Leading In and Out of Battle

I recently spoke to Col. John A. O’Grady (U.S. Army, Retired) about leadership lessons from his time inside and outside of the service. John played Division I at West Point, served in multiple staff assignments, commanded at every level from battery (150 people) through brigade level (3.5K people) culminating most recently with command of the 3rd Infantry Division Artillery (DIVARTY) and currently coaches high performing and high potential individuals, executives, coaches, players, teams and organizations. John’s awards and decorations include but are not limited to 2 x Bronze Stars, 2 x Legion of Merit, Defense Meritorious Service Medal, Meritorious Service Medal, Combat Action Badge and Parachutist Badge.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, set-backs, or challenges have been most instrumental to your growth?

John: Three fundamental things have got me to both where I am today and who I am today, and they are: My failures, my choices, and my relationships. If you look at any person and explore these three broad brush strokes, you can learn a great deal about them. I explore these buckets as a means of studying great leaders from all walks of life, chosen vocations or professions. It is an excellent exercise for your readers to use as they reflect on who they are and what got them to the here and now. So, the most significant failures would be my failed relationships, whether it be allowing a valued friend to slip into a distant space or my divorce and everything in between. My choices, so many in life but a watershed moment, was deciding to attend the United States Military Academy. The next one was made every day while there, and that was not to quit, to resolve to show up the next day. Relationships, because the best relationships require the qualities, I admire most that being, vulnerability, curiosity, faith, honesty, forgiveness and selflessness. 

Adam: What are the best lessons you learned from your experience in combat and experience leading troops in combat?

John: The best lesson I learned from my experience in combat and leading troops is two-fold. Pat one, no matter how good you are, and no matter how well prepared and trained you are, there will always be events outside your control – the enemy gets a vote. This fact becomes most evident in the darkest moments, sometimes a result of a loss of life. Part two, as a leader, you must do three things in this moment, first search for the opportunity and find it because one is present. Second, you must deftly balance the paradox that exists between optimism and harsh reality. The balance is between faith, things will get better, and with the responsibility as a leader to acknowledge and confront the harsh reality of the situation. Unfortunately, I had to do this in as a combat leader far too many times. Lastly, learn. Challenges, set-backs, hardships are all opportunities for learning, which begets growth and improvement. A guaranteed way to flip a negative experience into a positive is to learn from it, grow, and finally share that experience with those you lead.

Adam: In your experience, what are the defining qualities of an effective leader?

John: The defining qualities of an effective leader are the ability to influence people, humility, insatiable curiosity coupled with intellect, empathy, and the ability to create a psychologically safe space for those they lead by cultivating a culture of trust.

Adam: Who are the greatest leaders you have been around, and what have you learned from them?

John: The list is too long to enumerate. That said, the greatest leaders I have been around are those who made me better than I had I not met them. The single characteristic each one possessed was vision. I do not mean vision is the sense of a corporate vision statement. I am referring to the vision to see the full potential of someone, or some organization, before seeing it for themselves. I have been immensely blessed to be around great leaders my entire life. It started with my parents and brother, went on to sports coaches and teachers, then at West Point, and during a full military career. I have lived in a leadership lab my whole life, which is why I am passionate about sharing all those lessons and experiences with people in leadership positions now who perhaps have not been as fortunate. Here are few:

Mom and Dad – “there is no such thing as tough love, but we will love you tough.” What they believed and conveyed in this statement was, love is more than just a warm feeling. To love someone, you must be willing to hold them accountable as well. Additionally, they gifted me with an unrelenting faith that everything happens for a reason, and things always get better. Lastly, they gifted me with a sense to respect those less fortunate and be eternally grateful for all the blessings bestowed upon me. This sentiment is best summed up wonderfully in one of my Dad’s favorite sayings, “there but for the grace of God go I.”

My brother – looking out for the little guys matters. He always was, and still is, bigger than I am, so in this case, that works both metaphorically and literally.

Coaches (too many to list) – reflection and humility are required for growth. In the sports I played, we watched game tape, fairly and objectively evaluating performance against standards, learning, and resolving to improve. Micro-failures are stepping-stones to big wins. Today we refer to this concept as a growth mindset or infinite mindset.

Military Leaders – the best hands down for me was GEN (Ret) Martin Dempsey. I had the distinct honor to observe him both in and out of combat. I learned from him that leadership is as much about feeling as anything else. As a leader, no one should ever fear you because of your personality. Instead, you should inspire and motivate. They might be afraid you’ll hold them accountable when they do not meet the standard or behave in ways contrary to the values of the organization, but they should never fear you as a leader, as a person. That is an essential and nuanced distinction. If they fear you, then you are failing as a leader.

