Managing Difficult Conversations

The Conversations Nobody Wants to Have

In the previous lesson, we built conflict resolution skills for team disputes. Now let’s build on that foundation with the conversations that define your leadership: the ones you’d rather avoid entirely.

Telling someone their performance isn’t cutting it. Announcing layoffs. Explaining why someone didn’t get promoted. Addressing personal hygiene. Navigating a tearful reaction.

These conversations test everything you’ve learned about trust, feedback, and conflict resolution—under maximum pressure.

The Difficult Conversation Framework

Before: Prepare

1. Clarify your objective. What specific outcome do you need?
2. Gather facts. What evidence supports the conversation?
3. Anticipate reactions. How might they respond? (denial, anger, tears, silence)
4. Plan your opening. Write the first two sentences.
5. Choose timing and setting. Private, adequate time, not Friday at 5 PM.

AI: I need to have a difficult conversation with a team member about [situation].

Help me prepare:
1. What's the clearest way to state the issue in 2 sentences?
2. What facts and examples should I reference?
3. What are 4 likely reactions and how should I handle each?
4. What outcome should I aim for?
5. What should I avoid saying?

During: Execute

The Direct Approach:

1. State the topic. “I need to talk with you about your performance on the X project.”
2. Share the facts. “Over the past month, three deliverables were late and the client escalated twice.”
3. Explain the impact. “This is affecting the team’s credibility with the client.”
4. Listen. Pause. Let them respond.
5. Discuss next steps. “Here’s what I need to see change, and here’s how I can support you.”

After: Follow Through

• Document the conversation
• Schedule a follow-up
• Check in on the person’s wellbeing
• Monitor for changes

Scenario: Performance Improvement

When a team member is consistently underperforming:

Don’t: Wait until the annual review, collect a folder of evidence, and surprise them.

Do: Address performance issues early and regularly. If a formal improvement plan becomes necessary:

AI: I need to put a team member on a performance improvement plan.

Situation: [describe underperformance]
Previous feedback given: [when and what]
Duration of the issue: [how long]

Help me:
1. Draft the opening of this conversation
2. Structure specific, measurable improvement goals
3. Set a realistic timeline
4. Define what support I'll provide
5. Be clear about consequences without being threatening

Quick Check

You need to tell a well-liked team member that they’re not getting the promotion they expected. They’ve worked hard but aren’t ready for the next level. How do you open this conversation?

Scenario: Delivering Bad News

Layoffs, budget cuts, project cancellations—sometimes you deliver news you don’t agree with yourself.

Principles:

• Be direct. Don’t soften the news so much that the message gets lost.
• Be human. Acknowledge the difficulty and emotional impact.
• Be honest. If you can explain the reasoning, do so. If you can’t, say so.
• Be specific. What exactly is happening? What are the next steps? What support is available?

What NOT to say:

• “This is harder for me than it is for you.” (It isn’t.)
• “Think of this as an opportunity.” (Not helpful right now.)
• “Everyone is going through this.” (Minimizes their experience.)

Scenario: Emotional Reactions

When someone cries, gets angry, or shuts down:

If they cry:

• Offer a tissue and a moment. Don’t rush.
• “Take whatever time you need.”
• Don’t pretend it’s not happening.
• Continue the conversation when they’re ready.

If they get angry:

• Stay calm. Don’t match their energy.
• “I can see you’re frustrated. That’s understandable.”
• Focus on facts, not emotions.
• Offer a break if needed.

If they go silent:

• Don’t fill the silence. Give them space to process.
• After a reasonable pause: “What are you thinking?”
• They may need time and a follow-up conversation.

Using AI to Rehearse

Before any difficult conversation, practice:

AI: Let's role-play a difficult conversation.

Situation: [describe]
You play [the other person]. Be realistic—push back, show emotion, ask tough questions.

I'll practice my delivery. After each exchange, briefly coach me on:
- Was I clear enough?
- Was I empathetic?
- Did I stay on track?
- What would be more effective?

Let's start. I'll open the conversation.

Building Courage for Hard Conversations

The discomfort never fully goes away. But it gets manageable:

• Remind yourself of the cost of avoidance. What happens if you don’t have this conversation?
• Prepare thoroughly. Anxiety decreases with preparation.
• Practice with AI. Rehearsal builds confidence.
• Focus on the person, not your discomfort. They deserve clarity and honesty.
• Debrief afterward. Reflect on what worked and what you’d change.

Exercise: Prepare a Difficult Conversation

1. Identify a conversation you’ve been avoiding
2. Use the framework to prepare (objective, facts, reactions, opening)
3. Rehearse with AI in role-play mode
4. Refine your approach based on AI coaching
5. Schedule the real conversation this week

Key Takeaways

• Difficult conversations get harder the longer you avoid them—delay multiplies difficulty
• Prepare by clarifying your objective, gathering facts, and anticipating reactions
• Be direct and get to the point quickly—prolonged lead-ups increase anxiety
• Handle emotional reactions with calm presence: don’t rush, don’t minimize, don’t match energy
• Rehearse with AI before high-stakes conversations to build confidence and refine your approach
• Follow through after every difficult conversation with documentation and support

Up next: In the next lesson, we’ll dive into Building High-Performance Teams.