How to Have Difficult Conversations at Work

By: | Updated: August 21, 2023

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?

In the professional realm, challenging discussions are nearly unavoidable, whether conducted face-to-face or virtually. These exchanges are difficult due to the necessity of skillfully navigating potential negative sentiments that may emerge. Beyond the discomfort they entail, these discussions may create discord and animosity within the workspace if not handled with care. Here are difficult conversations examples commonly faced by both supervisors and employees.

1. Requesting a Salary Increase

Initiating a conversation about a salary increase is an uneasy task within the workplace. This discussion can be particularly intricate when requesting a raise beyond merit-based considerations. Balancing the recognition of your contribution with the desire not to appear unappreciative or solely motivated by financial gains can be challenging. To ensure your supervisor takes your request seriously, it is advisable to emphasize the value you bring to the company. Supporting your argument with data on industry compensation for similar roles and preparing for negotiation are also pivotal steps.

2. Addressing Suboptimal Performance

Confronting negative performance is an aspect most managers hesitate to address. Concerns often stem from a fear of fostering resentment, underappreciation, or demotivation among employees. While these concerns are valid, constructive performance evaluations are integral to organizational growth. Approaching such conversations with empathy and offering constructive feedback that avoids demeaning tones is essential.

Get our free team building toolbox

  • icebreaker games
  • bingo cards
  • DIY guides

heartby teams at FedEx, Amazon, Deloitte and 73,930+ others

Tool Box

3. Reporting an Underperforming Colleague

Addressing the shortcomings of a struggling colleague can feel challenging and potentially conflict-inducing. Raising concerns with a supervisor might evoke a sense of playing the antagonist, especially if done covertly. Yet, neglecting to address underperformance can hinder productivity and impact the overall team. A balanced approach entails first discussing the situation with the colleague to gain insight into their challenges and explore potential solutions. If issues persist, then reporting the situation to a superior while maintaining a focus on constructive resolution is advisable.

4. Discussing Micromanagement

Enduring micromanagement as an employee, where each aspect of your work is scrutinized, can be frustrating. Short of leaving the position, the optimal course is to engage with your manager about the issue. When discussing the matter directly with the micromanager, consider seeking to understand their motivations. Communicating how their approach hampers your motivation and productivity can lead to a constructive conversation, potentially guiding them toward more effective management strategies.

5. Concluding a Professional Partnership

Among the most challenging conversations in the workplace is the termination of a professional relationship. These dialogues are awkward and, at times, emotionally charged. It is essential to navigate these emotions in order to have a clear and respectful discussion. When facing the need to conclude a working relationship with an employee, engaging in a conversation about it might be daunting, yet it is preferable to evasion. A strategic approach involves providing a comprehensive and comprehensible explanation for the decision. Additionally, extending contacts and referring employees to potential employers can help alleviate the impact of such discussions. This strategy supports maintaining connections and reducing potential resentment.

6. Providing Constructive Feedback on Project Delays

Discussing project delays and offering constructive feedback can be a difficult conversation in the workplace. Addressing the reasons for the delay, while avoiding blame, requires tact and clear communication. Focusing on solutions to prevent future delays and maintaining a collaborative tone can help foster a productive conversation while ensuring projects stay on track.

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. Confront Urgent Matters

The significance of difficult conversations lies in their ability to facilitate open discussions. These conversations can happen between supervisors and employees regarding workplace issues impacting workload and performance. To begin with, it is important to recognize that conflicts or problems requiring attention do not automatically dissolve. Consequently, individuals involved may harbor resentment, potentially leading to disengagement or even turnover. Agreeing to address these pressing matters enables all parties to acknowledge their roles in the issue and collaborate toward finding a resolution.

2. Resolve Issues Effectively

A critical aspect of engaging in challenging workplace conversations is the acceleration of efficient and swift issue resolution. By directly addressing these concerns, colleagues can direct efforts toward discovering common ground and resolving conflicts that disrupt the office environment. Addressing disputes promptly typically results in reduced employee disengagement and turnover.

