How to Make a Hard Conversation more Productive: A Practical Guide for Dealing with Difficult People

There's a strange kind of intimacy between people that fight , the smallest bark will tell you their bite is worse than the bark, and there's much barking going on. Regular battles with very difficult people is part of standard professional life in Sydney, Melbourne, Brisbane and elsewhere. It's time consuming, it saps energy and if not handled well can damage trust. But it can also be a tool for change. If you have the right combination of practical capabilities and temperament, you can turn these exhausting interactions into clearer roles, better processes and (sometimes) more successful relationships. And I say this as someone who has seen frontline teams, C suite execs and HR leaders stumble through unnecessary disagreements , and then, with remarkably little effort, make them markedly better.

A blunt reality up front: not all conflict needs to be solved. Some rows are signal , they show misaligned purpose or structural problems that need addressing. Other rows are just noise. The first, underrated skill is knowing the difference between them.

Why bother

Because unaddressed conflict is costly and corrosive. "Lack of clear priorities and focus to too much time spent on dealing with conflict, these were the top five," said Tim Garrett, Interact's chief solutions officer. (Report Submitted by Tim Garrett) And this isn't just squandered time , it turns into real financial repercussions for Organisations. That number has become locked in my head; it's a useful line of demarcation when I'm working with teams who believe they can "just let it sort itself out."

Know the person before you solve the problem

Problematic behaviour is usually a pattern and unlikely to be born overnight. It helps to disentangle what people are doing from why they're doing it. Do they feel insecure in their personal lives? Is it overwork or ambiguous expectations? Are they deploying control tactics because their professional knowledge is not being taken seriously? A fundamental diagnosis , curiosity, not judgement , enables you to tailor your response.

Similar things tend to stick together: Overbearing control, passive aggressiveness, chronic negativity or manipulative game playing. Once you see the pattern, it's much easier to make a move. If someone has a habit of interrupting in meetings, don't assume malice , start with asking why they do so; it can be fear of being ignored than a desire to dominate. If someone is manipulative, then you will need stronger and more structural responses , clearer processes, less ambiguous authority, documented agreements.

Alas, a note many of you won't like: Yes, sometimes you will conclude that the easiest, most productive response is to reduce contact. Boundaries aren't defeat. They're strategy. The tricky part comes in applying them with professionalism, not pettiness.

Active listening and empathy are underappreciated weapons

Active listening and empathy dissipate conflicts, actually understanding others, leading to honest open dialogue. That sentence encapsulates one of the most useful tricks in the toolbox. Active listening is you turning up, paraphrasing back, open question probing and putting your own itch to respond aside while the other is talking. Empathy means for you to try to see the world from their viewpoint , not that you need to agree, but rather understand the forces behind their behaviour.

These two in combination give you an attack on defensiveness and keeps core issues from becoming the detonation it all blows up into. On the meetings I facilitate that cross industries, the most common reason for failure is partial listening. So people listen well enough to fire back with a response, but not so well as to resolve things. We're giving teams a simple habit: ask one clarifying question every time someone repeats a complaint. It decelerates the conversation and magic ensues , assumptions fall off.

Assertiveness with grace

There's a fine line to walk between conciliation and being a pushover. It is not appreciated enough in the corporate world of Australia. It's not about aggression; it is clearer. Use "I" statements , "I feel," "I've noticed," "I need" , and say what the consequences will be, without raising your voice. If you are interrupted by a colleague on a weekly basis, for example, you could say something like: "I feel sidelined when I'm not able to finish my point. I want us to let each other finish." Simple. Clear. Non personal.

To be assertive is also to watch the bottom line. I like a practical test: What changed after the hard conversation? If you can't point to a concrete next step, try setting the boundary more clearly. Too many conversations end at good intentions with no follow through , that's how patterns perpetuate. You should personify

Personality types

There is no such thing as the perfect solution. Different personalities need different strategies.

• The aggressive type: remain cool as a cucumber. Mirror back what they have said, then establish a boundary. "I can tell this is so important to you; I can see also that we are getting heated. Let's take a break and we'll come back with the facts."
• The passive aggressive kind: just don't play game of guess. Name common observations and request examples. "If meetings go too long, you talk about being so 'snowed under.' Could you tell me which meetings are the ones that does this?"
• The manipulative player: save all the things. After calls, short, concise and clear informational emails recap agreements. This reduces wiggle room for reinterpretation.
• The chronically negative: Reframe. Ask specifically for their idea rather than a gripe. It inverts the onus from criticising to contributing.

You'll see that I prefer concrete, action based solutions to personality typing, which leans towards psychoanalysis. Keep it concrete.

De escalation techniques that really work

When someone's volume or tone escalates, your move matters. Fast, effective strategies:

• Slow down your own voice. A measured tone cools down the emotional temperature.
• Decrease audience. If there's a public dressing down taking place, you can offer to take the conversation outside , resolutions come more quickly in private.
• Time Limited Agreements. Use time limited agreements. "Let's talk about this for 10 minutes, and then decide if we should take it offline."
• Pivot to interests, not positions. "You want this deadline; I want the quality to stay high; what's the acceptable trade off?"

