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.

What Mom and Dad Really Gave Me

 

Back in the early 1980s, I wanted a computer more than anything. It was a Commodore VIC-20, for those who are curious. The problem was that my family simply couldn’t afford one. We were of modest means, and there was very little disposable income. My mom and dad were honest with me about it. They told me they wished they could help, but the money just wasn’t there.

At the time, I had a paper route and picked up odd jobs at stores near where we lived. So I started saving. Before long, I realized that at the pace I was earning money, it would take years to buy a computer. To a kid, that was FOREVER.

I asked my parents again if there was any way they could help me get one sooner. Once again, they explained that they simply couldn’t afford to buy me a computer. But instead of leaving it there, they encouraged me to think differently. They suggested I use my paper route money to buy a lawn mower, rake, and basic equipment to start mowing lawns in the neighborhood. They explained that it would take time and work to get there, but it could eventually earn enough money for the computer I wanted.

So that became the plan.

For about five months, I saved every dollar I could. I got about halfway to what I needed for the equipment. Then my mom and dad surprised me. Quietly, without telling me, they’d been saving what little they could to help cover the rest. Looking back as an adult, I have no idea what they sacrificed to do that for me, especially knowing how tight money already was. But they somehow found a way.

Their sacrifice and guidance changed the direction of my life.

Together with my savings and their help, I bought the mower and equipment and started a lawn-mowing business during the summers. In the winters, I shoveled snow. What started as a way to earn money for a computer turned into a foundation for learning responsibility, discipline, customer service, and the value of creating opportunities instead of waiting for them.

By the age of 11, I finally bought that VIC-20.

More importantly, though, the experience taught me lessons far beyond that. Mom and Dad showed me what love looks like through sacrifice. They taught me the value of work, perseverance, gratitude, and ownership. They could’ve simply said no and left it there. Instead, they helped me find a path forward and quietly supported me however they could along the way.

I’ve never forgotten that and am forever grateful.

Thanks for reading.

Tim

Capital Discipline is Operational Discipline

 

If you have not read my earlier post, “Stability is Underrated,” I would probably start there first. This is really the financial side of the same conversation.

Healthy organizations usually think about money the same way good operators think about infrastructure.

Idle systems create waste. So does idle capital.

A lot of companies become so focused on controlling spending that they stop thinking carefully about whether their money is actually working once it reaches the balance sheet. Cash starts accumulating with no clear deployment strategy. Then six months later, leadership is simultaneously talking about cost pressure while large amounts of capital sit untouched, earning almost nothing because nobody wanted to make decisions around reserves, treasury management, reinvestment timing, or debt reduction priorities.

Conversely, sometimes organizations treat debt emotionally instead of operationally. Some leadership teams become so focused on eliminating debt entirely that they unintentionally restrict their own flexibility and delay investments that would have improved scalability or long-term operating health. Other environments go too far the opposite direction and operate as if cheap debt automatically excuses weak operational discipline underneath.

Usually, the healthiest organizations sit somewhere in the middle.

The strongest operators I have seen usually stay focused on flexibility:

• Enough liquidity to absorb problems without panic

• Enough discipline to avoid unnecessary exposure

• Enough operational consistency to keep investing during uncertain markets

• Enough structure that capital keeps moving intentionally instead of sitting untouched for years

That does not mean taking reckless risks.

Usually it means the opposite.

Some organizations quietly build strong long-term positions simply by staying disciplined while everybody else swings between overexpansion and overcorrection. Excess cash gets parked intelligently in low-risk instruments instead of sitting dormant. Capital projects get prioritized based on operational impact instead of internal politics or whoever speaks the loudest during budget season. Leadership stays realistic about what actually improves scalability versus what simply sounds impressive in a board presentation.

The environments that scale best usually understand a few things:

• Stability creates flexibility

• Predictability lowers operational stress

• Consistent cash management creates room for investment later

• Simple playbooks scale better than emotional decision-making

• Healthy debt and healthy liquidity can coexist

Most of this is not glamorous work. Nobody announces a major press release because reserve strategies became more disciplined or because treasury management quietly improved in the background.

