Introduction
Over my career and certainly during my time as a CISO, I’ve come to value the importance of authentic, purpose-driven leadership. These days I spend just as much time thinking about how I can improve my leadership skills to better serve those around me as I do on the functional and technical aspects of my job.
I’m hoping sharing my own experience of finding my “Why” might help or encourage others that are thinking about how they can better lead and inspire.
Starting With Why
I was recently brainstorming with my team about improving how we engage with our internal stakeholders across the organization. We’ve had success over the years with our awareness and outreach efforts and have had the privilege of working with a wide range of stakeholders on some amazing initiatives, but I felt we could do even more by communicating our purpose in a way that resonates with others.
There are several leadership and management books that talk about the importance of identifying your purpose or “Why”. I happen to like one book in particular:
In it, Simon points out that people don’t buy into “What” you do…they buy into “Why” you do it. The what is tangible, the Why is biological. It just “feels right”. It’s the Why that breeds loyalty. That’s the type of effect we want to achieve with our Why – but it has to be authentic.
As I thought about it in the context of our security program I was motivated me to go through the exercise of defining my own personal Why, so I referred to the companion book "Find Your Why" and got to work, starting by looking back over my life to identify stories that might help me define my personal Why.
Looking Back
As discussed in “Find your Why”, your personal Why is largely defined at an early age and you have to go back in your life as far as you can remember to find and study those “defining moments” and identify the connections.
I identified a number of these stories and, as I wrote about them, pulled out words and phrases to identify common themes. Obviously this exercise is meant to draw on very personal memories so I’ll do you a favor and spare most of those details and provide only a few stories/examples for context of how I arrived at my Why statement.
Early Years
As I looked back on my life to get a better understanding of my Why, one of the first memories I locked in on was of me on the front stoop of my house on Long Island as a young boy (probably 8 or 9) sitting next to my Dad. It was a hot summer day and we were both sweating and exhausted, having just completed several hours worth of outdoor yard work. I don’t remember any specific words that were exchanged, an exact day or even the exact year that it happened, but I do remember that sense of accomplishment as we surveyed the results of our hard work. Several other memories came to mind of us working together on various projects when I was younger (he would go on to lose a battle with Cancer when I was 14) and it was during that e that time I learned how much can be accomplished if you are willing to put in the effort. While I didn’t know it at that time, these early experiences played a signficant role in shaping my Why.
My First Job
Fast forward a few years, I was 16 and in High School and I took a job at a craft store named MJDesigns. For anyone that isn’t familiar with that name, the store has since been absorbed by the Michaels chain of craft stores.
I’ll start by saying that I knew nothing about crafts, nor was it a budding passion of mine. At first, I was just excited to have my first job. When I started at the store, I did a little bit of everything. I worked a cash register, helped with merchandising and restocking, worked in the warehouse, unloaded the trucks, swept the floors…pretty much anything they would let me do. Pretty soon I became very interested in learning all I could about how the place ran, what worked well, what didn’t, and what I could do to improve it. I wanted to be educated on everything from warehouse management to product placement and customer service.
I worked hard, showed my genuine interest, and soon I was offered a department manager position, where I was responsible for scheduling shifts, ordering product, visual merchandising and customer service. I did well enough that I was offered a second department to manage a short time later.
While managing two departments I was still helping with stocking the shelves, manning the cash registers, etc. I also took on night jobs like painting the warehouse and waxing the floors. In my senior year of high school I was required to do an internship and I arranged take an assistant bookkeeper role at my store. In addition to all of the other things I was doing, I was now also responsible for counting the registers, keeping the records, and filing the bank deposits. There was very little about the operations of that store that I didn’t get to see or have a hand in.
Looking back on it, at the time I didn’t appreciate that many of my peers at the store were several decades my senior and, for some, this was their professional livelihood. I, on the other hand, was seventeen years old and had no intention of working there beyond my high school years. It was never going to be my career but it was still more than just a job to me. I was motivated not by what was in it for me, but rather how big of an impact I could have. My Why was taking shape.
Air Force
Just before my senior year in college I was seriously considering what I wanted to do professionally. I was on track to graduate with honors with a double major in Business Management and Information Systems and a Minor in Computer Science. I felt pretty confident that I would have career options but I also knew I wanted to do something with a mission I could get behind…someplace that I could apply my work ethic and desire to help others succeed and feel like I was contributing to something great. My Dad was a Marine, as was my Grandfather and my younger brother. So naturally, I chose the Air Force. One week after graduation I got married and about six weeks later I was on the bus on Alabama for Officer Training School (OTS).
