The Art of Handling Difficult Conversations at Workplace

Although most of you tend to avoid conflicts, avoiding difficult conversations doesn’t make them go away. Instead, facing them helps us improve our professional and personal lives. Do you know why most people avoid such discussions? Because they are not aware of how to have them. Besides, most of you fear that having difficult conversations will harm your relationships or negatively influence your work environment. In reality, avoiding these conversations leads to resentment and creates significant rifts between people.

The article offers you a complete guide in dealing with difficult conversations at your workplace and practical strategies to navigate them successfully.

Difficult Conversations with Your Employees: What You Must Know

While most of you believe conflict is wrong, it is not. Difficult conversations are an essential part of working well with others. When you and your employees have an understanding, you put forth the first step to creating a better work environment. On the other hand, avoiding difficult conversations lead to lower employee engagement and productivity.

Do your employees hesitate to talk about work-related issues? If your answer is yes, you must address the problem immediately. Failing to do so might create a toxic culture, adversely influencing your organization’s success. A study reveals that approximately 40% of employees think their managers fail to have honest conversations about work topics, making difficult conversations even more intimidating.

As a manager or an organizational leader, you must learn how to have difficult conversations with employees and handle conflict at work. You must also demonstrate conflict resolution at the earliest whenever you identify a problem. Remember, not every conversation will lead to a solution. However, you might formulate an effective strategy to find a solution or reach a mutual understanding. You must aim for understanding, as it is the foundation stone of numerous solutions. Above all, prepare beforehand since it helps you focus on a productive conversation.

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Difficult Conversations with Your Boss: What You Must Know

Having difficult conversations with your boss or supervisors is essential. Why? It helps in creating opportunities to improve the situation you are addressing. Although difficult conversations are challenging, it enables you to achieve a positive outcome. A difficult conversation with your boss results in a better work-life balance, an increase in salary, fulfillment of responsibilities, and positive relationships with colleagues.

Enlisted are some aspects you must keep in mind when having a difficult conversation with your employer.

Request a Meeting

When you request a meeting, it signals to your manager that you are approaching them when it’s convenient for their schedule. It is when your manager is the most receptive to what you have to hear. Ensure to keep your message as simple as possible.

Control Your Emotions

However, you must control your emotions, which helps in creating fewer problems. We aren’t saying that your manager does not have faults. Instead, we tend to exaggerate the role others play when we experience any problem. It is essential to examine your behavior, as it helps in understanding your contribution. For instance, you admit to withholding information from your manager. This behavior might contribute to a vicious cycle, as your manager fails to receive the communication you require, ending up micromanaging or overstepping the boundaries.

Address the Issue Directly

When you start conversing with your manager, immediately address the reason for the discussion. Do not forget to thank your manager for taking the time to meet with you. When you express your appreciation instantly, you help set a positive tone for the meeting. Moreover, it also shifts the conversation to the purpose of the meeting, and you show them that you respect their time.

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Importance of Handling Difficult Conversations

A problematic conversation at your workplace requires you to control your emotions and information sensitively. When you create a psychologically safe environment during difficult discussions, you offer the following:

Employees Feel Heard and Valued

Everyone deserves respect, and having tough conversations at the workplace shows that you respect hearing about their experiences and feelings. The open dialogue further validates feelings, making employees feel heard and recognized at work. Through this approach, you create a supportive environment that values all your employees’ perspectives.

Recognize Uncomfortable Workplace Issues

When we engage in difficult conversations as a manager or a leader, we confront numerous uncomfortable and overlooked issues. These discussions shed light on reflective processes or sensitive topics, including harassment and discrimination. Addressing these concerns demonstrates your organization’s commitment to creating a healthy and inclusive work environment.

Improve Work Environment and Company Culture

Engaging in tough talks is more than allowing employees to speak their minds. A conversation succeeds when you achieve an understanding and a mutually desired outcome. Open communication between both parties about their feelings and working towards a common goal helps promote excellent collaboration and strengthen the work community.

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Effective Ways to Handle Difficult Situations in the Workplace

Undoubtedly, starting a difficult conversation is daunting for most of us. Often we expect the issue to resolve itself, which is not so. A report states that approximately 40% of managers put off a conversation for nearly six months or more. Unfortunately, it doesn’t work and makes the issue more prominent. Therefore, managers must navigate a challenging discussion well.

Here are some practical steps that you can adopt to make difficult conversations easier.

Consider the Situation from Your Employee’s Perspective

Do you often face difficulty in conversing with your employees or managers? It is because we often see the issue from our perspective. If something is fixed in our minds, we do not listen to others’ solutions and viewpoints. Setting your situation aside and looking at the problem from others’ perspectives is advisable. Imagine how they feel about having a difficult conversation with you. Since you might not understand their viewpoint immediately, you must get to where you feel interested in discovering what is happening with them.

Determine the Goals of the Conversation

With your approach to a difficult conversation, it is essential to identify your goals. Determine what you want to achieve through the discussion and the strategies you want to implement to achieve the result. It will help you feel prepared to enter the conversation and guide it with confidence.

Listen With an Open Mind

Often we enter a challenging discussion with divergent perspectives. Therefore, you must keep an open mind while engaging with others. The opposite offers an explanation clarifying the issues, helping you both overcome the problem quickly. You can practice active listening techniques, including paraphrasing, which enables you to understand the meaning.

Offer Empathy

Both of you are anxious when entering a difficult conversation, which often sparks emotional responses. With this, you must offer empathy to your partner throughout, reassuring them that you are conversing to reach a solution.

Focus On Resolution-Oriented Thinking

You might notice that the most challenging conversations begin with the goal of identifying a resolution. We must keep the goal throughout the conversation, avoiding the discussion becoming unproductive. Now, you can work together to find an answer that works for both parties. With the other person’s consent, you might take notes during the conversation, coming to a solution that meets all the demands.

Establish a Follow-Up Protocol

While the goal of a difficult conversation is to come up with an agreed-upon resolution and positive feelings, it never occurs. The conversation partner often requires time for emotional recovery and space to restore their relationship. When you end a conversation, establish a protocol for following up with the other person to confirm the developed resolution.


Although engaging in a difficult conversation is challenging, these tough talks are essential for your and your team’s growth. Try approaching sensitive topics with empathy and care. It helps create an uncomfortable discussion productive and produces a positive outcome.

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