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We Have to Talk:
A Step-By-Step Checklist
for Difficult Conversations

by Judy Ringer


Think of a conversation you’ve been putting off. Got it? Great. Then let’s go.

There are dozens of books on the topic of difficult, crucial, challenging, important (you get the idea) kinds of conversations. Those times when you know you should talk to someone, but you don’t. Maybe you’ve tried before and it went badly. Or maybe you fear that talking will only make the situation worse. Still, there’s a feeling of being stuck, and you’d like to free up that stuck energy for more useful purposes.


There are many well-written and informative books on how to have these important, crucial, and difficult conversations. At the end of the article, I list them. Get at least one and read it. They’re all great.

What you have here is a brief synopsis of best practice strategies: a checklist of action items to think about before going into the conversation; some useful concepts to practice during the conversation; and some tips and suggestions to help you’re energy stay focused and flowing, including possible conversational openings.

You’ll notice one key theme throughout: you have more power than you think.

Working on yourself: How to prepare for the conversation

Before going into the conversation, ask yourself some questions:

1. What is your purpose for having the conversation? What do you hope to accomplish? What would be an ideal outcome?

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