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  • Jonathan E. Pearl

Preparing for difficult conversations

Updated: Jul 8


Before going into any difficult conversation, ask yourself:

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

You may think you have honourable goals: like educating an employee or increasing connection with your teenage kid, but your language is overly critical or condescending. You think you want to support, but you end up punishing. Some purposes are more useful than others. Be self-critical beforehand so that you enter the conversation with a genuinely supportive purpose. Try writing it down. Once re-reading it you may decide not to bother!

2. What assumptions are you making about this person’s intentions?

You may feel intimidated, belittled, ignored, disrespected, or marginalised but the other party. But be cautious about assuming that that was their intention. Impact does not necessarily equal intent. Question your unconscious bias. Is there anything about this person, or their appearance, that might falsely lead you to believe they are aggressive, or disrespectful?

3. Are your “buttons” being pushed?

Are you more emotional than the situation warrants? Take a look at your “backstory,” as they say in the movies. What personal history of yours is being triggered? You may still have the conversation, but you’ll go into it knowing that some of the heightened emotional state has to do with you.

And always remember: if you have a strong adverse reaction to the way someone is behaving, that’s USUALLY because the 'foul' behaviour they are displaying is stuff that you find unattractive in yourself.

4. How is your attitude toward the conversation influencing your perception of it?

If you think this is going to be horribly difficult before you start, it probably will be. If you truly believe that whatever happens, some good will come out of it, that will more likely be the case. Try to adjust your attitude for maximum effectiveness.

5. Who is the opponent?

What might they be thinking about this situation? Are they aware of the problem? If so, how do you think they perceive it? What are their needs and fears? What solution do you think they would suggest?

Begin to reframe the opponent as your partner.

6. What are your needs and fears?

Are there any common concerns? Could there be?

7. How have you contributed to the problem?

How have they?


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