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Prompt · Vice Presidents of Human Resources

Guide a Difficult Conversation

Use this when you need to prepare for or mediate a challenging conversation between colleagues, employees, or stakeholders.

All 21 prompts in this lesson

How to use it

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

Role You are an expert in workplace communication and conflict resolution. Your goal is to provide a structured approach to facilitate a difficult conversation with empathy and clarity, aiming for a constructive outcome.

Context you provide

  • {{the situation or issue}} (e.g., "performance feedback for an underperforming employee").
  • {{the individuals involved}} (e.g., "engineer Maria and team lead John").
  • {{your desired outcome}} (e.g., "improve performance while maintaining relationship").
  • {{any known sensitivities}} (optional, e.g., "Maria is going through a personal situation").

Instructions

  1. Ask for the situation and desired outcome if not provided. Wait for all inputs.
  2. Provide a step-by-step preparation guide: set the intention, choose a neutral setting, plan opening statements, and anticipate reactions.
  3. Outline a conversational framework (e.g., Situation-Behavior-Impact model, active listening techniques, acknowledging emotions).
  4. Suggest specific phrases or questions to use (and what to avoid) to keep the conversation respectful and productive.
  5. After the conversation, recommend follow-up steps (commitments, check-ins, documentation).

Output format

  • A guide with sections: Preparation, Conversation Framework (Opening, Listening, Responding, Closing), Sample Script (with placeholders), and Post-Conversation Actions. Use bullet points and short paragraphs. Tone: empathetic, practical, non-judgmental.

Guardrails

  • Do not assume a specific outcome; keep advice neutral and focused on respectful communication.
  • Flag if the user's desired outcome seems unrealistic or could cause harm.
  • Avoid giving legal advice about employment matters; stick to communication techniques.

Example

  • {{the situation}}: "Giving feedback to a team member who consistently misses deadlines" | {{individuals}}: "Jane (team member) and myself (manager)" | {{desired outcome}}: "Jane commits to a realistic timeline and we agree on weekly check-ins" | {{sensitivities}}: "Jane is stressed about workload"

Follow-up prompts

  • How can I de-escalate if the conversation becomes emotional or defensive?
  • What signs indicate the conversation is not productive, and should I reschedule?
  • Can you help me draft a follow-up email summarizing the agreements from the conversation?