You’ve thought about it too much. It’s taken your time and attention. Perhaps you’ve lost sleep over it. Having THAT tricky conversation with a parent or co-worker or even your boss can be super uncomfortable.

Megan Dredge How To Have A Difficult Conversation 10 Practical Strategies


How do you handle tricky conversations?

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Here are ten strategies to help you navigate through a difficult conversation:

  1. Work on yourself first.

    Here are some questions you can ask yourself. (I referred to these in this episode).

    • Why do I want/need to have this conversation?
    • What is my desired outcome?
    • What ‘buttons’ are being pressed for me?
    • What attitude do I have towards the other person?
    • What incorrect assumptions might I have made about the situation?
    • What am I afraid of?
    • Where have I contributed to the problem?
    • What previous experiences with this person/situation are influencing me?
    • Why have I delayed dealing with this issue/person?
  2. Choose an appropriate time and place.
  3. Start positive.
  4. Get to the point.
  5. Use ‘I’ not ‘you’
  6. Include the other person.
  7. Listen.
  8. Take personal responsibility.
  9. Solve and Summarise.
  10. Reflect and Improve.

Episode Resources

Post – Feedback Sandwich, refer to point 6
Resource – Winning With Parents Super Pack
Post – Change Your Tomorrow In 60 Seconds Today


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QUESTION: In what ways have you been successful in having difficult conversations? You can leave your comments here.