Why You Should Ask Stupid Questions: How to Look and Act Like the Smartest Person in the Room

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.


  1. You have a right to your feelings.
  2. You have a right to set boundaries to feel safe.
  3. Anyone who attempts to revoke your right to your feelings or to set boundaries is someone scary.

Now, it may just be that the person is clueless, but lack of empathy on this is a danger signal that you cannot ignore.

Predators and bullies will try to negate your feelings and push you into situations where you don’t feel safe. The only defense you have is to own your feelings and to own your boundaries.

A predator will flatter you to let your guard down. A predator will cast you as a bitch if you don’t do what they are asking.

You know how this plays out in a bar: “I’m just trying to buy you a drink! You don’t want me to buy you a drink? Why are you being such a bitch?” No one has the right to argue with you when you say no. This is the clarion call of the predator. Hell, yes, I absolutely am such a bitch. I do not want your drink. I said so clearly. Now buzz off.

But a bar is an easy situation. What happens when this is your boss? “Can’t we just have a cup of coffee and talk this over just the two of us?” If you don’t feel safe, you have every right to request that a neutral third party is present. But for many it’s harder to set this boundary.

I think I am lucky that I do not find either of these situations ambiguous. Trigger my lack of trust, and I will take action to protect myself. Even so, I still get the arguments.

On this count, I am flabbergasted.

I am shocked by how many people are unable to see or unaware that when a boundary like this is set, that if you wish to reestablish trust, the only way to go about it is to be very very respectful of the boundary. No sneaking around it, no flattering your way out of it, just respect and forthrightness.

This is one of those topics that makes me see red.

If there is one book you should read on this topic, it is The Gift of Fear by Gavin de Becker.

Believe that they are all worthwhile

I wrote this after a conversation with a colleague that bothered me. This was probably a year or more ago. I never sent this. Honestly, I don’t think it would have been well-received. I ran across it again today. Rather than throw it out, here it is.

I think this goes well in partnership with this other blog post: http://smallpondscience.com/2013/04/23/student-quality/

Hi Colleague,

I couldn’t help thinking further on our conversation from yesterday. What I heard, and perhaps I misunderstood, was a lot of categorizing students into boxes. I think it is easy to put human beings into neat little boxes, especially when we are frustrated. These students are good. These students are bad, and they aren’t worth my effort.

If we can’t walk into a classroom with the belief that they are all good, all worthy, all human, then I think we’ve failed our first and most important job as instructors. Not every student is great at math. That doesn’t mean that they aren’t worthy human beings. And it often doesn’t even mean that they aren’t trying, even though we all know that some aren’t.

They are all incredibly young, and their mission here is to figure out what it is they have to give the world. Maybe it’s math. Maybe it’s not. But I have something important to teach them whether it’s math or it’s not. Sometimes it is how to try harder. Sometimes it is how to study smarter. Sometimes it is no matter what their struggles with math are, that they are valuable human beings. Sometimes it is that actions have consequences.

If I go into it with the true belief deep in my heart that they are all worthwhile, I better open the door for them to learn, whether they are gifted and hardworking or not. If I walk in with the attitude that many (or all) are worthless, then I shut the door for the learning; my attitude itself discourages my students’ best effort.

That doesn’t mean that I don’t find some students absolutely maddening and infuriating and lazy. I’m teaching a 300 person business mathematics class; that leaves me ample opportunity to get angry and frustrated. But I sincerely hope that even if I get angry and frustrated, that I still see them as worthy and capable of doing better than whatever it is they just showed me.

From our conversation yesterday, this is not what I was hearing. Maybe I misunderstood. Maybe you were having a bad day. But I hope that this is what you try to bring to your students — all of them — because I think that they and you are worth the effort.

I was terrified of that business mathematics class; of it being an unending battle in a hostile, math-hating environment. Like I said, there are students that irritate me, but overall, I would say, the concern and warmth I have brought to them has been returned by them. And that is a gift for me and for them.


Dr. Jinx


The question for you, my dear and knowledgeable friends and supporters, is if I would like the position although only at an appropriate rate of pay (and, hopefully, rank), does sending this help or at least not hurt the situation? I will refuse any offer that is below my salary for 2013.

Truth is my partner is going to have to do the real negotiating for me. The one power I have is to say no.

Thoughtful comments welcome and encouraged. My emotions on this are still strong.

Backstory. I didn’t put all the details of the conversation in. The chair was bragging at one point about forcing other women to take a pay cut to come to his institution. Then he argues that to do anything else to me would be unfair. There are other damning and insulting details. It was outrageous and grossly out of the usual rules of professional interaction.

Dear Chair and Protege,

I have to admit, I am still reflecting on our conversation Friday at wondering if that was an early April Fool’s Day joke that I just didn’t find funny.

With the exception of that conversation with the two of you, I very much enjoyed talking to the other people I met in the department, and in many ways I think the position would be a good match.

However, I am sure you understand that I cannot consider accepting an offer that is not at market value for my level of experience and qualifications. Given my current salary at Texas A&M, this would be between <$12,000 and $15,000 above the salary we discussed> per nine month appointment.

I am also concerned with the rank appointment. It is standard practice in faculty hires to keep employees at the same rank or even to hire them at a higher rank than they had in their previous institution. Given the tone of our conversation, I would like to speak with the dean or someone in higher authority about this.

I hope we can come to terms on this matter.