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14 Tips for Approaching Difficult Conversations With Employees

Have you ever had a team member who constantly showed up to work too late, struggled with intense body odor, posted something inappropriate on social media, or perhaps had a habit of missing deadlines? Addressing these issues can be delicate, and having these conversations is never easy. However, they are an essential part of being a leader. Leadership requires us to hold employees accountable for their actions, even though…

The Exactly What to Say Certified Guides can especially help with the latter, and here are some tips on how to approach these conversations so that in the future you know exactly what to say (or not to say).

Do your homework and prepare

First things first. These are not the kind of conversations you’d want to walk into blind. You must know precisely what the situation is and what you want to accomplish. Be prepared by doing your homework, knowing the facts, and providing specific examples. Ask yourself: 

Most importantly, are you able to have this conversation on your own, or do you need someone else to do it or join you?

Consult with Human Resources or Legal

Depending on the issue you are dealing with, it might be a good idea to consult with your HR department or Legal department in advance. They can advise you on how to handle it, if any disciplinary action can be taken, or if any company policies need to be followed.

Furthermore, some topics have legal implications, so it is better to be safe than sorry before discussing them. Among these topics are alcohol, drugs, religion, sex, violence, theft, fraud, or harassment and bullying. By walking into these kinds of conversations alone and unprepared, you are potentially creating considerable damage to yourself and your company, as they can lead to false accusations and even lawsuits.

Bring yourself into the right mindset

Remember that these conversations are not personal attacks against the employee. Instead, they are meant to be constructive and help your employee, team, and your organization improve. Also, remember that neither of you is probably looking forward to this conversation. It is likely that your employee is just as anxious as you are. So, take a few minutes to clear your head and remind yourself of that objective.

Choose the right setting for the conversation

These conversations are not meant to take place in hallways where others might hear or observe you. It is best to conduct them in a quiet and private setting where you will not be interrupted. Make sure you have enough time set aside to have a calm and constructive conversation.

Start the conversation with positive reinforcement

Start by acknowledging the employee’s past accomplishments but focus on measurable results. It will set the tone for the rest of the conversation and create an open line of communication by making your employee feel appreciated and valued. 

For example, say, “I wanted to have a quick conversation with you about your performance lately and some areas where I think you can improve. But before we dive into that, I wanted to let you know that I’ve been impressed with the progress you’ve made on project XYZ, where you helped increase our efficiency by XYZ %.”

Don’t say, “I don’t know how to say this,” or “This is really uncomfortable,” or “There’s no easy way to say this.”

Using these phrases will make the conversation more difficult, awkward, and uncomfortable for both of you.

Use neutral and straightforward language

When it’s time to move on to the main topic, clarity and conciseness are essential. Use concrete examples to illustrate your point and be as specific as possible. Rather than making assumptions, focus on the facts. It’s critical to use neutral language that is neither too harsh nor too soft.

For example, say, “I’ve noticed that in the past month, you’ve been late six times, and our team’s start time is 8:30 am.”

Don’t say, “You’re always late,” or “You never show up on time,” or “What’s your problem?” or “Can’t you just show up on time?”

Using accusatory or judgmental language will only make the employee defensive and less likely to listen to your concerns. 

Don't refer to others' observations

Avoid referring to what others have said or observed about an employee’s behavior when explaining why there is a problem. Focus instead on your observations and experiences. 

For example, say, “I’ve noticed,” or “It has come to my attention,” or “I was reviewing the reports from last month.”

Don’t say, “Bob said,” or “I’ve been getting complaints from others,” or “Your coworkers have been telling me.”

By referring to others, the employee will feel attacked and ganged up, which won’t result in a productive conversation.

Describe the consequences for the individual and organization

Indicate how the employee’s behavior is negatively affecting their work performance, their reputation, as well as the reputation of their team, department, and organization. It will give them a better understanding of why addressing this problem is essential for their career development and the organization’s success.

For example, say, “When you’re late for meetings, it disrupts our team’s workflow, and it makes it difficult for us to move forward with our projects.” or “Your lateness has been impacting your own work performance, and it’s preventing us from meeting deadlines.” 

