How to handle uncomfortable conversations

Knowing how to handle uncomfortable conversations begins with understanding the root cause of the discomfort. Here are eight expert tips and strategies to navigate difficult discussions effectively.

How to handle uncomfortable conversations: a coupe sit on the floor looking at each other.

“Cultivating empathy is a vital part of knowing how to handle uncomfortable conversations. It helps in fostering understanding, promoting effective communication, and building meaningful connections.” Credit: ©alfa27 / Adobe Stock 

How to handle uncomfortable conversations

The link between uncomfortable conversations and mental health

Uncomfortable conversations, though challenging, play a significant role in our overall mental health and well-being. In order to effectively handle uncomfortable conversations, it is essential to recognize that suppressing emotions and avoiding awkward conversations can adversely affect our mental and emotional states. By understanding and addressing our emotions through open dialogue, we can mitigate the risks associated with emotional suppression and create a healthier internal landscape.

When we avoid uncomfortable conversations, we often push aside our emotions, hoping they will disappear independently. However, feelings are not easily dismissed. In fact, we inadvertently give them more power by neglecting to acknowledge and address our emotions. Unexpressed emotions can intensify, leading to increased stress, anxiety, and even physical health issues.

Suppressing emotions can also impair our cognitive functions, including memory. When we avoid processing and discussing our emotions, they linger in our subconscious, taking up mental and emotional space. This can lead to difficulties in concentration, focus, and retaining information. By engaging in uncomfortable conversations, we actively confront and process these emotions, allowing our minds to operate more efficiently and effectively.

Additionally, avoiding emotions can contribute to developing aggression, anxiety, and depression. Unresolved emotional conflicts often manifest as heightened aggression or irritability. These suppressed emotions can build up, triggering disproportionate reactions to seemingly unrelated situations. Furthermore, persistent avoidance of uncomfortable conversations can fuel anxiety as we become apprehensive about addressing unresolved issues. Over time, this anxiety may develop into chronic worry and anxiety disorders. Similarly, repressed emotions can contribute to sadness, hopelessness, and even depression. Acknowledging and discussing our emotions creates an opportunity for healing, growth, and improved mental well-being.

Recognizing the link between uncomfortable conversations and mental health allows us to prioritize emotional openness and vulnerability. These conversations enable us to address underlying issues, improve communication and understanding, and foster stronger relationships. 

By embracing discomfort and actively participating in these conversations, we empower ourselves to navigate challenging emotions, enhance our mental resilience, and lead healthier, more fulfilling lives.

Understanding the importance of uncomfortable conversations

Uncomfortable conversations hold immense significance in our personal growth and the cultivation of healthy relationships. To effectively navigate these conversations, we must identify and understand the root cause of the discomfort we experience. By recognizing the underlying triggers, we can clarify our emotions, motivations, and reactions, leading to more productive and empathetic dialogues.

When faced with an uncomfortable conversation, it is common to experience a range of emotions such as fear, anxiety, frustration, or vulnerability. These emotional responses serve as signals, indicating that something deeper is at play. By taking the time to identify the specific aspects of the conversation that make us uncomfortable, we gain valuable insights into ourselves and the nature of the situation.

To identify the underlying cause of discomfort, introspection is critical. Take a moment to reflect on your emotions and ask yourself probing questions. What specific words or topics trigger unease? Is there a history or past experience that influences your reaction? Are there any unmet needs or unresolved conflicts connected to the conversation? Honest self-reflection enables you to uncover the root cause of your discomfort.

"Uncomfortable conversations create healthy relationships"

Understanding why you feel a certain way during an uncomfortable conversation involves exploring your thoughts, beliefs, and values. It requires self-awareness and empathy toward yourself. Consider how the conversation challenges your beliefs or values. Is there a fear of judgment, rejection, or confrontation? Identifying the underlying emotions and ideas will help you better understand your perspective and enable you to approach the conversation with greater clarity and empathy.

Sometimes, seeking support from a trusted friend, mentor, or therapist can provide valuable insights and help you explore your emotions further. Their impartial perspective can shed light on blind spots and assist in uncovering subconscious motivations or biases contributing to the discomfort.

Once you have identified the root cause of the discomfort, it is essential to acknowledge and validate your feelings without judgment. Recognize that discomfort is a natural part of growth and self-discovery. Embrace a compassionate mindset towards yourself, knowing that by engaging in an uncomfortable conversation, you are taking a proactive step towards personal and relational development.

