308. How To Have The Tough Conversations You Are Avoiding

Sure, tough conversations may be uncomfortable, but that's why they're called "tough conversations". It's time you learn that they don't have to be tough after all.

Feb 03, 2025

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When it comes to having difficult conversations at work, 70% of employees completely avoid them.

Seventy. Percent.

If you just play the odds, you’re one of those conversation avoiders.

You may even be one of the people who thinks you have tough conversations, but you really don’t. You sit in the meetings, but you never address the issues.

To be clear, avoiding tough conversations isn’t just a thing done by junior-level folks. It’s everybody.

Leaders are avoiding tough conversations with their direct reports, employees are avoiding talking to their bosses and most people are avoiding difficult conversations with their colleagues.

As Captain Cliche would say, our workplace culture has become more about “sweeping it under the rug” and less about “laying it all out on the table”.

The Tough Part of Tough Conversations

If you’re not used to them, tough conversations are tough to have.

How’s that for a blatantly obvious insight?
I mean, if the conversations weren’t tough to have they probably wouldn’t be called tough conversations in the first place. It’s right there in the name.

As a leadership coach, I encounter a lot of people (and I mean a LOT - with all caps) who have a tough time with tough conversations.

It happens for a variety of reasons, including:

Fear of conflict
A need to be liked, or,
A lack of confidence in knowing how to have the conversation

Actually, those are the only three reasons why avoiding difficult conversations happens. 70% of all workers suffer from one of those.

Which one is your downfall?

Whatever your reason, I gotchoo.

You are a good person and you deserve to be better at having these conversations.

So here’s what I’m going to do for you…

By the time you get to the end of this article, you’re not only going to understand why you are avoiding the tough conversations, but you’ll become a master of having them.

Sound good?
Good.

Now let’s talk about your fear of conflict.

Avoiding Tough Conversations Because Of A Fear Of Conflict

Conflict isn’t inherently bad – it’s just uncomfortable.

Being uncomfortable can feel icky. I get it.

Humans are hard-wired to avoid discomfort. That’s the whole basis for the fight-or-flight stuff we have built inside of us. It’s kinda what’s kept us alive for a few million years.

When you fear conflict, it’s just your brain saying “Don’t go in that dark cave, there could be a saber-toothed tiger in there that will bite your face off.”

Your fear of conflict is just trying to protect you from getting mauled.

So pay attention to when you are avoiding conflict. Begin to recognize what it feels like. And when you feel it, here’s what I want you to say to yourself:

“I am safe.
There are no saber-toothed tigers that will bite my face off.
I can have the conversation and I can do it now.”

In truth, tough conversations, if handled correctly, won’t have any conflict anyway. Instead, tough conversations are about jointly solving problems before they spiral out of control.

The first step is reframing them in your mind.

Avoiding tough conversations will create more conflict in the end. To ease your fear of conflict, have the conversation.

Avoiding Tough Conversations Due To A Need To Be Liked

The second reason people avoid tough conversations is because of an ingrained desire to be liked by everyone. The fear is that, by setting boundaries, you will no longer be liked.

Let me be blunt:

If you always want everybody to like you, you’re going to be a horrendous leader. You’ll probably be a pretty crappy parent too.

If tough conversations make people dislike you, then you’re not having the right conversation.

Done correctly, tough conversations will actually increase the amount of respect people have for you.

Avoiding tough conversations will cause people to not like you. So if you want to be liked, have the conversation.

Avoiding Tough Conversations Due To A Lack Of Confidence

Finally, many people just don’t know how to have a tough conversation. I understand that.

Companies don’t teach employees some of the most important business-related skillsets. They don’t teach you how to manage a budget or interview prospective candidates, and they certainly don’t teach you how to have difficult conversations.

They just expect you to be great. Like you’re going to learn the skills through some magical osmosis or something.

It’s ok to not know how to have a tough conversation. That’s why we’re having this easy conversation - to help you with the tough conversations.

Before we get to that, let me tell you 5 of the most common mistakes for you to avoid:

Don’t ramble. State your point and move on.
Don’t be too vague. Be clear on the issues and how they manifest themselves.
Don’t be too blunt and don’t sugarcoat. Stay in the middle ground of being direct but not harsh.
Don’t wait too long to have the conversation. Timing is important.
It’s a conversation, not a monologue. Don’t forget to shut your mouth and listen.

How To Have Tough Conversations

Now that you know WHY you are avoiding the tough conversations, let me spend a few seconds teaching you HOW to have them. It’s a pretty simple six step process. Here we go:

Step 1: Have Purpose

Before the meeting, make sure you know these simple things:

Are you addressing a behavior or giving feedback?
What outcome are you hoping to get?

Imagine you were in the other chair - how would you like to hear the information? How would you like that conversation to happen?

Step 2: Plan. But Don’t Over-Plan.

Be clear on the key points you want to get across.
Make notes but do NOT write a script. The notes are to remind you, not guide you.

It’s all about authenticity. Speak from your heart. Actually, speak from your mouth, but do it with heart.

Step 3: XYZ

Create a safe space from the get-go.
Acknowledge whatever good things you can say to the employee. If you believe in them, let them know you believe in them.

Be relaxed. Don’t forget to breathe.

Then clearly address the problem with the XYZ method

“When you do X, it impacts Y, and I’d like us to do Z.”

Ask them their opinion.

Do they recognize the problem?
Do they have thoughts on how to address it?

Step 4: Shut Up and Listen

Stop talking and let them process the information and respond.

Listen to their response with an open mind. Embrace your curiosity.

Remember, you’re on the same team. Assume that you both have good intentions and nobody is out to sabotage the other.

Step 5: Come To A Resolution

End the conversation with a clear path to resolution and accountability.

What will they do and by when?
What will you do and by when?

Reiterate that your goal is to help them succeed.

Step 6: Follow-Through

As they improve, acknowledge their improvements - even the small ones.

If they don’t improve, help them recognize where it’s not getting better

Schedule a follow-up discussion for you each to talk about how things are going.

The Tough Conversation Is In Your Hands. Or Mouth. Whatever.

You’ve made it this far, which means one of three things:

You’re ready to stop avoiding tough conversations
You just skimmed the article so you can say you read an article about it
You’re hoping there’s a magic pill like Ozempic but for tough conversations.

Sorry to break it to you, but there’s no magic pill. In the end, you kinda only have two options.

Keep avoiding the conversations, pretend the problems don’t exist, and watch it silently destroy your team’s morale and whatever remaining respect they have for you. Or…
Face the discomfort, lean into the tough conversations, and realize it’s not so hard after all to become a better, more respected, and more effective leader.

One of these options leads to growth. The other leads to a whole bunch of bad stuff.

Your call.

So go. Have the conversation. With a little bit of practice, you’ll realize that the tough conversations aren’t so tough after all.

I quickly transform teams into high-performing, collaborative units.
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