How to have a difficult conversation

Most people dread difficult conversations, whether they're about poor performance, bad body odour or the worst-case scenario - redundancy. Here's some tips to mastering the art of the tricky chat ...

by Emma De Vita
Last Updated: 09 Oct 2013

Get ready

As our Olympians know well, every hard feat is made easier with preparation. Start by considering what the ideal outcome of the conversation would be, whether it's getting people to change their behaviour or to keep their dignity after you've told them that they're losing their job.

'If you're nervous, practise at home until you find a form of words and a tone of voice which is firm, clear but friendly,' advises Kennett. 'The more you sound like a critical parent or a schoolteacher, the more resistant the other will be to your message.'

It's also important to pick the right location. Says Dr Stephen Harding [pictured], a director at HR consultant Towers Watson, 'it must be done face-to-face and privately'. And the location should match the message. The boss's office might be appropriate if you're giving a dressing-down, but a neutral place would be better suited to making a redundancy.

Stick to the facts

To avoid a confrontation or bitchy slanging match, you must keep things specific and never make it personal. Although it's difficult, try not to get emotional - avoid anger at all costs. A good way to start might be to admit that this will be a difficult conversation for both of you so the other person is warned and has a chance to prepare for it.

Describe actual behaviours and avoid the infamous 'feedback sandwich' (good-bad-good). It comes across as disingenuous and dilutes the impact of your message. 'The focus should be on the issue, not the person,' says Harding. If you spell out what is unacceptable, it gives the person something to work with.

Remember the best feedback is straightforward and direct. Speak with economy, do more listening than talking and articulate the message clearly. Says Kennett: 'I know of a boss who spent half an hour with an employee, who then left the room oblivious to the fact that he had been fired.'


After losing a job, 'an individual will go through a process akin to grief', explains Harding. There might be shock, denial, anger, depression, acceptance and then, ideally, rebuilding. Stay calm and remember that it's usual for someone being given bad news to have a fight or flight reaction. One person might become angry, while others can keep very quiet, suppressing their feelings until later. It's your job to keep emotions under control and to avoid argument. It's important to focus on the positive. If you're having a conversation about performance, it's because you want to improve it, so you must be optimistic and encouraging. 'Always be polite, willing to listen and affirmative. Don't dwell on the negative,' counsels Harding.


Start by allowing time for reflection. 'At the end of the meeting, let people explain what they're going to do,' says Kennett. If they don't want to say anything, don't force them: save it for later.

Finally, it's critical that you plan a schedule of progress meetings every two to three weeks to see if things are changing. If not, it's time for another difficult conversation ...

Find this article useful?

Get more great articles like this in your inbox every lunchtime

Is it favouritism to protect an employee no one likes?

The Dominic Cummings affair shows the dangers of double standards, but it’s also true that...

Masterclass: Communicating in a crisis

In this video, Moneypenny CEO Joanna Swash and Hill+Knowlton Strategies UK CEO Simon Whitehead discuss...

Remote working is no substitute for a good office

EKM's CEO Antony Chesworth has had no problems working from home, but he has no...

5 rules for work-at-home productivity

And how to focus when focusing feels impossible.

Scandal management lessons from Dominic Cummings

The PR industry offers its take on the PM’s svengali.

Why emails cause conflict

And what you can do about it.