Here's the toughest job interview question I have ever been asked.
Question: Tell me about a moral decision you faced where you came down on the wrong side.
Answer: (In real life, I paused here for a pretty long time.)
Here's the issue, though. I'll have to leave out names, to protect the innocent (and guilty).
We were working with company X, and they asked us to build a new shopping cart for their website. The client told us he really liked the cart on one of their competitors' sites. I passed the request and information along to one of our contractors.
The contractor gave a fair estimate, and we gave the green light. Everything was going swimmingly.
Then the contractor asked me for clarification -- which site was it, exactly, that the client liked? After we spoke, I realized that our contractor was probably just going to copy the code from that cart.
My failure: I let it slide. The contract was going well, it was profitable, it probably wasn't a big problem... So I just let it go. I forgot all about it, and didn't even bother looking at the code once the cart was delivered.
The consequence: Not two weeks after launching the new feature, our client got an unfriendly letter from the lawyers of their competitor. The cease-and-desist was followed with the threat of a lawsuit and some frighteningly specific damage claims.
Our client called me with the news, and I set about repenting. Which repentance involved immediately redesigning the offending cart myself -- staying late, shuffling other priorities, etc. -- for the next two days.
I also put together a defense of what we had originally produced, since it was largely based on open-source and other freely available code. (The competitor had made liberal use of free code, which he couldn't really claim to own.)
The end: The competitor dropped the matter, once he saw our new cart and the document we had prepared. We were lucky. He was not interested in pursuing a long, expensive legal battle. It could have been far worse.
I learned an important lesson from the whole experience. When I'm in charge of a project, I have to take responsibility for the actions of the entire team. It's not enough just to make sure that I don't personally do anything wrong; I have to make sure that everyone does what's right.