By understanding the underlying cause of your discomfort, you can approach the conversation with increased self-awareness and empathy. This awareness allows for more effective communication, as you can articulate your emotions and needs more clearly. Furthermore, understanding your triggers and motivations helps you actively listen and empathize with the other person's perspective, fostering a more productive and compassionate dialogue. Through introspection, self-reflection, and seeking support when needed, you can clarify why you feel the way you do. This understanding facilitates constructive and empathetic conversations, leading to personal growth, strengthened relationships, and improved overall well-being.

Starting an uncomfortable conversation: eight tips for handling them well

If you want to know how to handle uncomfortable conversations, you need to know how to prepare for them. Starting an uncomfortable conversation requires thoughtful planning and effective communication skills. Follow these tips to initiate such conversations in a constructive and considerate manner.

1. Choose an appropriate time and place

When initiating an uncomfortable conversation, it is crucial to consider the timing and environment in which it takes place. Selecting the right time and place sets the stage for productive dialogue and increases the chances of a successful outcome. 

The importance of choosing an appropriate setting lies in creating a safe and comfortable space where both parties can openly express their thoughts and feelings. Opt for a time when both individuals are relatively calm and free from distractions, ensuring that there is sufficient privacy to maintain confidentiality. By deliberately choosing the right time and place, you set the tone for a respectful and focused conversation, increasing the likelihood of understanding, empathy, and effective problem-solving.

2. Keep it concise

Prepare beforehand and clearly know what you want to convey and talk about. Like this paragraph, be brief in expressing your feelings about the issue and outlining your desired outcomes. Allow the other person to respond.

3. Practice active listening

While it's essential to clearly understand what you want to express during an uncomfortable conversation, actively listening to the other person is crucial for effective communication and building a collaborative environment. 

Active listening goes beyond simply hearing the words spoken; it involves engaging with empathy and understanding. By acknowledging and repeating the other person's points, you demonstrate that you genuinely comprehend their perspective, fostering a sense of connection and mutual respect.

Active listening is a communication technique that entirely focuses on and comprehends the speaker's message. It requires setting aside preconceived notions and judgments and actively engaging with the speaker's words, emotions, and non-verbal cues. It is a conscious effort to be fully present in the conversation and to genuinely understand the speaker's thoughts, feelings, and underlying motivations.

To practice active listening during an uncomfortable conversation, start by reminding yourself to be fully present and attentive. Maintain eye contact, face the person directly, and use open body language to signal engagement and receptiveness. As the speaker shares their thoughts and emotions, resist the urge to interrupt or formulate responses in your mind. Instead, focus on understanding their perspective by listening to both the content and the emotions behind their words.

One effective technique in active listening is to employ reflective listening. After the speaker has expressed a point, paraphrase or repeat their key ideas in your own words. This confirms your understanding and allows the speaker to feel heard and validated. For example, you can say, "If I understand correctly, you're saying that..." or "It seems like you're feeling..." This reflective approach encourages the speaker to expand on their thoughts, clarifies potential misunderstandings, and fosters a deeper level of conversation.

During active listening, pay attention to the words spoken and the speaker's non-verbal cues, such as facial expressions, tone of voice, and body language. These cues provide additional information about the speaker's emotions and feelings, enhancing your understanding of their perspective.

Practicing active listening creates a safe and inclusive space for open dialogue. It demonstrates your willingness to empathize with the other person's point of view. It fosters a sense of collaboration rather than confrontation. 

Active listening paves the way for effective communication, mutual understanding, and the potential for finding common ground or resolving conflicts. It promotes a positive atmosphere where both parties feel heard and valued, ultimately leading to more productive outcomes and strengthened relationships.

4. Be genuine and avoid filler phrases

A key part of knowing how to handle uncomfortable conversations involves being genuine.

Being genuine in the conversation means being true to oneself and others, expressing thoughts, feelings, and intentions sincerely and authentically. It involves aligning one's actions, words, and values with honesty and integrity, without pretense or hidden agendas.

When someone is genuine, they are not putting on a façade or pretending to be someone they are not. They present themselves as they are without wearing masks or adopting false personas. Genuine individuals are comfortable with their own vulnerabilities and imperfections and embrace their uniqueness rather than trying to conform to societal expectations.

Being genuine during an uncomfortable conversation is not about seeking validation or approval from others. It is about being comfortable in one's skin and embracing one's uniqueness. Genuine individuals are secure in who they are and do not seek external validation to define their self-worth. They communicate honestly without resorting to meaningless phrases that undermine the conversation's purpose. Avoid saying "It's fine" or "I know what you mean" when they don't align with your genuine thoughts and feelings.

