My Thoughts
The Difficult Person Playbook: What 17 Years in Melbourne Boardrooms Actually Taught Me
You know that person. The one who makes every meeting feel like a root canal without anaesthetic. The colleague who responds to "good morning" like you've personally insulted their mother. The client who treats customer service like a contact sport.
I've encountered more than my fair share over the years. And frankly, I used to be absolute rubbish at handling them.
Back in 2007, there was this procurement manager—let's call him Derek because, well, his name was Derek—who could turn a simple purchase order discussion into what felt like international peace negotiations. The bloke would challenge everything. Everything. If I said the sky was blue, Derek would demand three independent meteorological reports and a signed affidavit from the Bureau of Meteorology.
For months, I tried the textbook approach. Stay calm. Be professional. Don't take it personally.
Complete waste of time.
The Brutal Truth About Difficult People
Here's what they don't tell you in those corporate training sessions: most difficult people aren't actually trying to be difficult. They're usually dealing with something you can't see. Derek, as it turned out, was under enormous pressure from his CEO to cut costs by 30%. Every "unreasonable" question was actually him doing his job—protecting his company's bottom line.
The realisation hit me like a brick. I'd been so focused on how Derek was making me feel that I'd completely missed what was driving his behaviour.
This is where most people get it wrong. We assume difficult behaviour is about us. It rarely is.
Think about the last time you were "difficult." Maybe you were snippy with a shop assistant because you'd had a terrible day. Or you questioned every detail of a proposal because you'd been burnt before. Your behaviour wasn't really about them—it was about your circumstances.
The Three Types of Difficult People (And Why This Matters)
After nearly two decades of dealing with every personality type imaginable across Sydney, Melbourne, and Perth offices, I've noticed difficult people usually fall into three categories:
The Overwhelmed: These folks are drowning. They're short, defensive, or overly critical because they're struggling to keep their heads above water. I see this constantly with middle managers who've been given impossible targets or small business owners trying to do everything themselves.
The Burned: Someone has let them down before. Badly. Now they approach every interaction with their shields up. They're not really being difficult with you—they're being careful.
The Principled: These people have strong values or standards, and they're not willing to compromise. They might seem stubborn, but they're often just trying to maintain their integrity. Some of my best long-term business relationships started with someone I initially thought was being unnecessarily difficult.
Understanding which type you're dealing with completely changes your approach. With overwhelmed people, you need to reduce their cognitive load. With burned people, you need to rebuild trust slowly. With principled people, you need to find common ground.
What Actually Works (From Someone Who's Made Every Mistake)
Start with curiosity, not judgement. Instead of thinking "this person is being unreasonable," try "I wonder what's driving this reaction." The shift in your own energy is remarkable, and people sense it immediately.
I learned this the hard way with a particularly challenging client in Adelaide. She would nitpick every proposal to death. Instead of getting frustrated, I started asking questions: "What concerns you most about this approach?" "What would need to change for you to feel confident moving forward?"
Turns out she'd been burned by three consecutive consultants who'd overpromised and underdelivered. Once I understood that, everything changed.
Give them what they actually need, not what you think they should want. If someone seems controlling, they probably need more information or involvement in the process. If they're being aggressive, they might need you to acknowledge their frustration before moving to solutions.
I once had a project manager who would explode in meetings whenever timelines were discussed. Rather than trying to calm him down or defend the schedule, I started acknowledging his concerns first: "I can see you're worried about missing the deadline. Let's look at what we can do to mitigate that risk." Instant de-escalation.
Set boundaries like your sanity depends on it. Because it does. You can be understanding and empathetic without becoming a punching bag. Some of the most difficult people I've worked with actually respected me more once I started saying things like, "I want to help solve this problem, but I need us to keep the conversation professional."
Here's something that might surprise you: about 60% of "difficult" people become significantly easier to work with once they realise you're not going to be intimidated or manipulated. They were testing your boundaries, and once they know where they are, they often settle down.
The Emotional Intelligence Factor
This is where emotional intelligence becomes absolutely crucial. Most people think EQ is about being nice all the time. It's not. It's about reading the room, understanding what's really happening beneath the surface, and responding strategically rather than reactively.
The best investment I ever made was learning to manage my own emotional responses first. When someone's being difficult, your natural instinct is to match their energy—get defensive, argumentative, or withdrawn. That never works.
Instead, I started treating difficult interactions like a puzzle to solve rather than a battle to win. Game changer.
When Professional Help Is Worth Every Dollar
Look, some situations are beyond what you can handle on your own. If you're dealing with difficult behaviours that cross into harassment, discrimination, or abuse, that's when you need proper workplace training and HR involvement.
I've seen too many good people burn out trying to "fix" someone who actually needs professional intervention. There's a difference between someone having a bad day and someone with a pattern of toxic behaviour.
Trust your gut. If every interaction leaves you feeling drained, anxious, or questioning your own competence, that's often a sign the problem isn't just about communication styles.
The Long Game
The most counterintuitive thing I've learned? Some of my best professional relationships started with someone I found incredibly difficult to work with initially.
There's this developer I know—brilliant coder, but he used to challenge every single requirement like I was asking him to build a rocket ship instead of a simple website. Drove me mental for the first six months.
But his questions, annoying as they were, actually made our projects better. He was spotting potential problems I was missing. Once I stopped seeing his input as criticism and started viewing it as quality control, our working relationship transformed.
He's now someone I specifically request for complex projects. Turns out what I initially perceived as difficult behaviour was actually him caring deeply about delivering excellent work.
The Reality Check
Not every difficult person will become your favourite colleague. Some people are genuinely unpleasant, and no amount of understanding or emotional intelligence will change that. That's okay. The goal isn't to become best mates with everyone—it's to maintain your own peace of mind while getting the work done.
Sometimes the most professional thing you can do is limit your interactions with someone to what's absolutely necessary and focus your energy on the relationships that actually energise you.
After 17 years in business, I've learned that how you handle difficult people says more about your character than theirs. You can't control their behaviour, but you can absolutely control your response to it.
And honestly? That's usually enough.
Related Articles: