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Writer's pictureAriana Friedlander

4 Reflection Questions to Help You Prepare for Difficult Conversations

Updated: Mar 1, 2022

Have you ever procrastinated on having a difficult conversation with your boss or colleague or a loved one? I know I have! It’s a common scenario really. The anticipation of the conversation weighs you down.


Some of us fear what the other person will say. While other’s fear how we might show up in the conversation. Either way, the fear creates dread, the anticipation creates anxiety and we experience cortisol pumping through our bodies that tells us this conversation posses a threat to our well-being. If we let all that settle in, we might hold off entirely on having the conversation or even worse, approach the conversation on the defense to begin with.

But the reality of having difficult conversations is usually not as bad as our minds convince us it will be! This is especially true when we give ourselves time to prepare in a more rational and well thought out way. So, instead of playing out the conversation in your mind, I always suggest taking a moment to process, reflect and write in preparing for difficult conversations.

Here are four reflection questions I ponder in my journal to help me prepare for difficult conversations

  1. What’s happening?

  2. What have I been telling myself about this situation?

  3. What questions would I like answered by this conversation?

  4. What is the main point I really want to make?

What helps you prepare for a difficult conversation? Share your thoughts, reflections and suggestions with us here!

What’s Rosabella Consulting Up To?

Last week I had the pleasure of hosting and “speaking” to the Fort Collins Conscious Capitalism group about Embracing Your Inner Misfit for the Greater Good. I say “speaking” because the groups style is more conversational than Power Point driven, which fits my personality beautifully. We had an intriguing conversation about the corollaries between Conscious Capitalism and Misfit Entrepreneurs. Then we explored the deeper work around thought and consciousness that aspiring do gooders must embrace to embark on a successful journey. The event was such a hit that I was invited to speak at the Denver Chapter on August 17th!



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