The question-asking product II

Art of Message

Art of Message – April 26, 2023

The question-asking product II

I can’t forget a story I heard Malcolm Gladwell tell in his course

It was about a lifelong friend from New York who was very smart and knowledgeable and knew a lot about many things. Whenever someone brought up almost any subject, her response was, “Yep – I know about that already”, followed by an impressive display of her vast knowledge.

That behavior itself isn’t inherently “wrong”. But Gladwell made the point that it’s basically the exact opposite of the right way to interview someone as you do research.

The right way, in sum: listen actively, ask open-ended questions, solicit stories, be curious about everything, create a rapport, be patient with silences, minimize your own input, and cherish anything unexpected.

The last point hit hardest because it’s where he got the most intense. To paraphrase, he said:

“Don’t be the person that jumps to the conclusion that you already know, even if you do. Don’t ever say, ‘Oh I know everything about that’. Because you don’t, not fully. Even if you’re a world-renowned expert, there’s always something you don’t know – an odd detail, a turn of phrase, a personal anecdote, or a perspective you hadn’t heard before. Your job as an interviewer to fight like hell to find it.

To return to this question – how can a product ask the right question?

Maybe assume that customers know something – anything – about the product’s purpose that the product owner doesn’t. Not just about the product itself but about the category, industry, or market it lives in.

Products often attempt the low-cost approach – having an anonymous form, chatbot, support rep, etc, automatically ask something like, “Anything we missed?”.

Automated or not, perhaps there’s a better question and a better way of asking it.


The message above comes from…