The Day I Became the World’s Worst Supervisor

Some years ago, I supervised a team member who had been with the organization for over a decade. When he started, the company was small. But as we grew, the job grew too — and the pace eventually outgrew his capacity.

By the time I became his supervisor, there were quiet conversations about letting him go.

I didn’t want to do that. I valued his history with the organization and wanted to give him every possible chance to succeed.

So I did what many supervisors do when we don’t want to hurt someone: I started mentoring him slowly.

Every Monday morning, we’d meet to review progress. I’d offer feedback, set new goals, and try to encourage improvement one small step at a time.

My goal was to help him rise. But in truth, I was avoiding reality.

He was unmotivated — maybe even a little lazy — and I was too soft. I thought small corrections would help him improve without overwhelming him.

Then one day, he said something that stopped me cold:

“Anthony, it seems like every time I fix what you ask me to fix… you move the goalpost. I’m never doing a good job.”

He was right. My intentions were good, but my leadership was poor.

By trying to protect him from hard truth, I had made things worse. I was inconsistent, unclear, and afraid to have a direct conversation.

That’s when I learned one of the hardest leadership lessons of my career:

💡 To be clear is to be kind. 💡 To be unclear is to be unkind.

I wasn’t kind. I was cautious. And my lack of clarity hurt both him and the organization.

Eventually, I apologized. We finally had the difficult, honest conversation we should have had months earlier. It wasn’t easy — but it was the right thing to do.

💭 What I Learned

• Compassion without clarity is cruelty disguised as kindness.

• Avoiding conflict doesn’t save relationships; it erodes trust.

• Supervisors don’t fail because they don’t care — they fail because they care too much to be clear.

If you supervise others, remember: Don’t confuse patience with progress. The kindest thing you can do for your team is to define what winning looks like and hold them accountable to it.

That’s the moment I became the World’s Worst Supervisor — and the moment I began becoming a better one.

What about you? Have you ever avoided a difficult conversation that you wish you’d had sooner? Drop your thoughts below — your honesty might help another supervisor grow.