Difficult Conversations Still Need to Be Conversations

“I bitched out.”

That's how a woman at one of my childcare workshops described a conversation she'd been meaning to have.

Everyone was packing up. A couple of people had stayed back to talk about conflict and difficult conversations. She told me about someone in her kids' room she knew she needed to speak to. Not wildly junior, but a bit less experienced than her. I asked how the conversation went.

“I bitched out.”

She'd built herself up to do it, and when the moment came she didn't feel confident enough to go through with it.

I wasn't surprised. This comes up in nearly every workshop I run. Avoiding the conversation is one of the most normal responses there is. It doesn't mean you lack courage. It means the conversation feels overwhelming, so you avoid it.

She didn't spell out everything she was worried about, and I'm not going to pretend she did. But my gut said part of her wasn't sure it was really her place to give the feedback, and part of her was worried about how the other person would take it. When we dug a little further she got a bit reserved, so I left it there.

The reasons people avoid these conversations are all a bit different. Some worry the relationship will break. Some feel like they're stepping over a line that isn't theirs to cross. Some are scared they'll say the wrong thing, or that the message won't land, or that they'll end up known as “that person.” All of it is understandable. And all of it skips past the same quiet truth. The hardest part usually isn't the words. It's getting yourself to start.

We focus on “challenging” and forget “conversation”

We call them challenging conversations, or difficult conversations, or hard conversations. Fair enough. They are. But I reckon we get so caught up in the word challenging that we forget the second word.

A conversation needs dialogue.

It isn't one person unloading a list of problems onto another and walking off. It's questions, context, listening, working out what each of you actually knows, and figuring out what happens next. The moment it stops being a conversation and turns into a verdict, you've lost the thing that makes it useful.

Hold that thought, because it changes how you prepare.

I still get nervous before these

I want to be straight about something, because I don't want this to read like advice from someone who finds these easy.

I don't.

I still get nervous, sweaty, butterflies. I normally have a little script running in my head beforehand. That part hasn't gone away with experience, and I'm not sure it ever fully does.

What's changed is what I tell myself while I'm feeling all that. I try to remember that I'm doing this to help someone. Not to have a go at them, not to get something off my chest, but to help. When I can hold onto that, the nerves are still there, but I'm more willing to walk into it anyway. I haven't become someone who finds difficult conversations comfortable. I've just got more comfortable being uncomfortable.

Sometimes the person avoiding it is you

It's easy to talk about other people avoiding hard conversations. I've done plenty of avoiding myself.

I once had a yearly appraisal to complete with a staff member, and there were some behavioural issues that needed to be discussed. Part of what made it tricky was that a lot of the information was coming to me from other people, not things I'd seen with my own eyes.

But if I'm honest, that wasn't really why I sat on it. I sat on it because I didn't want the discomfort of the conversation. About a month went by.

When I finally sat down with them, they asked me a fair question.

“Why wasn't this brought up earlier?”

They were right, and I said so. “That's on me. I needed to have this conversation with you earlier and I didn't.” No defending it, because there was nothing to defend.

By sitting on it for a month I'd made things worse, not better. They felt hurt and undermined. They felt like people had been tiptoeing around them, which they had. That's not a safe place to put someone. Afterwards I made a commitment to myself that if concerns came to me in future, I'd talk to the person rather than let the same thing build up again.

The conversation still sucked. But avoiding it hadn't made it easier. It had just given the discomfort more time to grow.

If it feels awkward, that's okay

Some of this shows up in groups too, not just one on one.

You ask a question in a meeting and everyone goes a bit sheepish. Eyes start darting around. Everyone's waiting for someone else to say the thing they're all thinking, and if nobody does, the silence just gets heavier.

I've felt that in meetings I've led. Over time I've learned to get more curious when I sense something sitting under the surface. I'll try to lower the guardrails and make it clear that walking out without naming the thing doesn't get us any closer to fixing it. It felt clunky the first few times I said it. It still can. But usually all it takes is one person with enough courage to speak. Then someone adds their bit. Then someone else. Before long the awkward silence has turned into an actual conversation.

So if it feels awkward, that's okay. Awkward is good sometimes. It means it's real.

Make it about the behaviour, not the person

Now for one I thought was handled really well, because it's worth knowing what good can look like.

