Can I ask a stupid question?

I’m a big fan of stupid questions. 

And by stupid, I’m referring to the questions we often think of as too obvious to ask.

“Shouldn’t you know this already?”

Well, perhaps I do. Perhaps others in the room don’t.

Perhaps what seemed obvious, is actually, just stupid thinking. Automatic thinking. Continuing the thing we do, because we always do it that way.

“Why are we doing this?”

“What does that mean?”

Probably two of the most undervalued questions in life and the two we rarely feel comfortable asking in the context of work.

Yet, they are designed to challenge our automatic thinking. 

“That’s just the way we do things around here.”

“Ok, but why?”

A three-year-old often asks better questions than most of us. They’ll pursue you until they’re satisfied with your answer. But we forgive their persistence. After all, they’re just trying to learn more about the world, right?

As Edward De Bono said, "A conclusion is just a place where you stop thinking". 

The late, great Ken Robinson argued that we teach creativity out of our children. Perhaps, we are teaching them out of asking questions too. Is that why now we are all grown up, we’re scared of asking the obvious questions?

We shouldn’t be. 

Simply asking “why”, and pursuing it to a natural conclusion, can result in truly transformational thinking.

The photographer John Ingledew illustrates this beautifully.

“When industrial designer Kenneth Grange was briefed to develop new express trains for British Rail in the 1970, a seemingly na?ve question popped into his head: ‘What exactly are the buffers on a locomotive for?’ Expecting to be told ‘They’re to stop the trains crashing into stations, stupid!’, instead he learnt that they were for shunting carriages – a redundant activity from a bygone era. Liberated from the need to include them, Grange was able to design the streamlined trains that went on to revolutionise rail travel in Britain.” 

Sometimes obvious questions simply haven’t been asked openly before.

And sometimes these questions are actually new, or at least new to the people being asked. 

New questions frame the status quo differently and can result in very different outcomes.

As Dave Trott wrote in his Campaign article ‘The answer asks the question’, directing questions directly at the problem at hand is an obvious, yet sometimes underused strategy.

“Asking questions that hadn’t been asked before wasn’t silly, in fact, it won the battle of the Atlantic.” 

But something you will notice as you ask obvious questions is the reactions you get to these lines of questioning. There are subtle undertones to stupid questions. 

The awkwardness. 

I do have to say, I rather enjoy the awkwardness.  

Awkward questions make people nervous. Perhaps this is because you’re always meant to sound smart. We’re paid to know things, aren’t we?

You’ll notice others adjust themselves in their chairs or cut you a worried glance across the table.

Edward de Bono said the point of a question was to be provocative. I suppose that depends on whether the outcome of your questions is successful or not.

However, I’ve noticed that people say more interesting things when they feel awkward. They get defensive and say what they really mean. They clarify their position. They will feel challenged, and therefore want you to know exactly where they stand.

And with this, the truth reveals itself, perhaps to the benefit of others, who will chime in now. Building on the obviousness of it all. Catalysing the facts from the assumptions.

The main issue here appears to be culture.

In advertising, Planners are expected to ask difficult questions. It’s their job. It’s how they define the problem or sort fact from fiction. Yet, not everyone in the room seems to be aware of this. Perhaps, they don’t actually know what Planners do? And who can blame them? We aren’t the greatest self-promoters in the world of Advertising.

What a lot of people I’ve spoken to in preparation for this article seem to agree upon, is that we need to create cultures that empower people to speak up and challenge conventional thinking. 

Ask all the stupid questions and ask them earlier on.

Amelia Torode, Co-Founder of The Fawnbrake Collective explains, “I feel like at the start of every project we need a stupid question session - get them all out. Because as we all know there’s no such thing!” 

Bruce Clark of Northeastern University suggests we should create a culture that rewards asking questions, “I tell students that if someone asked a question they had, to go and thank that student after class. It can take some bravery to raise a hand.”

