How to Hold Tricky Conversations at Work
What to say when complete understanding seems impossible
“I don't think I slept the night before we had the call,” the manager told me. Her boss had told her to fire the employee, and with reason: the worker had made an error worthy of termination. Still, my interviewee found the call painful in the extreme: “Just hearing her plead for her job—she started crying on the phone. I had to tell her, ‘I’m going to hang up now.’” There was no way to end it otherwise.
Challenging conversations can stack up quickly in the average workplace. If you’re like most workers today, you spend roughly two hours a week dealing with conflict. Some of it, according to the study where I got this data, traces to people’s egos. Some of it derives from stress. Or overloaded task lists. Or generational differences.
How do you negotiate challenging conversations in situations where complete understanding and satisfactory resolution feel impossible?
The taken-for-granted wisdom today is that we should build bridges across chasms of workplace difference. But a weird thing happens on the way across that metaphor: somehow our approach to communication goes from being the bridge to being the chasm. (No one describes this better than John Durham Peters in his book Speaking into the Air. See especially pp. 5-6.)
Let me tell you a quick story. A few weeks back on the Mode/Switch Pod, we were holding our usual intergenerational chatter about challenges in modern American work culture. We were talking about Red Flag Moments, as it happens, and I commented that such moments made me, as a Gen-X guy, respond cautiously. Let’s just give this some time. Things might just get better in a few days. The Gen Z worker across the podcast table looked at me and said with pained gentleness, “That’s because institutions were made for you.”
I tell that story because it illustrates how good intentions to build a bridge aren’t always enough. Maybe I’m misguided, but, as I look back, I think I had good intentions. I was trying to identify how I experienced things in workplace life today. And yet, my well-intentioned bridge-building only pointed to a chasm deeper than I had imagined.
Challenging conversations at work make me wonder about a fundamental shift in the way we understand workplace exchange. Too often, we assume that communication is basically a way to Fix Things For Good. I think that’s some of the impulse behind the counsel to change up our communication media. Boomers prefer face-to-face conversation, and Xers prefer email. Millennials want you never to call them, and Gen Zs love them some reels. Make sense? Just choose the right tool!
If only it were that easy.
Sometimes, though, digital tech can offer us a way to rethink workplace communication. At least that’s what happened to me this week as I was listening to my favorite tech podcast, Hard Fork, about a new app called Bonk. This still-in-beta app offers friends a digital slap on the back. You don’t write them a thousand-world email. You don’t send a blunt telegram with dire news. You don’t communicate any information at all. You just see some blue dots next to a friend’s name; you tap a dot; and that friend gets a notification: “Your friend Bonked you.”
Okay, you’re right to be skeptical about a mode/switch from bridging to bonking. Even apart from the mildly raunchy connotations of the term, maybe this app strikes you as a pointless addition to the universe. “Why does this exist?” Kevin Roose asked his co-host Casey Newton on the episode.
But I think it’s easy to forget, when approaching a tricky conversation, just how much of life with other people entails a push notification acknowledging their existence. A lot of communication is just saying, “Hey, I see you.”
Maybe that simple moral fact provides help with tricky conversations at work. Sometimes you can find a bridge, sure. But sometimes you can only tap the Bonk button.
The Jewish communication scholar Michael Hyde might call it “the life-giving gift of acknowledgement.” For him, it isn’t just a digital tap. It is a deeply human call-and-response. One person’s existence calls out, Where are you? And another person’s response comes back: I’m right here.
It’s easy to forget how much of life with other people entails a push notification saying, “Hey, I see you.”
Believe you me, I often wish that workplace conversations would repair breakdowns and cross chasms. But sometimes the only possible thing to communicate is presence. If your job is to fire someone, you can’t always explain adequately how things got so messed up. If you are Gen-Xer boss with a blindspot, you might not ever be able to fully comprehend how your rising employees experience institutions today.
So let me ask, what would it sound like, in a challenging conversation, to communicate presence?
I got to talking about this with some of my Mode/Switch colleagues, and one of them scripted out a conversation that went something like this. The next time one of your coworkers makes a request and asks if it makes any sense, don’t rush to say, “For sure!” Instead, try saying, “Not exactly. I mean, your experience is so different from mine! But that’s okay. I don’t have to understand everything in order to do what you’re requesting.”
A simple script like that enables you to stay with people and work with people even when you don’t fully comprehend people.
-craig
