Difficult Conversations

by Barbara Buffton

How to get started

It’s often said that the first step is the hardest, but there are various ways in which you can make it easier.

Soft entry

Although it’s best not to beat about the bush when tackling a difficult topic with someone, it can be a good idea to gently ease into some topics rather than launching straight in. An element of small talk can be helpful to put the person at ease; for example, a simple ‘How are you?’ can suffice as a preamble, provided you are genuinely interested in the answer. Or, probably better still, there is what’s called a ‘soft entry’ into the conversation, where you say things like


I feel uncomfortable doing this...

I’m addressing this now because...

I’m afraid I have something to say that you may not want to hear...

I have asked to see you because I’d like to talk to you about x; but first, I’d like to hear what you have to say about it...

How are you? I was so sorry to hear about your wife. If you want to talk, I’d be willing to listen.


Write down some possible openers for your difficult conversations.

Giving bad news or unwanted messages

If you have something unpleasant to say to an employee, tell them that you need to provide feedback that is difficult to share. Then be straightforward with them.


I am talking with you now because this is an issue that you need to address if you want to succeed in this organisation.

I feel uncomfortable saying this to you, but I don’t feel I can carry on without getting it out into the open. The way you do/say x makes me feel y.

I’m afraid I have some bad news for you: we are reluctantly having to make you redundant.

As you can see, if you’re uncomfortable with your role in the conversation, you could say so. Most people are as uncomfortable providing feedback about an individual’s personal dress, habits or hygiene, as the person receiving the feedback. Knowing that you too are uncomfortable can strangely help the other person!

Take responsibility

Take responsibility for the message, rather than passing it on to someone else. For example, if you’ve been asked to tackle a question of someone’s personal hygiene, it is really not a good idea to start the conversation with ‘your colleagues have asked me to have a word with you’. This will ensure at worst a hostile environment and at best an awkward one back in the office.

Check out the situation for yourself first so that you can say instead ‘Listen, I don’t mean to embarrass or offend you. I’m not sure if you’re aware of a problem. I have noticed a certain body odour when I am working with you or near you. This makes me not want to work with you that closely. I feel this is something that needs to be addressed. What do you think can be done about this?’

How not to do it 

An artist asked a gallery how his paintings were doing.

‘We have some good news and some bad news. A guy asked if your paintings would appreciate in value after your death. When I told him yes, he bought all 15 of them.’

‘So, what’s the bad news?’

‘He was your doctor.’

Tackling your boss

If you have issues with a boss who has not been a good boss to date, it is imperative to address them first with that person. However, simply telling your boss that he or she is a bad boss is counterproductive and won’t help you to meet your goals. Instead, tell him/her what you would like and need specifically in terms of direction, feedback and support. Be polite and focus on your needs.


I enjoy working here very much and in order to make me even more productive and useful to the organisation, I wonder if we could agree on a few things/if you could help me with some things?

If you’ve done this and nothing changes, you may have to go over your boss’s head to his or her line manager and ask for help. However, your current boss may not appreciate you doing that, so do ensure you’ve done all you can with your current boss first, before taking your issues further up the line.

Asking for a pay rise

Maybe you’d like a salary increase or feel you absolutely deserve one? Try this:


I’d appreciate a discussion about my role and responsibilities and how I could enhance my salary package.

As with any topic you have put off addressing, ensure you’ve done your homework first. Focusing first on your roles and responsibilities leaves the way open for them to be linked to a pay rise – if not immediately, then in the future. Your employer will undoubtedly respond more favourably to this than simply to a request asking for more pay for doing the same job.


Practise your conversation opener with a friend. Ask them for feedback about how it felt to be on the receiving end and what would make your opener even better. Ask them to focus not just on the words you say, but on how you come across with your body language, tone of voice and expression.

Keep practising until you are happy with how you present yourself.

Taken by surprise?

What if someone comes to you with a difficult conversation? How would you handle this so that you deal with it competently?

The best way is to stall the person, saying something like, ‘Can you give me half an hour before we have this conversation? There are things I need to finish up first so that I can totally focus on what you have to say’.