The Leadership Conversation We Avoid

What 20 years of leadership taught me about the conversations that matter most

Early in my leadership journey, I absolutely dreaded corrective conversations.

I wasn't a fan of confrontation, and I worried about upsetting people. I didn't want to ruin someone's day or damage a relationship. Looking back, I realize I confused being liked with being a good leader.

If you're fortunate, you learn fairly quickly that pleasing everyone simply isn't possible. Over time, I learned something that changed the way I lead.

Many leaders actively avoid difficult conversations—not because they're weak, but because they care.

That distinction matters.

They see the best in their people. They convince themselves it's just a one-off mistake. They don't want to come down too hard, discourage someone, or dull their shine. But accountability still has to shine through. Without it, small problems become bigger ones. Left unchecked, they slowly erode workplace culture, team standards, and trust.

Later in my career, after learning some valuable lessons of my own, I decided to help prepare my junior members for the day they would become supervisors themselves.

We gathered in a conference room for a role-playing exercise. One person would play the supervisor, while another played a junior member receiving corrective feedback. I had written different scenarios for them, and during the first round, everything went about as expected.

People were understandably nervous. Giving corrective feedback in front of your peers isn't exactly comfortable. But they did well. Then I decided to throw a monkey wrench into the exercise.

Before the second round began, I quietly pulled aside each person playing the junior member. One by one, I gave them a secret instruction:

"You... be defensive."

"You... challenge everything the supervisor says."

"And you... get emotional."

What happened next was absolute chaos.

Apparently, I had unknowingly assembled a room full of aspiring actors. One junior member jumped out of their chair as if they were ready to flip the conference table. Across the room, another dramatically shouted, "You can't handle the truth!" in their best Jack Nicholson impression. Others interrupted, argued, folded their arms, or acted completely unreasonable.

Eventually, I had to step in. "Okay... okay... bring it back a bit." The room erupted in laughter.

Everyone realized they had embraced their roles just a little too enthusiastically. But once the laughter settled, the real learning began. We debriefed the exercise, and the biggest lesson wasn't about saying the perfect words - It was about empathy.

As supervisors, we're not sitting down with someone to ruin their day. We're there because we care about their success and because accountability matters. At the same time, we have no idea what the person sitting across from us may be carrying. They may be embarrassed, they may feel frustrated or caught off guard, they may be dealing with challenges at work or at home that we know nothing about, and that can shape how they respond in the moment.

That doesn't mean we avoid the conversation. It means we approach it with curiosity before conclusions. Understanding that changes everything.

In my experience, the best leaders don't walk into difficult conversations believing they have all the answers, they walk in prepared to ask questions, to listen, and to understand before they decide what happens next.

Accountability and empathy aren't competing priorities - they're partners, and the most effective leaders know how to balance both. And by creating an environment where honest conversations happen early, we foster trust, transparency, and a culture where people can learn, improve, and thrive.

If there's one lesson I'd pass on to every new leader, it's this:

Have the conversation.

Here are three practical ideas you can implement immediately.

1. Don't delay difficult conversations.

When you notice a performance or conduct issue, address it early.

The longer you wait, the harder the conversation becomes, and the more likely the behaviour is to spread. People pay attention to what leaders tolerate and if no action is taken, others begin to assume the behaviour is acceptable.

Think of it like removing a Band-Aid, It's uncomfortable either way, but it's far better to deal with it promptly.

2. Don't assume the worst.

Go into every conversation with curiosity instead of conclusions, don't assume someone is lazy, careless, or intentionally underperforming.

Ask questions.

Listen.

The more you understand what's really happening, the better equipped you'll be to coach, support, and adapt to the situation.

3. Remember the goal.

The objective isn't to win the conversation or to put someone in their place. The goal is to help your people succeed. After more than 20 years of leading people, I've learned that leadership rarely hinges on grand speeches or major decisions.

More often than not, it's built one conversation at a time, one moment, one interaction where understanding grows and relationships deepen.

Years ago, I believed avoiding difficult conversations protected relationships. I have since learned the opposite is true. The conversations we avoid today become the problems we inherit tomorrow. The best leaders don't have difficult conversations because they enjoy them. They have them because they care too much not to.

— Jason Alderson