Advice

The Truth About Difficult Conversations: Why Your Avoidance Strategy Is Actually Making Everything Worse

Look, I'm going to say something that might ruffle some feathers: most people think they're good at difficult conversations, but they're absolutely terrible at them. And I mean truly, spectacularly awful.

After twenty-three years in corporate training across Melbourne, Brisbane, and Perth offices, I've watched thousands of managers, executives, and team leaders completely butcher conversations that should've been straightforward. The result? Workplace toxicity, decreased productivity, and employees who'd rather quit than have an honest discussion with their boss.

But here's the controversial bit - I think this epidemic of conversation avoidance is actually a good thing. Wait, hear me out.

The Uncomfortable Reality Most Training Courses Won't Tell You

Every second week, some bright-eyed HR manager calls me up asking for managing difficult conversations training because their team "needs better communication skills." Wrong. Dead wrong.

The problem isn't that people don't know HOW to have difficult conversations. The problem is they don't know WHEN to have them, and more importantly, when NOT to have them.

I learned this the hard way back in 2009 when I was consulting for a major Sydney-based mining company. Beautiful offices, unlimited coffee, terrible management. I spent three months teaching their supervisors "active listening techniques" and "conflict resolution frameworks." Six months later, their turnover rate had actually increased by 14%.

Know why? Because I'd taught them to have conversations about everything. Every minor disagreement, every personality clash, every tiny frustration became a "learning opportunity" that required a formal sit-down discussion.

The Three Types of Difficult Conversations (And Why Two of Them Are Pointless)

After watching this play out across dozens of organisations, I've identified three distinct categories of workplace difficult conversations:

Type 1: Performance Conversations - These are non-negotiable. Someone isn't doing their job, deadlines are missed, quality is suffering. Have these conversations immediately, directly, and with clear consequences.

Type 2: Behavioural Conversations - This is where it gets tricky. Someone's attitude is affecting the team, they're being disrespectful, or they're creating tension. These conversations can be gold mines or complete disasters, depending on timing and approach.

Type 3: Personality Conversations - Stop. Just stop having these. You cannot change someone's personality through a conversation. I don't care how many emotional intelligence courses you've attended or how skilled you think you are at "coaching." Some people are just difficult, and that's not always a problem to solve.

The revelation that changed everything for me happened during a particularly brutal session with a telecommunications company in Adelaide. The CEO insisted we address "personality conflicts" between two department heads who'd been clashing for years. Three months of mediation sessions, team-building exercises, and individual coaching later, they still couldn't stand each other. But guess what? Their departments were performing better than ever.

Why Australian Workplaces Get This So Wrong

We've got this bizarre cultural thing where we think every workplace issue can be resolved through talking it out. Maybe it's our egalitarian streak, or perhaps we've been watching too many American self-help shows, but somehow we've convinced ourselves that the right conversation at the right time can fix anything.

It can't.

Sometimes people just don't get along. Sometimes someone's natural communication style rubs others the wrong way. Sometimes the issue isn't worth addressing at all.

I worked with a Brisbane-based logistics company where the operations manager complained that his assistant was "too cheerful" in the mornings. The HR department wanted to schedule a conversation about "workplace communication expectations." I suggested they reassign the manager to afternoon shifts instead. Problem solved, no conversation required.

The Real Secret: Knowing When NOT to Engage

This might be the most important lesson I can share after two decades in this field: your instinct to avoid difficult conversations is often correct.

Before you schedule that meeting, ask yourself:

Will this conversation change a behaviour that's actually impacting work results?
Am I having this conversation because I'm uncomfortable, or because there's a genuine business problem?
What's the worst-case scenario if I do nothing?
Is this really a conversation problem, or a systems/process problem?

Here's a statistic that'll surprise you: 67% of the "difficult conversations" I'm asked to facilitate shouldn't happen at all. Most workplace tension resolves itself naturally when people are given clear expectations, adequate resources, and sufficient autonomy to do their jobs.

The mining company I mentioned earlier? When we stopped focusing on conversations and started addressing their broken approval processes and unclear reporting structures, their culture problems disappeared almost overnight.

The Framework That Actually Works

When you DO need to have a difficult conversation (and trust me, sometimes you absolutely do), forget everything you've learned about "sandwich methods" and "active listening." Here's what works in real Australian workplaces:

Be disgustingly specific. Don't say "your attitude needs improvement." Say "yesterday during the client call, you interrupted Sarah three times and then checked your phone while she was presenting the quarterly figures."

Focus on impact, not intent. I don't care if they meant to be helpful or if they were having a bad day. What matters is the effect their behaviour had on the team, the client, or the project.

Set one clear expectation. Not three expectations, not five action items. One thing they need to do differently going forward.

Timeline it. When will you check in? What will success look like? How will you measure improvement?

That's it. No touchy-feely emotional processing, no lengthy discussions about underlying causes, no attempts to understand their perspective (unless it's directly relevant to the solution).

The Conversation Epidemic in Australian Offices

We've created a generation of managers who think every workplace challenge requires a heart-to-heart. Walk through any major Australian corporate office and you'll find meeting rooms booked solid with "check-ins," "alignment sessions," and "difficult conversations."

Meanwhile, the actual work gets pushed aside.

I was at a pharmaceutical company in Perth last year where the team leaders were spending more time having conversations about work than actually doing work. They had weekly one-on-ones, monthly team conversations, quarterly culture discussions, and annual performance conversations. When did they have time to develop new products or serve their customers?

The uncomfortable truth: some difficult conversations are just procrastination dressed up as leadership development.

What the Best Managers Actually Do

The highest-performing teams I work with have managers who are incredibly selective about when they engage in difficult conversations. They're not avoiding conflict - they're choosing their battles strategically.

Take Sarah, a operations director at a major Sydney retailer. She manages forty-seven people across three locations, and she has maybe one difficult conversation per month. Not because her team is perfect, but because she's created systems that prevent most problems from requiring conversations.

Clear job descriptions. Regular feedback loops. Transparent promotion criteria. Consistent consequences. Adequate training. Proper resources.

When conversations do happen, they're brief, specific, and followed by immediate action.

The Part Where I Admit I Was Wrong

For the first eight years of my career, I was part of the problem. I genuinely believed that better communication could solve any workplace issue. I taught elaborate conversation frameworks, role-played difficult scenarios, and convinced hundreds of managers that they needed to address every interpersonal challenge through dialogue.

What changed my mind was tracking the results. Companies that focused on conversation skills training showed minimal improvement in engagement, retention, or performance metrics. But companies that focused on clarifying expectations, improving processes, and giving people autonomy? Dramatic improvements across every measure.

The best difficult conversation is often the one you don't have.

Where This Leaves You

If you're a manager reading this, I want you to try something for the next month. Before scheduling any "difficult conversation," wait 48 hours and ask yourself: "Is this actually a conversation problem, or something else?"

You might be surprised how many issues resolve themselves when you focus on fixing the underlying systems instead of trying to fix the people.

And when you do need to have that conversation? Keep it short, keep it specific, and keep it focused on business impact.

Because at the end of the day, your job isn't to make everyone comfortable with each other. Your job is to get results.

The sooner we all admit that not every workplace problem requires a conversation, the sooner we can get back to actually doing our jobs.

Sometimes the most difficult conversation is the one where you decide not to have a conversation at all.