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A majestic Jimi Hendrix (left) and an unflappable Dick Cavett (right) circa 1969

Don’t you ever ask probing questions. Ever!

Yuri Zaitsev
Feb 21, 2020 · 4 min read

Never ask probing questions. Don’t even think about becoming genuinely curious about the people around you on a deep, anthropological level. Don’t pretend you want to. But let’s pretend that you do want to (for some reason), what would happen?

Well first of all you’d hear stories.

Second of all you’d begin to care about them.

And that’s it. Unless you work in the design industry, then you could also creatively inject a unique perspective into your work. Alright, so in conclusion you may want to sometimes ask strangers deep questions but only if you want those things. Actually, I’d say it’s super critical if you want to experience anything truly genuine, authentic, and full of personality. Only ask probing questions. Period.

Periodically I get to help people learn design fast. One time I was with a lady from [REDACTED] and we were trying to come up with how to #innovate in the beauty industry. We’d just finished the “drawing on whiteboards” phase of learning design and moving onto the “hot take” phase (sometimes called a point-of-view). This is the take that the team had come up with earlier from previous work:

Hair products should be about confidence.

That’s interesting but this insight wasn’t leading to the hottest new hair product of 2020. Alright readers-who-are-self-righeously-chuckling-to-themselves, consider this: when asked about what lead to this take, the team at [REDACTED] said,

“We did a few interviews and got to this insight, and after we do more interviews, this doesn’t really change. We are hearing a consistent story from the customer voice, so we are done.”*

You’d be surprised by how often people say this. Not just regular people, but super creative, centers of innovation excellence too. After spending a few years in the design industry, I’m surprised by how often I hear teams come up with “water is wet” points of view.

Actually, I’m not surprised because you should never ask probing questions to people. Ever! Unless you want that stuff that we already talked about and a good point of view.

*Scientific side note: The language in this type of response is actually consistent with the language of denial. Generally speaking you hear people talk this way when they are rationalizing and repressing some information and ignoring some implications. People not in denial usually speak differently. Here’s a book about it, I recommend skipping to Chapter 6.

Right? I’m actually not guessing because I’ve seen this before, all over the place, and my job is to fix this sort of thing. Here is how I figure out what’s going on.

“Hair products should be about confidence” is an answer to a question. We can work backwards from this to come up with questions that give this answer. I’m not saying Team [REDACTED] asked these exact questions, but I am saying that there is a 90% chance that these questions appeared in their interview guide.

“How do hair products make you feel?”

“When do you use hair products?”

“What do you want out of hair products?”


These questions are not tough. The only thing these questions probe is the confirmation bias implicitly hiding in there. I also guarantee that if you replace the words “hair products” with any other topic, then these questions will appear on many, many, interview guides and customer surveys. Evidently, lots of people think that they should never ask tough questions.

This happens when we are trying to get strangers to validate the idea we already have in our heads. We want them to say our idea is cool. Asking tough questions (if you want to) makes us pay attention to what the strangers want and aspire to be. Then our cool ideas stem from their wishes. Our preconceived idea falls off to the wayside, and that is scary.

Here is a list of very solid follow up questions if you manage to find those strangers again:

“When do you need to feel confident?”

“How do you act when you feel confident? How do you act when you are not?”

“When do you lose confidence?”

“When would you not fix up your hair?”

Fair warning: asking these sorts of questions runs the risk of changing your point-of-view and you may accidentally become interested in the people around you.

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Curious ruminations on human-centered design, by Amplifi Design and friends

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