How to Have Difficult Conversations (When Your Brain Keeps Talking You Out Of It)

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There’s a conversation you’re avoiding.
You know that.
I know that.
Everybody knows that.

You’ve probably thought about the conversation for a while. Days. Weeks. Maybe longer. Who knows.

You’ve played it out in your head – how it starts, how they might react, what you’d say next. You’ve even gotten close to having the actual conversation a few times. But, alas, something came up, or the moment didn’t feel right, or you decided to give it one more week because you really needed to clip your fingernails instead.

And you still haven’t had the conversation. Which means you still don’t know how to have difficult conversations in a way that actually sticks.

Meanwhile, you’re stuck with the knowledge that needing to have the difficult conversation and knowing how to have difficult conversations are completely different things.

And that’s exactly the reason we’re going to talk right now about how to have difficult conversations.

Let’s start with something most people get completely wrong.

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The Problem Isn’t the Conversation. It’s the Story.

Most advice you’ll get about how to have difficult conversations will tell you the problem is your behavior.
That’s not true.

They’ll tell you that you need better communication techniques or a better framework.
Not true either.

Some fancy framework – or even a specific script – are not the reason why you’re avoiding the conversation.

The reason you’re avoiding the difficult conversation is not because you don’t know how to have difficult conversations – it’s because your Unconscious Operating System has an idea in your mind about what will happen if you have the conversation. Maybe you’re convinced they won’t like you anymore. Or that you’ll say everything wrong and regret it.

There is some story you tell yourself that is all about self-protection. Regardless of whatever framework you’re given, the gravitational pull of self-protection will always win out. That’s the real obstacle to learning how to have difficult conversations – not the words, not the approach, not the timing.

So forget what those other people tell you – the way you’re going to learn how to have difficult conversations isn’t to learn more techniques. It’s to understand and accept the story that your Unconscious Operating System has convinced you about what happens if you have the conversation.

Remember, the story in your head is almost always more catastrophic than reality. Accepting that is where learning how to have difficult conversations actually starts.

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What the Avoidance Actually Costs

Every day you avoid learning how to have difficult conversations, its another day of making the situation worse.

The problem you’re not addressing isn’t like a plant – it doesn’t die off when you ignore it. Avoiding conflict is like an epidemic – the more you ignore the conversation, the bigger the problem grows.

That performance issue that you should’ve addressed in week 2, turns into a PIP conversation by month 4. The misalignment between you and your direct report that needed a 20-minute clarification, becomes a year of frustration, missed deadlines and an eventual resignation.

On top of that, relationships usually deteriorate when difficult conversations are avoided. And when I say “usually,” I mean “always”. You try to act all status quo, but the other person knows something is wrong. That causes a whole bunch of awkwardness with them, which turns into awkwardness with you, which eats away at the relationship like a caterpillar family at a leaf convention.

All the while, you’re going to lose your credibility.

The team notices when you avoid the difficult conversations. Trust me, they do. It doesn’t always seem like it, and they don’t always say it out loud, but they’ll change their perception of you. Over time, your avoidance will define who you are as a leader — and it won’t be the definition you really want.

Soooo… you ready to learn how to have difficult conversations now?

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Why Leaders Avoid Difficult Conversations

There are 3 reasons leaders avoid difficult conversations, and they’re not the reasons you usually hear out loud.

They’re conflict averse and don’t know it. Most leaders who avoid difficult conversations don’t describe themselves as conflict averse. They describe themselves as thoughtful. Maybe even diplomatic. They aren’t the kind of person who creates unnecessary friction. What they’re actually doing is using their “thoughtfulness” as a mask to shield them from having to have difficult conversation. The cost of conflict avoidance in leadership is real, and it accumulates quietly until it isn’t quiet at all.

They’re afraid of damaging the relationship. This one sounds noble. The reality is more complicated. The relationship isn’t protected by avoiding the conversation – it’s being slowly damaged by it. What you’re actually protecting is your fear of not being liked. And what you don’t yet realize is that a leaders job is not to be liked.

They’ve conflated two different things. There’s a difference between a difficult conversation and a destructive one. A difficult conversation is one where you talk directly about something that the other person might not want to hear. A destructive conversation is one where you’re attacking, demeaning, or acting out of anger. Most leaders who avoid difficult conversations are thinking that the destructive version is the same as the difficult version. They’re not the same thing. Not even close.

Any of these sound familiar? Good. Because recognizing which one is the reason for your avoidance is the first real step toward knowing how to have difficult conversations in a way that actually work.

