The Leader Guide: How to have a difficult conversation at work with your employee?

Aga Kokoszewska
7 min readJul 25, 2021


Leaders quite often hesitate, when it comes to having difficult conversations with their employees at work. No matter which management level they are on, people struggle to have a difficult, yet effective conversation many times. Fortunately, this is a skill that is easily trained and approach can be structured for best results. Not always fit for all scenarios, of course. Good background though makes a world of a difference and will improve any leaders skills pack.
You simply need to start from the main reason and what you would like to achieve, so the conversation will lead to a successful outcome for you and your employee. This is a win-win situation you should be aiming for.

Preparation is the first key to your success

As a leader, you need to determine what the end goal of the “catch-up” needs to be. This should look like a free-flowing chat between you and the person, but with the structure, that was planned by you beforehand. Think of key points to discuss to ensure they are not omitted. Write them down and keep them handy if you feel this will help. Allow enough time scheduled so you are not stressing about another meeting straight after in case you go over the planned time. If you are having this talk remotely, make sure your cameras are switched on for more personal effect and there are no external distractions. If it gets emotional, remember to take a pause or even reschedule for another time. You need to be in control throughout the meeting. Remember to stay on the topic should the discussion get sidetracked.

Awareness of the Topic

Ensure to start the dialogue by communicating the topic of the conversation. This way, you and your team member will have a clear picture, what to focus on. Let’s take an example, if the meeting is meant to address an increased level of recent absence, you may start with:
“I would like to speak to you today, as I have concerns related to your recent absences”.
Frustration from the employee side will appear if their leader does not make it clear what the discussion is about. You need to be open, honest and direct.

Leader Takes Responsibility

As a manager, your responsibility is to take care of your employees’ performance level and skills utilization within the department. Ideally, everyone contributes their best to the overall success of the company. If an employee is not meeting the business goals set, and you do not address them, the conclusion is simple: You are accepting poor behaviour at work. The important part is with you, the leader. Ensure that you are fully aware of your own actions taken to improve your team members performance.

Make a feel-good sandwich

When there are negative situations at work, that you need to address, one powerful technique is to soften the negative by sandwiching it between two positives.
What is something positive about the situation or the member of the team?
Such as something you appreciate or what is going well, that you can acknowledge before bringing up the issue?
What is the issue you are bringing up?
What is another positive statement, perhaps pointing out past obstacles that have been overcome or positive outcomes you already foresee, that you could bring up after approaching the negative topic?
One key thing to remember here, however, is that you want to make sure that you are praising and acknowledging others at OTHER times as well, not just when you need to create a feel-good sandwich. Otherwise, every time you begin to praise someone, they’ll assume a negative is coming.

Address Conflict Directly and Promptly

As soon as you have identified the need for a conversation with your employee, do not delay it and try to address it as soon as possible. Do not hold off a difficult discussion, although you might be trying to find several different reasons to do so. Delaying it does not work in favour of the employee, manager nor the company. Procrastinating on having these types of discussions is beneficial for no one and in reality doing your employee a disservice.

Use XYZ or “When, What, How” Statements

Instead of generalizing with always or never, using XYZ statements helps you get specific.
Here’s how it works:
X: When-identify a specific incident or example that you are referring to
Y: What-clearly identify the other person’s behaviour
Z: How to use an “I” statement to express how it made you feel or impacted you
Being specific will make the person feel like you are not judging their whole character, but rather looking at a specific behaviour.
Using the previous example, an XYZ statement would look like this:
Yesterday (when), when you were facing your computer while I was talking to the team (what), I felt like you weren’t listening to me (how).
This sentence clearly tells the other party how their behaviour impacted you and what they could do differently. The great news is this technique works great for POSITIVE statements too! When you want to acknowledge or praise someone, being specific helps reinforce positive behaviour. For example, once the person in this example changes their behaviour, you can respond by telling them: Today, when you were making eye contact during our meeting, I appreciated your level of engagement. Consider the issues or behaviours you need to address and rephrase them into XYZ statements:
Issue: …
When: …
What: …
How: …
Full statement: …

Two-way street

As a leader, you need to avoid making the meeting with your employee all about what you want to communicate. Not so easy conversations should be and feel just like a work chat or a catch up between you both. To initiate a two-way discussion, you will need to be asking questions as well as listening carefully and attentively. Asking questions will make the discussion easier and will help to understand the root cause of the issue. Finding the trigger to the problem will lead you and your employee to the desired solution.

“I” statements

Making “I” statements means focusing on your own feelings while taking responsibility for your part. It means NOT accusing the other party or directly naming their behaviour. Make it about you.
Instead of saying “You ignore me when I talk,” rephrase it as an “I” statement.
“Sometimes when I’m talking I feel like you aren’t listening to me.”
What behaviours do you need to address that the other party did? How can you phrase these as “I” statements?

Right place at the right time

The very important part for leaders to have an effective difficult conversation at work with their employees is the setting. First of all, it should take place in a private area or a meeting room, so no one will randomly pop in or be able to hear you. You should ensure enough time is scheduled for the chat. If the conversation takes place remotely, both parties should have the cameras switched on with a decent amount of lighting around for good video quality.
Trying to randomly coach members of your team in public will only make them uncomfortable and no message will be received positively.

When a witness is required

Sometimes a quick chat is not what is actually needed.
When it comes to policy violations, behavioural issues or any type of disciplinary coaching interaction, you should always aim to have a witness present. Get HR person involved as a third-party witness. If that is not possible, another manager could be your witness, never another employee. Brief the person on each other’s roles and responsibilities during the meeting.

Body Language

Keep an eye on your body language, as it says a lot, especially during a potentially stressful situation. You can say something but show a different message at the same time. Be careful and be mindful. Observe your employee, their body will also send you a message, learn how to read it.


Simple rule. Whoever is not involved in the situation, should not be aware of it.
If someone comes to you confidentially remember you cannot guarantee it 100%. Depending on what is disclosed during the conversation, you may have no option but be obliged to speak to someone else and take action.
If it comes to an employee complaint, always seek to speak with witnesses and remember that there is always more than one side of the story.
For example, advise your employee, that you have received feedback about their unacceptable behaviour. Be general to protect all parties involved. Keep in mind, there are 3 sides to the situation: the employee who complained, the employee who was complained about and the truth.


Leaders cannot forget to set up follow-up feedback sessions. By scheduling these sessions, you are getting closer to a positive change in the employee or impacting the results. The effectiveness of the conversation will depend on the steps taken after it happened. Lasting impact is the main goal to be achieved for success.
A person can feel discouraged, if they have an employee performance conversation with their manager, then work towards improving and never be recognized for it. Also, a person can become immune to these, if their performance does not improve on the other hand and they are not corrected for it in a timely manner or ever.
Follow up is a very important part of the process.

I hope these few steps will support you to build a structure of your own when performing a difficult conversation with an employee. The aim of this article is to be a guideline on how a leader can tackle issues at work in an effective way with clear communication and very little room for stress and misunderstandings.

Originally published at on July 25, 2021.



Aga Kokoszewska

I am a passionate and experienced Career and Leadership Coach