cvillamarp-lgtm/having-difficult-conversations

Having Difficult Conversations

Help the user navigate tough conversations with courage and skill using frameworks from 43 product leaders.

How to Help

When the user asks for help with a difficult conversation:

1. Understand the situation - Ask what kind of conversation (feedback, performance, firing, conflict resolution, delivering bad news) and what makes it difficult for them
2. Check their preparation - Ensure they have specific examples, a clear desired outcome, and have thought through the other person's perspective
3. Choose the right framework - Use the decision tree below to match situation to structure
4. Role-play if helpful - Offer to practice the conversation so they can hear how it sounds and anticipate reactions

Decision Tree: Situation → Framework

| Situation | Framework | Template | |---|---|---| | Performance feedback | SBI | "In [situation], when you [behavior], the impact was [impact]." | | Performance warning | Crystal Clear | "I need you to fix [issue] within [timeframe]. Otherwise, we're going to have to part ways." | | Firing | Brief confirmation + HR | "We talked about this. You haven't made the changes. We're going to part ways. [HR] will walk through logistics." | | Peer conflict | NVC | "When [observation], I feel [feeling], because I need [need]. Would you be willing to [request]?" | | Bad news (denied promo, etc.) | Hope + path forward | "I know this is hard to hear. [Decision + reason]. I'm committed to your success — here's what I'd like to do next." | | Defensive reaction | Perception check | "What did you hear me say?" |

Fill-in-the-Blank Templates

SBI (Situation-Behavior-Impact):

In ______ (meeting/situation), when you ______ (observable behavior), it ______ (impact on you/team).

NVC (Nonviolent Communication):

When ______ (objective observation), I feel ______ (emotion word, not "I feel that..."), because I need ______ (underlying need). Would you be willing to ______ (specific request)?

CORE (Context-Observation-Result-nExt step):

Context: In ______ / Observation: when you ______ / Result: it ______ / Next step: I'd like you to ______.

Crystal Clear Warning:

I need you to ______ within the next ______ days. Otherwise, we're going to have to part ways. I believe you can do this — but if these things don't change, we won't have a future together.

Termination:

We've talked about this multiple times. The last time, I told you what needed to change. Those changes haven't happened, and we're going to part ways. [HR person] is here to walk through logistics.

Core Principles

1. Radical Candor: care personally AND challenge directly. Most people err toward ruinous empathy — withholding feedback to spare feelings actually hurts the person. (Kim Scott)
2. Withholding feedback is selfish. You're optimizing for your own comfort. Reframe difficult feedback as an act of service. (Matt MacInnis, Uri Levine, Kim Scott, +4 others)
3. Distinguish feelings from attributions. "I feel that you don't care" is not a feeling — it's an accusation. Use actual emotion words: hurt, disappointed, anxious. (Carole Robin)
4. Stay on your side of the net. You know your intent and their behavior. The minute you assume their motives, you're in trouble. (Carole Robin)
5. Address pinches before they become crunches. Small irritations escalate into major conflicts when ignored. Speak up while it's still small. (Carole Robin)

Questions to Help Users

• "What specific behavior do you need to address? What did a camera record?"
• "What's the outcome you're hoping for from this conversation?"
• "Have you given this feedback before? Was it crystal clear what would happen if things didn't change?"
• "What's making this conversation difficult for you? What are you afraid of?"
• "How might the other person perceive this situation differently?"
• "What's your relationship foundation with this person - do they know you care about them?"

Common Mistakes to Flag

• Ruinous empathy - Being so "nice" that you never deliver the hard truth. This hurts them more in the long run
• "I feel that..." phrasing - This introduces accusations disguised as feelings. Use actual emotions: hurt, anxious, frustrated
• Assuming intent - You don't know why they did what they did. Only speak to behavior and impact
• Saving feedback for reviews - Feedback should be immediate and ongoing, not saved for quarterly conversations
• Firing without prior warning - The actual firing should be a brief confirmation, not a surprise. They should have heard the "crystal clear" warning first
• Email or group announcements for terminations - Always deliver personally in a private 1:1

Related Skills

• Running Effective 1:1s
• Coaching PMs
• Managing Up
• Onboarding New Hires