Top Tips – How to Approach a Difficult Conversation with your Employee

By Matthew Reymes Cole
12 Apr 2024

Part of being an employer is having difficult conversations with your staff.

It's never easy whether you’re making them redundant, conducting a disciplinary, or managing mental health issues. However, it is crucial that these conversations happen, and that they are handled right. Research conducted last year found that workplace conflict costs employers £30bn a year.

But where do you start?

employees having a conversation at work


How to prepare for difficult conversations at work

The first rule: don’t dive headfirst into a difficult conversation with an employee. Take time to prepare. Schedule a meeting and give yourself time to get ready.

How do you get ready for a challenging conversation? There are a few steps you can take. One, consider the desired solution. If the employee has an issue with their line manager, for example, ask yourself the question:

“What will get them back on the same page?”

Come up with at least one solution, if not more, and note them down. The eventual solution may not look like what you’ve noted down, but at least you can begin with a reference point. Do not force a resolution on the individual, as this will lead to resentment and further confrontation.

Next, note down any discussion points. Again, this isn’t so you can force an opinion on the employee, but so you can open a dialogue about the main issues.

Once you have your desired outcome(s) and talking points, you can do a run-through of the conversation. What could their objections be? What are some concessions you could make?

When you are happy, schedule a meeting with the individual and send them a breakdown of the talking points. Try to keep the email neutral and clear. You should avoid soundly overly emotional as this will set a bad precedent for the rest of the meeting.

How to have difficult conversations at work

So you’ve set a meeting, and you’ve thoroughly prepared for it. Now what?

Start by outlining the purpose of the meeting. Highlight the pre-planned talking points and go through them one by one. Remember, this should be a discussion, not a lecture. If you’re doing all of the talking, take a step back and allow them to speak. The same applies if they’re talking at you without a chance for you to respond.

You should finalise the meeting with some clear actions. Don’t leave the meeting without at least one thing you can both go away and work on. If not, you haven’t found a resolution, you have just let the employee vent their thoughts and feelings.

The employee should help build the action plan moving forward. Avoid assigning blame or proving a point. Go away with a solution, or steps you can take to improve things.

Finally, make sure you follow up on the meeting. New problems can arise, and people can fall back into old patterns. Checking in will help you keep track of how things are progressing.


tips on managing difficult conversations


Tips on managing difficult conversations

We’ve discussed the structure of the meeting, but not how you should manage it.

Emotion is probably the biggest issue in a difficult conversation. If you express too much emotion you risk escalating the issue. If you express too little emotion, you could come across as if you don’t care. The key is to stay calm and acknowledge how the employee is feeling.

This doesn’t necessarily mean you should accept or agree with what they are saying. You should always acknowledge the employee’s point of view, as this will make them feel heard. But, if they’re saying something that isn’t accurate or viable, you should express that. Remember, it’s not your place to get overly emotional. Stick with facts and figures

It can be good to allow the individual to vent during difficult conversations at work. They may have been carrying a lot of emotions and this is their chance to let them out. However, you shouldn’t allow this to derail the meeting. Allow them to speak and then calmly reorient the conversation. Only provide information where absolutely necessary, as a lengthy policy explanation at this stage is unlikely to have a positive effect.

It's also a good idea to be accompanied to the meeting. This will give you a sounding board. If the employee is accompanied, they also have another person to run thoughts and ideas by.

If the individual has mental health issues you are aware of, you should be accompanied by a mental health professional or first aider.

Following up on difficult conversations and crucial conversations

Follow up is crucial to the success of your meetings. It is key when considering how to handle challenging conversations, and to track the progress of the issue. In fact, it’s a good rule to follow in all of your meetings, not just the difficult ones.

To follow up, schedule a meeting a week or two in advance. Take the time in between to reflect on the discussion. If you feel the conversation has had an emotional impact on you personally, prioritise your mental health. Take a walk. Speak to someone about the experience. Practice breathing exercises. Utilise an EAP, or seek out a mental health professional to talk to.

In the follow-up meeting, review the action points you came up with in the last meeting. Evaluate their success and see how the employee feels now. If there are any lasting concerns, brainstorm new solutions.

Don’t handle challenging conversations alone

Every employer needs to have difficult conversations. This is something you will need to learn how to manage. Luckily, it’s not something you’ll have to manage on your own.

Croner’s consultants provide expert advice on all HR matters, 24/7, 365 days a year. Not only that, they can accompany you to meetings, or even conduct them for you. Find out how our service can support you with difficult conversations by calling 01455 858 132.

About the Author

Matthew Reymes-Cole

Matt joined Croner in 2007 as an employment law consultant and has advised clients of all sizes on all aspects of employment law. He has worked within management positions since 2017 and currently oversees a team within the litigation department, whilst continuing to support a number of clients directly.