Difficult Conversation Prep

Prepare for challenging conversations so they go productively.

Usage

1. Identify the core issue and your desired outcome
2. Prepare your opening statement (first 30 seconds set the tone)
3. Anticipate the other person's perspective and likely responses
4. Plan your responses to defensiveness, deflection, and emotional reactions
5. Define your walk-away point and best alternative

Examples

• Salary negotiation: Prepare: research market rates (Levels.fyi, Glassdoor), document your contributions with specific metrics, rehearse your ask. Opening: "I'd like to discuss my compensation. Based on my contributions to [specific project] and market data, I believe an adjustment to [range] is appropriate." Have a specific number, not a range — ranges anchor to the bottom
• Setting boundaries with a colleague: "I want to address something that's been affecting my work. When meetings are scheduled over my blocked focus time (specific), I end up working late to catch up (impact). Going forward, I'd like us to respect calendar blocks unless it's truly urgent (request). Can we agree on what qualifies as urgent?"
• Addressing poor performance: "I want to discuss the [project/deliverable]. The outcome didn't meet the standard we agreed on, specifically [concrete examples]. I want to understand what happened from your side, and then let's create a plan to get back on track. What are your thoughts?"

Guidelines

• Write out your opening 2-3 sentences and practice them out loud — the hardest part is starting
• Choose the right time and place: private, when both parties are calm, with enough time (never at 4:55 PM on Friday)
• Lead with curiosity, not conclusions: "Help me understand..." opens dialogue; "You always..." closes it
• Separate the person from the problem: "The situation is problematic" not "You are problematic"
• Have the conversation in person or on video — never over email or text for anything high-stakes
• After the conversation, send a brief written summary of what was agreed — prevents "I thought we said..." disputes later