There were times in my career as a manager when I avoided difficult conversations, none of which I am proud of. I can still remember specific people who were falling behind with expectations, and I did not step in soon enough. Looking back, I know it was no one’s responsibility but mine as their manager to be clear and honest. Because of my own fear of conflict at the time, I failed them. Those missed opportunities for clarity still weigh on me, because unspoken issues rarely resolve themselves.
Through my own learning and experience, I have learned that difficult conversations can become turning points in relationships if handled with honesty and care. Here are four lessons that continue to shape how I approach them.
Look inward before looking outward.
We often begin by putting blame on the other person. The truth is, starting with ourselves is far more powerful. Considering how we show up helps us move into the conversation as a support, not just as a critic.
Recognize differences in strengths.
Sometimes our frustration comes not from someone doing something “wrong” but from them doing it differently. Understanding where we differ in our strengths can soften our perspective. That awareness keeps us humble and reminds us that our way is not the only way.
Clear is kind. Unclear is unkind.
Brené Brown’s words ring true in every workplace. Avoiding honesty may feel easier in the moment, but it leaves others in the dark and robs them of the chance to grow. Harboring unspoken frustration is not kindness. It is avoidance.
Clarity and honesty build stronger trust.
Relationships do not crumble when honesty enters the room. More often, they strengthen. People want to know where they stand. When we approach tough conversations with openness, we create the possibility of deeper trust and mutual respect.
Practical Tools for Having Difficult Conversations
It is one thing to know why difficult conversations matter, and another to know how to begin them. Here are some practical tools to guide you:
Start with yourself
- “I realize I may not have been as clear as I should have been about expectations, and I’d like to revisit them with you.”
- “I want to check in with you because I’ve noticed some challenges, and I want to understand how I can support you.”
Name your intent
- “This might feel like a tough conversation, but my goal is to strengthen our work together.”
- “I want to be honest with you because I value our relationship and your contributions.”
Acknowledge differences in perspective
- “I see this situation through my lens, but I’d like to hear how you see it.”
- “We may approach things differently, and I want to understand how your strengths play into this.”
Point toward growth
- “Here’s what I’d like to see moving forward, and I’d love to hear your thoughts on what support would help you get there.”
- “What do you need from me to be successful?”
Bringing It All Together
I wish I could go back and actually have some of the conversations I avoided. I cannot change those moments, but I can use them as reminders of how important it is to lead with honesty, humility, and courage. Difficult conversations will never feel easy, but they do not have to be destructive. And when we have them, we create the possibility of stronger relationships and healthier workplaces.
The next time you feel the weight of a tough conversation, see it as an opportunity. With preparation, care, and courage, what feels uncomfortable at first may become the spark that strengthens trust, builds understanding, and moves everyone forward.
