Why Your "Difficult Conversations" Are Actually Just Bad Conversations

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Here's something that'll ruffle a few feathers: 87% of what we call "difficult conversations" aren't difficult at all. They're just conversations we're having badly.

I've been training executives, middle managers, and everyone in between for over 16 years now, and I'm bloody tired of hearing about "difficult conversations" like they're some mythical beast we need special armour to face. The truth is, most of these conversations become difficult because we make them that way.

Take last month when I was working with a manufacturing company in Brisbane. The plant manager was dreading a chat with his star foreman about safety compliance. He'd been putting it off for weeks, building it up in his head like he was about to negotiate nuclear disarmament. When we finally role-played it, the whole thing took eight minutes. Eight minutes! And the foreman thanked him afterwards.

The Real Problem Isn't the Conversation

Most professionals treat every serious workplace conversation like they're defusing a bomb. We psych ourselves up, rehearse scripts, and approach people like they're made of glass. Then we wonder why everything feels forced and awkward.

The conversations aren't the problem. Our approach is.

I've watched seasoned leaders who can negotiate million-dollar contracts turn into nervous wrecks when they need to tell someone their performance isn't cutting it. These same people who'll argue with suppliers all day suddenly can't figure out how to say "Sarah, we need to talk about your deadlines."

What's really happening is we've bought into this idea that certain topics are inherently difficult. Performance issues? Difficult. Workplace behaviour? Difficult. Budget cuts? Definitely difficult.

Bollocks.

The Three Myths Keeping You Stuck

Myth One: You need to be gentle about everything. Some feedback needs to be direct. Sugar-coating important messages doesn't make you kind – it makes you unclear. I've seen managers spend fifteen minutes dancing around a simple point that could've been made in two sentences.

Myth Two: People will automatically get defensive. This is self-fulfilling prophecy territory. Go into a conversation expecting drama, and you'll create it. Approach someone assuming they're reasonable and want to improve, and that's usually what you'll get. Companies like Atlassian have built entire cultures around direct, honest feedback, and their employee engagement scores are through the roof.

Myth Three: There's a perfect script for every situation. Those cookie-cutter conversation frameworks might work in training videos, but real people don't follow scripts. The moment someone responds differently than expected, your whole rehearsed approach falls apart.

I'll be honest – I used to be terrible at this myself. Back in my early consulting days, I'd avoid difficult feedback conversations for weeks. I'd convince myself I was being strategic, waiting for the right moment. Really, I was just scared of making things uncomfortable.

What Actually Works (And It's Simpler Than You Think)

The best conversations I've witnessed in the workplace have three things in common: they're direct, they're respectful, and they focus on the future, not the past.

That's it. No fancy frameworks or psychological manipulation required.

Direct doesn't mean harsh. It means clear. "Your reports have been late three times this month" instead of "I've noticed some challenges with timing recently." See the difference?

Respectful doesn't mean walking on eggshells. It means treating the other person like a capable adult who can handle honest feedback. Most people appreciate straight talk more than corporate speak.

And focusing on the future means talking about what you want to see moving forward, not rehashing every past mistake. People can't change what they've already done, but they can absolutely change what they do next.

The Perth Principle

I learned this lesson the hard way during a project in Perth about five years ago. The client's team was struggling with a particularly challenging employee – let's call him David. David was brilliant at his job but had a habit of shutting down any feedback with aggressive responses.

Management had been tiptoeing around David for months, having these elaborate strategy sessions before every interaction. They'd practically written dissertations on how to approach him about basic work issues.

When I finally met David, I found out something interesting: nobody had ever actually tried just talking to him normally. They were so worried about his reactions that they'd never given him a chance to react differently.

The solution? A straightforward conversation that started with "David, you're excellent at your technical work, but we need to address how you respond to feedback." No drama, no script, no elaborate build-up. Just a clear statement of the issue and an expectation for improvement.

David's response? "Finally! I was wondering when someone would just tell me straight up what the problem was."

He's still with the company, and his manager tells me their working relationship has never been better. The "difficult" conversation that management had been dreading for months took less than ten minutes and solved the problem permanently.

Why We Overthink Everything

Here's the thing about workplace conversations – we've professionalised them to death. We've created industries around "crucial conversations" and "radical candour" when really, we just need to remember how to talk to each other like humans.

The rise of remote work has made this worse, not better. Now every conversation feels formal because it's scheduled in a calendar invite. We've lost the art of the quick chat, the casual check-in, the spontaneous feedback moment.

But here's what I've noticed: the best remote teams I work with have figured out how to recreate those informal conversation opportunities. They're not having fewer difficult conversations – they're having more frequent, smaller conversations that prevent issues from becoming "difficult" in the first place.

The conversation that feels impossible today probably felt routine six months ago when the issue was smaller.

Making It Practical

Stop calling them difficult conversations. Start calling them important conversations. The language shift matters more than you think.

When you need to address something at work, ask yourself: "If this were my friend, how would I bring this up?" Then do approximately that, with a bit more professional polish.

Most of the time, that's enough.

I know this approach won't work for every situation. There are genuinely sensitive topics that require more finesse. Legal issues, personal crises, major restructures – these need careful handling.

But 90% of what we label as "difficult conversations" are just normal workplace discussions that we've built up in our heads. Performance feedback, project concerns, team dynamics, deadline issues – these are all part of regular business communication.

The sooner we treat them that way, the better off we'll all be.

Remember: the goal isn't to become a conversation ninja overnight. It's to stop making simple conversations complicated. Most of the time, people just want to know where they stand and how to improve. Give them that information clearly and respectfully, and you'll be amazed how "difficult" these conversations aren't.

Trust me – after sixteen years of watching smart people tie themselves in knots over basic workplace communication, the simplest approach is usually the right one.

Now stop overthinking it and go have that conversation you've been putting off.