they dramatically help change the trajectory of your career and achievements?

In the last six weeks, I’ve attended services for two remarkable Air Force leaders who have flown west. They were a half-generation older than I. Each served as my boss twice and both were my close friends for more than 40 years. They were crucial mentors who had a profound influence on me as a person and as a developing leader, so these losses have caused me to reflect on their impact on me (and many others) and the role that mentors play in our lives.

Character First  

After analyzing the lives of these two heroic leaders, I can see how they had very similar characteristics that made them so compelling. Most of all, they had great character and integrity—they led with honor. In this blog, let’s look at Col. Richard E. “Dick” O’Grady, and next month we’ll reflect on Col. Don Ellis.

The Early Days

Change of command when I succeeded Dick O’Grady as commander of the 560th Flying Squadron at Randolph AFB.

Freedom Flyers Reunion at the 560th FTS.

I met Col. Dick O’Grady professionally when we flew out of the same squadron back in the late 70s. It was at that time that I also got to know him personally when we headed north from San Antonio for a four-day pheasant hunting trip back to his family home, a farm in southern Iowa.  That was the first of many hunting and fishing trips we shared over the next 40 years.

It was our common values that was my first and sustaining attraction for Dick O’Grady. He lived his values consistently and I wanted to be that kind of person.

If you have read Leading with Honor, you may recall that I refer to some of the important lessons I learned from him as “O’Gradyisms.”

Let’s look at three fundamental (and somewhat paradoxical) characteristics of this amazing leader –

  1. Courageous, confident, and humble. Courage is fundamental to all character and leadership attributes. Without it we cannot keep our commitments—our doubts and fears will take us out. Dick was determined to live by the standards he promoted and that’s never easy. All humans have doubts and fears, but I never saw them in him. It seemed that his clarity about his values and standards gave him courage. His commitment was such that he just buckled up and marched into the fire with confidence that doing the right thing would take him where he was supposed to go. If he needed to confront a junior, he did it with firmness and grace. If he needed to confront a superior, he did it with respect and diplomacy. But in either case, he did not turn his head and let things slide without addressing them. His inner confidence and courage enabled him to be humble and strong and those quite often don’t go together.


  1. Optimistic and realistic. Dick O’Grady was a naturally upbeat, fun-loving extrovert, and his positive energy lifted everyone around him. He greeted others with a big smile and a warm welcome as if they were the most important person in the world. He was outgoing, but his extroversion was focused and purposeful—to lift up others, not himself. He certainly believed in himself (which is an essential quality of leadership), but it was clear that he believed in our purpose and mission, and equally he believed in others. The attitude and emotions of a leader cast either sunlight or shadows over the people around them. It was always bright, exciting and fun to be with this leader.

Paradoxically, he was also an extremely detailed planner. At the beginning of every day, he considered the mission, project, or challenge and planned the steps. I believe that knowing the way ahead helped sustain his positive expectations about success.


  1. Caring and confronting. Dick cared about his people. He was intentional about getting to know them, and he knew the name of every spouse in the unit and names of most of the kids. He knew who was hurting and made sure they were encouraged and supported. He communicated to his people in ways small and large that he believed in them and their potential.

But when someone was out of step, he did not hesitate to call them aside and give correction. This red-headed Irishman was direct and clear—he let you know quickly what the issue was and how to get back on track.

So this boss, mentor, and dear friend consistently evidenced another magnificent paradox of leadership behavior; he was both caring and confronting.

In some ways he was round and smooth, but when it was needed, he quickly clarified that square corners needed to be square. Beneath it all was a deep caring for others.

Col O’Grady’s Legacy

The legacy and memories of this great leader still inspire me. He was not perfect—none of us are—but his example reminds me that I’ve still got some room to grow. How about you? Who are your mentors? Are you still growing? And, who are you mentoring today?

Stop and reflect on the people in your domain that are watching you to see how you act, behave, and respond. I can tell you that if you model integrity of character, courage, optimism, and you can be both caring and tough, you will be an inspiration and create a legacy like my friend Col. Dick O’Grady. And like him when you fly west, you will leave a great legacy of leadership.


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Related Resources: Leading with Honor: Leadership Lessons from the Hanoi Hilton

Dick O’Grady Obituary:

Col Richard “Dick” Eugene O’Grady USAF (Ret) (1937-2018)

Richard Eugene O’Grady, age 80, of Grand River, Iowa, the son of Stephen Eugene and Dorothy Elaine (Fletcher) O’Grady, was born December 2, 1937, in Waterloo, Iowa. He passed away on Sunday, July 15, 2018.

