Back-to-basics: How to have difficult conversations

Few people look forward to having tough conversations. In fact, one survey found that 70% of employees avoid difficult conversations with their manager, colleagues or direct reports.  

You might need to address a colleague’s poor performance, tell someone their contract won’t be renewed, or ask for a pay rise or unpaid leave. Even the thought of some of those conversations might make you feel uncomfortable, anxious, or defensive.  

Here are some pointers to help you feel more confident and better prepared. While they won’t take away all the discomfort, they might help you to get a more positive outcome.

Reframe it  

If you think a conversation is going to be difficult, it’s likely to be just that. Anticipating that it will be tough could make you feel more anxious or defensive, even before it starts. Try to reframe the situation.

For example, rather than giving someone negative feedback, think of it as supporting someone with their development. Keeping the purpose of the meeting in mind can also help. You’re not having a difficult conversation for the sake of it, but to reach a certain outcome.

Don’t put it off 

It’s natural to want to avoid awkwardness, but putting off a tough conversation can make it feel more intimidating. It can also mean that a difficult situation will carry on brewing, rather than making steps towards resolution. Take action sooner rather than later.

Choose a suitable time and place  

It’s likely you’ll want to talk somewhere private, even if you’re speaking virtually. If the person feels that they’ll be overheard, it will be harder to have an honest and open conversation.   

Choose the most suitable time of day. That might be later on a Friday, to give time to digest what’s been discussed over the weekend. Or bright and early with a clear head. Whatever time you go for, make sure you block out enough time so you’re not rushed.  

Avoid having a difficult conversation if either of you are extremely stressed or if emotions are running high. And if there’s any chance it could get heated, consider having someone else present.  

Plan what you want to say 

Preparing what you want to say can help you to feel more confident. Gather together any information you need, and consider what questions you might get asked and how you could respond.

When you’re in the meeting, try to use clear, direct language – especially if you’re sharing information that the person won’t want to hear or is new to them.

Centre yourself  

We’re all unsettled by different things. You might hate confrontation, or feel uncomfortable if someone is crying. Get to know your personal triggers, and try to anticipate how the conversation might go.  

The calmer you can be, the less likely you are to be triggered. If you know, for example, that you’re walking into a potentially volatile situation, take some extra time to steady and centre yourself beforehand. Even a couple of calming breaths can help.  

And if during the meeting, either of you is getting overwhelmed it’s okay to take some time out, or delay it until you’re both calmer.

Listen carefully  

Listening carefully helps someone to feel deeply heard and understood. And that can only help to build bridges, even if the person is angry.  

Active listening means giving someone your full attention and putting your own opinions on hold. Ask questions if you’re not sure what they mean, use non-verbal cues to show them that you’re listening and engaged, and reflect back what you’ve heard. Showing empathy in this way can help to open up strong communication and build trust.

Take your time   

If you’re feeling awkward you may well want to get the conversation over and done with as quickly as possible. But that probably won’t leave anyone feeling that it was a positive experience. Rushing through might leave the other person feeling unheard, confused or angry.  

Slowing down your speech and introducing some pauses will give you both time to think and consider responses. That’s especially important if you’re working together to come up with some mutually beneficial solutions. It’s easy to feel that you need to talk constantly – especially if you’re nervous. But great ideas can come out of silence.

Give yourself some space afterwards  

If you didn’t take notes in the meeting, take some afterwards. Then, if necessary, email the person with a summary of your conversation and any follow-up actions. You might also want to reflect on what went well and what you’d do differently next time.   

And finally, take care of yourself. Tough conversations can be draining – even if they go better than anticipated. So give yourself some time out, go for a walk round the block or take a breather.