Difficult Conversations: How to Talk About Hard Things Without Making It Worse
Imagine you’re in a team, and someone keeps forgetting to finish their tasks. Or maybe you’re working hard on a project, but someone else does sloppy work—and you get blamed too. You feel angry, frustrated, or even a little hurt. Now what? Do you say something? Or do you stay quiet?
Difficult conversations are those moments when you think, “Uh-oh… how do I say this without starting a fight?”
Researchers have known for a long time that people aren’t always great at handling conflict. In fact, studies show that more than 85% of employees experience conflict at work. And nearly 30% say that it leads to worse performance—or even stress-related absences (source: CPP Global Human Capital Report, 2008).
Psychologist Friedrich Glasl even created a model for this: the Conflict Escalation Ladder. It shows how a simple disagreement can slowly turn into a full-blown fight if you don’t handle it early and well.
So yes—difficult conversations really matter. But here’s the good news: you can learn how to do them. Just like learning to ride a bike or bake a cake. You just need to follow the steps.
What exactly is a difficult conversation?
A difficult conversation usually means:
- You need to say something that feels scary (like giving criticism)
- You might hear something that hurts (like receiving feedback)
- Emotions are running high (anger, stress, sadness)
- Something important is at stake (like your job, your trust, or a relationship)
And the truth is: if you don’t handle it right, it often gets worse. People go on the defensive—or they shut down completely. And then… the real conversation never happens.
How to have difficult conversations: the basics
You can absolutely learn to have difficult conversations. Here are some basic tips to help you get started:
Start with yourself
If you’re angry or stressed, pause. Breathe. Don’t talk when your mind is stormy. You’ll say things you don’t mean.
Listen actively
Not just with your ears, but with full attention. It’s called active listening. You show the other person you’re really hearing them. Ask questions. Repeat what you heard. Want to learn how?
Be clear and kind
Say what you mean, but say it with respect. Don’t say: “You’re always messing things up!” Try: “I noticed the work isn’t finished. What’s going on?”
Look at the big picture
It’s not always just about “the one mistake.” It’s often about feelings, expectations, or confusion. That’s where Glasl’s Escalation Ladder can help.
Difficult Conversations: an example of addressing underperformance
The situation: Your colleague has submitted late and sloppy reports three times. You’re now doing extra work to cover.
How to say it: “Hey Sam, got a moment? I wanted to talk about something. I’ve noticed the last few reports came in late and unfinished. That’s meant I’ve had to do extra work to complete them. I get that things are busy—what’s going on? Can we find a way to fix this together?”
Why this works:
- You don’t blame—you describe the impact
- You invite a real conversation
- You offer to work on a solution together
Difficult Conversations: an example of confronting sloppy work
The situation: A team member delivers incomplete work without talking to you or asking for help.
How you might approach it: “Hi Lisa, can I share something with you? I saw that your part of the presentation wasn’t finished as we agreed. That surprised me a bit. Did you not have enough time? I’d like to understand what happened and see how we can get it back on track together.”
What you’re doing here:
- You stay totally calm
- You check your assumptions
- You keep the door open for collaboration
Tools that help with difficult conversations
At Toolshero, we’ve collected tons of methods and models to help you with conversations like this. Here are a few that are super useful:
7 Quick Tips for Better Conversations
Having difficult conversations is stressful, but with the right approach, it becomes a lot easier. These tips will help you to approach the conversation clearly and respectfully.
- Prepare, but stay flexible and open
- Start with your intent: “I want to talk about this because I care about our work together”
- Use “I” statements: “I’ve noticed…” instead of “You always…”
- Ask open questions: “How do you see it?” instead of “Why did you do that again?”
- Allow silence: Let people think. You don’t have to fill every pause
- Summarize: “So if I understand you correctly…”
- End with an action: “What can we agree on for next time?”
Final thoughts: difficult conversations are actually growth moments
They feel hard, yes. But they’re also your chance to grow, learn, understand, and connect better. And once you see it that way, they stop being something to fear.
So next time you get nervous about a talk you need to have, think this: “This is practice. I don’t have to be perfect—just honest, calm, and open.”
What’s one difficult conversation you’ve been avoiding? And what would happen if you tried? Share your experience and knowledge in the comments box below.
More information about the topic: Difficult Conversations
- CPP, Inc. (2008). Workplace conflict and how businesses can harness it to thrive: CPP Global Human Capital Report. CPP, Inc.
- Glasl, F. (2011). Conflict management: A practical guide to developing negotiation strategies. Verlag Freies Geistesleben.
- Patterson, K., Grenny, J., McMillan, R., & Switzler, A. (2012). Crucial conversations: Tools for talking when stakes are high (2nd ed.). McGraw-Hill.
- Rosenberg, M. B., & Chopra, D. (2015). Nonviolent communication: A language of life: Life-changing tools for healthy relationships. PuddleDancer Press.
How to cite this article:
Van Vliet, V. (2025). Difficult Conversations. Retrieved [insert date] from Toolshero: https://www.toolshero.com/blog/difficult-conversations/
Original publication date: 08/07/2025 | Last update: 08/07/2025
Add a link to this page on your website:
<a href=”https://www.toolshero.com/blog/difficult-conversations/”>Toolshero: Difficult Conversations</a>
Vincent van Vliet
Vincent van Vliet is co-founder and responsible for the content and release management. Together with the team Vincent sets the strategy and manages the content planning, go-to-market, customer experience and corporate development aspects of the company.
Related ARTICLES
Winners Triangle and Drama Triangle: the Basics
Thomas Kilmann Model of Conflict: the Basics and Test
ABCD model for de-escalation and control
Glasl’s Nine Stages of Conflict Escalation model
