How to handle the difficult conversation

As a manager, it is important that you take on all the tasks inherent in the leadership role – including the difficult conversations.

By Pernille Yde Planck, updated 2024

It can be both challenging and uncomfortable to have a difficult conversation with one of your employees. Sometimes these difficult conversations are therefore postponed.

As a manager, you might fear your employee's reaction, but it is important for the employee, the organization, you as a manager, and the team that these conversations are held continuously – because by having the conversation you correct the unwanted behavior and get everyone back on track.

The longer you wait, the more you turn a blind eye to inappropriate behavior – and the more that behavior becomes the new norm.

Different circumstances can be the starting point for a difficult conversation

A difficult conversation will often be a critical conversation related to an employee’s employment. It’s considered critical not only because it’s necessary, but also because it often involves delivering criticism — which is why it’s also known as a critical or challenging conversation.

The reason for the critical conversation could, for example, be a lack of professional competence, lack of engagement and effort, carelessness, too many mistakes, or poor collaboration skills.

Examples of behavior that require you as a leader to step in and initiate a difficult conversation include an employee who is disloyal or contributes to a toxic work environment. Other examples could be an employee struggling with alcohol issues or personal hygiene problems. Bullying, poor prioritization, sloppiness, and other signs of lack of engagement are also behaviors that you as a leader must address.

In addition, a difficult conversation can, of course, also involve having to demote or dismiss an employee.

Difficult conversations demonstrate visible leadership

When you, as a manager, issue a warning or have a critical conversation, you simultaneously have the opportunity to explain and help the employee understand what is needed for them to succeed. This makes it much easier for the employee to live up to the expectations.

Therefore, a successfully conducted critical conversation can have a positive influence on the employee's motivation, well-being, and efficiency.

For other employees, it is important that difficult conversations are held. When these conversations take place and behavior is corrected, it becomes clear that you, as a manager, are taking charge of difficult issues. For example, in a situation with a bullying employee, if you address the issue through a difficult conversation, the behavior stops and the psychological work environment improves significantly.

We’ve gathered five useful tips for handling difficult conversations

1. Prepare thoroughly

It’s important to prepare thoroughly before the conversation — both in terms of what you want to communicate and how the employee may react.

If there are aspects of the employee’s performance that are working well, be sure to acknowledge them. As for the issues that led to the meeting, be specific. Sharing concrete examples makes it easier for the employee to understand the feedback and respond constructively.

2. Criticize only behavior

Remember, you can only criticize aspects that the employee actually has the ability to change – that is, behavior. For example, this might be an employee who has sub-deliveries on a larger project and does not meet the agreed deadlines, or an employee who consistently works fewer hours than agreed.

3. Avoid distorted communication

When you have to hold a difficult conversation, it is important that you do not come across as overly forceful or "hammering" the employee. Sometimes, if the lead-up to the conversation has been long, you as a manager might rush to get everything said. If you do so, you will likely appear overly aggressive, and communication will become skewed.

Communication can also become distorted if the employee is caught off guard – perhaps even shocked because they were not given any prior warning. This may result in the employee not fully grasping the message. Avoid such skewed communication by considering and preparing for all aspects of the situation before the conversation.

4. Maintain a professional tone

During the conversation itself, it is important that you maintain an appropriately serious and professional tone. In other words, avoid using irony, sarcasm, joking, or humor as a cover-up for issues. Be professional. It is a good idea to start by stating that this is a difficult conversation and that there are things you believe are not working and that you would like to discuss.

5. Stick to what you have prepared

It is important that you adhere to what you have planned and communicate it in a clear and factual manner. Naturally, you should listen to the employee and allow them to process the message and ask questions. Be prepared for the possibility that the employee may need you to explain the issue in several different ways with various examples.

Benefits of holding difficult conversations

If you consistently hold difficult conversations, it will benefit you, your leadership, the collaboration within your team, and your organization. You will likely experience a better atmosphere, an improved psychological work environment, and better results.