Updated: May 11, 2023

How to Have Difficult Conversations at Work

You found our guide on how to have difficult conversations at work.

Difficult conversations at work are discussions centered on negative or sensitive topics. These conversations are often uncomfortable, tense, and sometimes heated. Examples of difficult conversations at work include firing an employee, addressing a negative behavior or performance, or even a possible delay in salary payment. Difficult conversations at work aim to access situations from different viewpoints and reach a mutual understanding or agreement.

Learning how to have difficult conversations at work is one of the first steps to developing workplace resilience and building a strong team. You can read communication books or conflict resolution books to learn these internal communication tools.

This article includes:

  • difficult conversations examples
  • why are difficult conversations important?
  • techniques for managing challenging conversations
  • how to have a difficult conversation with your boss
  • how to have a difficult conversation with an employee

Let’s get started!

What are difficult conversations to have at work?

Difficult conversations at work are almost inevitable, whether in person or virtually. These conversations are quite challenging because they require you to handle the negative emotions that may arise carefully. Apart from being uncomfortable, these conversations can lead to resentment and conflict in the workspace if mismanaged. Here are difficult conversations examples that most bosses and employees often have challenges discussing in the workplace.

1. Ending a Professional Relationship

One of the most difficult conversations to have at the workplace is ending a professional relationship. These conversations are awkward and, in some cases, emotional. It is important to navigate through these feelings to have a clear discussion. When planning to end a working relationship with an employee, having a conversation about it might be tough, but it is better than evading them. You could navigate this scenario by offering a detailed and understandable explanation of why you are ending the relationship. Providing contacts and referring workers to companies that need their services may also mitigate the effects of such conversations. This idea is a great way to maintain relationships and minimize resentment.

2. Asking for a Pay Raise

An uncomfortable discussion to have at work is requesting a pay raise. This conversation can be particularly tough when you ask for a non-merit increase. On the one hand, you know you deserve better financial remuneration for your efforts. On the other hand, you do not want to offend your boss and come off as unappreciative or only focused on financial benefits. If you want your superior to take you seriously, then the best way to navigate this type of conversation is to pinpoint the value you offer the company. You should also highlight the amount other companies pay employees in similar roles and be ready to negotiate your terms.

3. Addressing a Negative Performance

Most bosses avoid addressing or evaluating employees’ performance. According to an Interact Survey by Harris Poll, 37% of managers are uncomfortable giving direct feedback or criticism. Leaders worry these conversations could leave employees feeling resentful, under-appreciated, and demoralized. This feeling is understandable, as individuals may not handle a negative review about their performance well, and you do not want to be the villain. However, performance evaluations are essential to any organization. You can handle such conversations by being empathetic and giving constructive feedback without sounding demeaning or rude.

4. Reporting an Underperforming Colleague

When dealing with an underperforming coworker, pointing out their inconsistencies may sound offensive. On the other hand, reporting such a colleague to your boss or manager may make you feel like the bad guy, especially when you do this behind their backs. However, not reporting can affect your work process and, ultimately, the company. You can handle this situation by communicating with your colleague to understand their situation and how to help. If your coworker still does not seem to be in their game, then you can report them to your superior while ensuring you are not overly emphasizing this weakness.

5. Discussing Negative Behavior in the Workspace

At some point, you may need to address harassment, disruptive or distracting actions, lateness, or inappropriate behavior in the workplace. These conversations can be difficult without vilifying your colleague or employee. As a coworker, you can deal with this situation by talking to the erring colleague and explaining how their behavior makes you uncomfortable or affects you. If you are an employer, then you should carefully address the erring staff, focusing only on behavior contrary to the company’s policy.

6. Discussing Micromanagement

Micromanagement can be frustrating as an employee because every step of your workflow is under constant monitoring and scrutiny. Unless you plan to quit the role, the only option is to talk with the manager or boss about this problem. If you are directly conversing with the micromanager, then consider trying to learn the reason behind their action. You could also tell your supervisor how their micromanagement negatively impacts your motivation to work. At this point, the manager could show you what approaches you should incorporate that align with theirs.

Why are difficult conversations important?

Challenging conversations can be so stressful that most folks resort to avoidance because it often seems the best way to handle uncomfortable situations. However, not having these tough discussions, especially at work, has disadvantages. There are several reasons why difficult conversations are important, including the following.

1. Addressing Pressing Issues

Difficult conversations are important because they allow both boss and employee to air their opinions about workplace activities that affect their workload and performance. First, the conflict or issue that needs addressing does not automatically disappear. Therefore, the workers involved may get resentful, which can lead to disengagement or turnover. When you agree to address these pressing issues, it helps all parties involved identify their role in the problem and work toward finding a resolution.

2. Identify Dead Spots

Dead spots are the areas of your life in which you are either ignorant or insensitive to the pain and suffering you may be inflicting on others. Finding these blind spots helps you learn more about improving your interactions with others and yourself. Having an attitude of openness and a desire to learn and improve is crucial in these discussions, even if it means admitting your own inadequacies or errors. Sometimes, the parties involved in the conflict are unaware that their actions impact their colleagues negatively. When you have these unpleasant talks, most times than not, you would identify a dead spot and realize where you might have played a role in aggravating the problem.