3. Foster and Mend Work Relationships

Despite their tense nature and potential lack of immediate consensus, these challenging conversations contribute to the building and repairing of relationships within your team. Participating in such discussions conveys a sense of concern for the individual’s well-being by addressing tough situations. Through constructive dialogue that avoids judgment, parties involved understand their team acknowledges and empathizes with their concerns. These conversations underscore respect and a willingness to engage in uncomfortable discussions.

4. Facilitate Personal Development

While demanding, difficult conversations provide a unique opportunity for constructive feedback, enabling personal growth. These conversations assist teams in overcoming communication apprehensions, anxiety, and self-doubt. Comfortably navigating and handling these challenging discussions bolsters individual confidence and serves as a platform for personal development.

5. Enhance Collaborative Problem-Solving

Engaging in challenging conversations fosters collaborative problem-solving within the workplace. Rather than avoiding issues, confronting them directly encourages a team approach to finding solutions. This process allows diverse perspectives to come together, leading to more innovative and effective resolutions. Moreover, the willingness to address tough topics cultivates a culture of openness and transparency. In this environment, leaders meet concerns with proactive efforts to address them collectively.

6. Promote Continuous Learning and Adaptation

Difficult conversations are a vital avenue for promoting continuous learning and adaptation in a dynamic work environment. Addressing complex issues head-on encourages individuals to challenge assumptions and broaden their perspectives. As teams engage in these discussions, they become more adaptable and open to change, fostering an environment that encourages growth and improvement. Embracing difficult conversations as opportunities for growth enriches both individual skills and the overall organizational culture.

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 in Advance

When faced with challenging situations, the risk of speaking impulsively or becoming overly emotional is real. To avoid this, thorough preparation is key. Remember to take the time to analyze the situation carefully, consider what you want to convey, and plan how to express it effectively. This technique ensures that you communicate your grievances precisely without inadvertently hurting your team’s feelings. Strategic preparation empowers you to share your points concisely without sounding monotonous or robotic.

2. Maintain Composure

While preparation is a foundational step, maintaining composure during in-person interactions with involved parties can be daunting. It is essential, however, to remain composed while conveying your points. It is a balancing act to acknowledge your emotions, yet prevent them from escalating the conversation. You can employ techniques such as deep breathing and strategic pauses to avoid emotional escalation. Furthermore, focus on the emotions of the other party, guiding the conversation to reduce emotional tension.

3. Engage in Active Listening

A critical skill in navigating challenging conversations is active listening. Whether in a managerial or employee role, passive listening falls short. Be sure to actively listen with an open mind, genuinely seeking to grasp perspectives. Often, a straightforward explanation can clarify and expedite issue resolution. You can utilize approaches like asking open-ended questions, paraphrasing the speaker’s points, and refraining from interrupting to foster effective dialogue.

4. Utilize First-Person Communication

Employing first-person statements enhances communication during difficult conversations by providing an objective perspective. Utilizing “I” statements fosters addressing issues without an accusatory tone. Steering away from “you” statements avoids defensiveness or undue blame-shifting.

For example:

  • “I statement”: I feel overwhelmed when frequent changes to the project timeline occur, and I struggle to prioritize tasks.
  • “You statement”: You keep altering the project timeline, making it impossible to keep up.

In this instance, the “I statement” focuses on the speaker’s experience and feelings of overwhelm, eliminating blame toward the other party for timeline changes.

5. Steer Clear of Assumptions

In navigating tough conversations, avoiding assumptions is pivotal. Be sure to refrain from assuming, as it perpetuates misunderstanding and thwarts the resolution process. Instead, seek clarification when making statements, minimizing the risk of jumping to unwarranted conclusions.

6. Discover Common Ground

While consensus might not always be possible, identifying common ground is crucial for efficient problem-solving. For instance, identify areas of shared interest among parties, explore the reasoning behind points of agreement, and determine compatibility with your own perspectives. This practice showcases consideration for others’ interests and a willingness to compromise for the sake of resolution.

