Top Ten Checklist for Tough Conversations

Although the beginning of a tough conversation can be stressful, it can also be the best opportunity for you to influence the direction of where it is going.

Conversations become interactive when you are listening, asking questions, sharing your view, solving problems and getting back on track when it goes a little haywire. Thinking like a mediator and describing the problem between the two of you in a way that works for both sides is something that takes practice.

The top ten checklist for tough conversations are:

  1. Prep work. Sort out what happened and the impact that it had on you.

  2. Intention. What do you hope to accomplish by having this conversation?Top Ten Checklist for Tough Conversations

  3. Timing. Is this the best time to address the issue?

  4. Describe the problem. Include both viewpoints and describe the difference between your two stories.

  5. Listen, to understand their perspective.

  6. Ask open-ended questions.

  7. Acknowledge the client’s feelings.

  8. Paraphrase and reframe.

  9. Think of options that meet each person’s most important concerns.

  10. Determine for the future how you will keep the window of communication open. 

Rosemary Smyth, MBA, ACC, is a columnist and an international business coach for financial advisors. She spent her career working at leading investment firms before pursuing her passion for coaching. She lives in Victoria, BC. Visit her website at 

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