Leadership Lessons Observed and Learned from a Servant Leader

“Serving others prepares you to lead others.”

Jim George

You are considering or have been asked to serve in a role supporting a senior leader. What can you expect to observe and learn from this unique experience? This article isn’t a “how to be a great military assistant guide,” as those excellent articles have already been published here and here. Before I started in my first support role as an executive officer, it would have been nice to have been exposed to key practical aspects of the job and made aware of the bigger leadership lessons as described in this article to better inform how I approached the job.

Over the course of my military career, I had the “opportunity” to serve multiple senior leaders in support roles–executive officer, special assistant, aide-de-camp, executive assistant, and military assistant. They all have one thing in common–your job is to take care of your boss, so they can effectively do theirs, while also learning as much as possible about leadership, military operations, high-level governance, and everything about the current organization. It will serve you well on your own leadership path both in and out of the military.

“One of the wonderful things about being president is that it’s an unbelievable learning
experience. And one of the things I missed after the presidency was this: daily learning.”

President George W. Bush

Serving in support roles is truly an opportunity to learn at a high level every single day; you don’t have to be president to learn daily, and I would argue that President Bush is still a life-long learner based on his post-presidency agenda items—leadership development, veteran support initiatives, and painting portraits to highlight immigrants and veterans.

My purpose in writing this is to pass on big picture lessons learned while serving a senior leader, not how to prevent accidentally sporting a four-star general officer’s cover, like I did. The following are only a sampling of leadership lessons observed that I took away from working with multiple senior leaders in the Department of Defense, such as taking the long-view, value of in- person visits, importance of relationships, and even where fun can play a role in high-stakes work.

“The single biggest way to impact an organization is to focus on leadership development.”

John C. Maxwell

Leadership Laboratory:
Personally, I learn best by trial and error, especially when it comes to my own leadership development. However, working in support positions allowed me an opportunity to intimately observe senior leader decision making, interactions with their staff and peers, and their leadership styles. Many people read leadership books and non-fiction biographies for leadership tips. Instead of passively reading, even though I read too, I took a different leadership development approach. I was part of the senior leader story, the individual who was with them most of the day as they navigated daily challenges and opportunities. I was able to embrace the opportunity to develop my own leadership style while serving a senior leader. Not only have I been able to apply these leadership lessons in my own leadership roles, but I anticipate they will pay off for life—purely based on observing senior leaders implement similar leadership lessons.

“A leader’s role is to raise people’s aspirations for what they can become and to release their energies so they will try to get there.”

David Gergen

Leadership Long-View:
The leaders I was fortunate enough to closely work with all took a long-view approach to the organizations they led. I believe by taking a longer view, it allowed these leaders to deal with pop-up crises, while methodically working through more difficult challenges that require longer horizons, all while drowning out the noise that can easily sidetrack leaders. One leader decided to change a long-held base policy on limits to certain purchases at the on-base store because he viewed it as unfair for a small group of Air Force Airmen, even though it could have had other negative effects, but he took the long-view, and decided that it was more important to revise the policy for the affected Airmen. He believed that this policy change would have a positive cultural effect that would snowball to other aspects of the base culture over time. I can attest that this policy change eventually had the senior leader’s intended positive impact.

“Remember that it is the actions, and not the commission, that make the officer, and that there is more expected from him, than the title.”

George Washington

Leadership Visits:
There is no substitute to physically interacting with those that you are responsible for. Does it take resources, time, and commitment on the part of both the senior leader and host unit to coordinate a successful visit? Absolutely, but when senior leaders refrain from travel, protected by the confines of their office, the needs of units are routinely hampered by the “frozen middle.” I personally saw this multiple times, but one trip stands out. A unit’s infrastructure had been neglected for years–leaking roofs, inadequate insulation, and poor plumbing negatively impacted the units ability to perform the mission. It took my boss’ visit at the time to unlock the necessary resources to fix these shortfalls. There have been countless news stories in recent years that have shined a light on other neglected infrastructure issues, such as leaking fuel tanks and mold issues. In a perfect world, it should not take a senior leader’s visit to address mission-degrading issues, but until that time comes, in-person visits are key.

“Trust is the essence of Leadership.”

Colin Powell

Leadership Demands:
This observation might be intuitive, but it is worth reiterating. Senior leaders have their own families, stressors, goals, and aspirations like most other people. We typically want to view our leaders as perfect and infallible; when our utopian views of our leaders are burst, as long as the behavior isn’t illegal, immoral, or unethical, it is important to give them their own space to work through the challenges they too face—significant life events, professional challenges, heart
breaking issues, or day-to-day pressures. This type of relationship demands upmost trust from both the leader and assistant. This will look different for every situation, but being empathetic toward a senior leader goes a long way. They always showed me grace too when I needed it.

“If you work in government, you’ll see things that need doing. You can choose to stay out of trouble, or you can ask yourself, ‘If not me, who?'”

Bob Stone

Leveraging Leadership Relationships

I observed that senior leaders have an uncanny ability to identify relationships between activities that may not be apparent to most of us. Senior leaders have awareness, knowledge, and insights on a broad range of topics, so this gives them an edge. They are motivated to observe these relationships because they realize that to fulfill their long-view and to get things done, leveraging relationships, data, past experiences, and information is required to drive toward impactful results. One example is the importance of understanding how Congress impacts Department of Defense processes and funding through the National Defense Authorization Act and Appropriations, then developing a strategy to engage with Congress for mutually beneficial outcomes.

“Everyone wants to live on top of the mountain, but all the happiness and growth occurs while you’re climbing it.”  

Andy Rooney

Leadership Fun
We sometimes view senior leaders as stoic, lifeless, and distant but, from my experience, this was far from the truth. To maintain sanity, it is important to laugh and have fun when appropriate to do so. All eyes are on senior leaders, so it can be difficult, but when done appropriately, fun goes a long way for the senior leader’s overall health, their immediate staff, and others in the organization. One senior leader agreed to the ice bucket challenge, literally breaking the ice with the visited unit, resulting in a resounding success.

Leaders aren’t born, they are made. And they are made just like anything else, through hard work. And that’s the price we’ll have to pay to achieve that goal, or any goal.

Vince Lombardi

In conclusion, I observed and learned countless lessons while serving Department of Defense senior leaders as part of their front office staff. It was a luxury to gain a wide variety of perspectives from multiple senior leaders. I am much better off having served them. No senior leader ever told me what I should do after serving them; they did not have to. I knew, based on their own character, perspective, discipline, and loyalty to this nation, that I should do the same. In a meritocracy, why else would I and others be placed in these positions, but to lift others up by coaching, mentoring, teaching, following, and boldly leading as we continue our leadership journeys? It can be challenging working so closely with a senior leader, but what you learn in
these roles easily makes up for it.

What is holding you back from accepting a support role? Boldly make the most of it, because personal growth is bound to happen and it may just change your life.

Col Christopher P. Mulder, USAF is an active duty Air Force officer. He is a graduate of the
United States Air Force Academy, an Air Force F-16 pilot, former commander, and engaged in
national security and leadership topics.

The views and opinions expressed here are those of the author and do not necessarily reflect the
official policy or position of any agency of the US government or other organization.

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