3. Resolving Issues

An additional importance of having these tough discussions at work is that it helps you resolve issues more efficiently and quickly. When you address these issues head-on, you work toward finding common ground and resolving the conflict causing unrest in the office. You will likely experience less employee disengagement and turnover when you resolve disputes quickly.

4. Improve Communication

Difficult conversations are essential in the workplace because it helps both the boss and employees build their communication skills. Aside from resolving pressing issues, having these types of conversations teaches the parties how to express themselves articulately and learn to hear from other perspectives. During the talk, individuals also learn to listen to others actively.

5. Build and Repair Work Relationships

Although these unpleasant conversations are often tense and may not end with a consensus, they help build and repair relationships with your team. When you engage in these discussions, you let the individual know that you care enough to want to address a tough situation. By discussing your concerns constructively and being nonjudgmental, you show the parties involved that you understand and empathize with them but want a change in actions. These conversations also show that you respect these folks enough to want to have these uncomfortable conversations with them.

6. Improves Leadership

If you are a manager who is uncomfortable having direct or tough conversations with your team, then trying to have these challenging discussions can help improve your leadership skill. You can become comfortable addressing your staff when you consciously try to handle difficult conversations in person. This way, your team trusts you because they know that you value their feelings, improving productivity.

7. Aids in Personal Growth

While difficult conversations can be strenuous, they also provide an opportunity for constructive feedback that allows for personal growth. These difficult conversations help teams overcome the fear of communication, anxiety, and self-doubt. When you can comfortably handle and navigate difficult conversations, you build your confidence as an individual.

Techniques for managing challenging conversations

Unpleasant conversations can be daunting, but skillfully handling such discussions is important in ensuring a cohesive workplace. If you find it hard to communicate with your team, then here are some useful techniques for managing challenging conversations.

1. Prepare Ahead

When faced with tough situations, you may speak out of turn or become overly emotional when addressing the issue. You should plan ahead so that you can communicate precisely your point of grievance. An important technique is to take some time to carefully analyze the situation and think about what you want to say and how to express it. Tough conversations are already difficult, and you do not want to say words that would hurt your team’s feelings. When you plan ahead, you can deliver your points concisely without your emotions getting in the way. On the other hand, you do not want to sound monotonous or robotic when addressing the issue at hand.

2. Stay Calm

Although planning seems easy, dealing with the parties involved in person can be nerve-racking. However, you must remain calm when delivering your points. While your feelings are valid, you must not let your emotions or reactions escalate the discussion. You could take a deep breath and pause in between to avoid being emotionally charged. On the other hand, you should also pay attention to the other party’s emotions. You should know when to intelligently navigate the discussion in a way that makes the individuals involved feel less emotional.

3. Listen Actively

You should also learn to listen actively when having difficult conversations at work. Whether as a manager or employee, it is not enough to try to listen. You should also listen with an open mind and be willing to understand the situation from their perspectives. An explanation might be all it takes to clarify and resolve the issues more quickly. One helpful tip is asking open-ended questions, paraphrasing what the other party has said, and avoiding interrupting them while speaking.

4. Use First-Person Statements

Using first-person statements is important when having difficult conversations because it allows you to communicate well from your perspective. This technique helps you address issues objectively using the “I” statements so you do not appear to accuse the individual involved. If you keep using the “you” statement, then you may come off as being overly defensive or trying to avoid taking the blame.

​For instance:

  • “I statement”: I feel overwhelmed when there are frequent changes to the project timeline, and I am not sure how to prioritize my tasks.
  • “You statement”: You keep changing the project timeline, and it is impossible to keep up.

In this example, the “I statement” focuses on the speaker’s experience and feelings of overwhelm rather than blaming the other individual for changing the project timeline.

5. Avoid Assumptions

An additional technique for handling difficult conversations at work is avoiding assumptions. You should avoid making assumptions when discussing a difficult situation because it leads to further misunderstanding. As a result, you defeat the purpose of meeting to resolve the problem. Instead, you could ask for clarification when making certain statements so you do not appear to jump to conclusions easily.

6. Look for Common Ground

Although most difficult conversations may not end in a consensus, you must find common ground to resolve the problem efficiently. You should look for areas where parties involved share interests, explore the reason behind their points of agreement, and decide if it aligns with your ideas. Reaching a compromise shows that you care about the other individual’s interests and are willing to shift ground for resolution’s sake.

7. Take a Break

The goal of having difficult conversations at work is to come to an agreement. However, this may not always be the case. In such situations, taking a break may be the best step. When the conversation gets emotionally charged or does not seem to be going well, you could take a break to restrategize and find better ways to approach the issue.

How to have a difficult conversation with your boss

A conversation with your boss can be awkward, especially one involving a challenging topic. If you plan to have a difficult conversation with your boss, then you need tips for handling such discussions. Here are tips to help you have a difficult conversation with your boss.

1. Choose the Right Timing

If you plan to have a difficult conversation with your boss, then you must choose an appropriate time that works for them. Leaders undoubtedly have a busy schedule, and it would be impertinent to bring up such a conversation when they are extremely busy or stressed. On the other hand, the right timing makes them more receptive to your request, which takes some edge off the process.

