How to have Easy Conversations with Difficult People



We’ve all done it. We’re all guilty. Our phone rings, our door knocks, we receive a message “we need to talk”…we’re all guilty. We have all, in the past, shied away from the conversation. Either because the conversation itself is difficult, or the person we need to have it with is, well, let’s just say they have not won many prizes for being easygoing lately. But why do we shy away from them? Partly because we are afraid that we will end up fighting, or breaking up the relationship, partly because we are afraid of our own reactions perhaps, or the reactions of the other person. We are afraid to get hurt, to show weakness, to open up about our bottled-up feelings. To be vulnerable.


“Guys, could we have some space you think?”

I used to run a mile before confronting anyone, even when I felt wronged. But I realized that by running away, it was my own securities I was afraid of facing, my own weaknesses and not the other person’s. I wasn’t carrying my argument through and I wasn’t listening. As a result, I would get personal and shout. I would get angry, not knowing that by doing just that I was losing the argument and ruining my relationship with the other person as a consequence. Most importantly, I wasn’t getting my way. By looking at the issue at hand only from my perspective, I was on the highway to Nowhere.

Sometimes we have to ask difficult questions.


“Honey, could you take out the garbage?”

And sometimes we don’t want to hear the answer.

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“Do these feathers make me look fat?”

But unfortunately, life does not always indulge us and sometimes we just have to dive in and do that talk. So how can you make it easier? Here’s how in 5 easy steps:

  1. Acknowledge that the other person has a viewpoint. Just like you believe you are right, they believe they are right. Put yourself in their shoes. What would you have said or done if you were in their shoes?
  2. At the end of the day, we all want to be acknowledged and appreciated. Agree with your interlocutor before you try to explain your point of view.
  3. It’s the minimum sign of respect. Give the other person a chance to express themselves.
  4. Be honest about your feelings and your fears. No one likes to give in to someone who seems invincible. And frankly, none of us are. Show your vulnerabilities.
  5. Stick to the subject at hand. Don’t deviate. Don’t get personal. Don’t insult. That would only show weakness on your part. Stick to your point.

Sometimes, however, despite our best intentions and no matter what we do, we can’t seem to get through. But if you really care about the person, don’t give up! Maybe it’s just not the right time. In this case, it may be best to smile, retreat and try again. Here is a clip of bloopers from the king of difficult conversations himself, Jerry Seinfeld:


Do you feel you have changed in the way you handle difficult conversations or difficult people? How have they affected you in the past? How have you dealt with them?


Further reading

  • Dale Carnegie How to win friends and influence people
  • Brene Brown Daring Greatly





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