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Mastering Tough Conversations: Strategies for Leaders to Navigate Conflicts and Build Trust

Updated: Mar 20, 2023

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As a leader, one of the most challenging aspects of managing a team is having tough conversations. Whether it's addressing poor performance, delivering negative feedback, or handling interpersonal conflicts, these conversations can be emotionally charged and difficult to navigate. However, avoiding these conversations can lead to further problems and a toxic work environment.

As a Supervisor, I once had a tough conversation with one of my subordinates, let's call him Airman Smith. Smith was a great guy, but he had a tendency to let his personal life interfere with his work. He was frequently late, his uniform was always a mess, and he often forgot important details.

I knew I needed to address these issues with Smith, but I kept putting it off. I didn't want to hurt his feelings or make things awkward between us. Plus, I didn't want to be seen as the "bad guy" by Smith or the rest of the team.

One day, we were preparing for a high-profile inspection when Smith showed up late to work wearing his civilian clothes instead of his uniform. I was livid. I knew I couldn't let this slide any longer.

I took Smith aside and explained to him how his behavior was affecting the entire team and our mission. To my surprise, Smith started to laugh. I was taken aback. This wasn't the reaction I was expecting.

He explained that he had been up all night because his wife had gone into labor. He hadn't had time to change into his uniform, but he didn't want to miss the inspection. I felt like such a fool. I had been so focused on Smith's previous mistakes that I hadn't taken the time to consider what might be going on in his personal life.

At that moment, I realized how important it was to have those tough conversations but to also approach them with empathy and understanding. Avoiding them altogether had only made the situation worse, and it had created a toxic work environment for everyone involved.

From that day forward, I made a promise to myself to always take a step back and consider the bigger picture before jumping to conclusions. And, as a bonus, I also learned to always have a spare uniform on hand just in case.


In this blog, we will explore three strategies I have found that have helped me as a leader to have tough conversations in the workplace.

Emotional Intelligence

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Emotional intelligence is the ability to recognize and manage our own emotions and those of others. It's a crucial skill for leaders to have when navigating tough conversations. Studies show that leaders with high emotional intelligence are more effective in managing conflict and building trust with their team members.

One way to develop emotional intelligence is by practicing empathy. Empathy is the ability to understand and share the feelings of others. When having a tough conversation, take the time to listen actively to the other person's perspective and acknowledge their emotions. Use "I" statements to express how you feel, and avoid using accusatory language. This will help create a safe and supportive environment for the conversation.

Another way to develop emotional intelligence is by practicing self-awareness. Before having a tough conversation, take a moment to reflect on your own emotions and biases. It's essential to approach the conversation with a clear and calm mindset. Take deep breaths, visualize the conversation going well, and focus on the positive outcome.


Communication Skills

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Effective communication is key to having tough conversations in the workplace. Studies show that leaders who communicate clearly and respectfully are more likely to be successful in addressing sensitive issues.

One communication strategy is the "sandwich" approach. This involves starting the conversation with positive feedback, addressing the issue at hand, and ending with another positive statement. For example, "I appreciate your hard work on this project, but I noticed some errors in your report. Let's work together to fix them, and I'm confident we can create a better outcome."

Another communication strategy is active listening. This involves fully focusing on the other person's perspective and avoiding distractions. Use open-ended questions to encourage dialogue and avoid interrupting the other person. Reflect on what the person is saying and summarize their key points to show that you understand their perspective.


Conflict Resolution

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Conflict is inevitable in the workplace, but how you handle it can make all the difference. Studies show that leaders who use collaborative conflict resolution strategies are more effective in resolving conflicts and creating a positive work environment.

One conflict resolution strategy is to identify common goals. Focus on finding shared interests and values between team members to find a mutually beneficial outcome. For example, if two team members are in conflict over a project timeline, focus on the shared goal of completing the project successfully and finding a solution that works for both parties.

Another conflict resolution strategy is to encourage dialogue. This involves creating a safe and supportive environment for team members to express their perspectives and concerns. Use active listening skills and avoid jumping to conclusions or making assumptions.

Encourage team members to brainstorm solutions together and find a mutually beneficial outcome.


Having tough conversations is never easy, but with the right skills and strategies, it can be a positive and productive experience. As a leader, it's essential to develop emotional intelligence, communication skills, and conflict-resolution strategies to navigate these conversations effectively.

Here's a checklist to help you have tough conversations in the workplace:

  1. Develop emotional intelligence by practicing empathy and self-awareness.

  2. Use communication strategies such as the "sandwich" approach and active listening.

  3. Use collaborative conflict resolution strategies by identifying common goals and encouraging dialogue.

  4. Approach tough conversations with a positive and productive mindset.

  5. Remember to be respectful, clear, and honest during the conversation.

By using this strategy you are more likely to arrive at the outcome you desire when initiating these conversations. Let me know your thoughts and approaches below or on social media!


"Until Next Time, Climb Together!"


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