Showing posts with label Servant Leadership. Show all posts
Showing posts with label Servant Leadership. Show all posts

Wednesday, June 3, 2026

The Last Two Across the Finish Line

 


Many years ago, I attended the Ranger Indoctrination Program (RIP), which is now known as the Ranger Assessment and Selection Program (RASP).

One of the events was a five-mile run that had to be completed within a strict time limit. It was designed to create stress and accelerate attrition. 

About halfway through, I caught up to another candidate who was struggling and out of breath. He was in good physical condition, muscular and built more like a bodybuilder than a runner. He wasn’t a quitter, but this event just wasn’t his strength. I had a choice to keep my pace and finish comfortably, or slow down and help him. I slowed down and stayed with him. We spent the rest of the run pushing each other to finish. By the time we approached the finish line, everyone else had already crossed. Several candidates had already been dropped for not making it in time. The Black Hats (what our instructors were called) saw us coming from a distance. We were the last two across the finish line. And they informed us that we'd both passed. We’d moved on to the next round.

At the time, I didn’t think much about the decision, as during Infantry Basic Training, Advanced Individual Training, and RIP, one lesson was endlessly repeated: 

Never leave your buddy behind.

As you could probably guess at this point, this story isn’t really about running or about my experience as a Rippie. It’s about a lesson that has stayed with me for more than thirty years.

And I’ve seen the same principle apply in business: Some of the best teams I’ve been part of were built by people willing to invest time and energy in helping others succeed, even when there was no immediate benefit to themselves. Likewise, many of the best leaders I’ve worked with understood that their job wasn’t to win alone. It was to help the team cross the finish line together.

Monday, May 11, 2026

Words Carry Weight

 


Years ago, when I was serving in the 3rd U.S. Infantry Regiment (The Old Guard), a few of us had gone out to Murphy’s in Old Town Alexandria after payday. When we returned later that night, another soldier stopped me outside our barracks.

“Hey Gabaree!”

He asked why I was there. I assumed he meant why I was out that late and told him I was probably a little too inebriated and needed to go sleep it off.

He stopped me again.

“No. Why are you HERE?”

He meant, “Why I was in the Old Guard?”

At the time, the question felt oddly philosophical for the middle of the night after a few drinks, but I shrugged and answered honestly. I told him it was an honor to help provide funeral honors for families who had lost someone in service to our country. That it mattered to make every detail as perfect as possible so families knew their loved one was respected and honored properly.

Months later, that same soldier stopped me in a hallway and thanked me.

I was confused until he explained that the night we spoke, he had been planning to go AWOL. He was leaving for good and trying to decide whether any of what we were doing mattered. Something about that conversation changed his mind.

I’ve thought about that moment many times over the years.

Words carry weight. Most of the time, we do not realize when someone is searching for meaning, encouragement, or simply a reason to keep going. We are usually caught up in our own world and do not always realize how much impact a few words can have.

I’m thankful that conversation went the way it did. If I had answered differently, things might have turned out very differently for him.

It became a reminder to me to be mindful of what we say. Sometimes a few words can change the direction of someone’s life.


Tim

Sunday, December 21, 2025

Three Moments That Shaped My Leadership Philosophy

Three experiences across my career fundamentally shaped how I think about leadership. One reinforced that accountability always flows upward. Another revealed how gatekeeping limits organizations. The third demonstrated what happens when leaders create space for people to contribute beyond their job descriptions. Together, they continue to influence how I lead today.

Accountability Flows Up

When I was an enlisted soldier, our Executive Officer was known for keeping distance from those he viewed as beneath him. He rarely asked for help and tended to dismiss contributions that came from lower ranks.. One evening, as he prepared to attend a congressional dinner, his dress uniform was not properly pressed, and his brass was not shined. It would have reflected poorly on him and on our unit. 

I knocked on his open door and offered to help him press his dress blues and shine his brass. The offer was not received well. He took offense at the idea that an E4 would offer assistance and viewed it as a challenge to his authority. I was ordered to do push-ups and told I would be recommended for a summary Article 15 for insubordination.

