Difficult Conversations

by Barbara Buffton


Once you have faced up to the fact that you need to have that conversation, and the sooner the better, the next stage is to prepare for it. The following seven-stage process should help to keep you on track.

1. Think about it more positively

For example, if appropriate, you could reframe the words ‘difficult conversation’ in your mind to ‘a conversation where I get the opportunity to positively influence someone’s behaviour’. Notice how different that makes you feel about the whole thing. The very words ‘difficult conversation’ usually prompt a negative feeling. Seeing it differently, as something more positive, will change your mood for the better.

Also imagine the conversation having a positive outcome rather than turning out badly. This is likely to lead to you having that conversation instead of avoiding it. Thinking about the conversation having a positive and helpful outcome will lessen the anxiety you feel. After all, anxiety is just a fear of something bad that has not happened yet. So think about things turning out well.

Being in the right mindset for such a conversation is vital, because our mood affects how we are and what we do. It also affects someone else’s reaction to us. Have you noticed how being in a bad mood adversely affects your communication with others? And how being more cheerful and positive generally has the opposite effect on others?

2. Consider how you want to deliver the message

Some people prefer not to deliver bad news face to face and will do it via the telephone, email or even text. Email and text have the advantage of giving the other person time to prepare their response and it also means you avoid dealing with any immediate awkwardness or emotion. Hard as it might be, however, it is preferable, wherever possible, to have difficult conversations face to face. You can better gauge someone’s reaction by being in the same room as them. Their body language, facial expression and tone of voice all give clues as to how a person is feeling. Emails and texts cannot give you this information and can easily be misinterpreted. So, even if someone sends you an email that you don’t appreciate, pick up the phone or go and see them in person, rather than responding by email.

But what do you do when you can’t meet in person? Phone calls are better than emails as at least you have someone’s voice tone to add to the equation. It might even be possible to hold a conversation online using a webcam or via a video conference.

3. What do you want?

Be clear about what you want as a result of this conversation. What is it you want the other person to do or say? If the conversation is ultimately about performance at work, then focus on the behaviour you want changed rather than the person. In other words, make it impersonal and objective. This makes it much easier for the recipient to accept and to do something about.

For example: ‘What you said was difficult to understand. Let’s see how we can make it clearer for next time’. This separates the person from the behaviour. There is no judgment about the person’s character, only about the words used. We can change words much more easily than character. Contrast that with: ‘You were difficult to understand when giving that presentation’. This focuses on the person and can create feelings of resentment and antagonism.

4. Put yourself in the other person’s shoes

If you were on the receiving end of your words, how would you feel? Knowing the other person as you do, how might they react to what you have to say? Thinking about this from the other person’s perspective, does it change your message in any way? Does it change how, when or where you deliver it?


There is no one ‘right’ way of looking at things: different views may fit the facts just as well.

Remember that different cultures have different standards and in today’s diverse and multicultural society, these may create an issue. This is an area where we would advise caution, especially where items of dress are related to religion. The best thing to do is to speak with HR if you think there might be an issue that comes under the various regulations governing diversity. See also the topic on Diversity.

Of course, you may decide to approach things differently, depending on whether the issue is in-house or external. For instance, you may have an issue with a member of staff or with an external supplier. What will be different in how you handle these? Again, putting yourself in the other person’s shoes will give you clues about how to deal with this.

5. Practise your opening words and possible responses

If at all possible, role-play the conversation, with someone else acting as the recipient of your message. Become familiar with what you will say and how you will respond to different answers. Get feedback on how you come across and make sure that your verbal and non-verbal communication are aligned, so that, for instance, you are not smiling when giving bad news. Think about how you need to stand or sit, how your voice needs to sound and how you make eye contact. The devil is in the detail when you are having a difficult conversation!

Watch your ‘buts’

Notice which sentences are more motivating and which are demotivating:

  • I like what you’ve done here but it needs a bit more work.
  • I like what you’ve done here and it needs a bit more work.
  • This needs a bit more work, but I like what you’ve done.

The message we are left with is the one after the ‘but’, and not the one before it. So, be careful and practise the actual words you will use so that you get your ‘but’ in the right place. An alternative is to balance out both sides of the equation by using ‘and’ instead of ‘but’.

6. Anticipate concerns and questions

Make sure you have all the information you need to hand, especially exactly what message you want to give, any evidence, what impact it will have and why it matters.


Over the next day or two, practise describing problems and issues, without laying any blame. Catch yourself whenever you are about to say ‘but’ and check that the message you are giving is the one you want to give.

7. Practise your close

How do you want to end the conversation? What do you want to leave the other person with? Refer to How to close for more information.