When I got into graduate school I had to read a whole book called Difficult Conversations. It was a framework for navigating challenging conversations and served as a great baseline model when I was learning the skill of having and facilitating productive conflict.

I didn’t realize that the phrase “difficult conversation” would cover so many moments in my life from dish squabbles with my hubby, to client mediation, to expressing disappointment and regret to family members. It covered it all, and I had all of those conversations meaningfully and with purpose and intention all through my two years of school.

And it was fucking exhausting.

I was basically a bare nerve for those years, constantly hashing out my feelings/thoughts/wants and checking my intentions, making sure my wording was just so and digging through my own baggage set up by my family and cultural dynamics. It was exhausting, produced a ton of anxiety, and turned me into a paranoid freak where I was examining my motives and language constantly. Though I think the world could use a bit more self-examination, this was an extreme I don’t recommend for anyone for an extended period of time.

At a point about halfway through my second year I was having a lot of trouble with a classmate. I spent a lot of hours journaling and talking about it and thinking about it. We would have some conversation, but it never really altered our dynamic.

Finally, I realized that while my school environment encouraged me to make peace and seek resolution with everyone I came into contact with, that truly was just not a possibility in the real world. There would be times where relationships did not work for me and it was in my best interest to leave them rather than continue to beat my head against a wall. 

To figure out what the moments for discussion were, I came up with a short list of questions I needed to ask myself to quickly determine whether or not to have a Conversation with that person. (Note the capital letter. I’d like to think we all know the difference between a conversation and a Conversation.)

Here are my Qs:

  1. How much do I like this person?
  2. How likely do I think I am to be heard by them?
  3. Will my life be supremely difficult if I don’t get this resolved?

Pretty straightforward.

The first question always helps me identify the stakes I have in the relationship. If I don’t particularly like the person, then I’m unlikely to continue trying to have a relationship with them, which is what having a Conversation is all about.

The second question helps me get a sense of whether my efforts will be futile or not. I gauge this primarily by past experience with them and personal observations, not by my own feeling of not wanting to have the conversation. More objective measures and data points have to serve me here since I could easily throw up my hands and say, “Fuck it. They’ll never hear me so why even try.” I find that actually 9 out of 10 times, this isn’t true. The people I tend to surround myself with are very open to feedback and want to hear about times I’ve felt hurt or wronged.

Finally, I have to assess the difficulty of my life moving forward if I don’t address this. For my classmate, I had 2 more months of class with them and then little to no interaction in the forseeable future. They ultimately didn’t meet all my criteria, so I declared it not worth it and instead focused on self-management and self-soothing when I was with them. With my husband, if he didn’t do the dishes to my liking, my life would be more difficult (for some this might not be true!), so we had a series of conversations about how to split up this particular chore.

I try and use this as much as possible. As a serious ruminator, I could spend lots of time in acute anxiety over the state of something someone said or something I said. This way I nip it in the bud early and simply.

Do you use any criteria like this? If you do, I’d love to hear about it and if you don’t I’d love to know if you plan on creating some!