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7 Strategies for Mastering Difficult Conversations

communication leadership
Two women having a difficult conversation at work


By John Millen

In the workplace, we all encounter difficult conversations from time to time. 

Whether it's addressing conflicts with a colleague, giving constructive feedback, or negotiating a delicate issue with your boss, these interactions can be emotionally charged and challenging to navigate.

That’s why learning how to handle difficult conversations with grace and professionalism is an essential skill for any successful professional.

One of my clients and friends, let’s call her Taylor, recently had to tell her team that they would need to be in the office at least three days a week, even though a couple of them had moved away from the office. It was a company mandate that Taylor didn’t agree with but she had to implement for herself and her team.

I gave Taylor some informal coaching and sent her the tips below. It was still a messy outcome but Taylor said she felt she handled the situation as well as she could. Taylor also felt like she grew as a leader and future challenges will be easier to handle.  

With this in mind, here are seven effective strategies to help you master the art of managing difficult conversations. You’ll notice that these tips can help at home as well as at work:

1. Prepare yourself emotionally

Before entering into a difficult conversation, it’s crucial to take a moment to ground yourself emotionally. Acknowledge your feelings and any negative emotions that might arise, such as fear, anger, or anxiety. 

Take a few deep breaths to calm yourself and maintain a composed demeanor. It is essential to approach the conversation with a clear and focused mindset rather than allowing your emotions to take control.

2. Choose the right time and place

Timing and environment can significantly impact the outcome of a difficult conversation. Select a private and neutral space where you’ll both feel comfortable expressing yourselves openly. If possible talk face to face but of course you may have to make the most of a virtual call. 

Avoid approaching sensitive topics when tensions are already high or when either of you is stressed or preoccupied with other tasks. Instead, opt for a time when both of you can devote your full attention to the conversation.

3. Listen actively

Listening is one of the most critical skills when dealing with difficult conversations. Allow the other person to speak without interrupting, and give them your full attention. Active listening means not only hearing the words but also understanding the underlying emotions and concerns. 

Demonstrate empathy and validation, even if you disagree with their perspective. Acknowledge their feelings and rephrase their statements to ensure mutual understanding.

4. Use "I" statements

When expressing your thoughts or concerns, use "I" statements instead of "You" statements. For example, say, "I feel uncomfortable when..." rather than "You always make me feel..." 

This approach takes away the perception of blame and helps the other person see the issue from your perspective without becoming defensive. "I" statements encourage open dialogue and foster a more collaborative atmosphere.

5. Stay constructive and solution-oriented

Approach the conversation with the intention of finding solutions rather than dwelling on the problem itself. Be specific about the issues you want to address and focus on actionable steps to resolve them. 

Avoid personal attacks and remain respectful throughout the conversation. Aim to build bridges and create a positive outcome, even in the face of disagreement.

6. Be mindful of non-verbal communication

Remember that communication is not only verbal but also non-verbal. Pay attention to your body language and facial expressions as well as the other person's cues. Maintain eye contact to show you are engaged. 

Also, use open body language to demonstrate receptivity, and avoid crossing your arms or displaying signs of impatience. Similarly, watch for signs of discomfort in the other person and adjust your approach accordingly.

7. Be willing to compromise

In some situations, finding a middle ground or compromise is the best way forward. Be open to adjusting your viewpoint and be willing to meet the other person halfway. 

Compromise demonstrates your flexibility and willingness to work collaboratively to reach a resolution that benefits both parties.

Difficult conversations are an inevitable aspect of professional life, but with the right approach, they can become opportunities for growth and improved relationships.

Embrace these strategies, and you'll find yourself navigating tricky conversations with confidence and skill, ultimately enhancing your professional success and fostering a more harmonious work environment.

It will feel uncomfortable at first, but with practice you can master the art of handling difficult conversations.

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John Millen

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