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Why Most "Difficult Conversation" Training Is Rubbish (And What Actually Works)
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Seventeen years in business consulting, and I'm still amazed how many executives freeze up the moment they need to have what corporate trainers love calling a "difficult conversation."
Last month I watched a CEO—let's call him Dave—spend three weeks crafting the perfect email to tell his marketing manager she wasn't meeting expectations. Three bloody weeks! Meanwhile, his entire Melbourne office could feel the tension, productivity was tanking, and poor Sarah was oblivious to the fact she was apparently failing. This is the sort of corporate theatre that drives me mental.
Here's the thing most leadership gurus won't tell you: there's no such thing as a difficult conversation. There are only conversations we haven't prepared for properly.
The Real Problem With "Difficult" Conversations
The training industry has absolutely butchered this topic. Walk into any corporate workshop and they'll teach you the HEAR model, or the DESC method, or some other acronym that sounds clever but falls apart the moment real emotions enter the room. I've seen managers practise these scripts like they're auditioning for Neighbours, only to completely cock it up when their team member starts crying or gets defensive.
The problem isn't the conversation—it's that we've made it about us instead of them. When you're worried about being the "bad guy" or maintaining your image as the "nice boss," you're already stuffed.
I learned this the hard way back in 2018 when I had to tell my business partner we needed to part ways. Spent weeks rehearsing corporate-speak about "strategic misalignment" and "different visions." Complete waste of time. What actually worked was sitting down with a coffee and saying, "Mate, this isn't working for either of us, and here's why..."
What 73% of Managers Get Wrong
Most managers approach these conversations like they're defusing a bomb. They tiptoe around the issue, use euphemisms, and basically talk in riddles hoping the other person will magically understand what they're not saying. It's exhausting for everyone involved.
I watched this play out spectacularly at a Brisbane firm last year. The operations manager spent 20 minutes talking about "opportunities for growth" and "areas of focus" before finally—FINALLY—saying what everyone knew: "Your reports are consistently late and contain errors." Twenty minutes of corporate waffle for a sentence that could have saved everyone's sanity.
The truth is, clarity isn't cruel. Vagueness is cruel. When you dance around issues, you're actually showing less respect for the other person, not more.
The Three Pillars That Actually Work
Forget everything you've been taught about difficult conversations. Here's what actually matters:
Timing matters more than technique. Don't have performance conversations on Friday afternoons when everyone's mentally checked out. Don't spring serious discussions on people who've just walked in the door. And for God's sake, don't use the annual review as your first attempt to address issues that have been brewing for months. The best conversations happen when both parties have the mental space to engage properly.
Context is everything. Before diving into the issue, explain why you're having the conversation. "I'm bringing this up because I value your contribution to the team and want to see you succeed" lands very differently than launching straight into criticisms. This isn't about being soft—it's about being strategic.
Curiosity trumps judgment. Instead of assuming you know why something is happening, ask questions. "Help me understand what's getting in the way of meeting these deadlines" works better than "You need to be more organised." You'd be surprised how often the real issue isn't what you think it is.
The most successful "difficult" conversation I've facilitated wasn't difficult at all. A Perth warehouse manager thought he needed to discipline a worker for constant lateness. Turns out the guy's wife had been undergoing chemotherapy, and he'd been dropping her at treatment before work. Five minutes of genuine curiosity uncovered a solution that helped everyone: adjusted start times and better communication. No discipline required.
The Melbourne Mindset
Working primarily with Australian businesses, I've noticed we have a particular challenge with direct communication. We're so concerned with being "nice" that we often end up being unclear. This cultural tendency to soften everything actually makes conversations harder, not easier.
Compare that to how we handle things with mates. If your friend was consistently showing up late to footy training, you wouldn't spend weeks crafting an email about "punctuality opportunities." You'd say, "Mate, you're always bloody late—what's going on?" Done. Clear, direct, but still caring.
The same principles apply in business, just with slightly better vocabulary. You can be direct without being a dickhead about it.
When Scripts Actually Help (And When They Don't)
Here's where I probably contradict half the training material out there: scripts can be useful, but not for what you think. Don't script the conversation—script the opening. Having a clear, respectful way to start prevents you from rambling or losing your nerve.
Something like: "I'd like to talk about the project deadlines we've been missing. My goal is to understand what's happening and figure out how we can get back on track." That's it. After that, you need to actually listen and respond to what they're saying, not follow some predetermined flowchart.
The companies that excel at these conversations—think Atlassian with their legendary culture of direct feedback—focus on making them routine rather than rare. When feedback flows regularly, there are fewer "difficult" moments because issues get addressed before they become problems.
The Aftermath Nobody Talks About
One thing most training completely ignores: what happens after the conversation ends. You can nail the discussion, reach clear agreements, and still have it fall apart if you don't follow through properly.
I've seen managers deliver brilliant feedback sessions then completely fail to check in on progress or provide support. It's like teaching someone to drive then throwing them the keys to a Formula One car. The conversation is just the beginning, not the end.
The best managers I work with treat these discussions as the start of ongoing dialogue, not one-off events. They schedule follow-ups, offer resources, and actually notice when improvements happen. Revolutionary concept, I know.
Why This Matters More Than Ever
With remote work and hybrid teams becoming the norm, these skills are even more critical. You can't rely on corridor conversations or reading body language to understand what's going on with your team. Everything needs to be more intentional, more direct, and ironically, more human.
The teams thriving in 2025 are those where managers have learned to address issues quickly and clearly, without all the corporate theatre. It's not about being harsh—it's about being honest enough to help people grow.
Look, after nearly two decades of watching organisations tie themselves in knots over basic communication, I'm convinced this isn't actually about conversation skills. It's about courage. The courage to care enough about someone to tell them the truth, even when it's uncomfortable.
Most people actually want to know how they're doing. They want to improve. They just need someone brave enough to have the conversation that matters.
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