The Five Things I Wish Someone Had Told Me About Difficult Conversations Before I Stuffed Up 47 of Them

You know that feeling when you're walking to someone's office and your stomach's doing gymnastics because you know the conversation ahead is going to be... well, difficult?

I've been in workplace training for 18 years now, and I reckon I've seen just about every conversation go sideways that possibly can. Started as a fresh-faced HR coordinator in Perth back in 2007, thinking I had all the answers because I'd read a few books and done a course.

Spoiler alert: I didn't.

The Great Misconception About "Natural Communicators"

Here's something that'll ruffle feathers - most people who think they're naturally brilliant at difficult conversations are actually the worst at them. They're the ones who steamroll over concerns, mistake volume for authority, and confuse being direct with being harsh.

The best communicators I know? They're usually the quiet ones who listen more than they speak.

I learned this the hard way when I completely botched a performance review with Sarah (not her real name) back in 2009. Thought I was being "refreshingly honest" when I told her she had terrible time management skills. What I was actually being was unnecessarily brutal. Sarah left the company three months later - not because she couldn't improve, but because I'd made her feel like a complete failure.

That taught me something crucial: managing difficult conversations isn't about winning or being right. It's about finding solutions while preserving dignity.

The 73% Rule Nobody Talks About

Research I came across suggests that 73% of workplace conflicts escalate unnecessarily because people avoid the initial conversation. They let things fester until they explode. Sound familiar?

I see this constantly in Melbourne offices, Sydney corporate towers, and Brisbane small businesses. Someone's performance is slipping, or they're consistently late, or they're creating tension in team meetings. But instead of addressing it early when it's still manageable, managers hope it'll magically resolve itself.

It never does.

The other side of this coin is equally problematic - leaders who dive into difficult conversations without any preparation whatsoever. They wing it, thinking their good intentions will carry them through.

Big mistake.

Why Your Current Approach Probably Isn't Working

Let me share something that might sting a bit: if you're having the same difficult conversation repeatedly with the same person, you're doing it wrong.

I used to think persistence was the answer. Keep having the conversation until they "get it." What I discovered was that I was essentially having the same ineffective conversation over and over, expecting different results. That's pretty much the definition of insanity, isn't it?

The breakthrough came when I started approaching these conversations like a proper business consultant would approach a problem. You don't just keep applying the same solution when it's not working. You analyse what's going wrong and adjust your approach.

Emotional intelligence training changed everything for me. Suddenly I understood why some conversations worked and others didn't.

The Four-Phase Framework That Actually Works

Most training programs overcomplicate this stuff. They give you 47 steps and seventeen different models to remember. Who's got time for that when you're dealing with an upset employee or a defensive team member?

Here's what I use now:

Phase 1: Preparation (The Bit Most People Skip) Don't just think about what you want to say. Think about what they need to hear. There's a massive difference. Consider their perspective, their workload, their recent challenges, and yes, their personality type.

Phase 2: Connection Before Correction Start with genuine concern for them as a person, not just as an employee. "I've noticed you seem stressed lately" works infinitely better than "Your performance has declined."

Phase 3: Collaborative Problem-Solving This is where most conversations either soar or crash. Stop telling them what to do and start asking what they think would help. You'll be amazed how often they already know the solution.

Phase 4: Clear Follow-Up Commitments Vague agreements lead to repeated conversations. "Let's touch base soon" means nothing. "Let's check in Friday at 2pm to see how the new process is working" means everything.

The Goldfish Memory Problem

Here's where I'm going to contradict myself slightly, which drives my wife absolutely mad but seems to happen in most of my professional observations.

While I just told you to be specific about follow-ups, I've also learned that people have the attention span of goldfish when they're stressed or defensive. If you overwhelm them with too many action items in one conversation, nothing gets done.

Pick one thing. One clear, achievable thing they can work on. Then have another conversation later about the next thing.

This approach has saved me countless hours of frustration and probably prevented a few stress-related heart attacks along the way.

What the Training Manuals Don't Tell You

Training manuals love to pretend that every difficult conversation can be neatly resolved in 30 minutes with a tidy conclusion and handshakes all round. Real life is messier than that.

Sometimes difficult conversations need to happen in stages over weeks or months. Sometimes the person isn't ready to hear what you're saying the first time, and that's okay. Sometimes you need to acknowledge that the conversation didn't go well and start over.

I had a situation with a team leader in Adelaide who was struggling with delegation. Our first conversation was a disaster - I came across as preachy, he got defensive, and nothing was resolved. Instead of pretending it had gone well, I called him the next day and said, "That didn't go the way I hoped yesterday. Can we try again?"

That simple acknowledgment of failure opened up a completely different dynamic.

The Australian Context Nobody Mentions

Here's something specific to our working culture that international training programs miss completely - Australians have a particular relationship with authority and directness that affects how these conversations play out.

We don't respond well to corporate-speak or overly formal approaches. We appreciate straight-talking, but we also value fairness and giving people a fair go. This creates an interesting tension in difficult conversations.

You can't be too soft (we'll see right through it), but you can't be too harsh either (we'll write you off as a poor manager). Finding that sweet spot is crucial for Australian workplaces.

Technology Is Making This Harder

Everyone's doing difficult conversations over video calls now, and frankly, it's making everything more challenging. You lose so much nuance when you're staring at a screen instead of sitting across from someone.

Body language is crucial in difficult conversations. Being able to lean forward, maintain eye contact, and read subtle facial expressions makes all the difference. Video calls flatten all of that.

When possible, I still advocate for face-to-face difficult conversations. If that's not an option, at least pick up the phone instead of hiding behind email or Slack messages.

The Follow-Up That Makes or Breaks Everything

This is where most managers completely drop the ball. They have the difficult conversation, feel relieved it's done, and then... nothing. No follow-up, no check-in, no acknowledgment of improvement.

People need to know their efforts are being noticed. If someone makes genuine changes after a difficult conversation and you don't acknowledge it, you've essentially guaranteed that next time will be even harder.

I make it a point to catch people doing things right after we've addressed something that was going wrong. It reinforces the behaviour you want to see and shows them the conversation was worth having.

When Difficult Conversations Become Impossible Conversations

Sometimes, despite your best efforts, the conversation simply isn't working. The person remains defensive, dismissive, or completely checked out. This is when you need to shift from coaching mode to performance management mode.

It's not a failure on your part - some people simply aren't ready or willing to engage constructively. Recognising this early can save everyone time and frustration.

The key is being able to distinguish between someone who's struggling to understand and someone who's refusing to engage. The former needs patience and different approaches; the latter needs clear consequences.

---

Related Training Resources:

• Brand Local Blog
• Tag Group Posts