We recently had dinner with a friend who expressed frustration at her inability to engage her father in an authentic conversation about politics. “I told him I could see the reasons he supported his candidate — and I really could. I wasn’t just saying it. I thought that would create an opening for me to talk about my views so we could understand each other. But when I tried to tell him how I saw things, he shut the conversation down.”

It reminded me of a situation I ran into professionally several years ago. The newspaper where I worked had gone through a painful reorganization that put many people in jobs that they didn’t particularly want and for which they didn’t feel well suited. A colleague approached me about her frustration, and I suggested she have an honest conversation with her supervisor that explored ways to transition into a position that better showcased her skills.

She took my advice and later came to me on the verge of tears. “I will never do that again,” she said. “She had no interest in what I wanted. She just got angry and told me to deal with the situation the way it is.” 

Sometimes our desire to feel understood fuels a subconscious intention of creating an “epiphany” for the other person, which can lead to letdowns. I have embarked on countless conversations thinking that by expressing myself with goodwill, listening reflectively and arguing the other side, I would get a desired outcome: the other person would want to understand how I see things.

Unfortunately, authentic conversations don’t come with a money-back guarantee. 

In my experience, the first road we want to take is the one expressed by my colleague: “Well, I tried to be authentic and it didn’t work. I won’t try that again.” Our disappointment becomes data, another layer of evidence that being authentic is ineffective. 

How you choose to respond in the face of a disappointing interaction matters. Giving up is one choice, or you can make a choice to continue engaging others authentically and let go of the desire that people follow a desired script.

At the time, I felt guilty when my colleague told me about her conversation with the supervisor. I thought I had given her bad advice because she didn’t get an understanding response. Reflecting on it today, however, I am convinced she did the right thing. 

In the face of disappointing outcomes, it helps me to remind myself of who I want to be in the world. If I can re-commit to authentic conversations regardless of how they turn out, it is easier to pick myself up, dust myself off and try it again. 

And again.

And again.