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Why Your Difficult Conversations Training Isn't Working (And the Three Things They Never Tell You)
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Here's something that'll make your HR department squirm: 87% of managers who attend difficult conversations training still avoid the hard chats six months later.
I've been running workplace training programs across Australia for eighteen years now, and I can tell you right off the bat that most difficult conversations courses are about as useful as a chocolate teapot. They teach you scripts, give you role-playing exercises that feel like amateur dramatics gone wrong, and send you back to your desk with a folder full of "conversation frameworks" that you'll never bloody use.
Want to know why? Because they're teaching you to have fake conversations.
The Script Problem
Every training provider loves their scripts. "When discussing performance issues, start with 'I've noticed...' and then use the SOAR method..." Bollocks. Absolute bollocks.
Real difficult conversations don't follow scripts because real people don't follow scripts. Your team member who's been turning up late? They might come back with something completely unexpected like their marriage is falling apart or they're dealing with elderly parents. Good luck finding that response in your neat little training manual.
I learned this the hard way about twelve years ago when I tried to have a "structured feedback conversation" with a brilliant but chaotic project manager in Brisbane. Followed the framework perfectly. She burst into tears within the first two minutes because I sounded like a robot reading from a manual. Which, let's be honest, I was.
The best difficult conversations I've had in my career started with something like "Look, this is awkward, but we need to talk about..." No framework. No SOAR method. Just honesty.
The Empathy Myth
Here's where I'll probably upset some people: empathy isn't always the answer. Every training course bangs on about being empathetic, understanding their perspective, walking in their shoes. Sometimes that's exactly what you need to do.
Sometimes, though, you need to be direct and clear rather than endlessly empathetic. If someone's consistently missing deadlines and affecting the whole team, they don't need your understanding of their work-life balance struggles. They need clarity about expectations and consequences.
Medibank does this brilliantly - their managers are trained to separate understanding from accountability. You can acknowledge someone's challenges while still holding them responsible for results. Revolutionary concept, apparently.
The empathy-first approach often becomes avoidance dressed up as caring. "I don't want to upset them" becomes "I'll let the problem continue indefinitely." That's not empathy. That's cowardice with good marketing.
What Actually Works (Spoiler: It's Uncomfortable)
After nearly two decades of watching managers fumble through difficult conversations, I've noticed three things that actually make a difference:
First: Timing beats technique every time. The best conversation framework in the world won't help if you're having the chat three months too late. Most problems that explode into "difficult conversations" could have been handled with quick, uncomfortable chats weeks earlier.
I once worked with a team leader who was notorious for letting things fester. By the time he'd work up the courage to address an issue, it had usually evolved from a minor performance blip into a major team disruption. Meanwhile, his colleague down the hall would address things immediately - sometimes clumsily, but always quickly. Guess whose team performed better?
Second: Your discomfort is not their problem. This is the big one that nobody talks about in training. The reason these conversations are difficult is usually because you're uncomfortable having them, not because the other person is particularly difficult to talk to.
Stop making your anxiety their responsibility. Don't start with "This is really hard for me to say..." That immediately makes the conversation about you instead of about the issue that needs addressing.
Third: Most "difficult" conversations aren't actually difficult. They're just conversations you don't want to have. There's a difference.
A difficult conversation is telling someone their role is being made redundant or addressing serious misconduct. An uncomfortable conversation is telling someone their presentation skills need work or that they need to improve their punctuality. We conflate the two and end up treating every bit of feedback like we're delivering terminal news.
The Melbourne Test
I've got this little test I use with managers. I call it the Melbourne Test because I first used it with a client in South Melbourne who was terrified of giving feedback to her team.
If you can't explain the issue to your best mate over coffee without using any business jargon or frameworks, you're probably overcomplicating it. "Sarah's always late and it's pissing off the team" is much clearer than "Sarah demonstrates inconsistent adherence to our start-time expectations, which may be impacting team dynamics."
Use normal words. Address real problems. Stop hiding behind corporate speak and training frameworks.
The Follow-Up Factor
Here's what 90% of managers get wrong: they think the difficult conversation is a one-and-done thing. You have "the chat," everyone feels better, problem solved. Job done.
Nope.
The conversation is just the beginning. The real work happens in the follow-up. Most performance issues need three or four check-ins over the following months, not one dramatic clearing-of-the-air session.
I've watched managers pat themselves on the back for "finally having that difficult conversation" while completely ignoring whether anything actually changed afterwards. It's like declaring victory after the first battle of a very long war.
What Your Training Provider Won't Tell You
Training companies have a vested interest in making this seem complicated. If difficult conversations were just about being clear, direct, and timely, you wouldn't need their three-day intensive workshop, would you?
The truth is that most workplace conversations only become difficult because we avoid them until they become problems. Deal with things quickly and most of them never reach the "difficult" stage.
But that doesn't sell training courses.
I'm not saying all training is useless - there are some excellent providers out there doing great work. But if your difficult conversations training doesn't include practice with real situations from your workplace, role-plays with actual colleagues (not strangers), and multiple follow-up sessions, you're probably wasting your money.
The best managers I know learned through experience, not training manuals. They had difficult conversations, made mistakes, learned from them, and got better. They didn't become conversation experts by following frameworks. They became good communicators by communicating.
The Bottom Line
Stop looking for the perfect way to have difficult conversations. There isn't one. Start having imperfect conversations now, while the problems are still small and manageable.
Your team would rather have an awkward but honest conversation with you than months of passive-aggressive tip-toeing around issues. Trust me on this one.
And for the love of all that's holy, throw out those conversation scripts. Real people having real conversations don't sound like they're reading from a customer service manual.
Just be human. Be direct. Be timely. Everything else is just noise.
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