TRAIN Yourself for Difficult Conversations

Photo by  Tim Foster  on  Unsplash

Photo by Tim Foster on Unsplash


Driving the short route to school, bored with the radio and out of podcasts on my iPod, I imagine the questions. Softballs at first, gradually increasing in intensity until she asks the one that pierces my steely composure, the infamous question no one thought she’d ever ask again: “If you were a tree, what kind of tree would you be?”

I’ve been practicing for my Barbara Walters interview since I was about 12, but I think it’s time I start preparing for my turn to sit down with Oprah since Barbara’s “10 Most Fascinating People” isn’t an annual event anymore. 

Practicing for a fantasy interview may seem odd, but my (no longer) secret pastime is actually useful since I don’t just practice volleying words back and forth with the rich and famous. I also rehearse for conversations I dread. 

One-on-one conversations sometimes make me nervous. Thinking about having to ask a favor, discuss a problem, let a student know they’ve messed up…all of these can make me tremble.  Most of us are familiar with Malcolm Gladwell’s theorem that it takes 10,000 hours of dedicated practice to master a skill. The idea has been widely discussed since his book Outliers appeared. That kind of practice would be overkill for a conversation in our daily lives, but rehearsing for an interpersonal encounter we may help us calm down and approach difficult conversations with aplomb.

Think about what makes you nervous. Is it because you’re asking for a favor? Trying to convince someone to do what you want them to do? Letting someone know they’ve messed up? All of these are conversations I might have at work, whether it’s asking a teacher to judge a round of debate at our tournament, looking for funding for new headsets for the auditorium, or telling a student I’ve discovered their plagiarism. All of these conversations make me nervous, either for myself (am I too demanding?) or for the other person (how will they react?). Thinking about what makes you leery of the upcoming interaction allows you to move to the next step.

Rehearse what you’re going to say. Don’t just think about it. Say it out loud. What tone of voice will you use? Word choices matter whenever we communicate. In fact, Mark Twain once said “The difference between the right word and the almost right word is the difference between lightning and a lightning bug.” Choose wisely. It’s only practice, so if it doesn’t sound right the first time, try again.

Next, anticipate what the other person might say. Imagine the worst case scenario. Then imagine the best case scenarios.  For each of these exercises, the next step is the same.

Inventory your responses. If the person says no, how do you react? The teacher says they can’t judge because of a prior commitment. I thank them and exit the conversation gracefully. I’ve got other judges to recruit! If they seem interested but hesitate, I might reassure them they’re exactly the kind of person we need in the room.  When we have a plan, we take away part of the uncertainty of a stressful interaction and thus, make ourselves less anxious.

Finally, nail down a time and place to have the conversation and follow through. Putting it off often makes the anxiety grow. Sure, there are other ways you could use your time, but as my high school English teacher advised us when she compared completing a job we dreaded to enjoying dessert, “Eat the crust first.” How can you enjoy the rest of your day if a difficult task is hanging over your head?  

As a career theater educator, I know that practice is, as Malcolm Gladwell said, “the thing that makes us good.”  Rehearsal isn’t just for actors; TRAINing ourselves for conversations we dread will help us face them more positively and make the interaction itself easier.

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