How to have a difficult conversation that doesn't stress you out

Raising a concern without making it a thing

There’s more than one way to dodge a real conversation. Most of them look like subtlety wrapped in manners, rules, or performance.

The American form of subtlety is like a sledgehammer to your face. People insist on assertiveness so the wrongdoer knows exactly how they messed up. People need to feel ashamed about their actions so they’ll be motivated to improve themselves and reduce the chance of it happening again. You will be held to account for your actions.

The stereotyped Canadian form of subtlety is apologising for making someone feel bad, and reassuring them it’s actually all okay. The person wronged will sort it out themselves because the last thing they want is to be seen as a troublemaker.

The Australian form of subtlety is passive aggression delivered with a fake calm and a smile. You’re not quite sure if they’re pissed at you or giving you constructive feedback, or both. You’re also not convinced anything’s actually been resolved between you.

Most people just want to get it over with and launch straight into the criticism or their version of what didn’t go well.

This can catch the other person off guard. If their default is self-blame, they’re already in a shame response. It’s an amygdala hijack moment: their whole body’s on alert and now they’re hearing everything through their “they think I’m shit” filter.

On the other hand, you don’t want to walk on eggshells just to protect someone else’s fragility. You should be able to say what’s on your mind. It’s just about HOW you do it that gets the outcome you want. A realistic outcome is that you’ve raised their awareness of a character trait or habit that’s a barrier to connection. Even if it was hard to share and hard to hear, the trust you have for each other remains intact.

This process is especially useful when you’re speaking to someone who intellectualises everything to cover up their insecurity, or who spirals into shame and self-blame at the slightest hint of feedback. Both strategies are attempts to avoid vulnerability. This is why it’s important not to lead with confrontation, emotional intensity, or performance, which flies in the face of current feedback practice guidelines. These guidelines tend to focus on delivering your observations and emotional impact clearly and assertively, but that often makes the conversation about you, not the issue, setting off the exact defences you’re trying to avoid.

If you're thinking, this sounds like she’s setting up for an article on safe spaces, think again. Declaring something a safe space is often the quickest way to spike anxiety and send the wrong intention for a reflective conversation. The phrase has become code for “I’m about to say something intense and I expect you to handle it graciously.” Conversations that demonstrate respect aren’t always safe especially when clarity, insight, and growth require friction, tension, or discomfort.

There’s a way to say what you need to say without making it a performance…or a disaster.