In Praise of Stupid Questions

In Praise of Stupid Questions

"Could you say that again using normal words that we can all understand?" (Image: Robin Cave / UX Mastery)

That niggling feeling in meetings when you briefly consider speaking up, but choose not to? That’s one of your superpowers going to waste. This inaugural article in Joe’s monthly ‘Ask Anyway’ column for us explains why.

Why that ‘stupid’ question may be the smartest thing said.

This is the first article in Joe’s monthly ‘Ask Anyway’ column for UX Mastery.

At the intermediate and advanced levels of UX practice, work becomes more nuanced with higher stakes, responsibilities grow, issues like imposter syndrome go further underground, and work pressures increase. It’s less about the tools and more about managing people.

So, we want to settle in and have a conversation with you about how these things affect you, your work, and all of us as a community of practice.

What are the burning issues you wish people would talk more about? You can share them with us below and we’ll gladly respond.

“Man, I am SO glad you said something.”

If I had a nickel for every time I’ve heard that during a break in a meeting or consulting session, I’d be retired on an island somewhere, where the sun never stops shining and the drinks never stop flowing.

And if I had an additional nickel for every time at least five other people echoed that same sentiment, I’d own that island.

What did I do? Simple. I asked a stupid question.

You don’t get it (or do you?)

How many times have you sat in a meeting where a ‘leader’ says something ridiculous? Proposes a plan of action that has no chance of working unless you suddenly develop the power to bend time and space? Or something that’s dishonest, that takes advantage of the product’s users? Or that’s sexist? Or racist? Or just flat-out rude and disrespectful?

Everyone shifts uncomfortably in their seats. Eyes dart sideways around the room. But no one says anything.

You sit silent, with your hands folded, because you’re afraid that if you open your mouth, they’re all gonna laugh at you. Everyone will think s/he just doesn’t get it.

Here’s what you need to understand: you — and every other silent worrier in the room thinking the same thing — DO get it. In fact, you get it to a more thorough and much higher degree than anyone else at the table.

You get it because you’re not just blindly accepting what’s being passed around. You’re not assuming you know everything there is to know about the topic at hand. You’re not hiding behind your job title or your corner office or your tenure.

You’re not pretending to have all the answers.

And that’s what UX and Design are all about: assuming nothing and asking questions.

But both things require courage, and what you will find the longer you’re out in the working world is that courage is in unbelievably short supply. And you’ll also learn that what passes for courage is actually insecurity gone wild.

Fear of being human

When executive leadership is opposed to doing user research, it’s partly because they’re really, really scared of what that research might show them. That it will confirm the fears they already have, confirm the mistakes that they already know are being made. Confirm that customers have reached the apex of fed up and are done waiting for the company to do the right thing.  All of which may, unfortunately, require that they do something about it.

The research results will ask something of them they’d prefer to avoid: bucking the trend and speaking up. So you get resistance in the form of “sorry, no time, no budget, that’s a nice-to-have.” Urgency trumps importance.

But none of that is the real reason they’re stonewalling.

The real reason is a hell of a lot simpler; it’s because when they speak up at the next Knights of the Executive Round TableTM board meeting and advocate an unpopular approach…

They’ll be shut down.


Laughed at.

See, our reluctance to ask dumb questions isn’t just about not wanting to hear the answers — it’s about not wanting to be hurt.

It’s about our fear of being vulnerable, of taking off the armor and getting real.

This, in my opinion, is precisely what breeds situations like the one Twitter finds itself in now.

GIFs, loathing and Nazis

As I write this, Twitter’s design team just rolled out a new feature that allows you to add photos, videos, or GIFs in a retweet. They tweeted the hell out of this and talked about it like people have been camped outside their corporate offices, pounding on the doors with torches, screaming “WE WANT GIFS IN OUR RETWEETS!!”

When what those people have actually been screaming is “NO MORE NAZIS!!!” No more hate, no more abuse. Do a better job kicking out the hateful, predatory bullies who make being online an unsafe and increasingly scary experience for far too many people.

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But doing something about that would require Jack Dorsey and co. to have courage. To ask questions and get very uncomfortable answers. To fully admit just how fully out of control this is, how badly they’ve f**ked it up. But you see, that truth is scary.

That truth is something Twitter’s fearless leader and his bros do not, as my grandfather would say, have the stones to face.

So instead, they’re patting themselves on the back with “We heard you! We’re listening!” after rolling out a feature that maybe 1% of their user base asked for. They did the easy thing instead of the hard thing, because, at least inside the walls they work in, it didn’t make them look or feel stupid.

That’s fear, masquerading as courage.

That’s a refusal to ask the ‘stupid’ questions that are on everyone’s lips:

“What the f**k do we DO about this?”

“Where do we even start?”

“How are we missing this stuff?”

“What have we DONE?”

And when no one voices these things, the implication is that everyone agrees with what’s going down. That it’s OK, that it’s not a problem we need to address. As a consultant once said to me, “silence equals agreement.”

If you hear something you don’t agree with on any level, and you say nothing, you are, in fact agreeing with it. You are agreeing it’s OK, you are agreeing it’s the right thing to do. And in some cases, you are agreeing to DO IT.

You are also, in these situations, robbing every person in the room of the benefit of your intelligence, ability and talent. And that is extremely depressing, because you have a lot to offer, no matter how many unkind things you say to yourself on a daily basis.

If not you, then who?

Our assumption is often that the hard questions have been asked, but were ignored or dismissed. But what I’ve seen, time and again, is that while everyone certainly shared the same concerns, no one said a word. Instead, they sat silent and fearful, hoping someone else would say something.

The truth is simple, friends: someone has to do it.

Someone has to break the silence and voice the doubt that at least half the people in the room share. Someone has to be willing to endure whatever comes after they voice that ‘stupid question’ out loud.

And if no one’s going to do it, then you have to.

But Joe, they’re all gonna laugh at me.

Entirely possible. But here’s the thing: I’ve built an almost 30-year career on being that guy. On being the person in the room willing to say “could you say that again using normal words that we can all understand?”

Cue the laughter. And daggers in the eyes of the person speaking, who knows as well as I do how completely full of shit he is.

And a massive, collective sigh of relief that you can feel as six other people think to themselves “thank God.”

Is that hard for me? Yes. Always has been. Always will be.

I’ve been ridiculed, laughed at, insulted and threatened, in public and in private. None of that is anything short of painful.

But my career didn’t go anywhere until I started speaking up. Until I was willing to risk being shown the door for saying something I knew they wouldn’t like very much. I learned that when I told them the truth — or challenged its definition in the form of a ‘stupid question’ — one of two things happened. They either:

  1. Kicked me out of the room, or
  2. Cleared their schedule for the rest of the day (or month) to work with me.

Now, clients seek me out to do precisely that. I don’t market, I don’t advertise. They hear about how I roll from people in their network, and they find me. So I’ve been asking stupid questions for the entirety of my career. And I will continue to do so until I retire to that island I told you about earlier.

Because the truth is that nothing good happens for you until you learn to speak up. Until you’re willing to be seen, be honest and be vulnerable.

Until you’re willing to ask a stupid question.

‘Ask Anyway’ is a monthly column exploring collaborative teams, career survival and the heart and soul of good design practice. The only way to learn is to find the courage to ask. Send in your questions, and we’ll answer them here!

Written by
Joe Natoli
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