After OTS, I was assigned to the 509th Communications Squadron at Whiteman Air Force Base, home of the B2 Stealth Bomber. I was able to work with an amazing group of people and contribute to an equally amazing mission. As the Officer in Charge of the Network Control Center I was entrusted to lead some high caliber teams with a wide-range of IT Infrastruture and Operations responsibilities– server administration, long-haul communications, field technicians, help desk, network administration, security, and management, and more.
There were too few of us, we had too much to do, and we worked long hours and weekends…and I loved it. I learned a ton about the technical aspects of the job and even more about leadership and the importance of building and supporting a high performing team team. Regardless of my actual job description and techical requirements, I knew my primary responsibility was to make sure my Airmen were taken care of and successful. I would move on from Whiteman to other duty stations, but throughout the rest of my Air Force tenure I was solidly behind the mission and the people I had the privilege to learn from and lead. There were several stories that I pulled from this period of my life and I while I won’t go into them here, many of them were centered around sense of purpose, looking out for others and ensuring their success, which would also become core to my personal Why.
Healthcare CISO
I had originally planned to retire from the Air Force, but when I made the difficult decision to leave, I knew that a meaningful mission was still very important to me. In my search for my next opportunity, I happened upon a posting for an information security job at one of the top cancer hospitals in the world. To me, healthcare was about as noble of a mission as I could find and, like many, I had been impacted by cancer several times throughout my life.
The job itself didn’t have a well defined scope. I would have no management responsbilties, the team I would be joining was small, the function relatively new and not widely known in the organization, and there was no clearly defined career progression path or future. But it just felt right. And I was confident I could apply my skills, help the team grow and succeed, and have a postive impact on a great organization. It was the only place I applied.
Fast forward a decade and I’m still there. I’m now the CISO and I’ve had the privilege of building out that team and, together, we’ve designed a robust security program. I’m also a father to two beautiful children which has given me an even greater appreciation for wanting to help others succeed.
There were several other stories and memories from this period that I analyzed and it was these experiences (plus those identified previously) that would ultimately lead me to my Why statement.
My Why
All of these years I’ve had a Why. I felt it, I lived it, but I never took the time to put it into words. That can work for a long time (it did for me), but I found that as I was talking to my team about our vision and our Why, I needed to be able to articulate my own Why very clearly.
Here’s mine:
TO INVEST IN THE SUCCESS AND WELL-BEING OF OTHERS, SO THAT THEY NEVER HAVE TO SETTLE FOR ANYTHING LESS THAN GREAT
It seems like a simple statement but it took a lot of reflection, I analyzed a number of stories, and I wrestled with the words quite a bit to arrive at this.
I intentionally chose the word “invest” because it’s what I’ve always done with my time and my energy when I believe in someone or something. When I invest in something, I’m taking ownership; I have a stake in it; I’m all in.
I also kept success and well-being as two separate but equally important components. I celebrate in others’ successes and know that many of my own achievements were, in a large part, due to the efforts of others. I’ve always believed that I can consider myself successful as a leader when my team no longer needs me. I love what I do and will continue to do it for as long as I feel I can contribute, but I think that’s the true mark of success of a leader – when the values, the mission, and the team can continue to grow and succeed long after you’re gone.
I kept “well-being” distinct from “success” because I’m also invested in ensuring others are comfortable, healthy, happy, and protected. People deserve to be all of those things and if I can help contribute to someone’s well-being, I will. It’s a perfect fit for healthcare and I take great pride and responsibility in the service I’m providing to every patient that entrusts their care with my organization. I also look understand the importance of looking out for the well-being of my team and organization, and of course, I do the same for my own children.
I intentionally chose the word “others” rather than define it as “people” or something even more specific like “colleagues” or “team” because this Why statement applies to all aspects of my life. This is my Why for the people that I lead, the people I mentor, the organization I work for, and my family. My satisfaction and reward stems from from all of their satisfaction and reward.
I do all of these things because I believe that no one should ever have to settle for anything less than great. For those that want to be great, sometimes all they need is a little support and guidance; someone to invest in them, believe in them. Organizations are no different. A company should not have to settle for just so-so processes or output. If people are willing to invest in it, there is no reason why it can’t be great too. I’m certainly grateful to everyone that invested time and energy to contribute to my success over the years and I know wouldn’t be where I am without them, so it’s only right that I pay it forward for anyone else that is motivated to be great too.
Although it took me quite a bit of time to put my Why into clear, concise words, I’ve lived it long enough to know that it works for me and I’m glad I can finally articulate it. I think that it will help me better communicate my sense of purpose to others and also help me to align my pursuits with what truly motivates me.
Overall, this was a worthwhile excercise and for anyone that’s interested in doing the same, I hope this helps or motivates you to find your Why.
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