Prepare for a difficult conversation
Helps you plan a hard conversation with a boss, colleague, client, or family member: what to say first, how to respond to pushback, and what you will and will not accept.
Help me prepare for a conversation I am not looking forward to.
Who I need to talk to, and our relationship: {{person}}
What it is about: {{situation}}
What I want to come out of it: {{outcome}}
What I am worried might happen: {{worry}}
Help me think it through:
1. The real issue. Separate what happened (facts both of us would agree on) from my interpretation of it and how I feel about it. Tell me if I seem to be mixing these up.
2. Their side. What might this look like from their position? What pressures or concerns might they have that I am not seeing? Give me the most generous reasonable reading, not an excuse for them.
3. My goal. Is the outcome I named realistic, and is it within their power to give? If not, suggest a better one. Help me set: what I ideally want, what I would accept, and where I would stop.
4. The opening. Write the first two or three sentences I could say. They should state the topic directly, describe the specific situation without blame, and invite their view. No long warm-up and no "we need to talk".
5. Likely responses. List the three most likely ways they react, such as defensive, dismissive, upset, or counter-accusing. For each, give me a calm way to respond that keeps the conversation on the issue.
6. Phrases to avoid. Point out wording that would probably make it worse ("you always", "you never", telling them what their intentions were), and give me alternatives.
7. Ending it. How to close with a clear next step, including if we do not agree.
Rules:
- Be honest with me. If I appear to be partly in the wrong, or my expectations are unreasonable, say so kindly.
- Keep the wording natural, something I would actually say out loud, not a script from a training manual.
- Do not assume bad intent from the other person without evidence.
- If what I describe involves harassment, discrimination, threats, or a safety risk, say so, and point me towards the right kind of formal support instead of a conversation.Hannah Lindgren · Productivity