Difficulty of difficult conversations

Yogi Sharma
3 min readMay 25, 2022
Photo by Mateusz Wacławek on Unsplash

Hard conversations are hard. That is why we don’t have them. And delay them as much as possible.

I have been fascinated by hard conversations. I avoided them in my childhood, when there was tension around me. I avoided them in my young adult years. But for the past half a decade or so, I have grown to welcome hard conversations, and don’t shy away from them. And that has intrigued me even more — what changed?

In my coaching, the topic of hard conversations is central. In most challenges people face, there is a uncomfortable conversation or two they are avoiding.

Now, what makes hard conversations hard? I have been studying this through books, and also through my own experience working with people.

I don’t have one answer to this, but one thing that makes hard conversations hard is this: our desire to “win” in the conflict. We usually want an assurance to be right and win the fight (and let us face it, we view difficult conversations as a fight) even before we start the conversation or an argument or contention. We spend hours and days and weeks and sometimes months and years mulling over various viewpoints, and trying to come up with a good case. And in the mean time, the conversations and opportunities slip by.

The fear of failure in hard conversations is one impediment that keeps people from starting a hard conversation. We don’t want to get into conflict if we are not sure of winning.

What if we approached conversations as an exploration of the stories of the two people? What if we could go into a conversation with an open mind to understand the other person, instead of winning them over?

There are three resources that recommend a version of this:

  1. Nonviolent communication by Marshall Rosenberg.
  2. Difficult Conversations by Bruce Patton, Douglas Stone, and Sheila Heen
  3. Compassionate Curiosity framework from Finding Confidence in Conflict: How to Negotiate Anything and Live Your Best Life by Kwame Christian.

I have seen this in my own life and the lives of people I have worked with: when we are willing to go into a hard conversation without a need to win, what we get is usually better than a win.

Photo by Sebastian Bill on Unsplash

Are you willing to explore this?

  1. What conversation are you avoiding?
  2. What are trying to win?
  3. Are you willing to let go of the win, and willing to go into conversation to understand other’s story?

If you want any support in this, reach out. I love supporting people in having difficult conversations that matter.

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