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Difficult Conversations

There aren’t too many people who enjoy conflict. It is something that makes most of us feel uncomfortable. However, it is going to occur several times in your life. Sometimes it feels like it happens several times a day!

One super uncomfortable form of conflict is having a tough conversation with someone. Here are ways that can help you get through the situation.

  1. Get all the facts. Try to keep assumptions out of the equation. You’ll need to be a bit of a detective here as people won’t necessarily volunteer the information you need to handle the situation. If you make assumptions, you’ll end up having to apologize later when the facts become known.

  2. Don’t strive to be liked. While it is a nice feeling when people like you, when you need to have a tough conversation with someone, they likely won’t be as receptive as you hope. For instance, if you are faced with having to let someone go at work, they aren’t going to be your friend. Accept the fact that everyone won’t like you, and move on.

  3. Try to find a satisfactory solution wherever possible. If it’s in your power to do so, try to make the solution a win-win for everyone involved. This depends on the situation, of course. Coming up with a compromise will show you are making an effort to do as much as you can in a tough situation.

  4. Start the conversation with the good aspects of the situation. When you find something good the person has done, you can use that as a conversation starter. Then, when it is time to share bad news, or give criticism to the person, they will be more receptive.

  1. Don’t put off the conversation. If you let something go, you will lose the power you have when you finally get around to talking to the person. He or she will ask why you waited so long to discuss the situation. You will be left trying to justify your actions which puts you on the defensive. You’ll have less recourse in a tough conversation when this happens.

  2. If the conversation gets heated, agree to meet again at a future time and reschedule it. If things are really heated, and emotions are too high to even have a conversation, then you might want to consider rescheduling the conversation. It gives all parties involved time to calm down and think about the situation.

  3. Put yourself in the other person’s shoes. You need to approach the conversation with some level of empathy. How would you feel if someone were saying what you are planning to say? By doing this, you can be more sensitive to the needs of the other person. This increases the chance of the difficult conversation going smoothly.


  • Write down your talking points for a conversation that you need to have with someone. It’s easy to forget your thought process when you are in the heat of the discussion. By writing down what you want to say, you’ll be sure to cover all your points.

  • Write down counter-arguments that you feel the person may have. This is helpful to prepare for these arguments ahead of time. You probably won’t capture every argument, but the more you can, the better. This action can help you stay calm as you won’t be blindsided by a counter argument as much.

  • Try meditating before you need to speak with the person. If you find the time and space to meditate, it will help you relax. This will reduce your chances of getting agitated when the conversation is occurring.

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