Having difficult conversations with difficult people

by Christie on November 5, 2025

By Christie Mann, 889’s Resident Leadership Coach

We all have difficult people in our lives whether it is a boss, a colleague, a parent, a sibling, a friend or maybe even it’s ourselves. Having difficult conversations with difficult people is simply apart of life.

So how do you have a difficult conversation so that it doesn’t really feel that difficult?

My simple (yet not necessarily easy to do) answer is; courage, authenticity and compassion.

The more that we practice showing up this way, the less difficulty we experience (period), in conversations and in life.

In my practice I work with many leaders to prepare them for these “difficult conversations”. What I have observed is that people simply get in their own way and make the pending conversation seem a lot more “difficult” then it needs to be. I see people struggle with being completely honest with another person; afraid to hurt someone’s feelings or get in a confrontation. We project our own fears onto the situation and the other person and in some cases choose to suffer and not say anything at all.

What I have experienced through practicing myself and witnessing others be courageous, authentic, compassionate and simply saying what needs to be said, is that it actually deepens the connection between the two people. It instills a sense of mutual-respect and understanding in that relationship and helps both people to grow, develop and become better people.

Practice makes perfect. If you’re not accustomed to having the difficult conversation then challenge yourself, build this leadership and communication muscle.

Be courageous. Be your best self. Live from your heart. And don’t be difficult.

Care to share?

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