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How to Have Difficult Conversations, For Real

There are techniques worth knowing. But here’s the thing about how to have difficult conversations that most frameworks miss: the techniques only work once you’ve addressed the story first.

Start with the outcome, not the behavior. The conversation goes better when you open with what you’re trying to preserve or achieve, not with what the other person has done wrong. “I want to make sure we’re on the same page about what success looks like here” lands differently than “Here’s what you’ve been doing that isn’t working.” Both conversations need to happen. The first framing makes the second one receivable.

Name the pattern, not the incident. One-time feedback about a specific event is easy to dismiss. Feedback about a pattern is harder to argue with and more useful to the person receiving it. “In the last 3 meetings, I’ve noticed that when someone challenges your numbers, you shut the conversation down” is more actionable than “You were defensive in the meeting yesterday.”

Stay curious longer than feels comfortable. The instinct in difficult conversations is to make your point and defend it. The instinct that produces better outcomes is to be genuinely curious about the other person’s perspective before making yours. Not performatively. Authentic curiosity goes a long way. You might be missing context. That context changes what the conversation needs to be.

Separate the problem from the person. You’re not having a conversation about who this person is. You’re having a conversation about a specific behavior that needs to change. That distinction is incredibly important. Once you make it about the person, you’ll turn a difficult conversation into a destructive one.

Have the conversation sooner than feels right. The right time for a difficult conversation is almost always earlier than feels comfortable. The conversation that could have been a 10-minute check-in becomes a 2-hour reckoning when you wait 6 weeks. Smaller and sooner is almost always better than larger and later.

If you want to learn how to really master difficult conversations, check out the CARE Toolkit and learn why it’s not the conversation, it’s you. Because knowing how to have difficult conversations is one thing. Actually having them is another.

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The Thing Nobody Tells You About Difficult Conversations

Leaders who have made peace with difficult conversations consistently report the same thing: the conversation was almost never as bad as they thought it would be.

The relationship didn’t break. The person didn’t fall apart. Nobody ended up yelling or angry at each other.

People who have figured out how to have difficult conversations are people who realize that difficult conversations can actually be really easy. The sooner the situation gets addressed, the greater the relief on both sides.

In most cases, the other person already knew what was coming – they’d been waiting for someone to just say it out loud.

That’s the important shift in all of this. The most important thing isn’t a communication framework, or a script. It’s an understanding and acceptance of your Unconscious Operating System, and a desire to make things better.

You can do this. Knowing how to have difficult conversations isn’t a personality trait you either have or don’t. It’s a decision you make when the cost of avoiding becomes more uncomfortable than the conversation itself.

I believe in you.

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If the pattern of avoiding difficult conversations feels like something you want to understand better, the Leadership Diagnostic Workshop is a free 90-minute session that explains this type of pattern. Most leaders who come in thinking they need to learn how to have difficult conversations leave understanding what’s actually preventing them from having the ones that matter.

Frequently Asked Questions

Q: What’s the best way to start a difficult conversation?

Start with the relationship, not the problem. Something like: “I want to talk about something that I think is important for both of us, and I want to make sure we stay on the same side of the table while we do.” It signals intent and sets the tone before the hard part starts. Then get to the substance quickly — the longer you delay the actual point, the more tension you create.

Q: What if the other person gets defensive?

Defensiveness is usually fear. The person is protecting something — their competence, their reputation, their sense of self. When defensiveness shows up, get curious before getting firmer. Ask a question. Give them room to tell you what they’re actually worried about. The defensiveness usually drops when they feel heard. Fighting through defensiveness rarely works. Moving around it usually does. In fact, when it comes to how to have difficult conversations, one of the best ways is to proactively reveal your fears to help alleviate the same in others.

Q: Is there a different way how to have difficult conversations with someone senior to me?

The same way, but with more explicit framing about your intent. “I want to raise something that I’ve been sitting on, and I want to do it in a way that’s useful to you.” Most senior leaders respect directness more than people assume. The bigger risk is usually being too indirect, not too direct. Frame it as useful information, not a complaint.

Q: What if the conversation doesn’t go well?

It rarely ends as badly as the anticipation suggested it would. But when it does go sideways, the most useful move is to name it: “I don’t think this conversation is going the way either of us wanted. Can we take a step back?” Most conversations that derail can be recovered if someone is willing to acknowledge the derail. That someone is usually you. That’s why learning how to have difficult conversations is so important.

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Jeff Matlow is a leadership coach, mentor and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.