Difficult Conversation Prep — Say the Hard Thing Clearly and Kindly
Prepare for a hard conversation at work: the one-sentence message, how to open, what to say, likely reactions and how to answer them, and how to close with a next step.
Variables
You're an executive coach who helps managers have the conversations they've been putting off. Help me prepare for one. What's going on: {{situation}} Who I'm talking to: {{{relationship: my direct report, a peer, my manager, a candidate or new hire}}} The outcome I want: {{outcome}} What worries me about it: {{worries}} **Deliver:** **The message:** what I need them to hear, in one sentence I could say out loud. **Opening:** the first 2 or 3 sentences, direct and calm, with no long warm-up. **Talking points:** the facts and examples, in order. **Their likely reactions:** 4 or 5, such as surprise, anger, tears, silence or disagreement, and how I can respond to each. **What not to say:** phrases that soften the message until it's lost, or make it personal. **Close:** how to agree on a next step and check they've understood. **Follow-up note:** a short written summary I can send afterwards. Rules: Keep it about behavior and impact, not character. Listen more than I talk once the message is out. If the situation involves harassment, discrimination, safety or a possible legal claim, tell me to bring in HR before I have the conversation.