You're Not Going to Do That Again, Are You?

Early in my career, at Steals.com, I shipped a bug to production. It charged every customer 25 cents. Did not matter if their cart was ten dollars or five hundred. Twenty-five cents.

I still do not know how it got to production.

What I did next is the part that made my career. I owned it. We fixed it fast. Then I walked into the CEO's office and told him what happened, fully expecting to be fired. The CEO was Rett Clevenger.

He looked at me and said one sentence.

"Well, you're not going to do that again, are you?"

That was it. No firing. No write-up. Just a question that trusted me to be the person who learned from it.

He was right. I never made that mistake again. That is what a mistake like that does to you, when you own it. You learn it in your bones. From then on I double checked everything. Every charge, every deploy, every number. You stay on top of it because you remember exactly what it felt like to get it wrong.

But I took more than the lesson about the bug. I took his way of handling people.

Years later, as a Chief Technology Officer (CTO) running my own teams, that sentence became my template. When someone on my team shipped a bad bug, and they owned it fast, I gave them the same grace he gave me. Own it fast. Fix it. Learn it once.

Fear makes engineers hide mistakes. Grace makes them report them early, when they are still small.

I have carried that one sentence for twenty years. It built more good engineers than any code review I ever ran.