How to Handle Difficult Conversations at Work

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Editor’s Note: We’re excited to share this guest post from Annabelle Psychology, a trusted partner whose expertise perfectly complements our quarterly focus on employee wellness and health.

Let’s face it – awkward conversations at work are inevitable. Whether it’s raising a concern, giving feedback, or setting boundaries, these moments often feel uncomfortable and hard to navigate.

Thus, it is unsurprising that many of us actively choose to avoid them altogether. This is echoed in a survey where 7 in 10 employees reported avoiding difficult workplace conversations. Well, what if we told you that these difficult workplace conversations could actually strengthen your relationships and improve your work life? 

In this article, we understand why we avoid difficult conversations, how to shift our mindset around them, and some practical ways to approach them with confidence and care.

Why We Avoid Hard Conversations at Work and Why It Matters?

Avoiding uncomfortable conversations is a very human response, but such conversations are an essential part of life. From an evolutionary psychology perspective, our brains have evolved to detect and avoid threats. While this used to mean avoiding and running from predators, in modern times, emotional threats are included too.

This can include conflict, rejection, or social disapproval. Navigating conflict or challenging situations through conversation can trigger the same stress response (i.e., fight, flight, or freeze) as when we encounter physical danger. Therefore, choosing to avoid such conversations sometimes feels safer, even if it is just temporary. 

Other common emotional reasons for communication avoidance include:

• Anxiety about how others might react
• Worry about damaging relationships or professional reputation
• Concern about being seen as too emotional, aggressive or confrontational
• A previous negative experience with similar conversations
• Lack of confidence or uncertainty about handling the situation
• Discomfort with strong emotions, either our own and/or others’
• Desire to preserve harmony or keep the peace

What Happens When You Don’t Speak Up at Work

Avoiding difficult or uncomfortable workplace conversations could feel like the easiest and safest option. However, over time, it could lead to various negative effects for employees, teams, and the organisation. Here are some of the key impacts:

• Build-up of unresolved issues: Misunderstandings, performance issues, or interpersonal tensions do not just disappear, they grow. This can make future conversations even harder.
• Reduced trust and transparency: When things are left unsaid, feelings of uncertainty, resentment or suspicion may fester which erodes trust and hinders the fostering of an open, collaborative culture.
• Increased stress and anxiety: The emotional toll of unspoken concerns or unresolved conflict can cause chronic stress and negatively impact overall wellbeing.
• Poor team dynamics: Team morale can be affected due to unaddressed tension resulting in gossip, passive-aggressive behaviour, or disengagement.
• Missed opportunities for growth: When conveyed with care, constructive feedback can support personal and professional development. Avoiding these conversations can mean missing chances to learn, improve, or strengthen relationships.

How to Shift Your Mindset Around Difficult Work Conversations

With a small shift in mindset, difficult conversations can be viewed as opportunities for honesty, growth, and stronger working relationships, instead of fear.

Here are some mindset shifts to try:

1.  Confrontation to collaboration: You are not fighting against someone. You are working with them to find understanding. These tough conversations as chances to clarify, repair, and improve communication.
2. Personal to professional: It is not about criticising a person, it is about resolving an issue. When framed with respect, tough feedback can be constructive and solution focused.
3. Awkwardness to honesty: Some discomfort is normal and that does not mean the conversation is wrong. Honest dialogue is sometimes exactly what is stopping progression.
4. Fear to clarity: Instead of worrying about how things might go, focus on the clarity that comes from addressing things directly. Unspoken tension often does more harm to the working relationship than the conversation itself. 
5. Risk to growth: Difficult conversations can feel risky. However, with careful consideration, these conversations can lead to stronger relationships, better collaboration, and personal growth for both parties.

How to Start a Difficult Conversation at Work (Without Causing Drama)

Now that we have explored how to reframe our mindset around difficult conversations, what would it look like in practice? Here is a simple framework to ease into these conversations with confidence and respect:

1. Prepare and Plan
   • Ask yourself what your goals are for the conversation and what it is you want to achieve. Some examples of goals can be to seek clarity, resolution, or to set boundaries.
   • Choose an appropriate time and place. Have the conversation in a private, calm setting when neither party is rushed or overwhelmed.
   • Consider how you and the other person might feel during the conversation.
   • Write out your main points if needed as it can help organise your thoughts.
   • Regulate your emotions using grounding or breathing techniques if you find that you are feeling overwhelmed, anxious, or emotionally charged before the conversation. 
2. Start with Clarity and Respect
   • Open the conversation by sharing your intentions. For example: “I wanted to bring this up because I value our working relationship and want to be honest.”
   • Use “I” statements to express your experience without blame: “I felt overlooked when my input was not acknowledged in the meeting.”
   • Be curious, not accusatory. Invite their perspective on the matter: “Can you help me understand what happened?” vs. “Why did you ignore me?”
3. Stay Engaged with Openness and Care
   • Be open to listening. Provide the other person with your full attention and avoid interrupting, formulating a reply too early or jumping to conclusions. Allow the other person to speak fully before responding.
   • Acknowledge what you hear. Use simple affirmations like “I hear you” or “That sounds difficult” to show empathy without needing to solve anything.
   • Ask open-ended questions to invite dialogue.
   • Use nonverbal cues such as nodding and maintaining eye contact.
   • Keep your tone calm and aim for collaboration, not confrontation.
4. Reflect and Follow-up
   • After the conversation, take a moment to process and reflect. For example, how did the conversation go? How did you feel? What would you do similarly or differently next time?
   • Check in later with the other party, if needed. This helps to foster a positive relationship, ensure follow-through on key decisions or actions, and shows that the conversation was part of a larger goal of stronger teamwork and mutual respect.

Bonus Tools and Tips: 

• Helpful Sentence Starters
  • “This might be a bit hard to talk about, but I think it is important.”
  • “I am not trying to place blame, I just want to understand what happened better.”
  • “I appreciate you listening as I know this is not easy.”
• Calming Strategies When Emotions Rise
  • Breathe intentionally – Slow, steady breaths can help ease physical tension and emotional stress
  • Use grounding techniques – For example, plant both feet on the floor, notice your surroundings, or feel an object in your hand.
  • Label your emotions internally – For example, “I am feeling tense” or “This is uncomfortable but manageable” can help reduce emotional intensity.
  • Silently remind yourself – “I can stay calm. I do not need to have all the answers.”
• If Emotions Escalate
  • Suggest a break without shutting the conversation down – “This feels important. Would it be okay if we took a short break and came back to it later?”
  • Reassure the other person of your intentions
• Post-Conversation Self-Care
  • Give yourself time and grace to decompress after a hard conversation
  • Reach out to a trusted colleague, friend, or family for support if needed

For Managers: How to Support Staff Through Difficult Conversations

• Create a culture where feedback is normal, not feared
• Train teams in communication and conflict skills
• Model open, respectful dialogue yourself

Difficult conversations are never fun. But they’re often the key to better teamwork, trust, and growth. Speak up with care, not perfection. A little honesty goes a long way in creating a workplace where everyone feels heard and respected.