How to Have Difficult Conversations

I still remember the first time I got negative feedback on my work. The feedback was given from a trusted mentor-type figure. She has taught me so much, saw my growth firsthand, and went above and beyond to support me personally and professionally. I saw her as my champion until my manager, surprisingly, told me otherwise.

I was devastated. I felt so betrayed that I wrapped up work early, went home, and lay on the couch to watch Friends. Later that week, I counseled a few mentors and realized that part of my disappointment may come from hearing someone doubt me for the first time in my life.

I was shocked at how naive I was. Then, I told myself, “It’s time to learn about receiving and giving critical feedback.”

A year later, I was on the other end of the conversation.

Earlier this week, I decided to share a piece of critical feedback with my team member. I am going to reserve the details for my team, but the main challenge is that our fundamental values are at odds.

My intuition told me something was off early on, but I convinced myself to be more patient and give some chances. Unfortunately, we both realized that the value gap is not going away anytime and officially ended the apprenticeship today.

Crucial conversations are hard.

This is my first time letting go of someone on my team, so I consulted my leadership coach for advice. He helped me refine the message with clarity and specificity. In addition, he helped me develop a short and concise note to help my team understand what they need to know.

Here’s how you can do more hard conversations in daily life.

I encourage you to share feelings and have honest conversations with your partner, co-founder, and the team every week.

Having tough feedback is hard, but the feedback is meant to help you grow and get better. This tough feedback has exponentially accelerated my growth and gave me unique insights into life.