Last updated: 05.11.21

Tips for Having Difficult Conversations with Employees

Almost everyone has to take part in difficult conversations at work at some point in their career. Most people experience at least one challenging or uncomfortable conversation with a boss or a coworker, but those in management roles in particular may have to have these discussions more regularly as part of their role.

Having difficult conversations with employees can range from delivering a piece of negative feedback right the way up to telling someone that they are going to lose their job. It could also involve official warnings or ultimatums in response to bad behaviour or a lack of commitment to a role.

Whilst many people worry about and put off handling difficult conversations, they don’t have to be a negative experience. Being prepared and conducting the discussion calmly and sensitively will minimise any distress or discomfort for those involved and hopefully ensure that something positive can come from the interaction.

In this article, we offer practical advice on the best ways to have difficult conversations with employees in the workplace, helping to reduce negative outcomes and improve communication. 

What are Difficult Conversations?

In a workplace scenario, difficult conversations are any conversations that cover a sensitive, controversial or potentially emotional topic. People are often reluctant to engage in difficult conversations because they don’t want to talk about something challenging or because they are worried about the reaction that it will provoke, but they are often a necessary part of positive growth or change.

How to Start Difficult Conversations

One of the most important things to remember when having a difficult conversation is not to spring it on an employee unannounced. Let them know in advance that you want to talk to them and tell them if they need to prepare anything, so that they can enter the discussion feeling confident and hopefully more comfortable.

In some situations, it may be appropriate to let the employee know what you are going to talk to them about before the conversation. This can remove the initial shock or emotional reaction if you are delivering bad news, which can make the rest of the conversation easier.

Always begin having difficult conversations in a private and neutral space so that the employee doesn’t feel out of their depth. Ensure that enough time has been set aside to have a proper discussion so that nobody has to rush or feel under pressure to condense what they have to say.

You should always start difficult conversations at work by stating why you are there and what is going to be talked about. This removes any anticipation and will hopefully make the employee feel more comfortable and able to properly engage in the conversation instead of worrying about the outcome.

11 Tips for Having Difficult Conversations with Employees

  • Invite a Moderator

This might not always be appropriate, but some difficult conversations at work may benefit from the presence of a moderator or a neutral party. This can make the employee you are talking to feel more supported and will also ensure that the conversation remains unbiased by including a third party to point out any clear unfairness.

It can also be useful to have a moderator present if you anticipate that the employee may disagree with what you are talking about, as then you have someone who can impartially support the facts and keep things fair.

  • Acknowledge the Discomfort

There are some formal situations where this may not suit a situation, but sometimes it can be really beneficial to start a difficult conversation by acknowledging the discomfort. If you and the employee are able to discuss how you are both feeling and clear the air before you begin, it may remove some of the tension and help the conversation to be much more productive.

Acknowledging how you feel can also help to make you seem more approachable to the employee, which will make them feel more at ease and again help the conversation to run smoothly.

  • Be Direct

It can be tempting to beat around the bush when you are trying to discuss something difficult, as it may feel like skirting around the topic will make the impact less severe. However, it is always better to be direct when it comes to dealing with difficult situations, as this removes the chance that the employee might misunderstand what you are trying to say.

Begin the conversation by stating precisely why you are both there. Present the facts of what has happened or the purpose of the conversation clearly and concisely, and then allow the other person to clarify anything you have said.

  • Stay Focused

Again, when you’re having a challenging conversation you may find yourself skirting off-topic as a way to try and relieve some of the tension or discomfort. It’s an understandable reaction to difficult situations, but it tends to make things worse.

If you or the employee start to go off-topic, try and bring the conversation back as quickly and politely as possible. This is why it can be useful to have an agenda or at least a guide of what needs to be discussed, as you are much more likely to stay on track and avoid making small talk or discussing irrelevant points.

  • Exercise Empathy

Empathy is a key part of handling difficult situations in a positive way. Even if it doesn’t come naturally, you should make an effort to show the employee that you are trying to understand things from their point of view so that they feel like their situation is being acknowledged. 

You can demonstrate empathy by using phrases like “I understand that this must feel…”, “I appreciate that this may be hard to hear…”, or “I imagine that you are feeling...” to indicate that you are considering the employee’s feelings. If they voice any emotions that have been brought up, ensure that you repeat this back to them so they know that you have acknowledged their reaction.

