Behaviour is visible; intent is a guess

The most useful shift in dealing with a hard colleague is separating what you can observe from what you have decided it means.

You can observe that someone raised their voice, copied your manager on a reply, or went quiet in a meeting when your name came up. You cannot observe why. The moment you fill that gap — he is trying to undermine me, she doesn't respect my work — you have started responding to a story rather than a person, and the story is usually more expensive than the behaviour.

What is actually happening in the moment

Most difficult behaviour at work is functional. It is doing something for the person doing it: protecting them from blame, avoiding a difficult admission, moving a decision they feel stuck on, or simply being the pattern that got them promoted somewhere else in their career.

That framing sounds cynical and is actually the opposite. If a behaviour has a function, it is not random and it is not personal — and behaviours with functions can be worked with. Someone who shouts because shouting historically produced results is a different problem from someone who shouts because they are unkind, and the two need different responses.

The one who escalates

This person's reflex is to widen the audience. A question becomes a thread with four people copied in; a disagreement becomes a meeting. It feels like an attack and is often anxiety — a need for the decision to be shared so the risk is shared too.

The counter is not to escalate back. It is to answer the substance clearly, in writing, in front of the audience they chose. You cannot control who reads it; you can control whether your answer is calm and complete.

The one who never pushes back

Quiet is often filed under "no problem." It is frequently the opposite — the person who agrees in the meeting and doesn't deliver afterwards, because objecting in the room felt unsafe or pointless.

This is the pattern teams miss most, because it never creates a scene. The signal is not tone but follow-through: repeated slippage from someone who is consistently agreeable is not disorganisation, it is disagreement with nowhere to go.

The chronic complainer

Complaints about the same subject, repeatedly, without any change — this is usually not a request for a solution. It is often a request for acknowledgement, or a way of saying "this is not sustainable" in the only register available to them.

Solutions offered too early get refused, which reads as obstruction. What tends to land first is being heard properly, followed by one concrete question about what would make it workable.

Matching their tone. Escalating in the same register feels like fairness in the moment and reads as a loss of control to everyone else watching. Both of you end up defined by the exchange rather than the issue.

Avoiding it entirely. The most common response in Singapore's polite workplace culture, and the one that quietly costs the most — because the behaviour is working, and behaviour that keeps working keeps happening.

Winning the exchange. You can be right and still lose, if the other person now has a reason to make the next interaction harder. The measure of a difficult conversation is not whether you won it but whether the next one is easier.

Separate the behaviour from the person

"Your emails come across as blunt" is a usable sentence. "You are a difficult person" is not. The first invites a change; the second invites a defence. This sounds like a technique and is really about keeping the door open to a version of the colleague you can work with.

Ask what the behaviour is getting them

Before you decide how to respond, work out what the other person gains. If you can name the function, you can often offer it another way — the deadline protection they wanted, the acknowledgement they were looking for, the decision they were trying to force.

The same message, said two ways

Here is the difference in one line. First version: "You're always late with your updates and it's making my job impossible." The substance is a timing problem, but the sentence has been built as a character assessment — and the person now has to defend who they are rather than discuss the updates. Second version: "The last three weeks the updates have come after the cut-off and I've had to brief without them. What's making the timing difficult?" Same complaint, same facts, and now there is something to answer. It costs nothing extra to say it the second way. It just has to be practised, because under pressure almost everyone reaches for the first.

Rehearse the conversation before you have it

Most people prepare what they want to say and nothing about what they will do if it goes badly. Practising the difficult part out loud changes the outcome more than drafting the perfect opening line. It is also exactly the thing you cannot practise on your own from a book.

In a small firm of fifteen people, the difficult colleague is unavoidable — same meetings, same pantry, and no HR process to route around it. There, the leverage is the relationship itself. An honest one-to-one works because the two of you have to keep working together tomorrow.

In a larger organisation, the same behaviour arrives differently: it gets documented, escalated and absorbed by process. But the person at the receiving end still faces the same moment in the corridor. Here the lever is usually clarity — knowing exactly what you are accountable for, and what you are not obliged to absorb.

The difference is not who is more diplomatic. It is where the power to change the pattern actually sits — and that often has nothing to do with the person you are struggling with.

Information is not the missing piece

Almost everyone already knows they should stay calm, listen properly, and not take it personally. That knowledge has not solved the problem, which is evidence that knowing was never the gap.

What is missing is the ability to run those behaviours under pressure — while your heart rate is up and the person is mid-sentence. That is a skill, and skills are trained rather than remembered.

Practice with other people in the room

A course puts you in front of other adults who have the same problem, and gives you somewhere safe to try a response and get it wrong. That combination — practice, plus feedback from someone watching, plus other people's versions of the same moment — is what converts advice into reflex.

It also does something quieter and more useful. Hearing that a manager from a completely different industry has the same colleague, and the same difficulty, removes a lot of the personal sting. The problem becomes a workplace problem rather than something you are failing to handle.

Singapore's workplaces have their own texture — teams that switch between English, Mandarin, Malay and dialect within a sentence, four generations in one office, and a strong cultural preference for keeping things smooth. Advice written for an American open-plan office often doesn't survive contact with a Monday morning here.

When you look at what's available, the questions worth asking are fairly simple:

• Does it involve practice or just presentation? A course you watch is a lecture. A course where you rehearse a real conversation with your own difficult colleague in mind is training.
• Is it specific? "Communication skills" covers a lot and changes little. Something focused on handling difficult and negative people goes deeper into one problem.
• Does it give you something to use on Tuesday? A reusable structure for a hard conversation is worth more than five frameworks you can only describe.
• Who else will be in the room? A mixed room of supervisors, frontline staff and managers produces better discussion than a room of one job title.
• What funding applies? Ask directly about eligibility and what you need to submit — the answer changes the cost of the course considerably.

If you want one place to begin, Understand the Psychology behind Dealing with Difficult People is CBS's focused programme on this exact problem — it works on the psychology underneath the behaviour rather than a script to recite. The related sessions are worth knowing about too: The Stress Free Way to Deal with Difficult and Negative People at Work for those absorbing it daily, Writing Good Replies to Difficult Stakeholders for the written side of the same problem, and The Human Zoo: Care and Feeding of Challenging People in the Workplace for the manager trying to hold a team together around one difficult person.

Most people do not need to become experts in human behaviour. They need two or three responses that work, a way to stay steady while they deliver them, and the confidence that comes from having tried them once already.

Difficult people at work are not a personality problem you solve by being nicer. They are a behaviour pattern with a function, and patterns with functions can be worked with — but only by someone who can stay calm long enough to do it.

That is why the useful question is not "how do I deal with this person" but "have I ever practised doing it?" Most people haven't. That is the gap a good course fills, and it is a far more fixable gap than the person standing in front of you.