Difficult Conversations: It’s not just WHAT you say, BUT WHERE you say it
If you’ve ever been blindsided by feedback via Slack, had your stomach drop at a cryptic text from your boss, or—yes, it happens—been let go over Zoom, you’re not alone. One of the most common complaints I hear about difficult conversations is where they are held.
We talk a lot about what to say in a difficult conversation, and how to say it—but we don’t talk enough about where that conversation should happen. Venue matters. A tough message dropped into a chat app at 4:57 p.m. on a Friday can land very differently than the same words spoken over video with care and context.
Just Because They Should Know, Doesn’t Mean They Do
A few weeks ago I shared a (as it turns out, quite popular article and video) on building a Team Agreement—or what we like to call the Couth Code. It’s the set of unwritten-but-should-be-written rules that keep your team running with respect, responsiveness, and professionalism.
Managers often assume everyone just knows how to have a sensitive conversation. But as we’ve learned—just because something feels like common sense doesn’t mean it’s common practice.
And this is one of those places where alignment matters. Managers need to be talking with their HR partners, not just about policies, but about practice. About what’s couth, what’s not, and how we want to show up for people when things get hard.
Why Does This Keep Happening?
So why do people default to text or Slack for difficult conversations? Sometimes it’s a lack of confidence—they’re avoiding the discomfort of seeing the other person’s reaction. (If I don’t have to see them get upset, maybe it won’t feel so bad.) Other times, they genuinely don’t know any better. We “learn” from others. It’s statistically likely that managers who struggle with this got dumped over WhatsApp, ghosted after interviews, or fired by email themselves. They never had a model for what good looks like. And when no one teaches couth, people revert to convenience.
But just because it’s faster, doesn’t make it kinder—or more effective.
Let’s Talk It Through: Common Scenarios to Align On
Want to raise the bar on your team or org? Start here. Have a conversation around a few of these scenarios:
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Where do we give developmental feedback?
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What’s the right setting to deliver a layoff or performance warning?
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When is it okay to use text or Slack—and when is it definitely not?
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How do we want to handle interpersonal tension when it’s remote vs. in person?
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What’s our process when emotions are running high?
These are the kinds of norms that make it into your Couth Code. And once you’ve talked them through, you can teach them, reinforce them, and hold each other accountable.
A Few Quick Guidelines for Where to Hold Difficult Conversations
While there’s no one-size-fits-all answer, here are a few principles to help you choose the right room for the conversation:
Feedback should never be a surprise—especially in writing. If you’ve never had this particular difficult conversation before, don’t start with an email.
Use synchronous when the stakes are high. If there’s emotional weight or nuance, go face-to-face or camera-on whenever possible.
Ask yourself: “How would I want to receive this message?” Then adjust your approach to this difficult conversation to honor that same dignity.
When in doubt, say this: “This deserves a real conversation.” It’s a gentle way to pause the ping-pong of digital back-and-forth and elevate the dialogue.
The where sets the tone for how the message lands. So before you hit “send” on that tough message, take a beat. Choose a place that makes space for courage, clarity, and care.
If you’re a people leader or HR pro, talk with your team this week. Choose a few tricky situations and ask: What’s the couthful way to handle this here?
You’ll be amazed how much alignment (and relief) that one conversation can create.
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