I’m a little tired of your behaviour, she types.
Delete, delete. She’s dealing with a colleague, after all.
We need to talk.
That’s too vague, she wonders. Her colleague is abrasive, always backing her into a corner, stirring unnecessary trouble.
After several more deletions, she goes with, ‘We’ll talk tomorrow.’ She adds a couple of smileys and a ‘haha’, though there’s nothing really ‘haha’ about her situation.
Navigating difficult conversations feels like stepping into an emotional minefield. Dubai-based Anoushe Vijaysarthy, a marketing professional, admits that she spent a year of avoiding confrontation and straightforward communication with a particularly difficult colleague. “On the surface, he was friendly and amiable. We would laugh over tea breaks, and he felt like a friend, which only made it harder to admit why I had issues with him. He would barge into conversations that didn’t involve him, spread his things across my desk, make worrying errors at work, and expect us to cover for him. Each time I tried to address it, he would apologise, but then it would all start again. Finally, everything just kept piling up. My irritation showed in my behaviour, because I started snapping, and avoiding him, creating more awkwardness in the team.”
How do you tell someone when they cross the line, she wonders. Is there no easy way to have a difficult conversation? Sadly, no, the answer is in that statement itself. Annoying behaviours are just one part of this uneasy territory. These discussions cover a broad range: Explaining a delayed task, sitting through a poorly executed presentation, witnessing a micro-aggression in a meeting, or feeling slighted by a colleague. Awkward exchanges are a part of our professional lives.
So, how should you prepare for this kind of discussion? How do you find the right words in the moment? And, how can you manage the exchange so that it goes as smoothly as possible?
Assessing the difficulty of a conversation
First, ask yourself what makes the conversation seem so challenging . For example, Marianna Green, a sales professional based in Abu Dhabi, admits she finds it difficult to request two weeks of leave from her boss. Meanwhile, Judith Lin, a marketing manager in Dubai, often grappled with how to politely ask a colleague to stop borrowing money from her, knowing they would likely never repay it.
Dubai-based workplace mentor and business coach Theo Jackson puts it simply: Any conversation that dips beneath surface-level friendliness can come with a side of discomfort. “The moment you need to raise something that matters to you but may not align with someone else’s priorities, you’re stepping into the territory of a tough conversation,” she explains. People are afraid of having these conversations owing to the possibility of dealing with something less than pleasant at work, an argument, a disagreement, or just generally upsetting someone. “Most of us start thinking for the other person, and we get caught in our mental conversations.”
For Jackson, the trick lies in how you frame the scenario in your mind. “When you keep putting off the talk, skirting around the issue, the anxiety builds up inside you. That tension leaks into your behaviour, and trust me — people notice, which only stirs up more questions and unease at work,” she says. Her advice is to remind yourself it’s just a conversation. Ditch the ‘what-ifs’ and ‘maybes’, because those thoughts only serve to stress you out further.
‘Call people in, don’t call people out’
Don’t prepare for battle, instead, get ready for a conversation.
According to Todd Kashdan, author of The Art of Insubordination, when you call ‘people in’, you are ultimately admitting that we’re all of the same nature. “We all have flaws, make mistakes, and often don’t have the energy or mental capacity to do the things we care about. What’s important is we acknowledge it and choose to do better,” Kashdan had told the Harvard Business Review.
Meera Ramdas, a Dubai-based clinical psychologist, elaborates on this point. When someone is offensive or displays aggression, it’s natural for us to feel anger, humiliation, or condescension. After taking a few deep breaths and acknowledging that emotion, try to guide the person to understand their mistake, without publicly shaming them for it. Ramdas adds, “So, by saying, ‘I was rather hurt or taken aback by what you said’, you put the point across that you were offended, without sounding accusatory. Ask them for a conversation ‘Can we talk about this’.” When you call someone out, the issue becomes more about public accountability or criticism, which can often lead to defensiveness and strain relationships. By contrast, ‘calling people in’ focuses on reaching mutual understanding and improvement. This approach encourages the other person to consider the impact of their actions without feeling attacked or embarrassed.