  • Keep Positive

Unless the conversation you are having is very serious, you should try and keep positive during the interaction. Instead of focusing on what may have gone wrong, try and reframe this situation as an opportunity to do better in the future and identify an area for improvement.

You should also try and spend the majority of the conversation talking about the positive things that will hopefully get done in the future, instead of the negative things that have happened in the past. This will make the overall tone of the discussion much brighter and help the employee to feel less like they’re just getting told off.

  • Leave Time to Listen

An essential part of handling difficult conversations is leaving time to listen to what the employee has to say. Keeping things on track is important, but you want the conversation to feel two-way instead of just like you are delivering a lecture or warning.

Once you have established the purpose of the conversation and what has happened, give the employee a chance to tell the same story from their perspective. Clarify any complicated points and try to practice active listening so that they feel understood.

During this, try and leave your own opinions and assumptions about the situation at the door. Whilst it can be hard if someone has objectively done something wrong, understanding their perspective is much easier if you’re listening with an open mind, and this will lead to a more productive conversation.

  • Allow Questions

As well as giving an employee time to speak, you should also allow them to ask questions. If you’re coming to them with a complaint then it may not always be possible to disclose all the information, but they will likely have points they want to clarify or questions about what will happen next.

Allowing time to ask questions also ensures that you are both on the same page about what has gone on and what needs to happen next, which will hopefully make the rest of the conversation much easier.

  • Suggest Solutions

To try and keep a difficult conversation positive and productive, make sure that you enter into it with constructive feedback and solutions for how a similar conversation or situation can be avoided in the future. Closing a challenging conversation with a clear plan of action will make the discussion feel more productive and hopefully dissipate any negative feelings that may have been brought up.

It is important to have a two-way conversation about finding solutions with an employee, instead of just telling them what you think they should do. They’re much more likely to take action if they like or have suggested the next steps, so ensure that you factor in their opinions and wants as well.

  •  Finish with a Recap

At the end of a difficult conversation at work, it’s very useful to recap everything that has been discussed as a conclusion to the meeting. Not only will this clarify that you and the employee agree with all the points you have covered, but it also is a good way to finish on a positive note by summarising the next steps that will be actioned after the meeting.

  •  Keep Things Confidential

There are some cases where you may have to disclose what has been discussed in a difficult conversation with an employee, but if possible it is a good idea to try and keep the nature of the conversation confidential. Not only will this make the employee feel more relaxed whilst you are talking, but it also helps everyone to move on from what has happened and encourages forward progress instead of dwelling on negativity from the past.

You may have to share information with a superior, but you should never tell other employees what has been discussed unless they explicitly need to know.


How do you mentally prepare for a difficult conversation?

If you know that a difficult conversation is coming up, you will benefit from being in the right headspace beforehand. Even if you are not impacted by the news you are delivering or the discussion you’re having, it can still be draining or uncomfortable to have a challenging conversation with someone, especially if they take it badly.

The best way to mentally prepare for a difficult conversation is to ensure you know what you are going to say beforehand. This will make you feel more comfortable and help to keep the discussion on track, which will hopefully lead to less emotional fallout.

It’s also important to ensure you’re in a calm and positive headspace before dealing with difficult employees and challenging conversations. However you support your own positive mental health, try to avoid having these kinds of talks when you feel stressed, unhappy or distracted, as this could make the situation harder to deal with.

Why do we avoid difficult conversations?

Many people avoid having difficult conversations for as long as possible because they fear the consequences, whether that’s how the other person might react or how a situation might change. However, often by putting off hard conversations we actually tend to make situations a lot worse, which is why it is important to learn how to conduct them properly and get the best out of difficult discussions.


Many people dread having difficult conversations, especially in the workplace, but for some roles it is a key part of the responsibilities of the job. Preparing for these conversations, creating a safe and comfortable environment, keeping the tone positive and practising empathy and active listening are all ways that you can make handling difficult conversations much easier, and even start to enjoy them because of the positive outcomes they result in.

If you’d like more advice and guidance on how to have these kinds of conversations with employees, we offer a ‘Managing Challenging Conversations’ online course as part of our Leadership and Management resource collection, covering the key skills and approaches for having productive conversations.