What 17-Year-Old Me Learned About Leadership Blind Spots: How You Can Avoid a Common IT Leadership Trap

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TLDR: Leadership Blind Spots

• Leaders often make fast judgments about others while overlooking similar flaws in themselves.
• Assumptions about motives can quietly erode trust, culture, and team performance.
• What we label as weakness in others often shows up in us under a different name.
• Humility and self-awareness are strategic leadership strengths, not soft skills.
• The most dangerous blind spots aren’t technical gaps; they’re unexamined assumptions.

Read the whole article below the video.

A 17-Year-Old, a Bus Stop, and a Leadership Lesson That Lasted for Years

I was seventeen, standing alone at a bus stop in Denver late at night. Streetlights buzzed overhead. The city had gone quiet in that uneasy way it does after most reasonable people are home.

A man shuffled toward me. His clothes were layered but worn thin. He looked like life had taken more from him than it had given.

He asked if I could spare some money.

Seventeen-year-old me didn’t pause. I didn’t ask what he needed it for. I didn’t ask his name. I didn’t even consider that my assumption was wrong.

“I don’t have money for you to go buy booze,” I said. I was clear and confident, certain of my judgment.

He didn’t argue. He didn’t defend himself. He didn’t challenge me. “Well,” he replied evenly, “do you have a spare cigarette?”

Relieved to be generous on my own terms, I smiled. “I can always spare a cigarette,” and handed it to him.

He took it, looked at me, and said quietly, “We all have our vices, don’t we?”

No sarcasm. No anger. Just a statement of fact.

And in that moment, something shifted. He exposed my leadership blind spot.

My Leadership Blind Spot

Because I had just refused him money based on what I assumed he would do with it… while handing him something I used to feed my own habit.

I had judged his weakness while excusing mine.

That moment has stayed with me far longer than the bus ride that followed.

Now let’s fast-forward.

Most of us in leadership don’t stand at bus stops judging strangers. But we do something similar in conference rooms, in ticket reviews, and in performance conversations.

We assume motives.

Incorrect Assumptions and Misunderstood Intentions

We assign character based on behavior.

We tell ourselves a story about why someone did what they did.

“That tech is lazy.”

“That engineer just doesn’t care about the customer.”

“She’s resistant to change.”

“He’s not leadership material.”

And we’re often just as confident as I was at seventeen.

The Truth About Judgments

Here’s the uncomfortable truth: many of the behaviors we judge in others show up in us under different labels.

We criticize a technician for being abrupt with users while we justify our own impatience as “efficiency.”

We call a team member resistant while we quietly resist changes we didn’t design.

We dismiss someone as “difficult” while overlooking the ways we can be rigid, defensive, or territorial.

We all have our vices.

In IT leadership, the vice isn’t usually cigarettes or alcohol. It’s ego. It’s certainty. It’s the quiet belief that our position gives us clearer vision than everyone else.

Sometimes it does.

But sometimes it just gives us authority.

The man at the bus stop didn’t argue with me. He didn’t try to win. He simply exposed the double standard I didn’t know I was carrying.

That’s what strong leaders learn to do for themselves before someone else does it for them.

They ask:

• What assumption am I making right now?
• What story am I telling about this person?
• Where might I be guilty of the same behavior in a different form?

That kind of self-examination isn’t soft. It’s strategic.

Because cultures don’t fracture over technical disagreements. They fracture over judgment, ego, and unexamined assumptions.

A help desk technician who feels judged stops taking initiative.

An engineer who feels labeled stops offering ideas.

A manager who feels misunderstood disengages quietly.

And the leader who never questions their own certainty slowly becomes the bottleneck in the room.

The lesson from that bus stop wasn’t about generosity. It was about humility.

Humility doesn’t mean lowering standards.

It means raising self-awareness.

It means recognizing that before we correct someone else’s behavior, we’d better make sure we’re not excusing the same flaw in ourselves under a different name.

The seventeen-year-old version of me thought he had clarity.

The man in worn-out clothes had perspective.

And that’s the thing about leadership: wisdom doesn’t always come from the person with the title. Sometimes it comes from the person you least expect.

If you want to build high-performing IT teams that collaborate well, serve customers effectively, and actually trust one another, this matters.

Because the moment leaders stop assuming and start examining themselves first, everything shifts.

The culture becomes safer, feedback becomes more honest, conversations become more productive, and performance improves, not because people are afraid of being judged, but because they feel respected.

All from one sentence at a bus stop.

We all have our vices. The real question for leaders isn’t whether we do. It’s whether we’re willing to see them.

Oh, and in case you’re wondering, I quit cigarettes years ago.

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