Why we put it off, what it costs us, and how to walk into it without losing yourself.
Hello friends,
There's a conversation on your list. You've moved it through three weeks of calendars now, maybe more. It might be the underperformance one. It might be the one where you tell someone they're not getting the promotion. It might be the one where you ask your co-founder why they pulled back on a project without telling you.
You've thought about it on Sundays. You've thought about it in the shower. You've drafted lines in your head that you haven't said.
And every week, it stays on the list.
I want to talk about that.
Why we postpone
Most of the leaders I work with don't avoid hard conversations because they don't know what to say. They usually know exactly what to say. They've rehearsed it.
What they're avoiding isn't the words. It's the unpredictable bit. The face of the other person while they're hearing it. The silence after. The risk that they (the other person) might be hurt, or angry, or disappointed in you, in a way that doesn't resolve neatly in the same conversation.
That's the thing we're really putting off. Not the talking. The not-being-able-to-control how it lands.
And so we tell ourselves stories. "It's not the right week." "Things are stressful for them right now." "I want to be sure I've thought it through." Some of those stories are even true. But underneath them, almost always, is one quieter thing: I'm not ready to be the person who said the hard thing and didn't get to soften it afterwards.
I get it. I postpone too. (More than I'd like to admit.)
The cost (and why naming it matters)
Here's the part most of us don't track. Postponing a conversation is not free. It's not even cheap.
The conversation costs you energy every day it stays on the list. Every meeting with that person becomes slightly more complicated, because you're managing the thing you haven't said as well as the actual agenda. You start avoiding their messages. You feel slightly off in their presence. You sleep slightly worse. You probably don't even attribute the bad sleep to it. But it's there, doing its quiet work.
The person on the other end usually feels something too. They feel the avoidance, even if they can't name it. They become slightly more careful with you. The relationship gets a tiny bit smaller, week by week, without either of you choosing it.
By the time you finally have the conversation (and most of us do, eventually), it usually goes far better than the version we'd been imagining for three months. The other person is often relieved. The relationship gets bigger again. You wonder why you waited.
You waited because you wanted to wait until you were sure it would land softly. And that, it turns out, is not how truth-telling works.
What helps (a little)
I somehow love to put things into 4-5 steps, my mind loves these little controlly-structured things. So here we go:
One: name what you're avoiding, even if only to yourself. Write it down. Not the script. Just the situation. "I'm avoiding telling A. that their work isn't landing." Naming it removes about 30% of the weight. The other 70% is still there. But 30% is a lot.
Two: lower the bar. You don't have to have the perfect conversation. You have to have a true one. Try this opening: "I've been wanting to talk to you about something, and I've been putting it off because I wasn't sure how to bring it up. Can I share what's been on my mind?" That sentence does almost all the work. It says: this is real, I care about how this lands, I haven't been performing while we sat in meetings together.
Three: build in a follow-up. The most important sentence isn't the hard thing itself. It's: "Can we come back to this in a week?" Most difficult conversations don't resolve in one sitting. Giving the other person time to sit with what you said, without resolution pressure, almost always produces a better second conversation.
Four: tell yourself it's allowed to be awkward. The bar isn't "the conversation flows beautifully." The bar is "I said the true thing, and I stayed in the room while they received it." Awkwardness is a feature, not a bug. It's what real conversation looks like when it isn't rehearsed.
A different way of holding this
If there's a conversation that's been living rent-free on your to-do list for weeks (and I'd bet there is one, sitting there as you read this), I want to be honest with you about something. The reason it's still there isn't because you're avoiding it. It's because you care about the other person, and about your relationship with them, more than you care about getting it over with. That is actually a good thing. It's also why most leadership books, with their "just have the conversation" framing, feel slightly hollow when you try to apply them on a real Tuesday morning.
There is another way of holding this. Not a script. Not a frame. Just a slow, kind acknowledgement that the conversation will probably go better than you fear, will probably feel a bit awkward in places, will probably surprise you with what the other person actually says, and that walking into it imperfectly is still infinitely better than carrying it for one more week. The cost of postponement, paid in small invisible ways across both your nervous systems, is much higher than the cost of one slightly awkward Tuesday.
You're allowed to walk into it unsure. You're allowed to not know exactly how to start. You're allowed to be a person who says hard things imperfectly, and stays. 🫰
Have a lovely day,
P.S. The 1:1 mentoring work I do with leaders is built around exactly this. We rehearse the conversation you've been putting off, in your body, before you have it. We sit with the awkward bits. We figure out what's actually scaring you (it's almost never what you think). A 30-minute Chemistry Call is free. No sales conversation, just a feel-out. DM me, write to contact@zen-and-go.de, or schedule it right here: cal.com/sophie-bachmann/chemistry-call.