How Asking Basic Questions is a Superpower

Jeff Keltner
3 min readSep 15, 2020

I was having a conversation with a colleague recently and I gave them some advice that I thought might be useful more broadly — ask the dumb question. I honestly think this is one of the best superpowers you can have — and luckily it requires no skill except for a bit of confidence and a lack of ego.

Have you ever been in a meeting and heard something said and just not understood? And have you looked around the room and believed that everyone else knew what was going on? And did you decide not to ask your question because you didn’t want to look like you didn’t know what was going on? I most certainly have — and not asking those questions is one of my biggest regrets.

I took far too long to learn this lesson. I have been fortunate in my career to have tremendous opportunities which sometimes left my in jobs where I’ve been “ punching above my weight class “. However, that also meant that sometimes I was younger or less experienced than other people in the room. And when a topic came up that I didn’t understand, I would be worried that I didn’t know something that I was supposed to know. So I wouldn’t ask the question.

My current role at Upstart helped me to break out of this habit, for two reasons. First, I was entering a new industry in finance and lending and it felt safe not to know things which might even be considered basic. This helped free me of my worry that others would think I was in over my head if I asked a “simple” question — I was just new to the space! Second was our Co-Founder, Paul Gu. Paul always asks the question. Sometimes I would be thinking “I don’t understand that, but I assume Paul does” and then Paul would ask the question on my mind. Paul is incredibly intelligent, but he is willing to ask even simple questions. And because of that, he learns a lot.

Once I started being willing to ask the “dumb” questions, I was amazed at how useful a skill it was. I learned quite a bit very quickly and people started to think I knew a lot about areas that I had only learned about by asking. And I can’t count the number of times someone would come up to me after a meeting and say “I’m so glad you asked that, I was wondering the same thing.” Because quite often when you don’t understand something, you’re not the only one. It’s just that no one is willing to ask the question because they figure everyone else already understands!

Ultimately, success will depend on really understanding things. I believe the most successful people will be those who have a solid grounding in a wide range of topics and can apply that knowledge to new situations. There is probably no better way to build those skills, than by asking the questions whenever you have them!

Originally published at https://jeffkeltner.com on September 15, 2020.

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Jeff Keltner

father, husband, entrepreneur, geek. love fintech, edtech and startups. ex@Upstart ex-@google, ex-@ibm. studied computer engineering @stanford