Don’t say, “It makes me look bad when you’re late” or “It bugs me when you’re late.”

These statements are about you, not the employee. In fact, you should not have the conversation if the issue does not impact the company or its performance. 

Be clear about how you would like them to change

Rather than dwelling on the past, move quickly on to the future. Outline the specific steps you want the employee to take to improve their behavior or performance. Please don’t assume that they know. Often, leaders make assumptions about what they expect from their employees without being explicit about it. Thus, the employee is unaware of how to improve, and the problem persists. 

For example, say, “I would like you to arrive on time at the latest 8.30 am from now on.” 

Don’t say, “Can you try to be more punctual?” or “Do your best to arrive on time, please.” 

Unless you are specific in your request, there will be confusion about what needs to be done (or not) moving forward. 

Be careful when offering support

As a leader, you should always be supportive, but you must be clear that it is the employee’s responsibility to make the necessary changes, not yours. Therefore, avoid offering too much support or making excuses for the employee’s behavior. It will only enable their bad behavior and make it harder to address issues in the future.

For example, say, “I’m confident you’ll be able to meet this challenge and improve your punctuality.”

Don’t say, “I’ll try to work with you on this,” or “Maybe we can find a solution together,” or “It’s not easy for anyone to be punctual all the time.”

These statements shift the focus away from the employee’s need to improve their behavior. Moreover, it implies that you don’t trust their ability to change by themselves, which will only make it more difficult for them to do so.

Be prepared for pushback

As a matter of fact, this is normal and expected. Keep calm and stay focused on the issue at hand. Do not take the employee’s reaction personally, and do not let it derail the conversation. Instead, use it as an opportunity to reiterate your expectations and why meeting them is essential.

For example, say, “I understand the problem you described, but it’s important that we have this conversation because,” or “I hear your concerns; however, this doesn’t change the fact.”

Don’t say, “I know you’re upset, but” or “Are you going to be able to handle this?” or “This is hard for me too, but.” 

These statements make you appear more concerned with your feelings than with the issue at hand.

Summarize what was discussed

When wrapping up, take a moment to summarize what was discussed. A clear understanding of what needs to be done will help ensure both of you are on the same page, especially on what has been agreed upon.

For example, say, “So, we’ve agreed that you will arrive on time at the latest 8.30 am from now on,” or “To recap, you will work on being punctual, which means arriving at 8:30 am, and I’ll check in with you in a few days.”

Don’t say, “So, are you going to try to be more punctual?” or “Do your best to arrive on time,” or “I know you’ll do better from now on.”

These statements are too vague and don’t accurately reflect what was discussed.

End on a neutral note

The traditional way to end a conversation is on a positive note, but you need to be careful not to lighten up the conversation unnecessarily. Otherwise, the employee might leave feeling that their behavior or performance is not that big of a deal after all. It’s also not necessary to be overly negative, as this will only make the employee feel worse and make them less likely to change their behavior. A neutral tone is best.

For example, say, “Thank you for taking the time. Let’s go back to work.” or “I appreciate you being honest with me. We’ll talk again soon.”

Don’t say, “I’m so glad this is over because I really like you,” or “Again, I’m so happy to have you on the team.” or “You are amazing. Thanks for understanding.” or “Great, I’m so relieved we had this chat!” 

The statements will only make it more challenging to address the issue in the future if it arises again.

Don't forget to document the exchange

Documentation is critical in case there are future problems with the employee’s performance or conduct. Document everything related to the conversation so that it cannot be disputed later. 

No one ever said being a leader was easy, and sometimes it means having difficult conversations with employees. Following these steps will ensure that such conversations are productive and lead to positive changes for individuals and organizations alike.


Sylvie di Giusto

Sylvie di Giusto, CSP is an international keynote speaker for corporations, associations, and the public sector who uses her unique multicultural background and decades of corporate experience to work with professionals from all over the world who place great importance on themselves and their company’s brand, image, and reputation.

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