The Mistakes You’re Making in Difficult Workplace Conversations (Without Realising It)

We all know that awkward feeling when it comes to difficult conversations.

A conversation you’ve been deliberately postponing because you are dreading having it. Feedback you need to give, a boundary you need to set or explaining some tension you can’t ignore any longer.

Difficult conversations are unavoidable at work, yet sometimes we avoid them for too long (or forever!). We rehearse meetings in our heads instead of saying things out loud.   We prepare our arguments, choose our wording carefully and still sometimes walk away thinking, ‘that didn’t land the way I intended’.

Difficult Conversations Start Before Words Are Spoken

The reason is often not in the problem of what we say, but how we behave while saying it.

Most people think a difficult conversation begins when the sensitive topic comes up. In reality, it begins much earlier. It starts with how we prepare in advance. It’s in where we meet, how we enter the room, how we sit down and how we behave. The interaction starts before anything meaningful is said.

We often approach difficult conversations in ways that make them harder than necessary. Not because we mean to. But because we focus on the wrong things.

In my work with helping professionals and leaders, one pattern consistently emerges: difficult conversations in business rarely fail because of bad intentions; they fail because unconscious behaviour goes unnoticed. This is where I help people build awareness and deliberately change how conversations unfold.

Five Patterns That Make Difficult Conversations Harder

Based on what I see in organizations every day, here are some of the most common mistakes people make in difficult conversations and what helps instead.

1. You focus on what you want to say, not how you show up

It’s very important to prepare for difficult conversations. Most people do this by carefully choosing their words and the facts or opinions that need to be addressed. That makes sense, but it’s only one part of the picture.

Your tone of voice, posture, facial expression and timing often communicate more than the content itself. If your non-verbal behaviour doesn’t match your words, the message won’t land. Before the conversation, ask yourself: ‘How do I want to come across? Calm? Curious? Firm but open?’

Your approach also depends on the person you are dealing with. You should adapt to the person in front of you, rather than using a one-size-fits-all response. This could mean adjusting your tone, pace or language. An awareness of your own signals, verbal and non-verbal behavior, is one of the most powerful tools in difficult conversations.

2. You focus on the outcome instead of the interaction

People often believe that others must understand, must agree and that everything must be resolved immediately, but this does not help the conversation. Others can feel this pressure, the unspoken ‘must’. It shows through wording, tone and pacing and it often creates resistance rather than understanding.

A more effective starting point is curiosity: ‘What is happening between us right now?’ This creates space for listening rather than control. It helps de-escalate tension and keeps the exchange grounded in the present moment. You need to stay focused in the present moment because difficult conversations are not transactions: they are interactions.

3. You underestimate the role of comfort

When people feel uncomfortable, their behavior changes. They interrupt, withdraw, get emotional or become rigid. That doesn’t mean they’re unwilling; it often means they’re under stress or pressure. When people feel physically and mentally at ease, they listen more effectively, respond more openly and think more clearly.

I often say, ‘The best conversations take place with comfort for both parties,’ and this is something we should actively work on. People don’t communicate clearly when they don’t feel comfortable, including you.

Creating a sense of safety doesn’t mean avoiding the issue. It means being clear but also respectful. You can do this, for example, by:

• not responding immediately
• naming tension when you feel it or observe it
• staying present when it gets awkward
• giving yourself and the other person room to think and react

It’s important to pay attention to the setting, timing and your own state before starting a difficult conversation. If you don’t feel comfortable in their office, maybe you can meet on neutral grounds. If tension rises, you might want to have a coffee break.

Creating comfort doesn’t mean the conversation becomes easy. It means there is enough safety to stay present, congruent and real.

4. You try to “win” instead of understanding

Many difficult conversations turn into debates. Who’s right, who’s wrong or whose perspective is more important. The moment people see winning as the goal, listening stops, and that’s not an effective way of communicating.

Understanding doesn’t mean agreeing. It means genuinely wanting to know how the other person experiences the situation, even if that perspective surprises you or challenges your own.

That curiosity alone can change the entire conversation. It shows in asking thoughtful questions and truly listening. In tense situations, our brain is quick to fill in the blanks: ‘They are defensive. They don’t care. They won’t listen anyway’.  Those assumptions often influence how you enter the conversation, without you noticing.  Difficult conversations become easier when you replace assumptions with observation and listening. You can do this by asking questions like, ‘Can you tell me why you see it that way?, ‘Can you elaborate on that?’ or ‘Why is this important to you?’

When the other person speaks, focus on truly hearing them rather than formulating your reply. Allow their words to land before you respond.

5. You forget to look at your own behavior

When conversations derail, we’re quick to point outward, to that other person or the circumstances around us: ‘They reacted badly. They shut down. They escalated the situation.’

But effective communication starts with self-awareness. What did you signal when the tension rose? Did your voice speed up? Did your posture change? Did you stop listening? Developing awareness of your own behavior can increase the influence you bring into a conversation.

With greater awareness of your own behavior, you can respond better. When you notice that a conversation is not unfolding as intended, adjust your response and then reflect on how that change influences the outcome. The more you are aware of your own behavior, the more influence you can bring into the conversation with that behavior.

Difficult doesn’t have to mean damaging

Difficult conversations are rarely comfortable. But they don’t have to be destructive, either. That means making an effort to have the best conversation possible while reflecting on yourself and observing others.

When you slow down, observe with care and flexibility of both verbal and non-verbal behavior, conversations become clearer and therefore more effective. Difficult conversations don’t require perfect communication; they require awareness of yourself, the other person and what’s happening between you in the moment.

That is where conversations are productive and progress becomes possible.

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