Why you must ask more stupid questions

-: Four steps to turning stupid into a superpower :-

One of the worst things about starting something new is often feeling like the stupidest person in the room.

No matter how hard you work, what skills you bring or how quickly you learn, there will inevitably be many people who know far more than you do about your new world.

But whilst rookie status can be pretty tough on the ego, being ignorant can actually be a huge asset.

As an outsider, your fresh perspective and insights are likely to be incredibly helpful.

There is usually an established way of doing things.  Sometimes, it's broken.


Coming into a new world with an open mind and a blank sheet of paper allows you to question fundamental norms.

You're not being held back by convention; you never have to say "but it's the way we've always done it".

Getting excited about shiny new things is infectious. The grass is, of course, always greener on the other side.

And that rush of naive excitement about ultimate possibilities can often propel you - past frozen and jaded incumbents - into the art of the possible, breaking down outdated structures, taking bold action and birthing brand new ways of doing things.

And once you've recognised the blindingly obvious opportunity,  take a deep breath, get vulnerable, and ask a lot of stupid questions.


I have benefitted from asking very many stupid questions over the years.

When I was building my press agency, I realised the advent of digital cameras meant that many untrained people were capturing amazing breaking news photographs, but didn't know how to distribute them.  

I asked my colleagues "Why don't we just acquire these exclusive images rather than try to compete with them?"

So we pioneered the art of discovering newsworthy photography very quickly, negotiating the professional rights with the photographers, then licensing these images globally for them.

This meant that we didn't have to continue with the convention of sending photographers around the world in anticipation of breaking news (which is very expensive).

And it ensured our global news clients got the front page images they needed.

Simple, right? It doesn't sound like much, but this approach of finding the photos rather than commissioning them played its part in revolutionising how British newspaper websites covered major breaking news.

At another point, Sam Relph, one of our star young reporters, decided to take a career break to travel in India.  It was a poor country in transition, which many news outlets in Fleet Street didn't have great coverage from.  So I asked Sam - "Would you like to open an office in India?"

Hey presto, we had a bureau in New Delhi, much to the ensuing mirth of our competitors.

Sam and his team got the last laugh, breaking multiple world exclusives, and covering incredible news stories and making brilliant television for clients around the world for many years.

Then, I realised we were generating some incredible exclusive stories that many TV producers wanted to exploit as documentaries.  So, knowing no better, and with zero television experience, I started calling TV channels to pitch a partnership. The calls were all a waste of time - apart from one.  

When I called the Extreme TV channel, I had the great luck to be put through to their commercial director, Ben Barrett.

I asked Ben "Would you be interested in buying our documentary ideas?" and we organised a meeting.  

Not long afterwards, Ben moved on to ZigZag productions, where we successfully collaborated on selling and producing around a dozen TV documentaries together.

Ben's open-minded, entrepreneurial approach - which he has grown into his own brilliant company - kickstarted my career in television, for which I'll always be grateful.

I doubted my gut feelings for many years.

I often felt like an idiot for saying things that would make people laugh out loud, and ask if I was joking.

But after a few of these wins, I realised that I should trust the simple ideas that refused to go away, rather than dismissing them as stupid.

Finally, I learned that my dumb ideas were usually far more useful than my complicated ones.


So I prioritised leading with my gut and focussed on delivering the glaringly obvious ideas rather than beating myself up for having them.

This led to some of my best stupid questions:

"What is stopping us from growing faster?"
Getting completely miserable that all my TV ideas were being rejected by the networks, I realised that it was our clients not buying our shows which was blocking our growth.  So we started to commission our own shows instead of just trying to sell them to broadcasters.

"Why don't we just ask for amazing access"
Wanting to cover the growing racial tension in the USA, we decided to call up the KKK to make a documentary about their new generation. They accepted, and we went on to make Inside the KKK, a film that I am so proud of.

"Why haven't more people heard of us?"
Realising that we needed to get industry recognition, we stopped pitching for the outlier awards at ceremonies, and took on the major TV networks for the big awards, finally winning Factual Channel of the Year at the Broadcast Digital Awards, becoming the first non-broadcaster ever to win that accolade.

"Our clients are struggling - why don't we take them on?"
Under pressure from falling licensing income, we decided to stop prioritising selling our videos to clients and to become a publisher in our own right. This potentially jeopardised around half our company's turnover, but I knew that our clients' businesses were in decline and that news viewership was moving to social media.  So the simple/stupid move was to take them on instead of staying as a supplier, despite the huge fear.

These questions, and the resulting actions, transformed our company's fortunes for the better and positioned us as successful innovators.

Having grown our stupid questions approach into a useful methodology, here is my simple four-step guide to making being stupid into a superpower:

  1. Spot what's broken - people had been fed up with taxi travel for years. Then Uber happened.  Where are the areas you can make something much better, simpler or better value? They are probably staring you right in the face.
  2. Why hasn't it been fixed yet? If you can find that out, it will enable you to work around the blockers or offer you a valuable note of caution on your quest.
  3. What would this look like if it were easy? New things often feel incredibly complicated. But sometimes there is a blocker that - if removed - could make everything easy. Often this is something that feels like a holy grail, that no incumbent would ever consider changing.  This is actually your big entrepreneurial opportunity for positive disruption.
  4. Ask a lot of stupid questions - It is scary to ask people things that seem simple. Even journalists spend a lot of time skirting around asking the big question. But usually, the cringey question is the best one. If it makes you feel nervous or excited, it's the right thing to ask. The answers will be the ingredients for your next big production!

I've been asking some ridiculous questions recently. And this has led me into a fantastic new chapter of my life.

Having sold my company and taken a badly needed rest, I got increasingly interested in the dramatic changes happening in food and agriculture.

Living in the beautiful Golden Valley in the west of England, over the last decade I have been inspired by the beautiful landscapes and remarkable nature.

So, when an amazing farm came up for auction just ten minutes from home, I asked myself: "Why not buy the farm?"

Having never farmed before, being raised in a poor part of a huge city, with no experience of nature conservation or building restoration, this was indeed the latest in a long line of remarkably stupid questions.

But, after a lot of deliberation, I've seen an opportunity to do something positive, and my wife and I have bought a stunningly beautiful, but quite neglected, 98-acre upland pasture farm called Penymoor.

Penymoor sits on the side of Herefordshire's Golden Valley, close to Neolithic tomb Arthur's Stone © Photograph by Sam Barcroft 2021

I will now be asking my friendly and very experienced neighbours a million stupid questions as I figure out how to restore Penymoor into a successful part of the Golden Valley once more.

You can follow us on Penymoor's instagram to keep up with events on the farm.

And hopefully, I'll be able to answer a lot of your questions as our journey into agriculture and conservation begins!

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Sam Barcroft

Sam Barcroft

Creative entrepreneur and strategist with over 30 years experience of building media businesses
Herefordshire