The next day, I was called into the Commanding Officer’s office. Present were the CO, the XO, the First Sergeant, my Platoon Leader, Platoon Sergeant, and Squad Leader. The CO ordered push-ups. Two hundred each. Everyone in the room. Including himself and the XO.

Afterward, the CO explained the reasoning: 

If a problem reaches the CO without being resolved, leadership has already failed. Accountability does not stop at rank. It compounds as authority increases.

The Commanding Officer made it clear that leadership should never use authority to protect pride or avoid embarrassment.

That moment clarified something fundamental for me. Leadership means leading from the front and owning the environment you create. When problems reach the surface, leaders should first examine the environment they created before assigning blame elsewhere.  And sometimes individuals serve an important role by demonstrating what leadership should not look like.

Gatekeeping Limits Organizations

Years later, in a civilian organization, a peer shared his frustration with me. He served as a senior director for community outreach. He was effective in his role and deeply committed to the mission. Outside of work, on his own time, he had earned a PhD in organizational management.

There was no clear path for him to grow beyond his position.

At the time, I was leading several process improvement initiatives and saw an opportunity to leverage his expertise. I raised the idea with the CEO. The response was immediate and firm. I was told that I would not be authorized to matrix resources from other departments. Organizational management was her responsibility. If I needed assistance, I should come directly to her.

What stood out was not the decision itself, but its effect.

The organization already possessed expertise that could have advanced the mission, yet that capability remained unused because collaboration across organizational boundaries was discouraged.

Over time, I have seen this pattern repeat. Organizations rarely suffer from having too much talent. They suffer when existing talent is prevented from contributing. It limits them. When leaders confine people to narrow roles, they reduce institutional capacity. When problem-solving is centralized instead of shared, bottlenecks form. When potential is measured only by current titles, organizations quietly train their people to stop bringing their best ideas forward.

Creating Space for Capability

In another role, we were facing a growing attrition problem. Engineering teams were working excessive hours week after week. Burnout was setting in, morale was slipping, and we were beginning to lose people we could not easily replace.

One of my managers, whose formal role was in network engineering, approached me with a proposal. He suggested that we step back and revamp our processes. His idea was to document what was working, identify what was not, and put practical guardrails in place so engineers could focus on meaningful work without constant interruption, while still leaving room for innovation.

What the organization had never fully leveraged was that he had earned several ITIL certifications on his own. He had the training and the perspective, but had never been given the opportunity to apply it.

The proposal aligned well with a broader roadmap we were building. But even without that alignment, I would have approved it. It was a thoughtful solution to a real problem and a chance for someone to contribute beyond a job description.

We moved forward.

The impact was immediate and lasting. Processes improved. Rework declined. Engineering teams regained focus. Attrition slowed. Just as importantly, that manager grew. He became part of the solution, gained confidence, and expanded his role within the organization. Others noticed as well, up and down the leadership chain, from the CEO to the engineering teams. The success helped shift the culture. Staying in one’s lane mattered less than contributing to shared outcomes.

What stood out was not the framework itself, but the outcome of creating space for capability to surface. The organization benefited, the team benefited, and the individual benefited.

The Common Thread

In each of these situations, leadership either failed or succeeded for the same reason. Whether ego took precedence over responsibility, or responsibility created room for others to contribute.

Looking back, these experiences taught me that leadership is less about authority than stewardship. Authority can direct people, but stewardship develops them. The leaders I continue to admire are those who create environments where accountability is shared, expertise is welcomed regardless of title, and success is measured by organizational outcomes rather than personal control. 

Every organization already contains more potential than it fully utilizes. One of leadership’s greatest responsibilities is creating the conditions where that potential can emerge.


Tuesday, March 25, 2025

Leadership Does Not Require an Org Chart


One of the most important leadership lessons I’ve learned is that leadership is not granted by a title.

It is demonstrated through action.

Organizations often associate leadership with authority, reporting structures, or formal responsibility. Those things certainly matter, but they are not what make people choose to follow someone.

Leadership is ultimately measured by influence—by the ability to help others grow, solve problems, and move forward together.

Leadership Is a Daily Choice

Some of the strongest leaders I have known exercised influence without formal authority.

They mentored new employees.

