Leadership, Values, and Becoming Friends with Uncomfortable

Gerald Carter
10 min readNov 8, 2018

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“Our life tells its own story whether it is the story we want it to tell or not.”

Many events shape us, like a river that smooths a stone, but there are a few that set the direction for our life, as though we are moved from one part of the earth to another, sometimes gradually and sometimes violently. I was an only child and, I suspect like most only children, was surrounded by books, stuffed animals, and imaginary friends. One of my earliest school time memories, sometime around 3rd-grade, is being handed a math book and the opportunity to work through it at my own pace, all while sitting at a desk in the hallway outside of the class. I was alone in the cinderblock hallway sitting at a one-person metal desk focused intently on numbers with pencil in hand as only a 3rd-grader can, but I was happy. I completed the book in a much shorter amount of time than the curriculum allotted. I can’t entirely remember, but I think I was handed another book, this time full of 4th-grade material and began working my way through just as before.

For many years to come, my identity was defined by achievement. Coursework was nice, neat, and had a clear finish line I could race towards. Looking back I can see that the danger with rapid advancement is that you are likely to become addicted to it. In its absence, you begin to question your self-worth or even the organization’s competence to identify the right talent. I think that existing too much in such a highly structured environment can promote a “permission mentality” meaning that you grow accustomed to the comfort of knowing what the rules are, excelling at winning within the rules, but never being willing to go outside of the rules even when the situation requires you to color outside of the lines.

Achievement addiction can be illustrated with a simple example from my own life, one that I still cringe to recount. Sometime around mid-way through my 8th-grade year, one of my classmates, a girl that we’ll call Lisa, beat me out of an award for the highest academic average for the semester. My identity had been threatened, and I reacted badly. I remember telling her, in a fairly demeaning tone, that the only reason she won was that our band director didn’t give numeric grades. My “A” was normalized to a “95”, and that is what carried down my average. At the time, I’m sure that I believed I was being honest and stating the facts. In retrospect, I was mean-spirited but didn’t realize it. While she may not remember, it’s a memory that reminds me to support the achievements of others and celebrate their success as well as my own. Some things are important, and some things are not. Treating people with respect matters more than being recognized. Are you in it for yourself? Or are you in it for your team?

For close to twenty years I have worked remotely from a small rural town in Alabama. We have two traffic lights, and the nearest Starbucks (and Dunkin’ Donuts and Krispy Kreme) is thirty-five miles away. In high school, I had two close relationships. I remember thanking both of them during my valediction speech almost 30 years ago. Today, I am married to one of them, and continue to work with the other here at Dell. Other than my parents, my wife and my childhood best friend are the two constant relationships I cling to.

My wife and I met during high school in the town where we still live, and we recently celebrated our twenty-fifth wedding anniversary with our first trip to Ireland. She has a large extended family that I have come to love and appreciate. It’s not uncommon for fifty people to show up on the Fourth of July at my sister-in-law’s house for a good meal and a fun day at the lake. They have taught me how to laugh at myself rather than hide in embarrassment when I make a mistake, to remember to care for people you don’t always see, and how large families fit together by staying involved in each other’s lives. We don’t always interact with everyone in our organizations regularly, but it doesn’t mean that we should not acknowledge and support them.

My exit from academics into industry began on the west coast in 2000. VA Linux Systems, the first Linux OEM company, and creator of SourceForge had recently completed its IPO and was in a period of hyper-growth. I had been working in open source on the Samba project for a few years and had a friend that invited me to interview. I made my first trek to San Jose, CA, and they offered me a position in their professional services organization. Joining VA Linux was an overwhelming adventure. There were some great people, but it was a company trying to live up to the hype, and I was extremely green. It was the first time I had been confronted with a broad diversity in thought and opinion.

The people were amiable, but I was insecure. So much so that I stopped introducing myself as a resident of Alabama. I was trying to distinguish myself, and I believed that being from Alabama was not the type of recognition that I wanted. I was not prepared for my identity, my beliefs, or my way of life to be challenged, even in a non-confrontational manner. Looking back, I do not believe my perceptions were accurate and that people were more supportive than I remember. However, insecurity can taint our memories and even the best of intentions.

Earlier in my life during my teenage years, I had developed a deeply personal sense of faith, one that was shared with my closest friends. While I never wavered in those beliefs, sometimes they felt more comfortable to express than at other times. In my community at home, it was not a simple task to explain my job or career. Rather it was easier to tell people that I just worked in software which usually resulted in a nod and a shrug. Politically, I found myself living in a red state while working in a blue state. I was surrounded by diversity but felt more threatened than comforted. For a very long time, it felt like parts of me fit in different places but that they rarely come together in a common role.

The result was a fragmented worldview and a set of multiple “Jerry’s” each coming to play depending on the event. At my core, I was true to my values, but “Values are the stories we tell ourselves. Character [or culture] is the stories others tell about us.” By compartmentalizing myself, I had created a weaker version of myself. What I know now is that

Though one may be overpowered, two can defend themselves. A cord of three strands is not quickly broken.” (Ecclesiastes 4:12)

In his book “Authentic Leadership: Rediscovering the Secrets to Creating Lasting Value”, Bill George, former CEO of Medtronic, writes

“Being authentic is not just something you are at work. It must be reflected in all aspects of your life. Unfortunately, the pressures of society and work life often cause us to behave differently in the various aspects of life-work, family, social, spiritual. As a result, we wind up compartmentalizing our lives.”

