Avoiding Difficult Conversations at Work

Turn them into Crucial Conversation Skills for Leaders

The Conversation You Keep Circling Around

If you lead people, there’s probably a conversation you’ve been putting off. You may have heard the term, crucial conversations. These are the ones that you have to become a better leader and communicator.

The person you need to have that coaching conversation is waiting, but doesn’t know how to take the first step either. It might be about missed deadlines, poor attention to detail, tension on the team, or a tone that’s quietly draining energy from the room. You’ve seen it. Thought about it. Rehearsed how to bring it up. And still—nothing.

You may be just trying to protect the relationship. You’re hoping it resolves itself. You’re not alone—avoiding difficult conversations is one of the most common leadership traps.

But here’s the truth:

It’s not the person you’re avoiding. It’s the discomfort.

And when leaders avoid discomfort? That silence becomes part of the culture.

Why Avoiding Difficult Conversations Becomes the Default

Most leaders don’t avoid hard conversations because they don’t care. Quite the opposite—they care so much that they fear doing it badly.

You might have said:

“I don’t want to make it worse.”
“They’re going through a lot already.”
“Maybe it’ll sort itself out.”

And if you’re empathetic, the challenge intensifies. You feel what others might feel. But while empathy is a strength, avoiding performance conversations to preserve comfort doesn’t build trust—it creates confusion.

It also slowly chips away at your leadership communication skills. Be courageous and have those crucial conversations. It’s a skill that will change everything for you.

A Coaching Conversation That Changed Everything

In a former leadership role, I hired someone to run a high-stakes project. They had excellent interpersonal skills and a strong presence in meetings—but behind the scenes, delivery was slipping.

I delayed the conversation. I didn’t want to knock their confidence. Eventually, I said:

“You’ve got great people skills. I’m curious—how’s the technical side of the role going for you?”

That opened everything. They admitted to struggling with tools and structure. We added a bit of support, a quick training plan, and their performance lifted almost instantly.

They later told me how relieved they were to be able to speak openly without fear. That’s the magic of a well-framed, emotionally intelligent feedback moment.

The Problem with “We Need to Talk”

Want to raise red flags? Start with, “We need to talk.”

Better?

“You’ve been doing great work in [X]. I was wondering how [Y] is going for you. Let’s check in and see if anything would help support you better.”

This keeps it kind, curious, and clear. It’s what a coaching-style, psychologically safe conversation sounds like.

And it’s a habit you can build—one brave check-in at a time.

How to Approach Difficult Conversations with Confidence

Here’s a simple coaching framework for leaders who want to improve communication without confrontation:

1. Goal – What’s the outcome you want? Clarity, confidence, or a shift in direction?

2. Reality – What are the observable facts? Stay grounded in what you’ve seen or heard.

3. Options – What could support look like? Training? Clarity? Resources?

4. Way Forward – What’s a clear next step, agreed together?

This isn’t about control. It’s about building clarity and shared ownership.
Here’s how to use this in performance conversations.

When Emotions Arise During Difficult Conversations

Sometimes people shut down, get defensive or they just get quiet. You bring real value to the conversations when you sit with it, let the person process what’s happening with unconditional posiive regards, as we say in the coaching circles.

Allow them the space to feel what they feel. Your job isn’t to rush them through it—it’s to stay present.

Ask:

What’s happening for you? What would help you feel more supported as we talk this through?

You don’t need the perfect answer. Just your presence. And even add that you have been there and tell a story where you weren’t up to the mark, and what you learned from it.
This is what psychological safety at work looks like.

These Conversations Go Upwards Too

You may be just tolerating unclear expectations or a senior leader who’s out of step. Avoiding difficult conversations with your own boss is a silent barrier to progress.

Same tools apply:

Stay focused on shared outcomes
Frame with clarity, not blame
Lead up, as well as down

This is the foundation of emotionally intelligent leadership.

Final Thoughts: Avoiding It Doesn’t Work. Addressing It Changes Everything.

You might be just one conversation away from a performance breakthrough, a stronger relationship and a team that finally trusts what you say. Remember, avoiding difficult conversations isn’t a personality flaw—it’s a skill gap. And it’s totally learnable. So, when you lead with clarity and care, you become the kind of leader who’s safe to speak to—even when the topic isn’t easy.

Want Support Having These Conversations?

I work with leaders who want to lead well, communicate clearly, and build trust without avoiding the hard stuff.

Learn more about the Executive Coach behind this article, based in Dublin, coaching globally!