Adam: Thanks again for taking the time to share your thoughts on leadership. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?
Jack: I actually like to cook. I started about 20 years ago as a diversion from work, and began experimenting with a range of meals and desserts. My professional accomplishments in the military and my areas of expertise in life are limited, but in the world of grilled cheese I am a giant.
Adam: How did you get here? What experiences have been most instrumental to your growth as a leader?
Jack: I’ve known charismatic and innately talented leaders who have a commanding presence. But that’s not me. I’m fairly introverted and not a dynamic public speaker. I’ve learned that you basically start with who you are and, learning from other examples, work on developing traits that help you become as effective as possible.
I have also had a number of mentors who shaped how I operate as a leader. Some were peers, some were bosses, and some were subordinates. Perhaps the best was my first platoon sergeant. I was a new lieutenant just out of West Point and in subtle but thoughtful ways he helped me understand leadership in the real world.
Adam: What failures, setbacks or challenges have been most impactful in developing your leadership skills?
Jack: I could probably spend much of this interview describing mistakes or dumb things I have done over the years, from my days as a lieutenant to time as a general officer. Some notable and some not.
What was critical for me was to assess what I did wrong. From these experiences I took four things. First, I learned that significant efforts need to be collaborative efforts, and success is usually driven by building consensus as opposed to telling people what to do. Second, you need to stay focused on the essential and not get sidetracked. Third, you need to pursue a good solution, not working forever on a perfect solution. And forth, you need to be comfortable with who you are, knowing your strengths and weaknesses. Without exception, every time I failed in an effort I failed to follow these fundamental concepts.
Adam: In your experience, what are the defining qualities of an effective leader?
Jack: From my perspective there is one essential quality. There’s a difference between being in charge based on holding a certain position of authority, and leading an organization based on the trust and confidence that you’ve earned from your subordinates. An effective leader is able to establish this trust and confidence.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Jack: I think this goes back to looking at examples of leaders that you see on a daily basis and determining which traits might be effective for you. And thoughtfully using successes and failures to learn to be more effective.
Adam: What is the best advice you have on building, managing and leading teams?
Jack: Two points. First, you need to make sure that the effort is inclusive and everyone’s input and participation is valued. Part of this is recognizing that the best ideas and the best work may come from the most unlikely source. And second, you need to build a consensus to sustain the program over the long-term.
Adam: What are three leadership lessons from your time in the service that are applicable to a broad audience of leaders?
Jack: First, most people aren’t born natural leaders, but you can learn over time to be an effective leader. Second, part of being confident is actually knowing your business – being an expert. This requires a fair amount of lifelong self-study. And third, even though you can learn and evolve your leadership style over time, you ultimately need to be yourself. Trying to be something that you aren’t simply doesn’t work.
Adam: Who are the greatest leaders you have been around and why do you admire them? What did you learn from them?
Jack: I was fortunate to work with some really talented leaders at different ranks in the military. Since departing the service I’ve also been fortunate to interact with a number of talented civilian leaders such as school superintendents, midsize business owners, directors of nonprofits, and CEOs of small start-ups. Observing them reinforced my views on what constitutes a great leader.
Perhaps the best leader I have been around was a command sergeant major I knew as a lieutenant colonel. He clearly had the trust and confidence of everyone. His mere presence generated confidence. He also was comfortable operating in all environments, from assessing long-term strategic actions to leading troops in the field.
Adam: What is the biggest misconception people have about the military, the Army and military leaders?
Jack: When discussing the military and leadership most people tend to think about generals and admirals because they are most visible. But in reality the central strength of our military since the Civil War has been effective leadership and initiative at low levels. To this day it still differentiates our military from the rest of the world.
Adam: What do you believe are the three most important issues facing the country and the world? Are you optimistic about our ability to address them?
Jack: From my perspective the single greatest challenge the nation faces right now is our inability to collaborate on critical strategic issues. Issues that will affect the nation through the rest of this century. We need to regain the ability to have a reasonable open discussion and then decide on a course of action that most of the country can support.
Each of us would no doubt define “strategic issues” differently. To me there are three. First, we need to determine how to fund the future and meet the competing requirements of supporting an aging population, resourcing health care, investing in the future, and securing the nation. We have avoided this frank conversation for several decades.
Second, we need to redefine our role in the world and achieve some level of consensus in our foreign policy. We did this after WWII and, although the system had faults, our efforts prevented another world war and drove massive worldwide economic growth. But the world has changed. Working with our allies that actually share our values, we need to update our priorities and institutions.
And third, in a period of rapid technological and economic change that is driving what skills receive good wages, we need to find systemic ways to advance living wage America. Especially in the interdependent areas of employment, access to housing, and access to healthcare. This will prove to be the biggest domestic challenge of the next half century.
I’m actually optimistic that we can do all this. We increasingly possess the ability to creatively think our way through problems, and we still possess incredible advantages over the rest of the world. The best analogy I can think of is the 2012 US men’s Olympic basketball team. With LeBron James, Kobe Bryant, and Kevin Durant the team had every advantage the minute they walked on the court. All they needed to do to win the gold was to cooperate.
The United States is much like that basketball team. With our resources and advantages we can do remarkable things when we work as a team and focus on agreed upon challenges. But in our current divisive environment it’s as though Lebron and Kobe Bryant are refusing to pass the ball to each other. We just need to regain the ability to collaborate in essential areas.
Adam: What is the single best piece of advice you have ever received?
Jack: “Draw from your past – do not let your past draw from you.” We all learn from past experiences and they shape how we see the future. But you can’t allow negative experiences to constrain your future actions… they should inform your decisions and activities, but not hinder them.
Adam: What is one thing everyone should be doing to pay it forward?
Jack: This question gets back to my previous comment about collaborating on strategic issues. If we want to pay it forward I think that we all need to take a step back from TV news and social media and consider how we can collaborate to make our system of governance work. We owe this to a specific group of folks.
Most Americans are familiar with the Civil War battle of Gettysburg. Success at Gettysburg was central to the North winning the war and our survival as a democracy. And like most major events the outcome turned on a number of smaller actions, many of which are simply lost in history.
One small action occurred on the first day of the battle as Union and Confederate forces were fighting for the hilltops and ridges that might provide a tactical advantage. Late afternoon things started to look bleak for the north. A number of units were being overwhelmed and soldiers started to panic. In this chaotic environment, Charles Tilden, the commander of the 16th Maine Regiment, was ordered to hold a specific hill at all costs. His regiment needed to delay the Confederate forces long enough for several Union brigades to pull back and get organized.
Tilden, an extremely capable commander, understood the urgency of the moment. He quickly positioned his men on the best terrain and, facing overwhelming Confederate forces, they held out for about 20 minutes. At the end of that 20 minutes only 40 of the regiment’s 275 soldiers remained. The rest had been killed, wounded or captured. But this 20 minutes bought enough time for several other Union units to pull back and get organized, and as we all know the North went on to win the battle.
Most Americans have probably never heard of Charles Tilden and certainly wouldn’t recognize his face or the faces of the men he led at Gettysburg. But in a span of less than 20 minutes and in an area about the size of a football field they quite possibly saved the United States. At great cost.
When I watch the news on TV these days with the seemingly endless shouting matches I can’t help but think that we should be better than this. From Gettysburg to Iraq and Afghanistan, too many men and women have sacrificed too much to allow our political discourse to sink to these depths. If we want to pay it forward I think all Americans, and especially those elected at the national level, need to find ways to collaborate in essential areas. This would require having open conversations and occasionally compromising in a way that’s not ideologically optimal. It may also require forming temporary coalitions of like-minded individuals to address very specific challenges.
On a fundamental level I think we owe this to the 16th Maine and all the men and women throughout our history who have sacrificed much to allow us to control our own destiny.
Adam: What are your hobbies and how have they shaped you as a leader?
Jack: I’ve been interested in Roman history since I was a kid and have visited a number of Roman sites throughout Europe, the Levant and North Africa. The long history of Rome provides countless examples of good and bad leadership, both in the military and in public life.
I’m also an avid sports fan. I think sports highlights the mental aspect of success. The mental aspect of establishing and sustaining a high performing organization. We’ve all seen teams that are invincible at one point in the season but later struggle to compete. To me this illustrates the need for a leader to help build and sustain a culture of winning. An expectation of success. There are a lot of examples out there but I believe that Bill Belichick and Steph Curry are two great ones.
Adam: Is there anything else you would like to share?
Jack: Since the focus of this interview is on leadership I’d like to provide an additional observation on my take on the US leadership role in the world. To paraphrase the journalist Eric Sevareid, I believe that we need to serve as the source of material strength and moral force that men and women of goodwill can recognize and follow. If we don’t, someone else will fill the void.
I was fortunate in the military to see much of the world. And much of the world wants us to perform this role. Even with some of the horrendous mistakes, we have made our basic values resonate. I’ve been in villages and cities in multiple regions where our fundamental beliefs and values are seen as aspirational.
A couple specific incidents highlighted part of this to me. While stationed in Germany I met an elderly woman whose first husband was killed on the Russian front during WWII. Recognizing that Germany was losing the war, in his last letter he instructed her to find where the American army was operating and to take their kids there. They would be safe with the Americans. He had never been to the US but trusted us with what he valued most – his family.
While serving in Iraq I had several conversations that reinforced my view of the US. In a conversation with Tariq Aziz, Saddam Hussein’s former Deputy Prime Minister, he commented that he had surrendered to the US Army and not the Iraqis because our justice system was fair and honest. In a conversation with Saddam Hussein, while he was on one of his hunger strikes and in our hospital, he grudgingly acknowledged that we treated him better than his regime treated prisoners. I think it’s interesting to note that two totalitarian figures valued several attributes of an open democratic society.
As Americans I think we underestimate the power of the moral high ground.