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How to handle tough conversations at work

A psychologist provides a few tips for tackling tough conversations.

We may be living in a technologically advanced society, but most jobs are still reliant on your ability to connect with, and influence others. So part of our lives will always be taken up with tough conversations at work.

HR professionals know better than most that you can’t delete human emotion from your work life (as much as you sometimes might want to). So whether they be about differences of opinions or unacceptable or even strange behaviours – it’s best to prepare yourself for dealing with the pointier end of colleague relationships.

Improving our ability to get positive results from these tough conversations is worthwhile for any individual. Indeed, some predict that this alongside other human skills, will be the most desirable in the working world of 2030.

What do you mean by tough?

Firstly, it’s important to know what the tough conversations are for you. Everybody is different, so it’s no surprise that one person’s tough conversation is someone else’s lively chat.

For a lot of people, the most difficult subject is having to address poor performance. Others might be okay with that conversation, but they’re challenged by someone who’s crying at their desk. Being clear on what conversations are tough for you will help to know which skills you should perfect.


Achieving success in a tough conversation starts before you even utter a word. Walking into it in a state of heightened emotion is dangerous – so too is assuming you can just say your piece and leave.

Turning up feeling centred, aware of why the conversation is important, and giving yourself enough time to talk through the issues (and listen) provides you with a strong platform for a productive talk. So, as you step into the tough conversation, recognise that you may not feel completely comfortable or confident. And acknowledge that that’s okay.

Whether you realise it or not, the reason you have concerns about the conversation is because you care about the person and about the outcome. Having that awareness, and labelling which emotions you’re experiencing, will help you centre yourself before you talk through the issue.

Use behaviour-based language

As you begin the conversation, repeat this maxim to yourself: there are no difficult people, there are only difficult behaviours – and behaviours can be changed.

During the conversation, it’s wise to focus on those behaviours rather than generalisations. Conversational waters are muddied by “traits”, because they could mean different things to different people.

For instance, if you know a person is making their coworkers uncomfortable and you want to address the issue by talking to them about  ‘courtesy’ you could potentially be on the wrong track.

For you ‘courtesy’ might mean greeting with a smile and a nod, and being careful what you say around others. But for them, anything less than a firm handshake is rude and a bit of light swearing among colleagues just adds colour to the office.

Behavioural change – which is so often the aim of tough conversations – relies on a shared understanding of what specifically needs to change. Both parties need clarity on what new behaviours are required.

So in our example, it might be better to avoid the abstract notion of courtesy and instead address directly what they’re doing that others find discomforting. Talk openly and non-judgmentally about their swearing, and explain how it’s received by other people.

Use a Visual Medium

Where you physically direct the conversation has an impact on how personally the other party receives the information. The old adage of “tell ‘em to their face” will quickly result in defensiveness, especially if it’s a heated issue.

Instead, direct the conversation to a visual medium. It could be a whiteboard, or a report; regardless, using a visual medium allows you to depersonalise the conversation. It might sound silly, or too simple, but even having a walk and talk conversation allows you to direct the conversation to the path in front of you both.

Don’t avoid eye contact, but don’t use it confrontationally. Similarly, the visual medium is there to help you take some of the emotion and sting out of the conversation – not as a crutch with which you can avoid it entirely. If it’s antagonising the person you’re talking to, don’t keep using it.

Be courageous

In the HR world tough conversations might be business as usual, but the fact remains these difficult conversations take courage.

Tackling the tough stuff is an act of bravery based on deliberate decisions that require careful planning. Remember to give yourself a break, and not to beat yourself up even if the conversation didn’t go as well as you hoped.

Instead, take a moment to reflect and think about how you can prepare for next time. Because, even if it wasn’t your first conversation… it’s unlikely to be your last.

Alison Hill is a psychologist and co-founder of Pragmatic Thinking.

Learn how to have difficult conversations and maintain the relationship after, with the AHRI short course ‘Having difficult conversations’.

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