This was the first time I had experienced a C-level leader express the same challenge and conflict that I felt internally. It was the first moment I could put a name to my enemy — myself. Of all the obstacles I faced to become a leader who could inspire greatness in others, I was the one getting in my way the most. I failed to leverage every aspect of my experience, my personality, my spirituality, my purpose, my rationality, and my compassion when I come to work. I had failed to be authentic.

I will freely admit that my intuition is a much better fit for logical problems than emotional ones. People, myself included, are a fascinating puzzle to me. I prefer to maintain a tight circle of deep relationships with a few important people in my life. My wife is at the center of that circle and fortunately for me, has a deep value for people. She was able to help bring equilibrium to my principled dogma. It is something very special to be loved not for your achievements, but for who you are. She taught me that paying attention to the details in a person’s life are important. She demonstrated that love and respect are about honoring those details and showing people that you see them. She taught me to look outward rather than inward. She continues to teach me to this day.

My structured brain, however, still needed a language to be able to describe what I felt and what I observed in other people. Why did one person react badly under stress while another seemed unfazed? Why was I able to explain my ideas to one person in an elevator ride, and fail miserably in yelling match with another over the same topic? How do you interpret social cues? My leadership journey has been as much about understanding myself as it has been about understanding my teams and organizations. I was fairly inept early in my career. I remember embarrassing interactions with other managers unable to keep my cool with someone that just “couldn’t get it.”

Enlightenment often comes from the most unexpected places or experiences. My father has been involved in criminal justice for all of my life. I remember playing with his fingerprint kit in during classes while he taught at Troy State University as white dust covered my hands. I remember playing with the government issued red police light that sat in his car when he worked for the ATF. And I remember being hooked up the polygraph as he learned to read the charts while guessing which card I had picked up from a deck at random. As part of his interviewing research, he came across the idea of personality preferences, and he was the one that introduced me to the Meyers-Briggs Type Indicator (MBTI). This framing, while not perfect or necessarily exact, began my journey down the rabbit hole of cognitive, behavioral, and organizational psychology. We often need a different language to be able to talk about intrinsic motivations, values, and decision making. People can still be a mystery, but their reactions are less confounding when viewed through patterns of behavior. If anything, understanding tools such as this one allowed me to become much more pliable when dealing with and managing individuals.

In mid-2011, after having just stepped into my first executive leadership role as the CTO in a small start-up, our CEO sat me down for a 1:1. At this point, Barry and I were probably the longest employed people in the company having both joined sometime during 2005. I remember being in his office, both of us sitting at a small, round conference table, the kind that looked like it was delivered from Office Depot, when he gave me three pieces of advice. “First,” he said “build your executive presence. Second, learn to succeed through others. And finally, net it out.” My coach at the time, in a separate conversation, laughed a little and also agreed that I could benefit from some brevity.

In the spirit of ”netting it out,”

I believe that information is the most valuable asset that one person can give to another, followed closely by understanding. And that “Teaching is the highest form of understanding.” (Aristotle)

I believe in servant leadership, sometimes to a fault. So much so that I continue to struggle with delegation because of a deep belief in self-reliance.

I believe in playing the long game — build the world today that you want to live in tomorrow.

I believe in the value of and the best intent of people — a lesson I continue to learn through the patience guidance from my wife. I strive for building an organization where a person can be the best version of themselves, both personally and professionally, proud of what he or she has accomplished in collaboration with their peers.

I believe in systems — with all of their flows, stocks, and feedback loops.

I believe in the ability to improve — whether for an individual or an organization — if the motivation is present. And that continual improvement can only be sustained through a deep sense of purpose.

Finally, I believe in you — the people here in the room today. I believe that you belong here. And I believe that this opportunity will be what you, and I, make of it.

Every one of these points begins with “I believe”. It is a statement of value. The statements “I believe in” and “I value” are interchangeable. Our values must become verbs. I cannot say that I value patience unless I am willing to practice patience. Values must be encoded into daily practice. If I state that I believe in servant-leadership, I must decide each day how I will put that into effect and then act upon my decision. Once a practice is performed enough, it will become a habit. The collection of values that have become habits, the things that you do even though no one is watching but yourself, define your character. For a group of people, these organizational habits will define its culture. Values are embodied by a practice which becomes a habit which determines character. Remember that “Values are the stories we tell ourselves. Culture is the stories people tell about us.” Live your life to inspire stories told by others.

You should expect that a person, myself included, maintains alignment between their daily practices and their espoused values. You should expect that your growth and success is important to me. You should expect that I give you honest feedback in an effort to help you avoid blind spots and grow. You should expect that I believe the best in you, of you, and from you. And I will expect these very same things from you.

Stephen Covey says that “We judge ourselves by our intentions. We judge others by their behavior.” When I complete my journey, the story I want others to tell about me is simply this.

“Here is a man who was fortunate enough to have true friends and a truer family, and was able to contribute in part to their fullness of life.”

In closing, I will share these thoughts. Learn by imitating the greatness around you, but never become an imitation. We need more authentic leaders. Never become comfortable with being comfortable. Become friends with uncomfortable. Surround yourself with people who are more than you — more talented, more experienced, more compassionate, more honest — so that you can “be more” and “be better.” And know that your team wants you to succeed so never be afraid to lean on them. If you cannot, you have the wrong team.

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