These aren't tricks. They are structured methods for guiding the conversation back toward problem solving.

Boundaries and consequences: not up for negotiation

Boundaries are the scaffolding that prevent further damage from occurring over and over. Be explicit. By whatever name, describe what's acceptable and what isn't. If an employee misses deadlines, there must be clear understanding of what the effect is and what to do next. And if the behaviour continues, can follow through with those consequences you've said.

The fastest way to torpedo your credibility is with inconsistent enforcement. Here's where some HR teams start to get nervous , they fear escalating the situation. I frequently tell managers that they are the first line of enforcement. It's messy, yes. But it's also faster, and usually more effective than escalating every problem to central HR. (Unpopular opinion: HR should be strategic not the triage centre for every interpersonal hiccup.)

When to go through anyone

Sometimes you need a broker and oftentimes, you don't. Use your judgement. Call in HR or another impartial third party when a power imbalance is at play, or if legalities and safety become an issue. But don't weaponise HR over small slights. The best mediation occurs when both sides are also willing to engage. If one person declines to participate: the management must take a position regarding role changes or performance improvement.

Creating long term resiliency

Short term tactics are necessary. It's the long term resilience that prevents these issues from coming back. Educate teams on emotional intelligence: self awareness, self regulation, social awareness and relationship management. These are not just soft skills in theory; they result in hard benefits: fewer escalations, more productivity and higher retention.

In our practices, the best return in resilient training comes from a mix of practical roleplays and real case debriefs, combined with manager coaching. You don't learn how to manage difficult co workers from a slide deck. They learn by practising a difficult conversation, getting reactions and then doing it again.

Self care: not self indulgence but pragmatic strategy

You cannot negotiate well if you are tired or reactive. People who regularly manage conflict really don't get a choice about managing stress. Simple routines , reflecting, after a heated meeting, a few short breathing exercises, a walk around the block , bring capacity back. When I recommend this to busy managers, they give me sceptical looks; but the return on investment is instant: less knee jerk email, calmer meetings and clearer decision making.

Support networks matter too. Urge mentees and managers to debrief with a trusted colleague or coach. Perspective reduces reactivity.

When people become abusive: safety first

There's a line between difficult and abusive. Then, if someone is threatening safety, being discriminatory or bullying, escalate immediately. Document, act, protect the team. Organisations that stall lose trust quickly, and not without reason.

Actionable lessons you can use tomorrow

Meeting choreography: assign roles (facilitator, timekeeper) so one person isn't always in charge. Rotate who takes which positions so everyone gets the mechanics of arguing.

• Standardised wrap ups: summarise and assign action items in writing within a day of any heated conversation.
• Micro intervention scripts: develop polite one liners to deploy as deflection , "I'd like to hear that, but we need to refocus. Can we park that point?"
• Feedback training: train people to provide feedback that connects behaviour and impact, rather than about personality.

A couple of contrarian opinions

• Conflict is usually productive. Yes, really. Once you can see that a fight is nothing more than a misaligned process being surfaced, then you can work to fix the process instead of punishing personalities.
• Managers should resolve nearly all interpersonal problems before they become HR cases. HR is for systems, not every squabble.

Neither of those perspectives sit well with some readers. But having spent much of my adult life consulting in messy workplaces, the places that allow managers to take on responsibility for the care and feeding of relationships are also where teams thrive , and HR has enough bandwidth to design better systems.

The Organisational side , prevention is better than cure

Most Companies invest in soft skills once things have gone wrong. That's backwards. Bake conflict resolution into induction, leadership pathways and performance discussions. Reward those who find solutions, not those who "beat" others in an argument. You change incentives and people change their behaviour.

We see that a ton in our work and from our data: teams with regular calibration sessions and clear decision making rules are going to bat over fewer things. Their wheels turn more smoothly, with fewer burnt out people, and faster.

Final , and abrupt , truth

Dealing with difficult people is not a personality test. It's a process test. The better your processes , how you meet, delegate, escalate and follow up , the fewer damaging conflicts you will experience. Yes, empathy and being a good listener are incredibly important. But so do preparation, accountability and follow through.

You'll never remove all conflict. Nor would you want to. The goal is not so much silence but cultivation. Train for that. Expect setbacks. Learn. And when it clicks, it's an odd emotional upper: People who used to be adversaries turn into practical collaborators. That's the payoff.

Sources & Notes

CPP Inc., "Workplace Conflict and How Businesses Can Harness It to Thrive" (reporting that US employees average 2.8 hours per week dealing with conflict, estimating costs of $359B annually). CPP Inc., 2014.

Safe Work Australia, several publications relating to work related mental health and its impact on absence from work and productivity (cited for context of the cost of workplace stress; Organisations should refer to Safe Work Australia for current national data).

(For more visit, or to talk about how you can embed these practices into your team in Sydney, Melbourne and beyond we can design a practical scenario based workshop with you. We run what we teach.)