How to Have Difficult Conversations in Leadership

As leaders, we often encounter tough conversations—whether addressing underperformance or handling dissatisfied customers. These moments come with the territory, shaping us and the teams we lead.

Learning to handle these conversations will make you a great leader and get both parties the best results.

Here are some simple tips I use when going into a difficult conversation:

🗣️ Start of a Better Relationship: Approach with an open mind and curiosity to earn trust and respect. People want to be heard and seen, so avoid confrontational or dismissive behaviors.

💡 It’s Not Personal: I found this strategy especially true when it came to difficult conversations with unhappy patients. As the CEO of the health center, if they made it to me, they were very unhappy. I constantly reminded myself before the conversation that it wasn't personal; they just had a problem they needed help solving, and they didn't feel like their problem got solved. I would approach the conversation with curiosity rather than defensiveness, and nine times out of 10, that person would calm down and let me work through their problem with them.

🤔 Ask yourself a few questions before going into the conversation:

👉Are you willing to forgive this person?

👉In the grand scheme of things, does this really matter?

👉Is there a fair resolution that will meet both of your needs?

👉Do you have the facts, or are you making assumptions?

👉Are you open to the other person’s perspective and potential solutions?

Getting into the right mindset before the conversation will ensure a positive outcome. You must acknowledge your opinions and emotional state before the conversation begins.

🧘 Learn how to de-escalate: Nothing gets accomplished in a heated argument. Early in my career, I learned that staying calm (even if I was yelling in my head!) helped the other person stay calm, making the conversation productive. Use de-escalation tactics to keep things relaxed. If the other person can't remain calm, speak without yelling, or address the issue, be willing to end the conversation and reschedule. Sometimes, people need a cooling-off period before having a rational discussion.

A difficult conversation can be a positive and productive way to improve a relationship if handled well. Keep it a conversation, not a confrontation, and you'll see how far it can go to build trust and improve performance with the people you lead.