There’s a conversation you’ve been putting off. You know the one. It’s been sitting in the back of your mind for weeks — maybe longer. You’ve rehearsed it in the shower, talked yourself out of it over coffee, and quietly hoped the situation might just resolve itself.

It won’t.

And somewhere, you already know that.

Difficult conversations are the number one leadership challenge I hear from small business owners across Australia. Not strategy. Not cash flow. Not even finding good people. It’s this: the conversation they’re not having with someone who’s already on their team.

And I get it. When you run a small business, the relationships are close, the team is small, and everything feels personal. Telling a loyal employee their performance isn’t cutting it isn’t just a work conversation — it feels like it could unravel the whole thing. So you wait. You soften the feedback until it disappears. You convince yourself it’s not that bad. Or you drop the heaviest version of it all at once, after months of silence, and wonder why it doesn’t land well.

Here’s what years of working with business owners has taught me: the conversations you avoid cost you far more than the ones you have. You just don’t see the bill until it’s overdue.

Why we go quiet

In my work with small business owners, the same barriers come up repeatedly — and they have nothing to do with intelligence or intent. I explore these barrier to difficult conversations in my book Thriving Leaders,.

The first is the relationship. You’ve built something together. You know their kids’ names. You’ve celebrated their wins. The idea of damaging that by saying the wrong thing is genuinely scary. So you say nothing. But silence doesn’t protect relationships — it quietly corrodes them. When we don’t address issues, frustration builds under the surface. Respect erodes. You start managing around someone instead of with them. By the time you finally say something, months of unexpressed tension come with it, and the conversation is ten times harder than it needed to be.

The second barrier is the reaction. Will they get defensive? Will they cry? Will they threaten to leave? That uncertainty is paralysing, especially when you can’t afford to lose them. The thing is, most people don’t react the way we imagine they will. Our worst-case scenario plays on a loop in our head, but it rarely reflects reality. And even when a conversation is uncomfortable, discomfort isn’t damage.

The third barrier is time. You’re already stretched. A feedback conversation requires preparation, and preparation requires headspace you don’t feel like you have. So you file it under “I’ll get to it” — which, in a small business, often means never. But an issue left unaddressed doesn’t stay the same size. It grows. A twenty-minute conversation becomes a three-month performance management situation. Or worse, a resignation you didn’t see coming from someone you didn’t realise was already checked out.

A Harvard Business Review study found 44 per cent of leaders say giving constructive feedback is stressful and difficult, and 21 per cent avoid it altogether. In a small business where every single person has an outsized impact on your results, your culture and your clients, that avoidance has a very real price tag.

Three practical shifts to make

1. Lead with intent, not issue

Most difficult conversations fail before they begin because the other person doesn’t know why you’re having them. When someone doesn’t know your intent, they fill the gap with their worst assumption — and they spend the entire conversation defending against that, not hearing what you’re actually saying.

Before you raise the issue, name your purpose. Something like: “I’ve noticed something I think could really help you — when’s a good time to chat?” Or: “I want to make sure I’m supporting you properly. Can we grab fifteen minutes?” Asking for permission also gives the other person a degree of control, which matters more than people realise. When someone feels in control, they’re far more likely to stay open.

This single shift changes the entire temperature of the conversation before it even starts.

2. Focus on behaviour, not character

This is where most difficult conversations go sideways. The moment feedback sounds like a character judgement, the walls go up — and they don’t come back down easily.

“You’re unprofessional” is a verdict. “When you sent that message to the client before we’d signed off, it put us in a difficult position” is a fact. One threatens who someone is. The other describes what happened and gives them something concrete to work with.

Keep it specific. Keep it factual. Describe the situation, the behaviour and the impact — and use “I noticed” or “I observed” rather than sweeping statements like “you always” or “you never.” Those phrases are almost never accurate and almost always start an argument about frequency rather than a genuine conversation about change.

3. Ask before you conclude

Here’s the tip most people skip: after you’ve shared the situation and the impact, stop talking. Ask a genuine question. “What’s your take?” or “How did that land from your end?”

This is where the conversation either opens up or shuts down, and it depends entirely on whether the other person feels heard. You might learn context you didn’t have. You might find the issue is simpler — or more complex — than you thought. Either way, a two-way conversation is far more likely to result in actual change than delivering a verdict and waiting for compliance.

I won’t give you a script for what comes next, because that’s where the real skill lives — and it’s different every time. What I will say is that leaders who learn to stay curious in these moments, rather than rushing to resolve the discomfort, consistently get better outcomes. That curiosity is a learnable skill, and it changes everything.

The reframe that changes everything

Here’s the shift I invite every business owner to make: stop thinking of difficult conversations as something you do to people, and start seeing them as something you do for them.

When you hold back honest feedback, you’re not protecting someone. You’re withholding the information they need to grow. As a business owner, you’re not just entitled to have these conversations — you’re responsible for them. The people on your team deserve to know where they stand. They deserve the chance to improve. And your business deserves a culture where honesty is the norm, not the exception.

The businesses I see thrive are not the ones where everyone is always comfortable. They’re the ones where the leader has shown — repeatedly — that hard conversations lead to better outcomes, not broken relationships.

That conversation you’ve been putting off? It’s probably the most caring thing you could do.

This post first appeared on Flying Solo. You can read it here.

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