2. Be Concise

Being concise about addressing the issue starts from the moment you request a meeting with your boss. You only need to state simply that you must converse with them and why. When addressing the problem, you should be articulate and clear about the issue, using examples and real-life instances to prove your point further.

3. Focus on Facts

It would be best to focus on presenting facts when having a difficult conversation with your boss. For instance, a conversation where you are reporting an underperforming colleague or unruly behavior should be about the exact incidents backed by facts and evidence. Be sure to avoid assumptions, sounding judgmental, and using emotional statements, as these could ruin your argument.

4. Ask for Their Input

When you finish addressing the issue, ask your boss for their input or perspective to help with problem-solving. At this point, your boss may either agree with you or offer a different opinion. If their perspective or opinion differs from what you expect, then you can ask for clarification or negotiate. However, you should be careful at this moment to avoid appearing or sounding offended or defensive.

5. Follow Up

Whether you reach an agreement or not, you should follow up on the conversation to ensure a resolution. This step is important if you are looking to resolve an issue effectively and create a lasting impact on your boss. During the conversation, you can ask when would be a good time to follow up on your requests.

How to have a difficult conversation with an employee

A difficult conversation with an employee is just as awkward as one with a boss. Approaching this conversation with professionalism and empathy creates a more positive and receptive environment where you can resolve conflict efficiently. Below are tips you can follow when having a difficult conversation with an employee.

1. Address the Issue Quickly

Tough conversations are discomforting, but it is always best to address the issue immediately. The more time spent avoiding the issue, the more it compounds until it eventually gets out of hand. Avoidance only creates a breeding ground for resentment and further misunderstanding among the parties involved. If you notice a negative pattern among your team, then you should immediately request a meeting with the erring party and address the issue.

2. Avoid Sugarcoating the Issue

Although you require emotional intelligence when having a difficult conversation with an employee, you should not try to sugarcoat their action’s impact or the message. For instance, a discussion centered on the unimpressive performance of any employee needs direct address. Trying to sugarcoat this conversation gives the employee less opportunity to strive for better results because they may not recognize the impact of their actions.

3. Be Empathetic

When addressing an employee in a tough situation, you should be empathetic and let them know you are open to hearing their opinion. It would help to let staff know they can trust you enough to understand their perspective. This approach may help you connect with the worker on a deeper level and pave the way for a more positive and constructive discussion. As a bonus, the ability to empathize with others may help ease tension and prevent future disputes.

4. Listen to Their Perspective

After you must have addressed the issue, the next step is to let the employee respond. You should listen to the individual’s perspective with an open mind and stay engaged in their explanation. You can show that you are actively listening by asking for clarity on statements you do not understand, taking notes, and asking questions where necessary.

5. Focus on a Resolution

The main purpose of having difficult conversations with an employee is to provide a resolution. While you may want to air your grievance or hear from your employee, the focus should be resolving the conflict at the end of the meeting. When having an unpleasant conversation with an employee, it is best to focus on the problem and then explore alternatives to fix it.

6. Have These Conversations Often

Tough workplace situations will always arise that require these uncomfortable discussions. It would be best to establish a feedback culture where your employees can always contact you with their issues. A tip is to have regular personal meetings with each of your employees to make these difficult conversations less awkward.


Learning how to have difficult conversations at work is a vital ability that may boost communication, output, and team morale. Having these talks may be difficult, but there are ways to make the process more pleasant and productive. You can handle even the most difficult conversations with poise and confidence if you put in the time and effort to prepare for them, choose an appropriate setting, and keep your cool throughout. Avoiding confrontation might prevent you from resolving issues, addressing concerns, and working together. Instead, you can make even the most awkward discussion more fruitful and enjoyable with the appropriate attitude and approach.

This article provides insight into how to have difficult conversations at work, why it is important, and how to handle these tough talks as a boss or employee for a better outcome.

Next up, check out how to use active listening activities to create a sense of belonging and build a team mentality.

FAQ: How to have difficult conversations at work

Here are some frequently asked questions about how to have difficult conversations at work.

What are difficult conversations at work?

Difficult conversations at work are discussions centered on sensitive or contentious issues involving the boss or employee in a workplace. Individuals hold these conversations with the intent of reaching a consensus. Although difficult conversations at work can be challenging, having these discussions are ultimately the best way to achieve growth as a team or individual.

What are common scenarios that involve difficult conversations at work?

Common scenarios that involve difficult conversions at work include ending a professional relationship, reporting an underperforming colleague, and asking for a pay raise. Others include addressing negative behavior in the workplace or micromanagement.

Why should bosses and employees have difficult conversations in the workplace?

Bosses and employees should have difficult conversations in the workplace to ensure no tension and resentment among each other as a team. These difficult conversations also build trust and stronger relationships and improve communication.

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People & Culture Director at teambuilding.com.
Grace is the Director of People & Culture at TeamBuilding. She studied Industrial and Labor Relations at Cornell University, Information Science at East China Normal University and earned an MBA at Washington State University.

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