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The One Thing Nobody Tells You About Difficult Conversations (And Why Most Training Gets It Wrong)
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Here's what I wish someone had told me fifteen years ago when I was a fresh-faced supervisor in Brisbane, armed with nothing but a clipboard and misplaced confidence: difficult conversations aren't actually difficult because of the conversation itself.
They're difficult because we've been taught to approach them like we're diffusing a bloody bomb.
I've spent the last decade and a half training executives, managers, and supervisors across Melbourne, Sydney, and Perth on this exact topic. And frankly? About 73% of the "expert advice" out there is complete rubbish. Most training programmes treat difficult conversations like some sort of corporate choreography – step one, step two, maintain eye contact, use "I" statements, blah blah blah.
But here's the thing that'll make some people uncomfortable: the most effective difficult conversation I ever witnessed lasted exactly fourteen seconds. No sandwich method. No careful preparation. Just straight talk.
Why Traditional Training Misses the Mark
Let me paint you a picture. You know those role-playing exercises where everyone sits in a circle and practices "active listening"? Where someone pretends to be an underperforming employee whilst another person demonstrates textbook feedback techniques?
Absolute waste of time.
Real difficult conversations don't happen in sterile training rooms with name tags and laminated scenario cards. They happen when Sarah from accounts has been consistently late for three months and you've just discovered she's been covering for her colleague's mistakes. They happen when your best performer suddenly starts missing deadlines and you suspect there's something going on at home.
The problem with most conflict resolution training is that it assumes every difficult conversation follows the same neat little formula. It doesn't.
The Real Secret Nobody Wants to Admit
After facilitating hundreds of these conversations – and yes, I mean actually being in the room, not just theorising about it – I've noticed something fascinating. The managers who excel at difficult conversations share one common trait that has nothing to do with communication techniques.
They genuinely don't see these conversations as difficult.
Sounds ridiculous, right? But think about it. When you truly believe that addressing performance issues, setting boundaries, or discussing sensitive topics is just part of your job – not some special, anxiety-inducing event – your entire approach changes.
I learned this the hard way during my time at a major consulting firm in Sydney. (Can't name names, but let's say they have very shiny offices in the CBD.) I was sweating bullets before every "challenging discussion" until my mentor pointed out something obvious: "Mate, you're treating this like you're about to fire someone. You're just having a chat about work."
Where Most People Go Wrong
Mistake #1: Over-preparing Yes, you heard me right. Most people prepare themselves into paralysis. They script out every possible response, anticipate seventeen different scenarios, and end up sounding like they're reading from a teleprompter.
Mistake #2: Assuming everyone thinks like you Just because you'd prefer someone to "ease into" bad news doesn't mean everyone does. Some people actually appreciate directness. Revolutionary concept, I know.
Mistake #3: Making it about you This one drives me mental. Managers who start difficult conversations with long explanations about how "hard this is for me to say" or how they "hate having these discussions."
Nobody cares how you feel about it. Get on with it.
Mistake #4: Believing every conversation needs a resolution Sometimes the point isn't to solve everything. Sometimes it's just to acknowledge what's happening and set expectations moving forward. Not every workplace drama needs a happy ending tied up with a bow.
What Actually Works (Based on Real Experience)
After watching countless managers transform their approach – and seeing the results firsthand – here's what actually makes a difference:
Start with assumptions, not accusations. Instead of "You've been coming in late," try "I'm assuming there's something going on that's affecting your start times." Same information, completely different energy.
Be specific about impact, vague about motives. You know exactly how their behaviour affects the team, but you don't know why they're doing it. Stick to what you can observe.
Set timeframes that actually matter. Don't say "we need to see improvement" when what you mean is "this needs to change by next Friday or we'll need to discuss next steps."
The beauty of this approach? It works whether you're dealing with performance issues, personality conflicts, or those awkward conversations about personal hygiene that nobody wants to have but everyone's thinking about.
The Australian Advantage
Here's something I've noticed working across different cultures and companies: Australians are actually pretty well-positioned for difficult conversations. We don't tend to beat around the bush as much as our American colleagues, but we're generally more tactful than our British counterparts.
The challenge is that many Australian managers get caught up trying to be "nice" instead of being helpful. There's a difference. Nice is avoiding the conversation altogether. Helpful is having it properly.
I remember working with a team leader in Adelaide who spent six months trying to "gently encourage" an underperformer rather than addressing the issue directly. Know what happened? The rest of the team lost respect for both of them. Sometimes being kind means being clear.
The Follow-Up Nobody Talks About
This might be controversial, but most difficult conversations aren't actually that difficult. It's the follow-up that kills people.
You have the conversation, everyone nods and agrees, and then... nothing changes. So you have to have the conversation again. And again.
The managers who excel at this stuff understand that the conversation is just the beginning. They follow up consistently, they document outcomes, and they're prepared to escalate when necessary.
Because here's the uncomfortable truth: if someone doesn't change after a clear, fair conversation about expectations, it's not because you didn't communicate well enough. It's because they've chosen not to change.
When to Give Up on the Gentle Approach
Sometimes you need to abandon the collaborative approach entirely. If you've had the same conversation three times with no change, stop trying to find new ways to explain the same information.
Move to consequences.
This doesn't make you a bad manager. It makes you an effective one.
The One Question That Changes Everything
Before any difficult conversation, ask yourself this: "If this person's behaviour doesn't change, what will I do?"
If you don't have a clear answer, you're not ready for the conversation yet.
That question forces you to think beyond the immediate discomfort and consider actual outcomes. It also helps you approach the conversation with the right level of seriousness.
Final Thoughts
Look, difficult conversations will never be anyone's favourite part of management. But they don't have to be the anxiety-inducing nightmares that most training programmes make them out to be.
The best managers I know treat these conversations like any other work task – important, requiring attention, but not deserving of three sleepless nights and a PowerPoint presentation.
Start small. Pick one conversation you've been avoiding and just have it. No special techniques, no complicated frameworks. Just clear, direct communication about what's happening and what needs to change.
You might be surprised how straightforward it actually is.
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