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May 4, 2023 3 Min Read

Conquer Difficult Conversations With Confidence

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Difficult Conversations At Work


Difficult conversations are inevitable in any work environment, yet they remain challenging for many professionals. In fact, a recent study found that over 70% of employees avoid having difficult conversations with their boss, colleagues, or direct reports. This article provides practical steps and effective behaviors to help you navigate these conversations confidently and constructively. 


Adjust your Mindset: Remind yourself that this is just a conversation, not a confrontation. Approach the discussion with a positive outlook, assuming that both parties can reach a mutually beneficial outcome. 

Clarify your Objective: Determine what you want to achieve from the conversation. Be specific about the changes or improvements you hope to see. 

Be Mindful of your Emotions: Recognize your feelings and keep them in check. This will help you communicate more effectively. As the Harvard Business Review suggests, “Take a deep breath and focus on your goal.” Additionally, Coach Manon Rosenboom Alves adds that this is an often overlooked aspect that many of her clients fail to consider. Understanding your emotional state before engaging in a conversation is crucial in maintaining a composed and empathetic demeanor throughout the discussion, taking into account both the conversation itself and its broader context. 



Anticipate their Response: Difficult conversations can evoke stress and defensiveness. Be prepared for your co-worker’s reactions and maintain your composure. 

Ask if it is a Good Time: Ensure your co-worker is mentally and emotionally ready to engage in the conversation. If the timing is off, reschedule for a more suitable moment. 

Be Empathetic: Acknowledge that the discussion may be difficult for both parties. Show understanding and actively listen to your co-worker’s perspective. 

Be Prepared to Pause or Complete the Discussion at a Later Time: If emotions run high or the conversation becomes unproductive, suggest taking a break and reconvening when both parties have had time to reflect. 

Be Specific: Use “I” statements and focus on your observations, rather than making assumptions about your co-worker’s intentions. As Forbes recommends, “Describe the specific behavior or situation that is causing concern and explain its impact.” 

Give Them Control Over the Next Steps: Instead of making declarations, ask open-ended questions to involve your co-worker in the problem-solving process. 


Summarize & Follow-up 

Resist the Urge to Disengage: Difficult conversations can be emotionally draining, but it’s essential to remain present and focused until the end. 

Be Calm and Patient: Paraphrase what has been said and agreed upon to ensure clarity and understanding. Ask for agreement or alignment before concluding the conversation. Coach Manon advocates this as an effective way of displaying attentiveness and empathy as a means to conveying the significance of the conversation to you, and your genuine desire to understand their viewpoints accurately. 

Confirm Next Steps: Establish what actions will be taken and set a time for a follow-up conversation to review progress. 



Successfully navigating difficult conversations with co-workers requires preparation, empathy, and effective communication. By following the steps outlined in this article, you can turn challenging discussions into opportunities for growth and improved workplace relationships. To further develop these essential skills, consider reaching out to a coach who can provide personalized guidance and support as you integrate these new behaviors into your professional life, and even help you practice for an upcoming discussion. Remember, mastering difficult conversations is not only possible but can be transformative for your career and personal life. 

Book your session with Manon Rosenboom Alves or another TaskHuman leadership coach today!


Book Coach Manon →


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