I had to have a hard conversation with someone today, and it's got me thinking about those moments in life—God, they come more often than we'd like, don't they?—when we have to look someone in the eye and say the hard thing. Or, worse, when we have to look someone in the eye and let them say the hard thing to us.
I'm calling this "A Beginner's Guide" to scary hard conversations not because I think you're beginners but because I, myself, am one. But I've had some training in recent years—mostly thanks to my own failures—and it seemed the appropriate time to write some stuff down while it's still fresh.
My Dad likes to say, "The school of life goes like this: You take the test first, and then you get the lesson." What little I know about hard conversations—and it ain't much—comes almost entirely via this method. Maybe this guide will help yours go a little easier.
Rule the First: Wait, but Not Very Long
I got some really bad news on Friday. It was so bad, I gave myself a two-day hangover courtesy of a seventy-dollar bar tab at the Bunker Club. While waiting for some friends to join me there—the meetup was arranged before I got this bad news bomb dropped on my head—I whipped out my journal and started writing down my initial thoughts. Yep. I wrote in my journal at the bar. In front of human people. LIKE A BAWSE.
It was good to get some thoughts out right away, to do much of my initial reacting alone and where no one will ever see it. My problem when things go pear-shaped or when the unexpected happens is that, in the moment, I'm never sure how to respond. I'm smart, but I'm slow-smart. I think of so many devastating insults at three in the morning, but in the moment, I'm all "I KNOW YOU ARE, BUT WHAT AM I? YOUR MOMMA IS WHAT."
Being reactive is almost never a good idea. When we don't have the time to let our bodies, minds, and souls absorb a shock, we're prone to all kinds of acts of stupidity. We lash out. We say things we don't mean. We make big decisions we can't take back. In my post-bad-news stupor, I not only Googled ways I could move away from Oklahoma—in the interest of escaping this particular problem—I also looked into how it would work to go spend the rest of my days in a Tibetan monastery. I also ordered the first of three beers and a shot of Buffalo Trace, neat, and imagined all the clever, devastating things I'd say when confronted with the person at the heart of my distress. I had the kind of thoughts that'd make Jesus mix up a batch of Purple Drank.
Thing was, I also, at the core of me, knew I had to have a difficult conversation—and that I had to do so as soon as possible. So I gave myself the weekend to cool down and get all my reacting out of the way. My brother and I had planned a day trip to Arkansas, so I also knew I had eight hours of driving ahead of me and someone to talk to who understands me about as well as anybody. So we drove, I talked, I listened, and I spent a fair amount of time crying, mostly in the shower, which is my favorite place to have tears. I let my feelings go wherever they wanted to go, and Monday morning, I got up, put on my big boy pants with a coat and tie, and stepped right into a tough conversation before going to work.
You can't put these things off. The longer you put them off, the harder they get, and it doesn't take too long for them to become impossible. Get your reacting out of the way, feel your bad feelings, and then go for it.
Rule #2: Have A Plan
This is one of the most important things I learned in therapy. Because I'm not good at reacting in the moment, I need a plan. I need to know at least how to get the plane off the runway. It's another important reason you have to wait at least a little while before having a tough conversation: You have to rehearse.
Some might say doing so makes the whole thing less authentic. I couldn't disagree with this more if Hitler had been the one to say it. It's not inauthentic to search for the very best, clearest, and most concise way to say what's really on your heart. If I jump right in, I'm bound to forget things, misstate stuff, and not be fully present in what's happening, because I'll be second-guessing myself.
I rehearse conversations mostly in the shower and in the car. When I feel them going off the rails—for me, that looks like imagining crazy scenarios I know will never happen and saying things I'd never actually say or even really think—I reset. Okay, let's start over. I don't usually get very far before I have to restart, but that's okay: What's important is starting off the right way.
Rule #3: Set the Right Tone. Then Listen.
