How a Cup of Coffee Changed My Perspective on Leadership

The year was 2000.

I still remember the moment I felt the most scared and anxious in my life.

It was my first “real” job after graduate school, and reality was setting in. The excitement of starting my career had faded, replaced by the monotony of office life.

Monotony of Work Life

After two years of working at an architecture firm, I found myself stuck in a routine: waking up at the same time, walking the same New York City streets, taking the same subway, and doing the same tasks at work—only to repeat it all the next day.

I started wondering: Is this all there is to life?

Just as I was wrestling with this question, I heard rumors of a new project our firm might take on. The problem? I had no idea how to get involved. I didn’t even know if I was allowed to know about it.

Eventually, I learned the name of the partner who might be leading the project—my boss’s boss. (a stranger who I have never met before). But as a junior employee at the very bottom of the office hierarchy, I had no reason to interact with him.

More importantly, I had no idea how he would react if I showed up in his office, uninvited.

Still, I knew one thing: if I didn’t speak up, I’d be assigned to the next available project—whether I liked it or not.

As terrifying as it was to approach him, the thought of drifting through my career without any direction was even scarier.

So, I knocked on his door.

What happened next was a lesson in leadership that has stuck with me for over two decades.

Curiosity: Why Great Leaders Ask More Questions Than They Answer

As soon as I stepped into his office, I was ready to blurt out my name and my request before he could kick me out.

Feeling anxious for what the other side holds

I had mentally prepared for every possible negative response:

  • Make an appointment with my assistant first.
  • Talk to your direct boss instead.
  • You can’t just barge into someone’s office like this.

But instead, he simply said: “I was about to have a cup of coffee. Want one?”

Wait… coffee?

That was not on my list of anticipated responses.

In that moment, my nerves settled. I wasn’t just some junior employee wasting a partner’s billable time. I was a person, sitting across from another person, having a conversation over coffee.

When I finally got to my point—asking to be part of his project—he stopped me midway. But not to reject my request. Instead, he asked about me.

Where had I studied? How long had I been at the firm? What kinds of projects had I worked on?

I had assumed he only cared about my qualifications for the project. Instead, he was simply curious—about who I was and what I had done.

That was the first lesson in leadership I learned that day. Great leaders aren’t just focused on what people can do for them. They take the time to understand the people around them.

Being Direct: The Leadership Skill No One Likes, But Everyone Needs

After letting me talk, he got straight to the point.

He told me that while the project would be starting soon, many key decisions were still up in the air. Then, he said the word I had been dreading: inexperience.

The project needed senior team members, and I simply didn’t have the experience yet.

At the time, I was disappointed. But looking back, I respect him for being upfront.

Being Direct: Leadership skill

Over the years—through my work in architecture, teaching, and serving on boards—I’ve realized that directness is a rare leadership quality. Many leaders avoid tough conversations, hoping issues will resolve themselves. But in reality, avoiding difficult discussions only creates bigger problems later.

I recently experienced this firsthand while working with a more senior colleague.

I assumed my approach was fine—until one day, I learned she had issues with how I worked. The problem? She had never mentioned it before.

If she had been direct earlier, we could have had a conversation. I could have adjusted my approach, or at least explained my reasoning. Instead, we wasted time and energy on misunderstandings that could have been avoided.

Good leaders don’t shy away from tough conversations. They make decisions, communicate clearly, and set expectations—whether people like the answers or not.


Final Thoughts

We hear words like leadership and leaders all the time in the workplace. But what do they actually mean?

For me, leadership is about two things: curiosity and directness.

My boss’s boss showed me that great leaders take the time to understand the people around them. They ask questions, they listen, and they make others feel valued. But they’re also direct. They don’t avoid uncomfortable conversations or sugarcoat reality.

Now, years later, I think about that moment every time someone knocks on my door—whether they have an appointment or not.

And yes, I offer them coffee first 🙂

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