What makes conversations difficult?

According to the book "Difficult Conversations" by Stone, Patton, and Heen, challenging conversations involve three layers: the "what happened" conversation (facts), the "feelings" conversation (emotions), and the "identity" conversation (what this says about us).

Examples include: telling someone their performance isn't meeting expectations, addressing a colleague's behavior that's affecting the team, giving notice to your employer, or saying no to a request from your boss.

The difficulty comes from fear: fear of hurting the relationship, fear of retaliation, fear of being wrong, or fear of how we'll be perceived. These fears cause us to avoid, sugarcoat, or fumble important conversations.

Why we avoid them (and shouldn't)

Avoiding difficult conversations feels safer in the moment but creates bigger problems later. Unaddressed issues fester, resentment builds, and what could have been a small correction becomes a relationship-ending blowup.

→Problems compound. The longer you wait, the worse it gets. Small issues become big ones.
→Silence implies acceptance. If you don't speak up, people assume there's no problem.
→Your reputation suffers. People notice when leaders avoid conflict. It erodes respect.
→Relationships deepen through honesty. Counterintuitively, having hard conversations often strengthens relationships.

Signs you're avoiding a needed conversation

🚨 You're venting to others instead of addressing the person directly

🚨 You're hoping the situation will resolve itself

🚨 You're waiting for the "right time" that never comes

🚨 You're mentally rehearsing arguments in the shower

🚨 You feel tension around someone you should feel comfortable with

How to prepare

1. Get clear on your goal

What outcome do you actually want? "I want them to stop doing X" is clearer than "I want to tell them how I feel." Focus on the future, not relitigating the past.

2. Separate facts from stories

"You missed the deadline" is a fact. "You don't care about this project" is a story you've told yourself. Stick to observable facts.

3. Consider their perspective

What might they say? What pressures are they facing? Empathy doesn't mean agreement—it means understanding. You'll be more effective when you see their side.

4. Choose the right setting

Private, neutral, unrushed. Not in passing, not in a group, not at the end of a long day. Give the conversation the space it deserves.

5. Open with shared purpose

"I want us to work well together" or "I care about this relationship" sets a collaborative tone. You're not adversaries—you're two people solving a problem.

Common mistakes to avoid

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Leading with blame

"You always..." or "You never..." triggers defensiveness instantly. Start with curiosity, not accusations.

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Sandwiching

Fake positives around criticism ("Great work, but...") feels manipulative. Be direct.

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Letting emotions take over

If you're too emotional, wait. Venting feels good but damages trust. Cool down first.

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Having the conversation by email

Tone is lost in text. Difficult conversations deserve face-to-face (or at minimum, video).

Techniques for tough moments

1When they get defensive: Acknowledge their feelings. "I can see this is hard to hear. I'm not trying to attack you—I want us to figure this out together."
2When they deny: Stay factual. "I understand you see it differently. Here's what I observed..." Don't argue about intent—discuss impact.
3When you're triggered: Pause. "I need a moment to think." Breathe. Don't respond from anger.
4When it's going nowhere: Suggest a break. "Let's both think about this and continue tomorrow." Sometimes distance helps.

Practice before the real thing. Skillbase lets you rehearse difficult conversations—from performance reviews to conflict resolution—with AI that responds realistically, so you're prepared when it counts.

Try difficult conversation scenarios

Frequently asked questions

How do I start the conversation?▼

Be direct but warm: "There's something I've been wanting to discuss with you. Is now a good time?" or "I'd like to talk about [topic]. My goal is to understand your perspective and share mine."

What if they react badly?▼

Give them space to react. Don't try to fix their emotions or argue. Acknowledge: "I can see this is upsetting." Sometimes people need time to process. You can always pause and continue later.

How do I stay calm when I'm nervous?▼

Prepare thoroughly—nervousness often comes from uncertainty. Breathe slowly before and during. Remind yourself of your positive intent. Accept that discomfort is part of the process.

What if the relationship is damaged anyway?▼

Sometimes that happens, but avoiding the conversation would have damaged it too—just more slowly. At least now you have the information you need to decide how to move forward. And often, relationships strengthen after honest conversations.

Key takeaways

✓ Avoiding difficult conversations makes them harder, not easier
✓ Separate facts from the stories you tell yourself
✓ Start with curiosity and shared purpose
✓ Focus on the future, not relitigating the past
✓ Practice makes these conversations easier

Difficult conversations: the complete guide

⚡ Quick answer