Why Your 'Difficult Person' Training Is Probably Making Things Worse

The bloke in accounts who snorts every time someone mentions change. The woman in marketing who somehow turns every team meeting into her personal therapy session. That supervisor who treats every suggestion like a personal attack on their leadership credentials.

Sound familiar? If you've worked in corporate Australia for more than five minutes, you've met them all. And chances are, your organisation has spent thousands on "difficult person" training that's about as effective as a chocolate teapot in the Simpson Desert.

Here's the thing that most trainers won't tell you because it doesn't sell courses: 87% of workplace personality conflicts aren't about difficult people at all. They're about systems, expectations, and communication breakdowns that we've dressed up in psychology speak to avoid dealing with the real issues.

I've been running workplace training programs across Australia for seventeen years now, and I'm going to share some uncomfortable truths that might save you from another round of role-playing exercises that everyone forgets by Tuesday.

The Problem With Most "Difficult Person" Programs

Let me paint you a picture. You've got Sarah from HR facilitating a session where grown adults practice "active listening" with someone pretending to be an angry customer. Everyone's nodding sagely while thinking about their lunch plans. The real "difficult person" - let's call him Dave - either hasn't shown up or is sitting in the back corner radiating the kind of energy that could power a small wind farm.

This is where most programs fall flat on their face.

They assume the problem is skill-based. "If only people knew how to communicate better!" they cry. But here's what I've learned after watching thousands of these interactions: Dave from accounting isn't difficult because he lacks communication skills. Dave's difficult because he's been promoted twice in fifteen years while watching less experienced people leapfrog over him, and now he's supposed to smile and nod while some consultant half his age tells him how to "manage his emotional responses."

The real issue? No one's addressing the elephant in the room.

What Actually Works (And What Doesn't)

The Approach That Fails Every Time: Treating personality conflicts like individual deficiencies that can be fixed with a workshop. I've seen organisations spend $50,000 on programs that basically amount to expensive group therapy sessions. One mining company in Western Australia flew in a "conflict resolution specialist" from Sydney who had clearly never worked a day in an actual workplace. Absolute waste of money.

What Actually Moves the Needle: Understanding that most "difficult behaviour" is actually predictable response to poor systems, unclear expectations, or leadership that couldn't organise a piss-up in a brewery.

Take the case of a manufacturing plant in Adelaide where the "difficult person" turned out to be reacting to a promotion system so opaque that nobody understood how career progression actually worked. Once they clarified the criteria and created transparent pathways, their "personality problem" magically disappeared.

But here's where it gets interesting - and this is something that might ruffle a few feathers.

The Uncomfortable Truth About Workplace Personality Types

Not everyone is going to get along. Not everyone should get along. Some personality combinations are like mixing mentos with Coke - explosive and predictable.

I worked with a tech startup in Melbourne where they kept trying to force their detail-oriented financial controller to "collaborate more effectively" with their big-picture creative director. After months of mediation and team-building exercises, the breakthrough came when they stopped trying to make them best mates and instead created systems that leveraged their natural friction productively.

The finance guy's skepticism became a valuable checkpoint for unrealistic projects. The creative director's impatience pushed the finance team to streamline their approval processes. Instead of trying to eliminate the tension, they channeled it.

Revolutionary concept, right?

The Three Types of "Difficult" That Actually Matter

Forget the personality assessments and colour-coded behavioural frameworks. In real workplaces, there are really only three types of challenging behaviour that matter:

Type 1: The Competent Complainer These are your high performers who've become cynical. Usually because they've seen too many initiatives fail or watched mediocrity get rewarded. They're not actually difficult - they're burned out. The solution isn't communication training; it's giving them meaningful challenges and showing them their feedback actually influences decisions.

Type 2: The Insecure Micromanager
Often newly promoted or in roles where they feel out of their depth. They compensate by controlling everything they can. Most training programs try to teach them to "let go" without addressing why they're gripping so tightly in the first place. Better approach: clear success metrics and regular check-ins that reduce their anxiety about being caught off-guard.

Type 3: The Genuine Problem About 5% of workplace conflicts involve someone who's genuinely toxic. These aren't training issues - they're HR issues. No amount of workshop role-playing will fix someone who's fundamentally incompatible with professional behaviour. But most organisations spend months trying to train around these people instead of addressing them directly.

The trick is knowing which type you're dealing with before you waste time and money on the wrong solution.

What Your Training Should Actually Cover

If you're going to invest in difficult person training (and you probably should), here's what actually works:

Start with systems analysis, not personality analysis. Before you assume someone's being difficult, map out what their actual experience looks like. Are they getting conflicting instructions from multiple managers? Are the tools they need to do their job actually functional? Is their performance being measured on things they can't control?

Teach managers to spot the difference between skill gaps and motivation gaps. Someone who doesn't know how to do something needs training. Someone who knows how but won't do it needs a different conversation entirely. Most managers treat both situations the same way, which is why their "coaching" conversations go nowhere.

Focus on early intervention rather than crisis management. The best time to address difficult behaviour is in the first two weeks, not after six months of everyone walking on eggshells. This means training supervisors to have uncomfortable conversations early and often.

I remember working with a logistics company in Brisbane where they'd let a team leader's behaviour deteriorate for eight months before bringing in external help. By then, three good people had resigned and the team dynamics were poisoned. What could have been a simple conversation in month one became a six-month rehabilitation project.

Early intervention isn't just more effective - it's dramatically cheaper.

The Real ROI of Getting This Right

Here's something most training providers won't tell you because it complicates their sales pitch: good difficult person training doesn't eliminate workplace conflict. It reduces the time and energy spent managing preventable conflicts so you can focus on the productive disagreements that actually drive innovation.

The best teams I've worked with argue regularly. They disagree about priorities, approaches, and solutions. But they do it efficiently and professionally, without the personal drama that derails less mature teams.

That's the real goal - not workplace harmony, but productive conflict management.

Making It Stick (The Part Most Programs Skip)

The dirty secret of corporate training is that most of it has the staying power of a New Year's resolution. People leave motivated, implement changes for about three weeks, then gradually slide back to old patterns.

The programs that actually create lasting change do three things differently:

They build the training around real situations specific to your workplace, not generic scenarios that everyone recognises as artificial. They include follow-up sessions at three and six months, not just a one-day workshop. And they train managers to reinforce the concepts, not just the people who attended the training.

But here's the thing that surprised me most after all these years: the organisations that get the best results from difficult person training aren't usually the ones with the worst conflicts. They're the ones that invest in this stuff before they desperately need it.

Related Resources: Check out some excellent perspectives on Business Supervising Skills and Managing Workplace Anxiety. For those dealing with particularly challenging conversations, Managing Difficult Conversations offers practical frameworks you can actually use.

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The author has delivered workplace training programs across Australia for over 15 years, specialising in practical solutions for organisational behaviour challenges. He currently splits his time between Melbourne and Perth, working with companies ranging from mining operations to tech startups.