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The Truth About Difficult People: They're Usually Not The Problem (And Why That Should Terrify You)

Nobody wants to hear this, but most "difficult people" are actually showing you something about your workplace, your systems, or yourself that you don't want to face.

After 18 years of working with teams across Melbourne, Perth, and Sydney—from mining companies in the Pilbara to tech startups in Surry Hills—I've watched thousands of professionals point fingers at the "difficult" person in their office. The one who asks too many questions. The colleague who pushes back on every decision. That team member who seems perpetually unsatisfied.

Here's what I've learned: calling someone difficult is often the first sign that your organisation lacks the tools to handle healthy conflict.

The Uncomfortable Reality

Most people I meet want a magic formula. They want me to tell them how to "fix" Janet from accounting or how to "manage" Steve from the warehouse who won't stop questioning procedures. But here's the thing—the moment you label someone as difficult, you've already lost half the battle.

I was guilty of this myself back in 2009. Had a project manager who questioned everything I proposed. Made meetings run longer. Challenged timelines. I spent months complaining about him to anyone who'd listen. "He's just being difficult," I'd say.

Then the project launched. On time. Under budget. With fewer bugs than any rollout we'd done before.

Turns out, his "difficult" questions had caught problems I'd missed. His pushback had strengthened our approach. I'd been so focused on managing his personality that I nearly missed the value he was bringing.

What Makes Someone "Difficult" Anyway?

Let me be blunt about something most consultants won't tell you: there's no such thing as a universally difficult person. There are people who don't fit your systems, your communication style, or your expectations. But that's not the same thing.

Take someone who asks "why" repeatedly during meetings. In a hierarchical organisation, they might be labelled difficult. In a research team, they'd be considered thorough. The person hasn't changed—the context has.

I've seen this play out countless times. A marketing manager at [a major retailer] was considered difficult by the finance team because she wanted detailed explanations for budget cuts. Same person was considered brilliant by the creative team because she asked probing questions that improved campaigns.

Context matters. Culture matters. And sometimes, what you're calling difficult is actually someone trying to do their job properly in a system that doesn't support it.

The Four Types You'll Actually Encounter

Forget the personality tests and behavioural assessments for a moment. In my experience, people get labelled "difficult" for four main reasons:

The Questioner challenges decisions and wants to understand the why behind everything. They slow down meetings but often catch problems early. Companies like Microsoft have learned to channel this energy into quality assurance and risk assessment roles.

The Perfectionist never seems satisfied with "good enough" and keeps pushing for improvements. They can frustrate teams focused on speed, but they also prevent rushed decisions that cost money later.

The Avoider seems to resist change or new initiatives. Often, they're actually protecting institutional knowledge or highlighting implementation challenges that others have overlooked.

The Confronter speaks up about problems others prefer to ignore. They make people uncomfortable, but they also surface issues before they become crises.

Here's what's interesting: none of these behaviours are inherently problematic. They become "difficult" when they clash with your organisation's communication style or decision-making process.

The Real Problem (It's Probably Not What You Think)

After working with over 200 teams, I can tell you the real issue: most organisations have terrible conflict resolution skills. We've created workplaces where any form of pushback or questioning is seen as problematic.

I was running a workplace harassment training session last month in Brisbane when a manager complained about an employee who "always finds problems with everything." When we dug deeper, it turned out this employee had identified three major safety issues that had been ignored. But because they delivered feedback bluntly, they were labelled difficult.

That's not a difficult person problem. That's a communication skills problem.

We've become so focused on maintaining harmony that we've forgotten how to have productive disagreements. We label anyone who rocks the boat as difficult instead of teaching people how to navigate choppy waters.

What Actually Works (And What Doesn't)

Here's where I'm going to contradict most HR advice: you cannot manage a difficult person into being easy. You can't workshop someone's personality into compliance. I've tried. It doesn't work.

What does work is changing how you interact with different communication styles.

For The Questioner, set clear boundaries around when and how questions get asked. I worked with a team in Adelaide where the project manager was driving everyone mad with constant questions. We implemented a "question window" - 15 minutes at the start of each meeting specifically for clarifying questions. Suddenly, the questions became valuable input instead of frustrating interruptions.

The Perfectionist needs clear definitions of "done." I've seen teams waste months because a perfectionist team member kept pushing for improvements while everyone else thought the project was finished. Define completion criteria upfront. Make it explicit.

The Avoider often needs more information about why change is happening. They're not resisting to be difficult—they're protecting something they value. Figure out what that is.

The Confronter needs appropriate channels for raising concerns. Create formal processes for feedback. Make it safe to surface problems.

But here's the key: these aren't techniques for managing difficult people. They're good management practices that work for everyone.

When You Actually Do Have a Problem

I'm not saying all challenging behaviour should be accommodated. Some people are genuinely disruptive, disrespectful, or destructive. But that's different from being difficult.

If someone is consistently undermining team morale, refusing to follow reasonable procedures after clear communication, or creating a hostile work environment, that's a performance issue, not a personality clash.

The difference is impact. A Questioner improves outcomes even if they slow down processes. A disruptive person damages outcomes regardless of their intentions.

The Bottom Line

Here's what 18 years in this industry has taught me: the organisations that thrive are the ones that learn to harness difficult people, not eliminate them.

Some of my best business relationships have been with people I initially found challenging. They pushed me to think differently, caught my mistakes, and forced me to articulate my ideas more clearly.

If you're spending significant time managing "difficult" people, ask yourself: are they actually the problem, or are they exposing weaknesses in your systems that you'd rather not address?

Because until you answer that question honestly, you'll keep having the same conflicts with different people. And that's a pattern worth examining.

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