33. 3 Reasons Difficult Conversations Go Wrong (And What to Do Instead)

One of the hardest skills we're never taught? How to have difficult conversations well. So we put them off… until they're living rent-free in our heads. When we finally do have them, we wing it, things get awkward or defensive, and we end up avoiding them even more next time.

But every difficult conversation is actually three conversations happening at once. When you understand what they are, you stop treating hard conversations like a minefield, and start approaching them with more clarity and control.

What is a difficult conversation?

You usually know it by how it feels.

The dread, the rehearsing in your head, the hoping it just resolves itself. Most people walk away from difficult conversations feeling worse — and so does the other person. The relationship takes a hit, and nobody is quite sure what a “good” outcome was meant to look like.

What’s missing is a North Star.

Most people go into difficult conversations with one goal: avoid a terrible outcome. But trying to avoid something is not the same thing as knowing what you are trying to create. Without clarity, you are just hoping for the best.

Difficult conversations do not have to end badly. It’s possible to come out the other side with the relationship intact, or even stronger. But that requires a different approach than most of us have been taught.

The framework that helps

This breakdown comes from Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen (Harvard Negotiation Project). Their insight is simple and powerful: negotiation is, at its core, a difficult conversation, and the same dynamics show up everywhere.

Their core idea is this:

You are never having just one conversation. You are having three.

Conversation 1: The “What Happened?” Conversation

This is where most difficult conversations derail before they really begin.

On the surface, it seems straightforward: “We are here because of X.” But the other person thinks you are here because of A, B, and C. You do not fully agree on what happened, even when you are talking about the same event.

That’s because we all fall into three common traps.

1) The truth trap: “I’m right, you’re wrong”

We treat our version of events like it has been ruled on by the International Court of Justice.

But difficult conversations are rarely about objective facts. They are usually about perceptions, interpretations, and values. The same incident can land completely differently depending on someone’s background, context, or cultural lens.

A better move than arguing over who is right is to get curious about how the other person made sense of what happened.

Share your interpretation, then invite theirs.

2) The intention trap: “I know why you did that”

We assume we know what the other person meant, and those assumptions shape everything: how we feel, how we speak, and whether we come in defensive, suspicious, or angry.

The problem is that intentions are invisible, so we are often guessing. And to make it trickier, people are not always clear on their own intentions in heated moments. Someone can react in a way they do not fully understand themselves.

If you’re not careful, you can make a hard conversation much harder by projecting intentions that were never there.

3) The blame trap: “Whose fault is this?”

Blame turns the conversation into a binary game: hero vs villain, right vs wrong.

Once someone feels blamed, they stop engaging with the problem and start defending themselves.

A more useful shift is from blame to contribution:

• How did each of us contribute to getting here?
• What can we do differently going forward?

When one person names their part, it often gives the other person permission to do the same.

Conversation 2: Feelings

Many people try to skip feelings entirely, especially at work.

Feelings can seem unprofessional, risky, or like opening a door you will not be able to close. And sometimes, strategically, it genuinely makes sense not to centre feelings in the conversation.

But other times, if you skip the feelings, you miss the point.

I’ve seen this play out in my own life. A disagreement that looks like it’s about something small, like laundry, is rarely about the laundry. One person is talking about clothes being put away, but underneath it’s about feeling unappreciated, overlooked, or like you don’t have a say. Until someone names what’s happening emotionally, the same argument just repeats in different forms.

This happens in workplaces too. People argue about process or decisions when what’s really underneath is feeling disrespected, overlooked, or unsafe.

Feelings are not a soft extra. Often, they are the actual issue.

Conversation 3: Identity

This one is the most subtle, and often the most powerful, because it runs under everything else.

The identity conversation is about what this situation means about who you are.

For each person, something beyond the topic is at stake: competence, fairness, being a good leader, being kind, being respected, being independent.

This shows up all the time for leaders.

You may see yourself as kind and fair, someone who wants the best for your team, and now you have to give hard feedback, enforce a boundary, or make a decision that will upset someone. Those two truths can feel like they cannot coexist. That tension can lead you to soften the message too much, hesitate, or avoid the conversation entirely.

And the other person has an identity at stake too. If they feel their competence or value is being questioned, they may become defensive, shut down, or push back.

Noticing the identity layer does not make it disappear, but it gives you more compassion and more control.

Next steps

Awareness is the starting point. Before your next difficult conversation, take a moment and run through the three layers:

1. What’s my version of what happened, and how might theirs be different?
2. What am I assuming about their intentions, and could I be wrong?
3. Is there something emotional underneath this that needs to be acknowledged?
4. What’s at stake for my identity here, and what might be at stake for theirs?

This changes your posture going in.

Instead of arriving with a message to deliver, you arrive ready to have an exchange. Instead of trying to prove you are right, you try to understand. And instead of telling someone what their story is, you share the story you currently have, and give them space to correct it.

That’s the difference between a difficult conversation that damages a relationship, and one that can actually repair it.

If you want to go deeper into this framework and hear real examples of how it plays out, listen to the full episode. And if you’re navigating a difficult conversation right now, email me at [email protected] to share what’s going on.