Why Your "Difficult Person" Strategy Is Probably Making Things Worse

Karens. Micro-managers. That bloke in accounts who still uses Internet Explorer and emails in Comic Sans. We've all got them—the people who make us want to fake our own deaths just to avoid Monday morning meetings.

After seventeen years running training workshops across Melbourne, Brisbane, and Perth, I've watched thousands of well-meaning professionals completely stuff up their approach to difficult personalities. And here's the uncomfortable truth: most of the time, you're making it worse.

The Problem With Being "Professional"

Everyone tells you to "stay professional" when dealing with difficult people. What a load of rubbish. Professional often translates to passive-aggressive, which is about as useful as a chocolate teapot in resolving workplace conflicts.

I learned this the hard way back in 2009 when I was dealing with a particularly challenging client—let's call him Derek. Derek was the type who'd argue with a stop sign if given half the chance. For months, I tried the traditional approach: polite emails, diplomatic language, and endless patience. Result? Derek got worse, my team got frustrated, and I ended up stress-eating Tim Tams at 3am.

The breakthrough came when I finally dropped the fake politeness and had a real conversation with him. Turns out Derek wasn't difficult—he was terrified of looking incompetent in front of his board. Once I understood that, everything changed.

The Three Types You're Dealing With (And Getting Wrong)

The Control Freak These people aren't power-hungry monsters. They're usually drowning in responsibility and desperately trying to keep their heads above water. Give them information early and often. Make them feel involved in decisions, even small ones.

I once worked with a GM in Sydney who insisted on approving every single expense over $50. Drove everyone mental. Instead of complaining, I started sending her a weekly summary of upcoming expenses. Problem solved. She relaxed because she felt informed, and the team stopped wanting to throttle her.

The Attention Seeker These folks aren't narcissists—they're often insecure and seeking validation. The worst thing you can do is ignore them or give them minimal responses. That just escalates their behaviour.

The Perfectionist Here's where most people get it completely wrong. You think perfectionist equals high standards. Wrong. Perfectionism is usually fear-based behaviour. They're terrified of making mistakes, so they obsess over details and drive everyone else mad in the process.

Stop trying to convince them to "just let it go." Instead, help them identify what "good enough" looks like for different situations. Set clear parameters. "For this project, two rounds of revisions is our limit." Boundaries, not battles.

What Actually Works (Spoiler: It's Not What HR Tells You)

Stop trying to change them. Seriously. You can't turn a control freak into a laid-back hippie, and you shouldn't try. Work with their personality, not against it.

Get curious about the why. That annoying micromanager? Maybe they got burned by a direct report years ago. The colleague who questions every decision? Perhaps they've seen too many projects fail due to poor planning.

I remember working with a team leader who seemed impossible to please. Nothing was ever right. Turns out she'd been promoted into the role without proper training and was completely out of her depth. Once we addressed that underlying issue through some supervisor training, her "difficult" behaviour disappeared almost overnight.

Set boundaries early and stick to them. This isn't about being mean—it's about clarity. "I'm happy to discuss this, but not via 47 emails. Let's book a 15-minute call instead."

The Uncomfortable Truth About Difficult People

Here's something that'll make you squirm: sometimes, you're the difficult person. I know, I know. But think about it. That time you were sleep-deprived and snapped at everyone? When you were dealing with a family crisis and couldn't focus on anything? We've all been that person.

The difference is, we know our reasons. We can justify our behaviour because we understand the context. Other people don't have that luxury. They just see the behaviour.

My Biggest Mistake (And How It Changed Everything)

About five years ago, I was working with a company that had a "problem employee"—let's call her Janet. Everyone complained about Janet. She was negative, argumentative, and seemed to hate every new initiative. Management wanted to performance-manage her out.

I spent weeks trying to "fix" Janet's attitude. Coaching sessions, communication workshops, the works. Nothing budged. Then, during what was supposed to be our final session, I asked her something different: "What would need to change for you to actually enjoy working here?"

Her answer floored me. The company had restructured eighteen months earlier, eliminating Janet's previous role and forcing her into a position she never wanted. She felt like her expertise was being wasted and her concerns were being ignored. She wasn't being difficult—she was grieving the loss of a job she loved.

We ended up managing difficult conversations differently after that. Instead of trying to change Janet, we found ways to utilise her expertise in her new role. Result? Janet became one of the company's most valuable contributors.

The Australian Way: Practical Solutions That Actually Work

Forget the American self-help guru approach. Here's what works in real Australian workplaces:

Be direct, but not brutal. "Mate, when you interrupt everyone in meetings, it makes it hard for us to get through the agenda. Can we try something different?"

Address issues quickly. Don't let resentment build. That casual Friday drinks session where everyone bitches about Steve from IT? That's not solving anything.

Focus on behaviour, not personality. "When you send emails at 11pm, it creates pressure for people to respond outside work hours" is better than "You're such a workaholic."

When to Walk Away

Sometimes, despite your best efforts, it doesn't work. And that's okay. Not every difficult relationship can be salvaged, and you shouldn't destroy your mental health trying.

Signs it's time to disengage:

• You're losing sleep over their behaviour
• Other relationships are suffering because of the stress
• They're actively undermining you or the team
• Your manager won't support reasonable boundaries

Related Resources: Check out Core Group's advice for more insights on workplace dynamics, or explore Evolve Force's blog for additional professional development resources.

The Bottom Line

Difficult people aren't going anywhere. Every workplace has them, every family has them, and every friendship group has them. The question isn't how to avoid them—it's how to deal with them without losing your sanity.

Most "difficult" behaviour isn't personal, even when it feels like it. It's usually someone struggling with something—fear, insecurity, lack of skills, or past trauma. That doesn't excuse poor behaviour, but understanding it makes it easier to respond constructively rather than reactively.

And remember: the goal isn't to become best friends with everyone. It's to create an environment where work gets done without unnecessary drama. Sometimes that means having tough conversations. Sometimes it means setting firm boundaries. And sometimes it means accepting that not everyone will like you—and that's perfectly fine.

The real skill isn't learning to deal with difficult people. It's learning to stay true to yourself while adapting your approach to get the best outcome for everyone involved. Master that, and you'll find those "difficult" people become a lot more manageable.

Now stop procrastinating and go have that conversation you've been avoiding.