Difficult Conversations

by Barbara Buffton

The when and where

There is no magic formula for deciding the best place and time to have ‘that’ conversation. But there are questions and issues you need to consider that will help you decide.


Deciding when to have a ‘difficult’ conversation is crucial. Remember that there may never be a right time, so check that you are not using this as a delaying tactic. However, it is important to think about the individual concerned and when they might be most receptive to what you have to say.

You cannot afford to wait for perfect conditions... opportunities are easily lost while waiting.

Gary Ryan Blair

Taking them completely by surprise is not a good idea! You might alert them first by saying something like, ‘I wonder if we could meet up later as I’ve got something important I want to discuss with you.’ Schedule in the time and make sure you’ve allowed long enough.

Consider the actual time and day of the conversation. Is Friday at 4pm appropriate? Or would Monday morning first thing be better? If it’s a hygiene issue, for example, late Friday might give the person the chance to go home without having to face the colleagues who they may suspect have complained and come in on Monday with the matter dealt with. On the other hand, if someone is coming back on Monday after a bereavement, then the sooner you make the appropriate comments, the better.


A private space to speak where you will be uninterrupted is very important. Is the office the best place? Or would it be best to go somewhere neutral? Think about it from the other person’s point of view – where might they feel more comfortable? Think about whether the other person is likely to react emotionally to your message. Is the chosen location safe from prying eyes or ears?

Set-up of the environment

Is the set-up of the room conducive to the discussion that is going to take place? Do you want to be behind your desk? Or is it better that you sit side by side with the person? Sitting down rather than standing can ease any tension.