🦋 The Most Productive Conversation is the One You're Avoiding

About ten years ago, I was leading a campaign team of nine people. A few days before a big meeting, three of my team members came to me individually. They were frustrated with another member, let's call him Mark, who was micromanaging them and speaking condescendingly.

My reaction? Avoidance.

Fearful that confronting the issue would derail our momentum, I told them it was just "Mark's style" and that we should ignore it to focus on our work. That was a bad mistake. Within months, two of those three team members quit. The underlying tension finally erupted in an open argument during a meeting, and the team collapsed.

By avoiding one difficult conversation, I had engineered a much larger conflict and guaranteed our failure. I learned my lesson the hard way: Avoiding difficult conversation now, creates even bigger problem in the future. It's a missed opportunity to solve, reconcile, and grow.

🤦‍♂️ The Most Common Mistake in Leadership

The most common mistake in leadership is solving the wrong problem. We often consciously or subconsciously avoid the real problem and define the challenge from the perspective of least resistance—to avoid conflict and discomfort. Guess what? Having the right solution for the wrong problem will get you nowhere.

Let me give you an example of how we often frame problems to avoid real challenges: In my story, I framed the problem as the team's ability to adapt to Mark's leadership style. Why? Because then the team needed to do the work of changing. In reality, the real problem was Mark's attitude. This meant that I, as the team leader, had to have that difficult conversation with him. I avoided that work by placing the problem somewhere else. And you saw what happened.

Take any big challenge you have right now and ask yourself: Are you placing the challenge where it really should be placed? Or are you avoiding the real work by placing the problem where it's more convenient for you? This is the way to identify some difficult conversations that you have been avoiding.

🛑 Obstacle is the Way

If you feel uncomfortable about a particular conversation that you know you need to have—with your boss, colleague, sister, or friend—that is the path forward. That emotion of heaviness, that fear, actually marks the real issue you need to explore.

Difficult conversations are the engine of effective leadership because they are an opportunity to build trust and psychological safety, by demonstrating that honesty is valued more than artificial comfort. This makes it possible to solve the most critical underlying problems, maintain accountability, and clarify expectations without letting resentment build. These conversations are the only way to foster genuine growth through honest feedback and drive innovation by challenging ideas and debating solutions.

⚔️ The Clash of Values

Difficult conversations are crucial for leadership because they point to the clashes where leadership is most needed—where competing values like speed & inclusion, or candor & harmony, or tradition & innovation, collide. These tensions are the most common obstacles to growth and progress, and your job is to surface and reconcile them so that trust and work can move forward.

In any conflict, each side is protecting something valuable to them. The purpose is to turn a fight into a choice by acknowledging this truth and asking what trade-offs are acceptable. Avoiding this talk ensures everyone stays stuck—standards drift, resentments grow, and decisions stall as unspoken feelings leak into the personal or team's tone and performance.

🤔 Which conversations are worth having?

You can't tackle every hard conversation. There are plenty you could have, but chasing all of them is exhausting and unwise. I use these questions to decide:

1. Is it a pattern, not a blip? If you've seen it 2–3 times or it's affecting others, it's worth addressing.

2. What's the long-term cost of avoiding it? If staying silent increases the odds of a bigger blow-up, lost trust, or repeat mistakes, have the conversation soon.

3. What are the gains if I do it? If the potential benefits—clarity, better results, stronger relationship—are meaningful (and not just about your ego), it's worth having.

🙈 Why We Dodge the Discomfort

If you've ever put off a tough conversation, you're not alone. It's not a character flaw; it's a deeply human response. We dread these conversations because:

• Fear of Negative Outcomes: What if it goes badly? We worry about damaging relationships, hurting someone's feelings, being hurt ourselves, or loosing something (resources, position, relationship)

• Threats to Identity: These conversations can feel like a referendum on our competence, our kindness, or our value. We fear uncovering a personal insufficiency—that we aren't smart enough, capable enough, or good enough.

• Apathy and Exhaustion: Sometimes we think, "What's the point? Nothing will change." Or we simply don't know where to start.

These fears push us to see conflict as a threat. If you intend to exercise leadership, a big part of it is having skin in the game and taking risks worth taking in order to make progress.

🔍 The Mindset Shift: From Certainty to Curiosity

The single most powerful shift you can make is moving from a mindset of certainty to one of curiosity.

When we enter a difficult conversation, we usually believe we know everything we need to know about the problem. We've judged the other person's intentions based on how their actions made us feel. When your colleague misses a deadline, you assume they're irresponsible. When you miss one, you're just overworked. We infer intent from impact, and we are very often wrong.

Instead of assuming, get curious. Catch yourself in your own certainty and ask:

• I wonder what information this person has that I don't?

• How might they see the world that makes their view make sense?

• What important experiences have shaped their perspective on this?

This shift moves you from a posture of blaming to one of exploration. It changes the goal from persuading to understanding.

✅ Action Item

Nothing beats real-life action. Here what I propose you do:

1️⃣ Choose one difficult conversation worth having

2️⃣ Write down what makes it difficult for you? What are you afraid off?

3️⃣ What triggers you in the other person's view and how can you have a more empathetic understanding of their position? Prepare to stay calm in the face of triggers.

4️⃣ Find time to have that conversation (in person is always better)

5️⃣ Enter the conversation with curiosity mindset. Focus on listening and understanding, fostering trust and connection, before sharing your opinion. The goal is not to be right, but to make progress! 

6️⃣ Reflect after the conversation - what did you learn about the problem, about yourself?

💡 There is a lot more to unpack & learn about this topic. I'm considering developing an online course 👇

💭 Final Thought

The fear of a difficult conversation is really a fear of the consequences. But as my story shows, the consequences of avoidance are often far worse. Building this skill requires practice. It will feel uncomfortable at first, but it is one of the most crucial skills for leadership, collaboration, and meaningful relationships.

So, have that difficult conversation you know you need to have ✊