Two white blocks with people drawn on them. Between them are several red blocks with exes, symbolising difficult conversations at work.
Image: © Andrii Yalanskyi/

Manager tips: How to have difficult conversations with employees

17 Jul 2023

Need to schedule a difficult conversation with a member of your team? Here’s how to do it in a way that will be constructive without leaving a bad taste in the mouth.

People managers often have to have difficult conversations with employees, whether it’s addressing a slip in standards or talking to someone who is not a team player.

Whether you’re newly promoted and are now leading a team for the first time or you have simply always struggled with confrontation or difficult work conversations, it’s important to be able to address issues in the workplace the right way.

As the old adage goes, people leave bad bosses, not bad jobs and if you don’t address difficult topics in the right way, you could end up leaving a bad taste in your employees’ mouths.

A difficult conversation could be anything from pulling someone up for being constantly late to meetings or having a negative attitude to missed deadlines or a slip in standards. When that time comes, take the correct steps to ensure it goes smoothly.

Put yourself in the right frame of mind

If the difficult conversation is in relation to a particular incident that has made you mad, it’s important not to pull that person into a meeting straight away. It’s never a good idea to talk about things when you’re annoyed or upset so the first thing you need to do is get into a calmer state of mind so that you’re able to think about the incident logically.

If it helps, write down exactly what happened and the impact it had so that you have your facts straight. This will help with the next step and it will give you a more holistic view of the problem.

Write down the points you want to make

Once you are in a calm place, write out a few bullet points that you want to say in the meeting. This should not be a script of what you plan to say but a short list of essential points you need to hit.

Stick to the facts of the matter, that is, what happened or what behaviour needs to be corrected, the impact the person is having on you or the rest of the team as a result of the behaviour and what or how this needs to change.

Ask for their thoughts first

Once you’ve got the situation straight in your head – and on paper – schedule a meeting for a reasonable time, not too far in the future. It’s important to address the situation while it’s still fresh.

Before launching into your list of bullet points, ask for their thoughts first. Present or highlight the situation or issue that has arisen and actively listen to their thoughts on the matter. There might be struggles you don’t yet know about or they might be unaware of the impact they’re having so it’s good to really hear their perspective first.

Be specific and seek understanding

When taking them through your own points, it’s important to have specific examples – especially if it’s a case of recurring behaviour. This helps to ground the problem in reality and helps them better understand what you’re referring to and how it had an impact.

The goal is not to force them to agree with you automatically, but to ensure they understand where you’re coming from or how the issue might be affecting other members of the team.

Actively listen to their response

Listening to your employee is essentially on this list twice for a good reason. While you as a manager may have an important issue that you need to address with this person, it should still be a two-way conversation.

The initial thoughts from them will help you understand where they’re at coming into this discussion and how aware they are of the problem. Having outlined specific examples or points and explained the impact in a calm, factual way, now is the time to listen to their response to ensure that they have heard you, that you understand how they’re feeling about the situation and any external factors that you may not have been aware of.

It’s also a good time to note their physical response. So much conversation happens through body language, and while remote working can make it a little harder to spot signals, it’s not impossible.

Discuss potential solutions

If the issue you are discussing requires a change in behaviour or a challenge that needs to be addressed, it’s important to discuss potential ways to overcome these issues together.

The employee will be best able to talk about how they can go about changing the way they work, while also highlighting potential blockers or struggles they have. That’s where you as a manager can come in with experience and knowledge that may be able to help them further.

Schedule a check-in

Once you’ve had the conversation and set out solutions or have reached an understanding that something needs to change, it’s important to schedule a check-in shortly after the initial conversation.

How long into the future that will be depends on the situation, as some things will see measurable results within a week or two, while others may take a month to show steady improvement. Decide the nearest time that is fair to see something change for the better and book a meeting for then to show that you will continue to engage with the employee on this.

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Jenny Darmody
By Jenny Darmody

Jenny Darmody became the editor of Silicon Republic in 2023, having worked as the deputy editor since February 2020. When she’s not writing about the science and tech industry, she’s writing short stories and attempting novels. She continuously buys more books than she can read in a lifetime and pretty stationery is her kryptonite. She also believes seagulls to be the root of all evil and her baking is the stuff of legends.

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