Shared knowledge freely.

Made introductions that helped someone else’s career.

Offered thoughtful feedback.

Recognized potential in people before others saw it.

None of those actions required permission.

They simply required a willingness to serve.

Influence Exists Everywhere

Leadership opportunities appear far more often than most people realize.

Helping a colleague navigate a difficult decision.

Connecting two people who could benefit from knowing each other.

Sharing lessons learned from a challenging project.

Volunteering professional expertise within the community.

Taking time to coach someone earlier in their career.

These moments rarely receive recognition.

They often create the greatest long-term impact.

Growth Is Part of Leadership

Every season of a career offers opportunities to learn.

Some periods involve building organizations.

Others involve developing new skills, expanding professional networks, reflecting on experience, or exploring different perspectives.

Growth is not something leaders pause until circumstances become ideal.

It is part of leadership itself.

Leaders who continue learning remain better prepared to help others when new opportunities emerge.

Service Builds Credibility

Leadership rooted in service creates trust.

People remember those who invested in them without expecting immediate return.

Organizations remember leaders who shared credit, developed talent, and strengthened teams rather than protecting personal status.

Those habits build credibility that extends well beyond any individual role or organization.

Leadership Is Portable

Titles change.

Organizations change.

Responsibilities evolve.

The ability to influence, encourage, teach, and develop others travels with you.

That may be the most enduring form of leadership.

When leaders focus less on position and more on contribution, they discover that opportunities to serve exist in every stage of a career.

Leadership is not defined by where you sit on an organizational chart.

It is defined by the positive impact you leave on the people around you.

What Crafting Espresso Taught Me About Developing Teams

Outside of technology, one of my favorite hobbies is making espresso.

Good espresso is remarkably unforgiving. Small adjustments to the beans, grind size, water temperature, or extraction time can dramatically change the result. At first glance, it seems like a hobby built around precision.

The longer I’ve practiced it, however, the more I’ve realized it is actually about understanding potential.

Every coffee bean is different.

The goal isn’t to force every bean to behave the same way.

The goal is to understand what allows each one to perform at its best.

I’ve come to believe leadership works much the same way.

Great Teams Are Not Built from Identical People

Technology organizations often focus on finding the “perfect” candidate.

In reality, high-performing teams are built by combining people with different experiences, perspectives, and strengths.

Some excel at solving complex technical problems.

Others communicate exceptionally well with customers.

Some thrive under pressure.

Others quietly improve processes that make everyone around them more effective.

Leadership begins by recognizing those differences rather than trying to eliminate them.

Development Requires Intentional Investment

Coffee does not become exceptional by accident.

Neither do people.

The strongest leaders invest time in coaching, mentoring, and creating opportunities for others to grow. Sometimes that means technical development. Sometimes it means giving someone responsibility before they feel completely ready. Often it simply means believing in someone’s potential before they believe in it themselves.

People usually rise to expectations that are supported with trust and opportunity.

Leaders Create the Environment

An espresso machine cannot compensate for poor beans.

Likewise, talented people often struggle in environments where priorities are unclear, collaboration is discouraged, or leadership creates unnecessary obstacles.

One of the most important responsibilities of leadership is creating conditions where people can succeed.

That includes clear expectations, psychological safety, meaningful feedback, and the freedom to solve problems rather than simply execute instructions.

When those conditions exist, performance improves naturally.

The Best Leaders Serve the Team

The phrase servant leadership is sometimes misunderstood.

It does not mean lowering standards or avoiding accountability.

It means recognizing that a leader’s responsibility is to help others perform at their highest level.

Leaders remove obstacles.

They develop capability.

They create opportunities.

They recognize potential that others may overlook.

The success of the team becomes the measure of the leader.

Excellence Is Never Finished

One of the reasons I enjoy making espresso is that there is always something to improve.

A slightly different grind.

A better extraction.

A new bean.

Leadership follows the same path.

No team is ever truly finished developing.

No leader is ever finished learning.

Both improve through curiosity, patience, thoughtful refinement, and the willingness to keep making small adjustments over time.

The goal is never perfection.

It is creating an environment where people—and the organization—continue getting better.

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