Middle School Drama and Adult Wisdom on "Difficult" Conversations

“Difficult conversations” has been my spontaneous theme these last few weeks. The topic came up at a conference, I’ve been asked to give a training on it, it’s surfaced in several 1:1 and group coaching sessions, popped up in podcast episodes, and appeared in the books I’ve been reading. So—let’s talk about difficult conversations!

There’s so much to unpack.

They’re not just a workplace thing. Often, the most difficult conversations are with the people we love.

One of my earliest memories of a difficult conversation was at the tender (and confusing) age of 13.

For a few weeks—what felt like months—I was shunned by my friends. I hid in the library (ah, middle school… wasn’t it fun?!?! NOT). Eventually, I worked up the courage to ask what was going on. I had no idea. I was agonizing over what I might have done wrong.

Turns out, I hadn’t done anything wrong. One of my friends was jealous (I was good at sports and academics, and this annoyed the sh*t out of her—understandably so), and she’d spread a bunch of lies about me. She later apologized and painted me a beautiful horse poster. I forgave her, and we moved on.

Reflecting on this now, with everything I’ve learned as an adult, a few things become clear.

Lesson 1: Don’t wait.

I avoided the conversation, like many of us do, because I was afraid—afraid to be hurt or to hurt someone else. But waiting made things worse. My out-of-control, unrealistic ruminations, the isolation I felt, and the tension in the friendship group all made the situation much bigger in my head than it was. Dealing with it earlier would have saved everyone a lot of grief.

Lesson 2: Know how you react.

Hiding in the library made me feel like a victim. Some might say I was a victim of bullying—and yes, maybe so—but I also let myself be put in that situation. I fled and froze. Besides avoidance, two other typical responses are fight (going in hard and aggressive) or fawn (doing anything to placate, even at the cost of your own values).

These reactions—fight, flight, freeze, fawn—make total sense when we feel threatened. But from a relationship standpoint, they disconnect us. If we want to continue to live, work, and lead with others, we need to respond from a place of empathy and curiosity.

Becoming aware of how you react—what happens in your body and mind—is powerful. Once you know your patterns, you can self-regulate and make more empowered choices.

Lesson 3: Control what’s yours to control.

In that middle school blowout, I couldn’t control what was being said or how others reacted. I could only control myself. And that’s the reality. We know this intellectually, yet we often still try to control others. When we truly accept that we’re only in charge of our own thoughts and actions - not those of others - we can make intentional choices about who we want to be—and practice being that person.

Difficult people and difficult conversations? They’re our best teachers. They help us grow. We should thank them.

Lesson 4: Reframe.

If I have a choice in how I approach difficult conversations, I can start by changing the words I use. What if it’s not a “difficult” conversation, but a crucial one? (Grenny, Patterson, MicMillan, Switzler, Gregory in Crucial Conversations). That subtle shift helps me focus on why it’s important to talk, rather than why it’s hard.

In my case, I had been good friends with this girl. She was going through a rough time. Her behavior reflected her own pain, and I happened to be her trigger. What mattered was understanding what was being said about me so I could decide what to do next.

Eventually, I did the brave thing. I asked my other friends what was going on, and then I confronted her—not aggressively or submissively, but curiously. I told her I was hurt and that I missed my friends. She cried, felt terrible—and, as you know, made me the horse poster. (Which I then dramatically tore up into tiny shreds in front of her… nah, just kidding!)

Lesson 5: It’s usually not as bad as you think.

And then—often—it’s not that bad. You think, “Really? THIS is why I spent so many lunchtimes alone, reading in the library instead of laughing and gossiping with my friends?” What a waste of time and energy.

And folks, time and energy are precious. So let’s have the conversation and move on to better things.

So that was my middle school version of unpacking difficult conversations. Here's the quick summary:

1. Don’t wait.
2. Know your reactions.
3. You can only control yourself—so take responsibility.
4. Reframe from “difficult” to “crucial.”
5. It’s usually not as bad as you think.

On to more fun! Middle school boys seemed to be great at that.

Hope this was helpful!