Yesterday, I did something I’d been dreading for months: I let go of a teammate who had been with Cver AI for a year and a half.
She was our designer. When she started, her work was exceptional—executive-minded, innovative, fresh thinking for every problem we faced. Her designs were clean and polished, the kind of work I would have created if I’d taken my UI design classes seriously. Her approach resonated with how I think, and I genuinely valued what she brought to the table.
This isn’t about throwing shade. She’s a talented designer. But somewhere along the way, something shifted.
In recent months, she gradually disconnected from the product we were building. I can’t place all the blame on her—yes, she had a commitment, and yes, she could have walked away instead of letting things deteriorate for both of us. But my managerial skills deserve scrutiny too. As a founder, I failed to maintain that connection. I didn’t know how to reach her, to reignite her energy, to help her see the vision we were working toward. This person had shares in Cver AI. There should have been ownership, commitment. But that feeling had evaporated.
I stayed quiet. I forgave shortcomings in execution, delivery, time management, and self-direction. Until I couldn’t anymore. Then I’d complain and express my displeasure. Things would improve briefly. Then the pattern would repeat. Again and again and again.
I knew I couldn’t continue like this. There’s something about a new year that crystallizes clarity—you realize what you can’t carry forward anymore. This was one of those things. I kept wishing circumstances were different. Maybe if we’d been working together in an office, things would have turned out differently. Perhaps the lack of in-person connection contributed to her disengagement from the work. I’ll never know for sure.
When I finally decided to end our agreement, I prepared thoroughly for several days. I scheduled a meeting. She said no problem. Minutes before the call, alone in the virtual meeting room, my heart was pounding. She joined. I started mumbling, stumbling through the words. I led with the termination—those were the very first lines I managed to get out. I tried to explain the reasons, though I didn’t go deep. I told her I’d send a document with the full explanation afterward.
Her response? “Okay.”
One word. That’s it. Days of rehearsal. Minutes of heart-pounding anxiety. One word.
I learned something crucial: I’d been terrified of this confrontation for so long, building it up in my mind. The other person simply received it with an “Okay” and moved on.
Moving forward, I’m committing to being more upfront with any team member whose work quality or frequency isn’t meeting expectations. I’ll give clear warnings. I’ll try to prevent the mistakes I made this time—the silence, the sporadic complaints, the cycle of frustration. And if things still don’t improve? I won’t overthink it. I won’t rehearse for days. I’ll confront it directly and do what needs to be done.
Genuinely, I’m thankful for what Cver AI is teaching me. It’s pushing me to become a leader I didn’t think I could be. I’m still learning—hell, I don’t know where I’ll be in one or two years—but I’m certain I’ll be much better at managing people, tasks, delivery, and everything else that comes with this role.
The hard conversations don’t get easier. But avoiding them makes everything harder.