How to Prepare for a Difficult Conversation

September 15th, 2021 | in Articles
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How to Prepare for a Difficult Conversation

From time to time, we all find ourselves in situations where we feel stuck and a difficult conversation needs to happen in order to free up energy for more useful purposes. Whether it’s at work or in your personal life, these discussions can make us feel very uncomfortable. Are you holding off on having any important conversations right now?

Do You Avoid Difficult Conversations?

There are many reasons why we avoid difficult conversations. Some people feel they don’t have the skills, or they fear all the emotions that may arise. Others may feel things will eventually get better or are afraid of making things worse. Either way, avoiding or delaying a difficult conversation can damage your relationship and create other negative outcomes. Conversely, launching into a difficult conversation without preparation can be equally disastrous.

Build Your Confidence and Influence

The best way I know to build your effectiveness and confidence is to thoughtfully prepare for the conversation by setting your intention for how you will show up. You will find that you have a better understanding of the situation and more potential to influence the outcomes than you think.

Here a list of questions to ask yourself before going into the conversation:

Setting Your Intention

Before going into the conversation, take some time to think through the answers to the following questions:

  • What are you hoping to accomplish? Ideally, what is the outcome you would like to achieve? Are all of your goals supportive and honourable or do you secretly want to punish the other person? If you want to avoid negative outcomes, focus on a supportive purpose and commit to discarding the others.
  • What assumptions are you making about the other person’s intentions? It might not have been their intention to make you feel hurt, belittled or disrespected. Intentions don’t always align with what we say or do, and this can impact how others receive what we say or do.
  •  Did the other person push any of your “buttons”? Did something they say or do trigger you in any way? If they did, it was likely difficult to control your emotions at the time, but with a few deep breaths and a little reflection time, you’ll be able to assume some responsibility for your reaction and have a more constructive conversation.
  • Are you feeling negative about the conversation? When you expect something to not work out, it typically doesn’t. If you want a more positive outcome, start with an attitude of curiosity, respect and vulnerability. Set an intention to respect the other person’s point of view, and they are more likely to respect yours.
  • How might the other person be feeling about the situation? What do they see as the problem? What are their fears and concerns? What are yours? Is there any overlap? Think about their perspective and imagine if you were in their shoes.

The key to initiating difficult conversations is setting a conscious intention to guide the dialogue. Without this critical step of conscious intention setting, it’s easy to get sidetracked by unconscious intentions—our own or other people’s. The more we become aware and actively prepare for difficult conversations, the more meaningful conversations we’ll be able to have.

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Difficult Conversations, by Douglas Stone, Bruce Patton, and Sheila Heen
Crucial Conversations, by Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler


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