I reckon stupid questions are among the smartest things to ask.

Andy McLeish
March 17, 2021

In meetings, often I find people preface a question with the phrase “This is a stupid question but…” It made me wonder – what is a stupid question? I’d say it’s one where the answer seems obvious or already known. And the problem with that is often there’s one or more of these factors at play:

  1. Assumptions (apparently they’re the mother of something)
  2. Heuristics (mental shortcuts our minds take – like assuming people with glasses are more intelligent)
  3. Institutional knowledge (it’s how we’ve always done it so no need to question it).

All of these are an issue for anyone who wants to get to the bottom of a problem. More often than not, they stand in the way of the truth. So it’s really important to deliberately break through them.

This topic isn’t new by any stretch. It’s well trodden territory in behavioural economics, human centred design and other areas. But my observation is that in practice it is still seriously underdone. Stupid questions are not asked enough and as a result many businesses end up doing the same things they’ve always done and the same things that their competitors do. The solutions might be perfectly adequate, but rarely are they optimal.

Strategists are often encouraged to look beyond the obvious. Go past the big insights and find ones that were previously undiscovered, perhaps buried in a single comment from a focus group participant. We then apply it universally to everyone and expect it to transform the fortunes of a brand. Sometimes there’s gold in those hills but it’s often a long shot.

I reckon it’s more useful to look directly at the obvious. Look at it for a long time, look at it from every possible angle. Study it, question it, pull it apart. Go deep on it. Ask ‘why’ more than once, even if it sounds stupid. I think this is one of the most important things to do, especially at the start of a process. So much so I’m having packs of playing cards made, with all of them featuring one word; ‘why?’ We’ll hand them out in kick off meetings and ask people to play them on the table often. Hopefully it’ll encourage the asking of silly, obvious questions. And hopefully that will lead to less silly, less obvious solutions.

Make no mistake, it’s harder than it sounds. I’ve been around a while, and I still feel silly asking obvious questions – I worry that people will finally work out that I’m really an idiot. But I’m trying to get better at asking them. And I think you should too. In fact, if you have stupid questions you’ve always wanted to ask, I’m quite good at answering them. So I’d be happy if you send me some stupid questions you’ve always wanted to ask but had been afraid to. And I’ll attempt to give you a not stupid answer in my next post, or directly.

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