When Dick was young, his family moved to a farm north of Grand River, Iowa. He attended country school and graduated from Grand River High School in 1956. Upon graduating, he attended Drake University in Des Moines. On July 25, 1958, Dick O’Grady and Rosalie Harger were united in marriage in Des Moines. They were blessed with four children, Steven, Michael, Douglas, and Kathleen. Following college graduation in 1960, he joined the United States Air Force and served 29 years. He completed Squadron Officer School in 1968, and IND College of Armed Forces in 1972. His military career included two tours in Vietnam and service on Okinawa. A few of his major assignments were Commander of the 560th Flying Training Squadron in San Antonio, Texas, Commandant of Squadron Officer School in Montgomery, Alabama, Vice Commander of Tech Training School in Biloxi, Mississippi, and Chief of Standardization Evaluation in San Antonio. He retired in 1989, as Assistant Deputy Commander of Operations at Randolph Air Force Base in San Antonio. His awards of accommodation include Legion of Merit with oak leaf cluster, Bronze Star, Air Medal, Meritorious Service Medal with two oak leaf clusters, AF Organization Excellence Award, and others.

Dick and his wife, Rosalie

After military retirement, Dick worked for EG&G in Las Vegas, Nevada, flying Boeing 737’s for 15 years. He and Rosalie spent several years between their home in Boulder City, Nevada and the farm north of Grand River. In 2004, they built a house north of Grand River and made it their full-time home.

During his free time Dick enjoyed hunting and fishing. Additionally, he loved spending time with his grandchildren, projects on the farm, community service, and traveling. He was an active member of St. Andrew’s Catholic Church in Boulder City, Nevada and St. Patrick’s Catholic Church in Grand River, Iowa. He served in the Grand River American Legion and was on the board of directors for the Grand River Community Center for five years.

Dick was a loving and committed husband, father, grandfather, and friend who will be deeply missed. He never knew a stranger and was dedicated to building relationships with others. His kind and hardworking character added greatly to the legacy that will continue in the hearts of his children, grandchildren and friends.

Preceding him in death were his parents, Eugene and Dorothy O’Grady, and sons, Douglas and Michael O’Grady. Survivors include his wife, Rosalie O’Grady; children, Steve (Lauralee) O’Grady, Kathy (Steve) Ralph; daughters-in-law, Cindy (George) Holmes and Kathryn O’Grady; grandchildren, Rowdy (Nicole) O’Grady, Michaela O’Grady, Julie (Patrick) Youells, Justin O’Grady, Gage and Savannah O’Grady, Megan and Rachael Watkins; great grandson, Hoyt Michael O’Grady; brother, Jim (Karen) O’Grady, three nieces and nephews, other relatives, and many, many friends.

Funeral services were held at St. Patrick’s Catholic Church in Grand River, Iowa at 10:30 a.m. Thursday, July 19, 2018, with Father David Polich officiating. Burial was in the Grand River Cemetery, Grand River, Iowa. A visitation with a time for Memory Sharing was held at the Slade – O’Donnell Funeral Home on Wednesday evening.

Memorials may be given to the Grand River Community Center in Dick’s memory.



6 Comments on “3 Leadership Characteristics of My Mentor, Col Dick O’Grady

Steve O'Grady
August 27, 2018 at 1:29 pm

Godspeed Dick from the U. S. Navy

Robert Reih
October 26, 2019 at 4:45 pm

Steve, if Dick your dad then I can only say my sincere condolences. What a fine man your dad was. Flying and helping others was his passion. He made all of us feel that we made a difference and we only wanted to do better because of him, our mentor. I can still hear his command voice encouraging me, guiding me in my quest to do the best that I could. And everyone that knew your dad couldn’t say enough good things about him. He was a terrific guy. And your mom too just opened her home to me at Laughlin AFB back in 1975. Please express my thanks to your family for me…

Robert Reish

Anna Areyano
September 17, 2018 at 6:27 pm

I had the honor and privilege of working with Dick O Grady at EG&G for a few years. He was the kindest and most approachable person in command there! He will be missed by all who worked with him and for him..I salute him and thank him for being my friend!!.

Kevin Light
September 18, 2018 at 10:16 am

Anna – thanks for sharing your kind words about Col O’Grady. I know it was a privilege to know him in person. Kevin from the Leading with Honor team

Robert Reish
February 13, 2019 at 3:01 am

Then Major O’Grady, he was my Flight Instructor in the T-38 at Laughlin AFB, Del Rio, Texas. What a fine man, friend, and teacher. I thought of him often but was never able to track him down. His wife was such a wonderful person too both opening their home to me back in 1975. He was so positive and always encouraging me in every way. Because of his help I graduated top of my class, 75-06. I eventually ended up as a Captain flying the Boeing 777 for American Airlines and then carried Dick’s positive attitude with me always. Thank you Colonel O’Grady for your friendship and positive Spirit. You are missed… Robert Reish

Kevin Light
February 13, 2019 at 8:28 am

Robert – thank you for sharing your personal tribute about Col O’Grady–what a great legacy that he has left with so many leaders. We’ll also make sure that Col Ellis sees your comments, too. Kevin @ Leading with Honor


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