For instance, a team member has stolen credit for your work. Instead of snapping at them (as tempting as it might be) and saying, ‘You always steal my ideas’, try approaching the conversation with, ‘I’ve noticed often now, that I’m really not being acknowledged for my contributions. Can we talk about this?’
Don’t sound rehearsed
Don’t memorise and beat around the bush.
Dubai-based Rebecca Dawson, a public relations professional recalls a colleague who was livid with her teammate, as he would constantly interrupt her during meetings. A non-confrontational person at heart, Dawson’s colleague spent days wondering how exactly she could have this conversation. So, she rehearsed with Dawson several times, made notes, and even imagined what he would say, tried timing herself and went to talk to the person. However, it was clear that she was ‘frightfully’ nervous, and when her friend went ‘off the script’, she grew even more hassled. Dawson just watched while the person continued staring blankly at the entire performance.
So lesson here is, don’t plan meticulously in advance. Note down key points if you must, but remember, you don’t know what your counterpart will say, adds Ramdas. Otherwise, you are left frazzled, and wondering what to do next, just like Dawson’s colleague. Be flexible, and prepare for a plethora of varied responses, regardless of the situation. Be clear, direct and natural.
Listen to their perspective
It’s really not your way or the highway. If you try entering a conversation with that mindset, you’ll just create a wider rift, than actually bridging it.
Ask yourself, what’s the problem, says Jackson. Consider what the other person thinks as the problem. With a little compassion, express your interest in understanding how the other person feels, and process the other person’s words and tone. Once you do, look for a meeting point between your view and theirs.
When I have colleagues that perhaps overstep the boundaries or continuously make mistakes, I find that there is usually something going on behind the scenes - either at work or at home. My approach would be to have a private chat with them in a relaxed environment....
And don't forget to be empathetic. Louise Heatley, the owner and managing director of Exclusive Links Real Estate Brokers, Dubai, echoes this sentiment and shares her views, "I’ve found that handling tough conversations effectively and with some compassion can make all the difference." When a colleague oversteps or repeatedly makes mistakes, she emphasises on approaching the discussion calmly, focusing on clarity and respect. You aim to understand their perspective and underlying challenges, set clear expectations and provide constructive feedback, which is helpful, and where necessary, engage the staff member in more training if required. Similarly, Catherine Hawkes, owner of Salon 91, says that whenever she notices her colleagues overstepping boundaries or continuously making mistakes, her approach would be to directly ask them what's going on and point out what situations are not acceptable. "In most cases, I find that the person usually opens up about what is concerning them, and why they have been behaving in such a way. If they are continuously making mistakes, I'll evaluate if it's more training that they need or if it's a behavioural issue," she adds.
Try to build trust, people wont open up if they don’t sense trust. So little acts of kindness goes a long way. It could be a message and concern about something at work or personal life
In order to get people to open up, you need to build trust. As Nathalie Khouri, Creative Director from Ralee Design House, explains, look for common ground. Listen to them and ask personal questions. Show interest in them. "Try to build trust; people won't open up if they don’t sense trust. So, little acts of kindness go a long way. It could be a message expressing concern about something at work or in their personal life," she says. Khouri shares her method for handling conflicts: "Show the person the impact the issue can cause. Get the team involved. Show how the issue can impact the team and try to find ways to work together. Finally, ask the person for solutions and feedback. Be open to receiving feedback and solutions from the other person."
Give something back
When a conversation could put someone in a difficult position or mean taking something away from them, ask yourself, ‘Is there something I can offer to ease the situation?’ says Jackson. For example, if you need to turn down an assignment from your boss, suggest a suitable alternative. Be constructive. No one wants more problems. Offering options provides a sense of direction and shows respect, helping the other person find a positive way forward. "Try to find solutions and take your time," adds Khouri. "Take your time to speak, and give the meeting some value."