The Unnoticed Majority – these are the people who go unnoticed every day yet get up and simply do their best to contribute to society in whatever manner God and they see fit. Day in and day out, the perseverance of these heroes is remarkable to me. Whether it’s the trash collector, a custodian in a hospital, bus driver, or day worker, these people complete necessary tasks every day, which, if not completed, society as we know it and many of the comforts and conveniences we all enjoy would unravel. I hold them all in esteem as excellent examples of leadership, it is easy to see if you only stop a moment and look, really look.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

John: A commonality amongst the best leaders I have worked with and observed is that they routinely seek to multiply their experience. They recognize they do not know everything and try to know as much as they can. They multiply their knowledge by reading, seeking mentors, hiring a coach, participating in experiential leadership events such a taking themselves and their C-suite leaders to a historic location so they can draw parallels to their current context. In doing all these things, they accelerate their growth as a leader and prepare themselves to recognize threats and opportunities better, shift through complexity and lead in a manner far beyond what their personal experience might have otherwise allowed. 

Adam: How can leaders cultivate a culture of trust?

John: I will share the basic tenets of what I refer to as the “Trust Framework.” I have developed this is a practical tool anyone can use to cultivate trust within their organization and relationships. 

Recognizing that building and maintaining trust is continuous and evolving, the heart of the framework is “Trust Equation.” A simple-to-follow method that transforms trust from a feeling to something practical that we can get our arms around shows you how to set realistic expectations clearly and continuously measure those expectations against demonstrated behavior, all of which is the process by which trust is cultivated. Finally, I discuss the various directions in which trust flows so we can develop trust with intention instead of an ad hoc manner.

As a result, leaders create the ultimate sustainable competitive advantage that helps individuals, teams, and businesses better withstand hardship and adversity, enhance or save relationships, and attract and retain top talent and clientele, and helps individuals become both better leaders and teammates.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

John: Number one, resist if placed in, or feel like you are in, a binary moment. I have had to learn, and relearn, too many times, either based on my actions, or observing other leaders, that the decisions I most wish I could get a re-do on were those where I believed the choices available were binary. Always look for the space between. My good friend and accomplished musician, Freddie Ravel, shared a revelation he experienced while collaborating with renowned cellist, Yo-Yo Ma. Freddie revealed, it is not the notes themselves that are nearly as important as the space between the notes. So, entrepreneurs, executives, and civic leaders should always avoid binary situations and find the space between them. This space is likely where the most significant opportunity and best choice exists. 

Second, invest in developing your high-human skills and those of the people you lead. What do I mean by high-human skills? Simply they are the same skills that most other people refer to as soft-skills. I say this for several reasons. First, there is nothing soft about these skills; they can be both incredibly hard to develop and put into practice. Second, the fourth industrial revolution is the current and developing environment in which disruptive technologies and trends such as the Internet of Things (IoT), robotics, virtual reality (VR) and artificial intelligence (AI) are changing the way we live and work. In this environment, many of the hard-skills of successful businesses are supplanted by these technologies. However, these technologies have limited at best efficacy in replacing the high-human skills. So, those who are best at these skills will further differentiate themselves as leaders as well as their organizations. Lastly, leadership is, and the art of influencing people is a profoundly human endeavor. Those who are most adept at curating high-human skills and practicing them with those they lead are positioned to have the influence and impact that most elicits positive and healthy responses from those they lead. It also leads to higher employee and client engagement, satisfaction, retention, recruitment, conflict mitigation, and many more tangible benefits that directly affect the financial bottom line.

The third bit of advice is a Tom Pollack quote, “It’s never as good as it looks, and it’s never as bad as it seems.” As a leader having an emotional balance and awareness to keep this in mind will be of great value to deal with one of the paradoxes of leadership. It will help you relate to people with dignity and respect, exude a calming effect in moments of great difficulty and doubt, and serve as an inhibitor to complacency and laisse faire behavior and attitudes when things are going well.

Adam: What is your best advice on building, leading and managing teams?

John: Alignment of Vision, Mission, and Values is everything because it creates the environment, direction, and mandate for people to drive culture. I like to apply an aerodynamic metaphor when explaining the importance of this alignment to corporate executives. When engineers design cars or planes, they are seeking the highest degree of aerodynamic efficiency, attempting to reduce drag, or that which reduces the efficiency and effectiveness of the object. Well, think of your organization and your people within it for a moment as an object. Well-crafted and aligned vision, mission, and values produce the most aerodynamically efficient people and organization, the ones with the least drag on fulfilling potential, meeting objectives, and out-performing the competition.

Adam: What is the single best piece of advice you have ever received?

John: Listen to understand, rather than to respond and be right.

Adam: Is there anything else you would like to share?

John: Given that we are amid the COVID-19 pandemic, it is understandable for leaders to experience doubt, despair, perhaps even fear, and so on. I would simply say, stay confident in crisis. In many cases today, the leader’s confidence is shaken, and the same is true of the people they lead. I would simply remind them that they would not be where they are today had they not already survived and thrived after the previous worst day or period of their lives. They overcame that time in their life, and so too will navigate their way through this period. Stay confident in crisis.