The Power of "Dumb" Questions

Fresh out of Stanford with a psychology degree, I was focused on clinical work. But as a foreigner in the U.S., hospitals weren’t hiring. I’d followed every rule, checked every box. But still, no job.

Meanwhile, an acquaintance kept pestering me to help her nonprofit. One night, stressed and frustrated, I blurted out, “Do you have a job for me?” It felt rude. But I thought, “Why not ask?”

She lit up. “We’re hiring!”

It was the dot-com boom, and I started Monday.

The office had a bedroom and Subway sandwiches on repeat. I had no background in software and felt completely out of place. But being an outsider has its advantages, especially if you’re willing to ask questions.

We were building what became 𝗬𝗮𝗵𝗼𝗼! 𝗠𝗮𝗶𝗹, the first web-based email to support attachments. The engineers called them “Part 2 of 2.” I thought that was confusing and asked if we could change the name. They refused until I asked Kimmy, our beloved receptionist, if “2 of 2” made any sense to her. She had no idea.

Probably to please her, but possibly because they saw my point, we found a better name. Today, every email platform calls them “attachments.”

Sometimes the outsider sees what the experts can’t. Sometimes the “dumb” question is the smartest one.

Now, as a coach and psychologist, I still ask those kinds of questions. I just do it for a living.

Dr Jonathan Marshall