I had assumed that feedback would be hardest with difficult relationships. The ones where trust was thin or tension was present. Those conversations would obviously require more care.
What I didn’t anticipate was the conversation I needed to have with someone I genuinely liked and respected. Someone who was talented, well-intentioned, and had been part of building something real. Someone whose strengths I admired and whose efforts I had watched up close.
Telling that person something hard was harder than almost anything I’ve done as a leader. Not because the feedback wasn’t true. Because the relationship made me want to protect them from it.
That instinct, to protect the people we care about from discomfort, is not kindness. It is a form of withholding. It says, quietly: I don’t trust you to handle this. I value our ease over your growth.
The most caring thing I could have done was to have that conversation earlier, more specifically, with more trust in their capacity to receive it.
Feedback delivered with love is still feedback. Genuine care for someone includes being honest with them. Especially when it’s hard. Especially when you like them.