Why Difficult Conversations Go Wrong (and How Managers Can Change the Outcome)

Even after years of studying difficult conversations, I still don’t like having them. 

Whether you're addressing poor performance, resolving tension between colleagues, or working through competing priorities, these discussions can feel uncomfortable before they even begin. Often, we rehearse what we'll say, anticipate resistance, and brace ourselves for conflict long before we sit down with the other person.

Ironically, that preparation may be one of the reasons these conversations don't go as planned.

According to leadership coach Victoria Rennoldson, we rarely enter challenging conversations with a clean slate. We bring assumptions, past frustrations, and emotional baggage that shape how we listen, respond, and interpret what the other person says. The good news is that managers can learn to recognize these influences and create conversations that build understanding instead of deepening conflict.

The Hidden Weight We Bring Into Every Difficult Conversation

Most workplace conflicts aren't difficult simply because people disagree. They're difficult because every person arrives carrying their own experiences.

Victoria explains that past disagreements, cultural influences, organizational norms, and even family dynamics all shape how we think about conflict. Some people naturally avoid it. Others see it as an opportunity to prove a point. Neither approach necessarily leads to productive outcomes.

As managers, Victoria urges us to ask ourselves an important question before any difficult conversation:

Am I reacting to what's happening today or to everything that's happened before?

If this is the third or fourth conversation you've had with someone about the same issue, it's easy to walk in expecting another frustrating exchange. Unfortunately, those expectations often become visible through your tone, body language, and assumptions before the conversation has even started.

Taking time to reset emotionally isn't about pretending the past didn't happen. It's about making sure previous experiences don't prevent you from hearing what's actually being said today.

Clarify Your Intention, Not Just Your Goal

Most of us prepare for difficult conversations by focusing on the outcome we want such as improved performance, acceptance of feedback, commitment to a decision, or changing a behavior.

Those goals matter. But according to Victoria, they're only half the picture.

Before the conversation begins, it helps to consider another question:

How do I want this person to leave this conversation feeling?

That shift changes everything.

Instead of viewing the discussion as something to "win," Victoria suggests you begin thinking about preserving trust, strengthening the relationship, and ensuring the other person feels respected, even if the conversation itself is uncomfortable.

When managers focus only on getting agreement, they often damage the relationship they're trying to improve. When they balance results with empathy, they're far more likely to achieve both.

Your Environment Shapes the Conversation

Managers spend a great deal of time thinking about what they'll say, but far less time thinking about where they'll say it.

Yet, notes Victoria, the environment can have a surprisingly powerful influence on how people communicate.

If every difficult discussion takes place across a conference table in the same meeting room, the setting itself can reinforce an adversarial dynamic. Victoria points out that sitting directly opposite one another can unintentionally make the conversation feel like a negotiation rather than a collaboration.

Sometimes a small change is enough to shift the tone.

Meeting at the corner of a table instead of directly across from each other, taking a walking meeting, grabbing coffee, or even choosing a phone call instead of a video meeting are all ways Victoria identifies that can reduce tension and help both people engage more openly.

The goal isn't to make the conversation less serious. It's to make it easier for both people to think clearly instead of becoming defensive.

Don't Assume the Other Person Is Ready

One of the simplest, and most overlooked questions managers can ask is

"Are you ready to have this conversation?"

Victoria underscores that just because you've scheduled a meeting doesn't mean the other person is emotionally prepared to have a productive discussion.

They may still be processing a previous interaction. They may be dealing with personal challenges you know nothing about. Or they may simply need more time before they're able to engage constructively.

If the answer is no, rescheduling isn't avoiding the issue. It's increasing the likelihood that the conversation will actually accomplish something when it does happen.

Giving people space often leads to better conversations than forcing immediate resolution.

Listen Before You Solve

Managers are natural problem solvers.

Unfortunately, that strength can become a weakness during conflict. We often spend so much time preparing our own points that we forget to fully understand the other person's perspective.

Curiosity should come before persuasion, says Victoria.

Open questions like "Can you tell me more about your perspective?" or "What's been influencing your thinking?" create room for understanding rather than defensiveness.

More importantly, genuine listening helps uncover something many managers miss: sometimes people aren't actually working toward the same goal.

Victoria highlights that when both sides define success differently, no amount of debating will resolve the disagreement.

Only after those underlying goals become visible can people begin working toward a shared solution.

Look for a Third Option

Many workplace disagreements become trapped in either-or thinking.

Either we choose my solution or yours.

Either we move forward or we stop the project.

But effective managers know that innovation often begins by challenging those assumptions.

Victoria offers that instead of asking which option should win, try asking:

"What would it look like if we combined the strongest parts of both ideas?"

Often the best solution isn't replacing one idea with another. It's building something neither person had considered before.

Even if a complete solution isn't immediately obvious, agreeing on one small experiment or next step can move the conversation forward without requiring either person to fully commit before they're ready.

Better Conversations Start Before the Conversation

Managers often believe difficult conversations succeed because they choose the right words.

In reality, success usually depends on everything that happens beforehand.

Managing your emotions. Clarifying your intentions. Creating the right environment. Making sure the other person is ready. Listening with genuine curiosity. Looking for shared solutions instead of victories.

None of these steps eliminate conflict.

But they transform conflict from something to avoid into an opportunity to strengthen relationships, improve collaboration, and make better decisions together.

For managers, that's a skill worth practicing, because every difficult conversation handled well builds trust that makes the next one a little easier.

Watch or listen to the full interview here.

Keep up with Victoria Rennoldson

- Connect with Victoria on LinkedIn: https://linkedin.com/in/victoria-rennoldson

- Listen to the Cultural Communication Confidence podcast: https://culturecuppa.com/podcast

- Check out her book Become a Global Leader: https://culturecuppa.com/book

- Visit the Culture Cuppa website: https://culturecuppa.com/

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The Modern Manager is a leadership podcast for rockstar managers who want to create a working environment where people thrive and great work gets done.

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