The Time I Was Coaching Without Even Realizing It

Sometimes, we have a knack for something long before we realize it. In my case, I didn’t fully understand that I had an instinct for coaching until I found myself in a rather unexpected situation.

About 8 years ago my friend “Steven” invited me for drinks at a bar near his former workplace. He had recently been laid off due to a company-wide restructuring, and this bar was a spot he frequented after work. He knew the bartenders well, and it was a place of comfort for him after what he had gone through.

That evening, Steven introduced me to one of his best friends from his time at the company—a woman he referred to as his "work wife." She worked in HR and, as I would later discover, was the person who ultimately had to deliver the news of his layoff. I was immediately struck by the complexity of their relationship. On one hand, they were close friends, but on the other, she was the bearer of life-changing, painful news for him. How could they still maintain their friendship after such a difficult encounter?

Curious, I asked her a direct question:
"How are you and Steven still able to be friends, despite the fact that you were the one who had to tell him he no longer worked for the company? How do you reconcile remaining close with someone whose life you’ve disrupted, even if it was just part of your job?"

At first, she laughed it off, as if the question was inconsequential. But I pressed further, not out of judgment, but because I genuinely wanted to understand how someone in her position navigated the emotional complexities of such a situation. I had been told by managers in the past that it was important to disassociate emotions from certain business decisions, but I always struggled with that. I saw this as an opportunity to learn from someone who appeared to have mastered that skill.

However, my persistence didn’t have the desired effect. As our conversation progressed, her demeanor shifted. What I intended as a thoughtful question about professional boundaries and emotional intelligence came across to her as an accusation. She felt as though I was implying she had been a bad friend to Steven or had betrayed him. That was never my intention, but miscommunication in emotionally charged situations can sometimes lead to unintended consequences.

Later, she told Steven about our conversation, and he was upset with me for questioning his friend in a way that made her uncomfortable. He didn't see that I was not only intellectually curious about the situation, but I was also looking out for him as a friend. The evening ended on a sour note, and we didn’t talk for almost a year.

Fast forward to a different event, and I ran into Steven again. To my surprise, he pulled me aside and shared something I wasn’t expecting. He said that evening’s conversation had triggered a series of realizations for him. He had started to reflect on the people he trusted with his career and his life, and he came to the conclusion that he had been relying too much on others to have his best interests at heart. That conversation, as uncomfortable as it was at the time, had set him on a path toward taking better control of his own career.

He thanked me for pushing the issue, even if it had cost us our friendship for a time. He explained that after that night, he distanced himself from his HR friend and began focusing on his own goals and priorities. He realized that no one would advocate for him as strongly as he could advocate for himself.

Looking back, I realized that night was a moment of unintentional coaching. I didn’t set out to provide Steven with life-altering guidance, but by asking the uncomfortable questions, I helped him reflect on his situation and take action. I wasn’t giving him direct advice or telling him what to do. Instead, I was helping him find his own clarity by challenging the way he saw things.

This experience taught me that coaching isn’t always about formal sessions or structured advice. Sometimes, it’s about having the courage to ask the hard questions, even at the risk of discomfort. It’s about helping people see their situations from a new perspective, and empowering them to make decisions that are aligned with their true goals.

That night, I didn’t realize I was coaching—but looking back, it’s clear that I was. And that’s when I started to understand that I had a natural inclination for helping people unlock their own potential. Sometimes, the most valuable lessons come from the conversations we don’t even realize we’re having.