I was in a manager role and a senior nurse educator needed to speak with a student who was underperforming on a clinical placement. I was asked to be the second person in the room.

What stood out was her approach. Her tone stayed consistent. She was empathetic but firm. She knew the facts, and she kept the conversation on the behaviours and the performance concerns rather than turning it into an attack on who the student was. She explained why she was worried about whether they were ready to step into a registered nurse role, then laid out what would happen next, including speaking with the university and what needed to be achieved.

She asked the student questions. She talked through goals that were actually achievable. She checked they understood how serious the conversation was. English wasn't the student's first language, so she also made sure what she was saying was landing, and when something wasn't clear she said it again rather than assuming.

The outcome wasn't “you're not good enough.” There was a plan. The student got an extra two weeks of placement and ended up meeting the requirements to complete it.

That conversation taught me something simple. Empathy and firmness aren't opposites. You can care about someone and still be honest with them.

The trap I see people fall into is the opposite. The conversation becomes “you did this,” “you always do that.” The moment someone hears that, their defences can go straight up, and now you're not having a conversation, you're having an argument. So I try to start with curiosity instead. “Can you help me understand what happened here?” Or just, “I've got a question about something.” It's not a magic phrase, and it doesn't guarantee the other person takes it well. But it gives them room to explain before the whole thing turns adversarial.

There's one more part to that. Don't just hand someone a problem and expect them to sort it out on their own. If I'm raising something because I actually care about someone's development, I've got to take some ownership of helping them improve. The message underneath should be closer to this. I've noticed something, I'm worried it won't serve you well over time, and I want to help you fix it. That's a very different thing from offloading your frustration onto someone. It's also the difference between a conversation that damages a relationship and one that builds it.

When it gets emotional, get curious

Sometimes you go in to talk about one thing and the other person gets really emotional, more than the situation seemed to call for.

When that happens, I don't think the answer is to push harder on the original issue. I get curious instead. Something like “are you okay?” can be a better place to go than ploughing on. We don't know everything that's happening in other people's lives, and everyone's carrying something. Sometimes the difficult conversation ends up showing you that the behaviour you noticed isn't the real problem at all. There's something deeper going on underneath it.

That doesn't mean a personal struggle makes an ongoing issue disappear. It still needs dealing with. But you'll deal with it a lot better once you understand what you're actually looking at.

A phrase I lean on a lot when things start heating up is “what do we know?” I like it because it hands the other person the first word. They tell me what they know, I tell them what I know, and from there we can work on what happens next. When a conversation is going in circles and getting more emotional, that question can act as a reset. It pulls both of us back towards the facts instead of going another lap around the feelings.

Say it before you go home

Speaking up doesn't mean every issue has to be dealt with this second. If someone's flustered in the middle of a chaotic shift, or clearly overwhelmed, that's probably not the moment. Waiting for both of you to be in a steadier state isn't the same as avoiding it.

But I've got a rough personal measure for the ordinary stuff. If something needs to be said, I try to say it before I go home.

Once you start carrying it into tomorrow, and then the next day, two things happen. There's a good chance the conversation just quietly never happens. And the specifics start to blur. You lose the exact behaviour, the exact moment, the thing you were actually going to talk about, and it all softens into a vague feeling that something's off. That's much harder to raise well.

So once I've decided today's the day, the way in is often pretty simple. “Can I talk to you about something?” Or naming it honestly: “This isn't going to be an easy conversation.” Setting the expectation early helps both of you understand what you're walking into.

The word we forget

If someone came to me and said, “I know I need to have this conversation, but I really don't want to,” here's the question I'd put back to them.

If you were on the other end, and nobody was telling you the hard truths, nobody was pulling you aside to help you get better, how would you feel?

Most of us would want to know. Done with a bit of care, having the conversation is usually the more respectful thing, not the crueller one. It's an act of caring about someone enough to be honest with them.

Which brings me back to where I started. The goal isn't to win. It's to create enough dialogue that you can actually talk about the problem, instead of letting it turn into a personal attack that damages the relationship. Questions help. Curiosity helps. “Help me understand” helps. Context matters. Listening matters.

We call these things challenging conversations, and we spend most of our energy bracing for the challenging part. But a conversation needs dialogue and context to be a conversation at all. So maybe we could worry a little less about the first word, and pay a bit more attention to the second one.

Conversation.