5. Embrace silence

Be prepared. During an uncomfortable conversation, silence can feel incredibly painful. The natural inclination is often to fill the void with unrelated chatter or hasty remarks. However, embracing silence as a valuable communication element can offer a powerful opportunity for reflection, deeper understanding, and thoughtful processing of new information. Resisting the urge to talk during these moments of silence is essential for maintaining the integrity and effectiveness of the conversation. Here are some tips to help you resist the urge to speak and fully embrace the silence:

  • Pause and breathe: When confronted with a pause in the conversation, take a moment to pause and take a deep breath. This simple act allows you to collect your thoughts, regulate your emotions, and center yourself in the present moment. It provides a valuable buffer that prevents impulsive responses and will enable you to approach the conversation calmly and composedly.
  • Practice active listening: Instead of using silence as an opportunity to formulate your response, use it to actively listen to the other person's words, emotions, and non-verbal cues. 
  • Reflect on your emotions: Silence can be ideal for introspection and self-reflection. Use this time to check in with your own feelings and thoughts. Are any underlying fears, biases, or assumptions driving your discomfort or desire to speak? Reflecting on your own emotional state helps you gain insight into your reactions. It enables you to respond in a more empathetic and constructive manner.
  • Allow time for processing: Uncomfortable conversations often involve new information or differing viewpoints that require processing time. Instead of rushing to respond, use the silence to allow the information to sink in and consider its implications. Let the silence work as a pause button that gives both individuals the space to digest and integrate what has been discussed. This allows for a more thoughtful and informed response when the conversation resumes.
  • Embrace curiosity: Rather than feeling pressured to fill the silence with your thoughts, adopt a mindset of curiosity. Use the quiet moments to generate meaningful questions that can deepen the conversation or clarify points of confusion. Embracing curiosity keeps you engaged in the conversation and demonstrates a genuine interest in understanding the other person's perspective.
  • Be comfortable with discomfort: Silence can evoke discomfort, but embracing and normalizing it within the conversation is crucial. Recognize that discomfort is a natural part of growth and learning. By allowing the discomfort to exist without trying to immediately alleviate it, you create space for authentic and transformative dialogue.

Handling silence during uncomfortable conversations requires practice and mindfulness. Positive silence helps create an environment that fosters more profound understanding, reflection, and the potential for meaningful resolution.

6. Stay centered amid emotional reactions

Knowing how to handle uncomfortable conversations means that you need to be prepared for intense emotions to arise, potentially derailing the dialogue. It's essential to recognize the role of mirror neurons, which can amplify emotional responses in both ourselves and the other person. Staying centered amidst emotional reactions is crucial to maintain a productive and constructive conversation. Here are some strategies to help you navigate overwhelming emotions while remaining engaged in the conversation:

  • Validate your emotions: First and foremost, acknowledge and validate your emotions. It's okay to feel a wide range of emotions during a difficult conversation, including sadness, anger, or frustration. Recognize that your emotions are valid and natural responses to the situation at hand. Validating your emotions allows you to honor your feelings without judgment or self-criticism.
  • Create a safe space: Establishing a safe and supportive environment is vital for navigating intense emotions. Ensure you and the other person feel comfortable expressing yourselves openly and honestly. Encourage empathy and understanding by listening to each other's perspectives without judgment. A safe space promotes mutual respect and allows for a more compassionate exchange.
  • Accept tears as healthy and natural: Crying is a natural emotional response and can be a healthy way to release pent-up feelings during a conversation. Recognizing that shedding tears does not undermine your ability to engage in the dialogue effectively is essential. If you feel tears welling up, remember that it's okay to let them flow. Allow yourself the space to express your emotions authentically without feeling embarrassed or ashamed.
  • Take a pause if needed: If you find yourself overwhelmed with emotions and struggling to maintain composure, it's perfectly acceptable to pause briefly. Excuse yourself politely, step away from the conversation temporarily, and give yourself a moment to collect your thoughts and regain emotional balance. Use this break to practice self-care techniques, such as taking deep breaths or engaging in grounding exercises that help calm your mind and body.
  • Practice self-compassion: Be kind to yourself and practice self-compassion throughout the conversation. Recognize that experiencing intense emotions is a part of being human and that it's natural to have emotional reactions during difficult discussions. Avoid self-judgment or harsh criticism for feeling overwhelmed. Treat yourself with gentleness, understanding, and acceptance as you navigate your emotions.
  • Refocus on objectives and intentions: When overcome with emotions, staying focused on the conversation's objectives can be challenging. Remind yourself of the purpose and goals of the discussion. By realigning your attention to the desired outcomes, you can regain perspective and prevent emotions from derailing the dialogue. Remember that maintaining open communication and seeking a mutually beneficial resolution should remain at the forefront of the conversation.

