In Praise of Difficult Questions

You know the moment. You’re discussing the work you’ve poured your soul into for the past few weeks and someone asks a question. Normally, that’s no problem because you know your stuff and you have rationale for all of the choices you’ve made. But this is a question that you just hadn’t anticipated. Someone has exposed a hole in your thinking.

For many this is a nightmare scenario. All through life we’re taught that we need to be in control; we need to be on top of things; we need to be… right. What do you do with one of those questions?

I had this experience recently on a large, highly complex project for an application to be used by clerks in the courtroom. After many design iterations I was asked how a clerk would search and filter a certain portion of the data. My response: “Um… I don’t know. They can’t. Why would they need to do that?”

It turns out there was an important scenario we had never investigated. After much discussion we decided that clerks actually needed a couple of simple easy-to-run reports instead of search and filter. But the key to uncovering that was my willingness to say “I don’t know. I missed that. Tell me more”. If I’d been unwilling to expose my ignorance; if I’d said “Oh, yeah – I’m working on that now. I’ll have it to you tomorrow” we never would have gotten to the bottom of the need.

It’s taken me years, but I’ve learned to love difficult questions. I’ve learned to seek them out. Because they’re gateways to massive learning. They’re keys to making my work better.

Donald Rumsfeld famously said “There are known unknowns; that is to say there are things that we now know we don’t know. But there are also unknown unknowns – there are things we do not know we don’t know.” Despite the somewhat garbled delivery, he makes a great point. There are often questions that we don’t realize we should ask.

Difficult questions reveal the things you didn’t know you didn’t know. And they’re worth their weight in gold.



Dennis Breen


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