But those things compound over time.

The same way operational debt compounds when organizations ignore process problems too long, financial inefficiency compounds when capital stops moving with purpose.

Good operators usually understand that stability and growth are not opposites.

Consistency creates room for growth.

- Tim

Stability is Underrated

 

A lot of leadership discussion today revolves around disruption, rapid transformation, aggressive scaling, and moving faster than everyone else. Some of that absolutely matters. Markets and technology change and organizations have to adapt.

But most environments do not actually fail because they lack another transformation initiative.

Usually, they struggle because basic operational consistency starts breaking down underneath them.

Sometimes processes and expectations change depending on who is leading the meeting that week. Different teams have different ways to solve the same problems. This leads to inconsistent reporting. Escalations can become emotional instead of procedural. Onboarding playbooks don’t stay up to date, and institutional knowledge lives inside individuals instead of an operational structure. This makes steady growth hard.

The organizations that tend to scale well are often the ones that become a little boring operationally. Good onboarding. Predictable governance. Defined and consistent ownership. Repeatable processes. Stable escalation paths. Consistent communication. People know what success looks like and how decisions get made without needing constant interpretation from leadership every single time something changes.

That kind of stability creates room for organizations to actually grow.

Without it, scaling usually means multiplying confusion.

I think this is part of the reason some organizations keep hiring smart people and still struggle operationally. Intelligence alone does not create consistency. A strong operating model does. So do simple playbooks that people can actually follow under pressure instead of beautifully designed processes nobody uses after the consultants leave.

The funny part is that this kind of operational discipline rarely gets celebrated publicly because it’s not exciting. Nobody announces a major press release because the escalation process got cleaned up or reporting structures finally stabilized across departments.

But those things matter.

Especially in environments trying to scale without burning people out or creating constant operational chaos underneath the surface.

Most organizations do not need more drama.

They need more consistency.

-Tim

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

Complexity Compounds

After enough years in IT, you start noticing that most technology problems are not really technology problems. Usually, the systems already exist. The engineers know the issues. The business has known the pain points for years. What’s usually missing is ownership and consistency.

A few years ago, I was in an environment running ServiceNow, Salesforce, and NetSuite with overlapping functions spread across all three. None of them were bad platforms. The problem was years of growth and departmental decisions had blurred responsibilities between systems. Teams were entering the same data multiple times. Reporting varied depending on which platform someone trusted more that week. Integrations became fragile. The software itself was only part of the cost. It took time and discipline to consolidate responsibilities and simplify workflows, but once that happened, operations got noticeably smoother almost immediately.

The more environments I work in, and the more mistakes I make and grow from along the way, the less interested I am in shiny platforms and giant transformation announcements. Most organizations run better when things get simpler.

Leadership Lessons Learned from What Not to Do

Three moments across my career shaped how I think about leadership. One reinforced that accountability always flows up. Another showed how gatekeeping limits organizations. The third demonstrated what happens when leaders create space for people to apply what they already know. Together, they form some of the standards I still operate by.

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 XO was reprimanded in front of the group and warned never to discipline a soldier out of pride or embarrassment again.

That moment clarified something fundamental for me. Leadership means leading from the front and owning the environment you create. When people fail, leadership failed first. 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 the mindset behind it.

Instead of serving the mission, she put her own ego first. The organization had capability, motivation, and unused expertise. Yet growth was constrained by territorial ownership rather than by ownership of outcomes.

Over time, I have seen this pattern repeat. Gatekeeping does not protect organizations. 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.

Strong leaders invite contribution, welcome challenge, and remain accountable for the systems they oversee. Weaker leaders protect status, restrict access, and confuse control with effectiveness. When someone brings effort, intent, and capability to the table, my responsibility is to create space for that contribution to matter. That is how trust scales. That is how organizations grow without breaking. And that is how leadership earns credibility over time.