Remember, staying centered amid overwhelming emotions is a process that takes practice. By validating your emotions, creating a safe space, accepting tears as natural, pausing when needed, practicing self-compassion, refocusing on objectives, and seeking support when necessary, you can navigate intense emotions while remaining engaged and constructive in the conversation.

7. Cultivate empathy

Cultivating empathy is a vital part of knowing how to handle uncomfortable conversations. It helps in fostering understanding, promoting effective communication, and building meaningful connections.


Empathy allows us to acknowledge and validate the experiences and perspectives of others, even when they differ from our own. If you find empathy challenging, there are practical strategies you can employ to cultivate empathy at the moment and enhance your ability to connect with others on a deeper level.


  • Put yourself in their shoes. Imagine yourself in the other person's position and try to understand their feelings. Consider their life experiences, values, and beliefs that have shaped their perspective. This exercise helps you broaden your understanding of their point of view and cultivates empathy by allowing you to see the situation from their vantage point.

  • Ask open-ended questions: Encourage the other person to share more about their thoughts and feelings by asking open-ended questions. These questions prompt them to provide detailed responses beyond "yes" or "no." You create a space for them to express themselves fully by showing genuine curiosity and interest. This demonstrates empathy and helps you gain deeper insights into their emotions and experiences.

  • Reflect on shared humanity: Recognize that, as humans, we all experience a range of emotions and face challenges in our lives. Remind yourself that the person you're conversing with has their own unique struggles, desires, and fears, just like you. Reflecting on our shared humanity can foster a sense of connection and compassion, making it easier to approach the conversation with empathy.

  • Practice mindfulness and self-awareness: Cultivating empathy requires self-awareness and the ability to be present in the moment. Practice mindfulness techniques such as deep breathing or grounding exercises to help you stay focused and attuned to the conversation. By being fully present, you can better understand the emotions and needs of the other person and respond with empathy.

  • Seek common ground: Look for areas of commonality or shared values between yourself and the other person. Find points of agreement or mutual understanding, even if your perspectives differ. Identifying common ground helps bridge gaps and establishes a foundation for empathy and constructive dialogue.

  • Educate yourself: If you struggle to empathize with specific perspectives or experiences, take the initiative to educate yourself. Read books, articles, or personal narratives that explore diverse viewpoints and experiences. Engage in conversations with people who have different backgrounds or beliefs. Increasing your knowledge and exposure can broaden your empathy and enable you to connect with a broader range of individuals.

Remember, cultivating empathy is an ongoing process that requires practice and openness. You can develop and enhance your empathy by actively listening, putting yourself in others' shoes, asking open-ended questions, reflecting on shared humanity, practicing mindfulness, seeking common ground, and educating yourself. Over time, empathy will become more natural, enabling you to approach uncomfortable conversations with a greater understanding and a deeper connection to those around you.

Concluding an uncomfortable conversation: key considerations

Knowing how to handle uncomfortable conversations includes knowing how to end them. All productive uncomfortable conversations should have a clear endpoint. Here are some essential considerations for concluding such discussions:

  • Maintain positivity and relevance: Strive to end the conversation on a positive note, focusing on relevant aspects. Avoid dwelling on negative aspects or assigning blame. Emphasize mutual growth and understanding. It is okay to pause an uncomfortable conversation and restart it later.
  • Embrace "I statements": A reminder. Express your thoughts and emotions using an "I statement" rather than accusatory language. This approach encourages personal accountability and reduces defensiveness.
  • Embrace the learning process: Not all uncomfortable conversations will go perfectly. It's important to be kind to yourself and remember that these discussions require courage. Each conversation, regardless of its outcome, offers personal growth and improvement opportunities.

Handling uncomfortable conversations is a vital skill that contributes to our mental well-being and strengthens our relationships. By following the tips outlined in this article, you can confidently navigate these conversations, fostering understanding, growth, and healthier connections with others. Embrace the learning process and recognize the positive impact these conversations can have on your personal and emotional development.

Article by
Brendan McDonald

Brendan McDonald, the author of "How to handle uncomfortable conversations," is a former humanitarian aid worker who has ventured into challenging territories such as Kosovo, North Korea, Sri Lanka, Libya, Jordan, and Iraq. He has gained extensive experience in information management, staff wellness, and communications. In early 2014, after dedicating a year to the Syria Crisis, Brendan experienced burnout and was subsequently diagnosed with clinical depression. Brendan lives with several medical conditions, including chronic myeloid leukemia (CML), peripheral neuropathy, and bicuspid aortic valve disease (BAVD)