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.