I’ve got a little story for you, so sit right down and make yourself comfortable.

A while back, I worked as a software developer for a fairly small but very profitable company. The owner of the company is one of those geniuses. He was interested in computers back when desktop computers first became available. He started playing with the idea that they could be used to do statistics and mathematics. Eventually the program he wrote to do that was paying his bills. In the present, that software package has since likely made him many millions of dollars. At a guess? Tens of millions of dollars.

I remember one day, we were sitting in a meeting discussing the future of documentation for this product. Our documentation was (at the time) printed in the dead tree edition: a set of about 12 books or manuals. Online documentation, it was becoming clear, was the way things would be in the future. And the standard way to do documents like that is PDFs.

At some point in the conversation, my boss, the genius, the owner of the company, the man who had been in computing since desktop computers first became available, spit out the question, “What does PDF stand for?”

PDF, very simply, stands for Portable Document Format.

It might not strike you, Dear Reader, that this is a stupid question, but at that time in that context, PDFs had been around for a decade or so. Surely, anyone who was anyone in commercial software development would know what this is. Especially someone who had seen these evolve over the past decade. For goodness sake, he had been into computers when the first PCs came out! How could he not know what PDFs are?

Apparently he didn’t know what PDF meant.

I sat there in my chair thinking, very rudely, to myself, “That is the stupidest damn question I have ever heard in my entire life.”

You know what happened next?

Someone, maybe even me, answered him. I don’t remember who.

The conversation continued as if nothing unusual had happened.

No one ever mentioned it to him again. I certainly didn’t let loose with my opinion.

But I was keen to observe and think about the dynamic of what I had just seen.

I came to a few conclusions.

1. If you are the smartest person in the room, you can ask whatever stupid question you want, and someone will give you an answer.
2. So rather than worrying about whether or not a question is stupid, maybe you should act like you are the smartest person in the room, and just ask it.

I’ve put this into practice. If I have a question, even if I have that little nagging doubt in my mind about whether it is a stupid question, I ask it. What have I found out from this?

1. Almost always, others have the same questions that I do.
2. I get more respect from asking questions than I do from keeping silent.
3. People tend to think I’m smarter when I ask questions than when I don’t.

Dear Reader, I conclude with my advice to you. Act like the smartest person in the room. Have courage, and ask your stupid questions.