7. Consider Taking a Break

The overarching aim of challenging conversations is to find agreement, but this is not always feasible. In such instances, recognizing when to take a break is essential. When emotions intensify or communication stagnates, a break offers an opportunity to recalibrate and devise more effective approaches for addressing 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 Time

It is important to start by selecting the right time and setting for the conversation. For instance, choose a time when your boss is likely to be available and not overwhelmed by other tasks. Additionally, opt for a private and quiet location where you can have an uninterrupted and confidential discussion.

2. Come Prepared

Before the conversation, prepare and plan ahead. Be sure to clearly define the issue you want to address with your boss and outline the key points you intend to cover. Also, anticipate potential questions or objections your boss might raise and formulate thoughtful responses.

3. Be Clear and Concise

When you request a meeting with your boss, be clear and concise about the purpose of the conversation. It is good practice to use straightforward language to express your concerns without delving into unnecessary details. During the conversation, focus on presenting facts and specific examples to support your points. Sharing concrete incidents or situations that highlight the issue can provide clarity.

4. Use Active Listening Techniques

Active listening is essential during the conversation. For example, pay close attention to your boss’s responses and feedback. Then, avoid interrupting and give them the space to express their viewpoints fully. Once you have presented your concerns, invite your boss’s input and perspective on the matter. Be sure to remain receptive to their insights, even if they differ from your own.

5. Collaborate on Solutions

This conversation will go well if you work collaboratively with your boss to seek solutions and find common ground. To address the issue at hand, propose potential resolutions and suggestions. Flexibility is key, as not all issues will have straightforward solutions. Most importantly, stay focused on the topic at hand, and avoid bringing up unrelated matters.

6. Follow Up

As the conversation concludes, summarize the key points and any agreed-upon actions. Remember to express appreciation for your boss’s time and willingness to engage in the conversation. If necessary, set a timeline for follow-up or any next steps that need to be taken.

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 Promptly

Difficult conversations may be unsettling, but it is important to promptly confront the matter at hand. Procrastination only exacerbates the situation, allowing it to escalate into something unmanageable. Avoiding the issue fosters resentment and misunderstandings among those involved. If you detect a recurring problem within your team, then arrange a timely meeting with the individual responsible to directly tackle the issue.

2. Avoid Sugarcoating the Issue

Emotional intelligence is crucial for navigating challenging conversations with employees. However, refraining from excessive positivity when discussing the impact of their actions or the underlying message is key. For example, when discussing an employee’s underwhelming performance, it is essential to be forthright. Softening the conversation with too much positivity might hinder the employee from fully comprehending the consequences of their actions and striving for improvement.

3. Attentively Acknowledge Their Viewpoint

Following your initial address of the issue, it is imperative to allow the employee to respond. Remember to actively listen to their standpoint with an open mind and remain engaged in their explanation. For instance, you can seek clarification on unclear points, take notes, and ask pertinent questions as needed.

4. Prioritize Problem Resolution

The primary objective of engaging in challenging conversations with employees is to arrive at a resolution. Although expressing your concerns or hearing the employee’s side is important, the ultimate focus should be on resolving the conflict by the end of the discussion. In navigating unpleasant discussions, it is most effective to center on the problem and then collaboratively explore viable solutions.

5. Have These Conversations Regularly

Instances of complex workplace scenarios that necessitate uncomfortable discussions are inevitable. Establishing a culture of open feedback where employees feel comfortable approaching you with their concerns is advantageous. Consider conducting routine one-on-one meetings with each employee to foster an environment where difficult conversations become less awkward and more commonplace.

6. Maintain Confidentiality

It is essential to respect the employee’s privacy and keep the details of the conversation confidential. Sharing sensitive information with others can damage trust and morale. Remember that upholding confidentiality safeguards the individual’s personal dignity and strengthens your credibility as a trusted manager. By treating sensitive matters with discretion, you create an atmosphere where employees feel secure discussing their concerns openly. This environment contributes to a more harmonious and productive workplace.


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.

Book wildly fun team building events with expert hosts

View experiences
team building event banner

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.

Author avatar


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


Share this article:
Leave a Reply

Your email address will not be published.

Get our free team building tool box

$49 value at no cost.

Tool Box

Enter your email for instant access