You may be furious. You may be hurt, disappointed, panicking, or unsure of yourself, and you may have great reason to be any or all of these things. At one point or another this weekend, I was all of the above and then some. That's why it was good I got my catharsis out of the way early: The problem in this scenario wasn't my feelings, and my feelings weren't this person's problem.
So when I went in, I was direct and authentic but cool. "I understand we have a problem, and I'd like to talk about that," was how I began. And truthfully, our conversation didn't get very far: My conversation partner didn't really have time to unpack everything we needed to, so I said, "Okay, can you give me the broad strokes really quick?"
Some of what was said to me wasn't the easiest stuff to hear, and several times during the conversation, I heard some inner, hurt, frustrated, insecure part of myself raise its hand like Hermione Granger during a Bobby Riggs press conference. I HAVE SOMETHING I NEED TO SAY IN RESPONSE TO THAT.
But I mostly kept it shut. I listened. I heard. I put my pride in time out. Did I share my cohort's perspective on everything? Did it matter if I did or not? No, and no. But when I spoke, I did so respectfully. When I had a request, I shared it calmly. This wasn't the time for feelings; this was the time for hearing.
Am I saying hide all your feelings? No. But when they must be discussed—so many of our hard conversations boil down to, "You did this, and it hurt my feelings"—we don't get anywhere by being fire hoses of emotion left untended. Had I gone in to this conversation guns blazing, I'd have made a tense situation much, much worse. There may be a time to discuss my own hurt feelings, but this wasn't it. This was a chance to try to build a bridge to something better.
Rule #4: Make a Plan to Follow Up
As I said, my conversation today began with a notice that we didn't really have the time in the moment to hash things out the way they needed to be hashed out. So, as politely as possible, I made sure to ask for a follow-up conversation to get into details. I asked for specific examples rather than generalities, so I'd know how to identify a mistake before I make it the next time.
A couple hours later, I sent a follow-up email: Thanks for sparing me some time this morning. Here's a window of time it'd be convenient for me to meet back up like we discussed, but I can make time whenever it's convenient for you. I look forward to our next conversation.
The scary part of this, of course, is that you leave it in another person's hands how things will go. I may have to follow up again to get my second conversation (though I doubt it). So often, we bind a lot of emotional energy up in whether or not we feel the people in our lives are doing their share of the work, and in general, that's energy best spent elsewhere. If I have to follow up, then so be it. If not, great. But in this scenario, I'm determined to hash things out and improve this situation to everyone's satisfaction. I'm in it for the long haul. If you get in a pickle in your life and decide, no, I'd rather let this relationship go than gut it out, peace be upon you. We all have those decisions to make.
Not So Scary Hard
You get used to it, after awhile. I noticed something in myself this morning. I was waiting to meet this person with whom I had this conflict, and I was feeling around inside my shaking little heart. Mostly what was there was fear.
Fear's a tricky thing. There are those in the self-help community who'd tell us it's always bad, always wrong, always lying. Those people are wrong. I have a very reasonable fear of jumping out of planes, riding my bicycle without a helmet, and throwing rocks at black bears, because each of those things is a deeply unwise thing to do. Fear teaches us how to preserve ourselves. It's baked into our DNA to want to do so.
The trick is to know what's worth preserving and what's not. Today, I had the choice to preserve a longstanding conflict or to try to break open the ice in which it's been frozen and extract it. We never know how change is going to go, which is why we're so scared of it. Maybe things will improve; maybe they'll grow infinitely worse. In this case, I'm determined to try to improve them. So fear didn't get the final say. I took some deep breaths, knocked on the door, and said, "Do you have a minute to talk to me?"
Nothing was resolved. The bad news is still the bad news, and I don't know the way forward. But I know a next step, and all those negative feelings begging for catharsis have grown silent. Had I not had this conversation this morning, I'd have spent the entire day the way I spent this weekend: full of anxiety and dread. But I cracked open the door, and a little light got in—just enough to see by, which doesn't always feel like enough but always is.