Save the Empire: the art of asking better questions

Empire Records has a lot to answer for.

For a kid, heading into their teenage years and obsessed with music, it meant there was no option but to pursue a job in a music store.

When the film version of High Fidelity came out, teenage years waning and the security of home lost to the freedom of university, any change to that direction was a lost cause.

So, obviously, in 2002 I started work at Sounds, one of New Zealand’s now long-lost music stores.

Aside from the free CDs, DVDs, and band meet-and-greets, Sounds gave me my first exposure to job interviews. Company policy said two people needed to conduct them, and my manager toed the company line, in so much as I was invited to be the second person, albeit with no speaking lines.

Except for this one time.

We flew through an interview with a Scottish guy as he nailed all the “tell me about a time when…” behavioural questions. So, with his name all but on the contract, my manager turned my way and invited me to ask a question from a list we’d been joking about.

“If you were an animal, which animal would you be?”

I don’t have any data, but I’d expect most people would say tiger, and if they didn’t say tiger they’d say dolphin. Not this guy.

“I’d be a seagull.”

The reason?
(Content warning: it’s not for the faint-hearted)

“Well, back home in Scotland, the seagulls sit on top of the high rises and wait for smaller birds to fly between the buildings.
Then they swoop in, at speed, crashing into the birds, sending them flying into buildings and knocking them out cold.”

Oooooooooooooookay.

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Interviews are the most obvious example of where we need to construct good questions, but they’re not the only example. In truth, we’d probably all benefit from being able to ask more, good questions, in many more situations.

If you’re wanting to further understand the ROI on investing in better questions, Warren Berger outlined the case for it in his book, A More Beautiful Question. He argues that questions can improve decision-making, provide a spark for creative problem-solving, enhance leadership skills, and help strengthen personal relationships.

So, what stops us, and how do we ask better questions?

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‍What stops us asking questions?

There are many reasons why we don’t ask questions. It might be that we don’t want to look dumb at work, or that we don’t want to look dumb to our friends, or we don’t want to look dumb to the mechanic who just explained, using all the car jargon they could, why our Toyota Corolla won’t start.

Wait.

Is it just that we don’t want to look dumb?

Yes, dummy, it’s that simple: the easiest way to break this down is to say, yes, we’re all a bit scared of looking dumb. Which is, well, dumb.

We can’t expect to know everything relevant to our job, or our friends, or our Corolla. 

More importantly, no one, no one, expects us to know everything about those things.

As an added bonus, everyone, everyone, likes it when people take an interest in the things that matter to them, that they’re good at, that set them apart. They want you to ask them questions about these things.

I know you’re not a total dummy, and you want some data to go with these anecdotes, so let’s hit up Harvard - coincidentally, the same school Corey was heading to after finishing up at Empire Records. A 2017 study by the Ivy League university found people who asked questions were more likeable and seen to be more responsive and caring. 

They also found speed daters who asked more questions were twice as likely to get a second date … do what you like with that bit of intel.

Other research, and I’m paraphrasing, found that men were more likely to ask questions in a professional setting and less in a personal one, whereas women were the opposite.

So, it’s gender, it’s situational, it’s being dumb-dumbs, it’s the overall complexities of the human condition.

The good news is, while Rex Manning cannot change, we can.

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First off, we’re going to need a little confidence. We’ll all find that in different places, but here I’m going to argue for two things: a growth mindset and the assertion that being a dumb-dumb is ok, great … awesome, in fact.

Let’s run through these real quick, starting with a growth mindset: we have to want to be better, and be prepared to invest the time to do that. Having a growth mindset is centred, in the words of Carol Dweck - who came up with the concept, on believing our skills can be developed, they’re not innate, fixed things. It’s nurture over nature. 

Chances are, if you’ve made it this far, you have that mindset … or you’re a massive Empire Records fan.

Now, I’m going to park the bus on calling you a dumb-dumb here, shifting to some more positive reinforcement. You are awesome. I am awesome. We’re all awesome. But we’re also pretty hard on ourselves, and we tend to define our internal perspective by some pretty inconsistent metrics.

I like Eric Barker’s perspective on this one, which he framed uniquely in his Barking Up The Wrong Tree newsletter,

“Why do you love a baby? 
Do you love them less when they cause you problems or fail at something? 
No. The love is unconditional. 
We might not love when the baby vomits on grandma, but that doesn’t make you love the baby any less. 
Apply the same principle to yourself.”

Apply the same principle to yourself. I’ve ditched the quotes because this excerpt from Eric is now my advice to you. We are all dumb-dumbs, and we’re all brilliant, and in any situation we might be one, or the other, or a bit of both. 

That means we’re all human, and that’s the best thing to be.

So, let’s take these mindsets: we believe we can grow and learn, and we know that being a human means being fallable, and that is great.

Now, how do we use these concepts, and this confidence boost, to ask better questions?

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‍How do we ask better questions?

First off, practice makes perfect.

Nobody strolls into Empire Records on Rex Manning Day and nails life first try: Lucas didn’t practice and he lost nine grand. 

Start small. 

Ask questions in low-risk situations: a friend about their weekend, a colleague about a project they're proud of, your local coffee shop about the best thing on the menu. Pay attention to the answers. Test different types of questions and watch how people respond. Notice which questions make people light up, or give you fuller, more interesting responses. Those are clues about what kinds of questions you should ask, and when you should be asking them.

Second, buy them dinner first.

You probably aren’t opening with "What’s your five-year plan?" on a first date, and you probably wouldn’t hit a new boss with “What’s the deepest regret of your professional career?” in your first week. 

Start casual. Build trust. Understand who you’re talking to, and when. Warm people up with smaller, easier questions before you get to the big, juicy ones. 

There’s the added bonus that you just might strike some unexpected gold, via some unexpected gold questions, in your warmup.

Third, good questions have a job to do.

A good question pulls its weight. It should either deepen your understanding, help you see a new angle, or open a door for connection. 

Are you trying to learn? Can you walk me through that process again? 

To challenge? Have we considered the potential downsides to this approach?

To connect? What are you most passionate about right now?

If you don’t know what you want a question to achieve, neither will the person answering it. Being intentional, even just quietly in your own head, makes it easier to ask something that matters and avoid conversations that fizzle out into awkward silence or vague shrugs.

To recap: practise in the shallow end, read the vibe before cannonballing into the deep end, and aim your questions at something real to get the most impact out of the splash.

Inadvertently, “what animal would you be?” ticked all these boxes.

And if all else fails, just remember: no one at Empire Records really knew what they were doing either, and they still saved the store.

As Corey implored,

“You have everything it takes!
More than everything it takes!”

So, start asking questions now. You just might save the Empire.

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Jamie is the Head of Experience at Redvespa. With a background in museums and heritage - and long-closed music stores, he loves to share a good story. The more outlandish, forgotten, or hidden, the better. As you're reading this, he probably has a tab open following live baseball scores.