I was reading a blog the other day about difficult conversations at work… and, as tends to happen, I absolutely hijacked it.
Because here’s the thing — we all know difficult conversations matter. No one is out here saying, “You know what makes a great team? Avoidance and passive aggression.”
And yet… we still avoid them.
We avoid them like that one cupboard at home that you just keep shoving things into, hoping no one opens it. Until one day it explodes and now you’re dealing with a much bigger problem than you started with. (One cupboard, who am I kidding, I have 4 cupboards and a 3rd drawer down!)
Workplace conversations can feel a bit like that cupboard.
The Mental Gymnastics We Do Instead
Instead of having the conversation, we:
- Rehearse it 47 times in the shower
- Write the email… delete the email… rewrite the email
- Decide it’s “not a big deal” (while thinking about it constantly)
- Or my personal favourite — become exceptionally good at being polite while quietly irritated
Because saying the thing feels risky.
What if they get upset?
What if I say it wrong?
What if it makes things awkward?
(Newsflash: it might be awkward. That’s not actually the worst thing in the world.)
What Happens When We Don’t Say the Thing
Here’s the less-fun truth: the issue doesn’t go away.
It just… evolves.
Small things turn into tension.
Tension turns into frustration.
Frustration turns into stories we tell ourselves:
“They don’t respect me.”
“They never listen.”
“They should just know better.”
Meanwhile, the other person is often completely unaware there’s even an issue.
So now we’ve got a disconnect and a narrative… which is not a great combo for healthy teams.
Let Me Reframe This (Because It Helped Me)
Healthy teams are not the ones skipping around conflict like it’s lava.
They’re the ones who can say, “Hey, this isn’t working” — and then actually talk about it.
Not perfectly. Not without a bit of awkwardness. But honestly.
Because when you do have the conversation:
- Things get clearer
- Misunderstandings get sorted (often quicker than expected)
- Trust builds — the real kind, not the “we’re all smiling in meetings” kind
- People actually get the chance to improve and feel supported
It turns out, avoiding the conversation is usually more damaging than having it.
A Few Things That Help (From Someone Who Also Finds This Hard)
I’m not going to pretend this suddenly becomes easy. It doesn’t. But it can become doable.
Talk about what happened, not who they are
There’s a big difference between “that deadline was missed” and “you’re unreliable.” One opens a conversation, the other shuts it down.
Be clear (kind, but clear)
Hinting is not a strategy. It just creates confusion and resentment on both sides.
Actually listen
Not the “nod while waiting to jump in” kind. The kind where you might hear something you didn’t expect.
Stay a bit curious
Going in with “help me understand what happened here” lands very differently to “here’s everything you did wrong.”
Focus on what happens next
We’re not here to win. We’re here to make things better.
The Culture Piece (Because It’s Never Just One Conversation)
This isn’t just about one awkward chat in a meeting room.
It’s about the kind of environment we’re creating.
Because when people feel safe to speak up — respectfully, honestly, without fear of being shut down or judged — everything changes.
Issues get addressed earlier.
People feel less alone in their frustrations.
Teams become… well, teams.
And leaders (formal or informal) play a huge role here. Not by getting it perfect, but by going first. By showing that honesty and respect can sit in the same conversation.
Final Thought (The One I Keep Coming Back To)
Difficult conversations aren’t a sign that something is broken.
They’re often a sign that people care enough to try and fix it.
Yes, they can be uncomfortable. Yes, you might fumble your words. Yes, it might feel awkward.
But a slightly awkward conversation now is almost always better than a full-blown issue later.
(And a lot less messy than that exploding cupboard.)