Dreading that conversation with a colleague? Your stomach’s already in knots. But here’s the thing—avoiding it won’t make it disappear. In fact, it usually makes things worse.
I’ve had plenty of difficult conversations go sideways, and I’ve learned exactly what NOT to do. More importantly, I’ve figured out the approach that actually works: one that preserves the relationship while solving the real problem.
The Cost of Avoiding Difficult Conversations
Avoidance is comfortable in the moment. But it’s expensive long-term. Research shows that employees who feel unable to have honest conversations are 2.2 times more likely to leave their jobs. That’s not just a morale issue—that’s retention bleeding out.
When you avoid a difficult conversation, the problem doesn’t shrink. It grows. Resentment builds. Misunderstandings multiply. And by the time you finally address it, you’re dealing with a crisis instead of a conversation.
Here’s what I’ve discovered: the difficulty isn’t in the conversation itself. It’s in the fear leading up to it.
The Psychology of Difficult Conversations
Before you even open your mouth, your brain is working against you. It’s running worst-case scenarios. Your colleague might get defensive. They might cry. They might get angry. They might tell everyone what you said.
All of these catastrophes live in your head, not in reality. And they’re keeping you stuck.
Here’s the truth: Most people respond well to conversations when they’re approached with genuine intent, clarity, and respect. When you show up as someone trying to improve the situation (not punish or blame), people usually meet you there.
The Framework: 5 Steps to Difficult Conversations That Work
Step 1: Prepare Like You Mean It
Don’t wing this. Preparation is 80% of the battle.
Why: When you’re prepared, you’re calm. Calm people communicate better.
What to do: Write down exactly what you want to say. Not a script (that sounds robotic), but the key points:
- What’s the specific issue? (Be concrete, not vague)
- Why does it matter? (What impact has it had?)
- What outcome do you want? (Change behavior, clarification, repair the relationship?)
- What are you willing to compromise on?
Example: Instead of “You’re always undermining me in meetings,” write down: “In the last three meetings, when I’ve proposed ideas, you’ve said things like ‘that won’t work’ without asking questions first. This makes it harder for me to build confidence in front of the team. I’d like us to discuss ideas together before shutting them down.”
Benefit: You sound reasonable because you are. You’re prepared.
Step 2: Choose Your Timing and Setting
Location matters. Timing matters. A lot.
Don’t have this conversation:
- When either of you is rushed
- In front of an audience
- When emotions are peak-high
- Over email or chat
Do have it:
- In a private, neutral space (not your office—that’s power-dominant)
- When you both have 20-30 minutes minimum
- When you’re both calm
- Face-to-face if possible
Example opening: “I wanted to talk about something that’s been on my mind. Do you have 30 minutes this week to grab coffee? There’s nothing to worry about—I just want to clear the air on something.”
Benefit: You’re signaling this is important and respectful.
Step 3: Start With Empathy, Not Criticism
Your opening sets the tone for everything else.
Instead of: “I need to talk about how you’ve been handling the project.”
Try: “I’ve been thinking about our working relationship on the XYZ project, and I realize we might not be on the same page. I know you care about doing good work, and so do I. Can we talk about what’s not working?”
See the difference? The second one signals that you respect them AND there’s an issue to solve together.
Benefit: You’re inviting collaboration, not confrontation.
Step 4: Use “I” Language and Specific Examples
Vague criticism creates defensiveness. Specificity creates understanding.
Vague: “You don’t listen to me.”
Specific: “On Tuesday, when I mentioned the timeline concern, I felt like it wasn’t heard because the response was about budget instead of timeline. That made it hard for me to move forward.”
Notice: You’re describing impact and feelings, not attacking character. This is crucial.
Benefit: They can actually respond to what you’re saying, not defend against vague accusations.
Step 5: Listen More Than You Talk
This is where most people mess up. They deliver their piece and leave. But this is a conversation, not a speech.
After you’ve shared your perspective, actually ask: “What’s your take on this?” Then shut up and listen. Really listen.
They might have context you’re missing. They might agree with parts and push back on others. Either way, listening shows respect and often resolves the issue faster because they feel heard.
Benefit: You might learn something that changes your approach.
Common Pitfalls (And How to Avoid Them)
Pitfall 1: Getting Defensive When They Get Defensive
Them: “Well, you weren’t clear about the deadline!”
Your Brain: “Are you kidding me? I sent THREE emails!”
Stop. Pause. Breathe. Then say: “I hear you. Help me understand what you need from me to be clear next time.”
Pitfall 2: Bringing Up Old Stuff
Keep it about THIS issue. Not the April incident. Not the thing their friend said. Now.
Pitfall 3: Assuming You Know Their Intentions
You: “You deliberately excluded me from that meeting to make me look bad.”
Reality: Maybe they forgot. Maybe they thought you were in another meeting. Don’t assume.
How to End On a Good Note
Even if the conversation is awkward or tense, end with clarity:
- What did you agree on?
- What’s the next step?
- When will you check back in?
Example closing: “So it sounds like you didn’t realize how X was landing with me, and I understand now that you were coming from Z. Let’s agree to flag issues sooner instead of letting them build. Can we touch base in two weeks to see how this is going?”
FAQ: Difficult Conversation Questions
Q: What if they get angry?
A: Stay calm. Validate without giving in: “I see you’re upset. That’s okay. Let’s take a break and come back to this.” Anger often passes once they feel heard.
Q: What if they deny the issue?
A: Stick to facts: “I can show you the emails/chat history.” But be prepared that denial might mean you need to involve a manager or HR.
Q: What if nothing changes?
A: Document the conversation. If behavior doesn’t improve, escalate to your manager. You did your part.
Q: Is this conversation going to ruin our working relationship?
A: Probably not. Ignoring problems ruins relationships. Addressing them strengthens them.
The Real Truth About Difficult Conversations
After every one of these conversations I’ve had, I felt this sense of relief. Like a weight lifted. Because when you address something directly—with respect and clarity—the awkwardness disappears. The relationship improves or stabilizes. And most importantly, you can move forward.
The conversation you’re dreading right now? It’s probably not as difficult as your mind is making it out to be.
Your turn: What difficult conversation have you been avoiding? Share in the comments—I’d love to help you think it through.