Martin Davies, Director at Smarty Pants Consultancy Limited, reflects on the importance of leaders creating the space for stupid questions, “When I had a team, I used to encourage asking a stupid question at least once a day. It’s amazing what can follow from asking that question. And it builds confidence, too. The challenge for businesses is, how do you cultivate a culture that values the stupid questions?”

Dan Wieden framed the importance of asking better questions by highlighting the dire consequences of becoming complacent, "When you don’t know, you try desperately to find out. But the minute you think you know, the minute you go – oh, yeah, we’ve been here before, no sense reinventing the wheel – you stop learning, stop questioning, and start believing in your own wisdom, you’re dead. You’re not stupid anymore, you are f*****g dead."

This culture of asking obvious, or difficult questions, seems to evaporate though when you look client-side. There appears to be an expectation that people should already know the answers, and so there is less opportunity to challenge convention through stupid questions. This is often evidenced by the reactions of clients when you challenge their way of doing things. 

Have you ever noticed how the eyes of junior clients light up when you ask their boss, “why are you doing it that way?”. 

It’s like being telepathically fist-bumped across the boardroom table.

But in any working environment, it’s rare for people to notice why you’re asking stupid questions. They may not realise that you’re creating a climate where the truth can reveal itself naturally. The conversation prompted by an obvious question may lead to an unexpected answer, but you will never be credited for starting that chain of events. Nobody will track back through the conversation and understand that the obvious, stupid question you asked at the beginning prompted the unexpected outcome. That is the curse of deliberately choosing not to appear clever.

The truly stupid questioner will, however, ask questions that are designed to make themselves appear clever. Their questions will be met by equally vacuous, intellectual answers that lead you and your quest for understanding nowhere. Many of you will probably recognise this trait in some of your colleagues whose true ambition is self-promotion and not the pursuit of truth or indeed, original thinking.

It’s worth considering the role you play as the questioner and being clear on your intentions. As Mark Hancock pointed out to me, “the jester was the only one who could tell the King he was being a dick and get away with it.” 

Here are a few questions that may help frame your own questions.

Are they directed at the problem at hand?

Are other people thinking them, but not saying them?

Do they challenge conventional or automatic thinking?

Are your questions new?

Your questions lead you closer, or further away from the truth, so be clear in your own mind on your intentions.

What appears clear is that the truth isn’t always the thing held in your head. Or the thing you’ve convinced yourself of. It is often waiting to be discovered. But it has to be collectively agreed upon. Truth alone, held by one person is merely inert potential. A diamond buried deep in the mountain. Asking the right questions, the sometimes-obvious questions, and yes, the stupid ones, can unearth the truth and share it for everyone’s benefit.

Andrew Willshire, Founder of Diametrical Ltd, perhaps put it best, “As one of my lecturers used to say, if you have a question that you think is too stupid to ask, it's guaranteed there are another ten people in the room with the same question. So, ask it, and help everyone out."

Here are a few stupid questions I think we could ask more.

What does that mean?

Why did it work?

Why didn’t it work?

What happened?

Why haven’t you changed it?

Why do you do it like that?

Are there any other stupid questions you like to ask, or feel we should ask more?

So, in conclusion, we should all be asking more stupid questions. 

Ask them early on. Ask them for everyone else in the room. 

Be provocative. Be the jester who challenged the King. 

You might not be rewarded personally, but your work will be. And the people who understand why that matters will always reward you for asking.

Acknowledgements

My thanks to Mark Hancock, Dave Trott, Amelia Torode, Andrew Willshire, Martin Davies, Rory Sutherland, Richard Shotton, Zack Gardner, Paul Bailey, Jill Dudones, Matt Phil Carver, Steven Sullivan, James Hankins, Tom Lewis, Cameron Broadway, Andrea Ciulu, Simone Bocedi and Matt Krygowski for their contributions to this conversation and help writing this article.