The Worst Question You Can Ask

The saying is, there’s no such thing as a bad question. But there’s one question, one we’ve all been asked and often hear, which really is the worst question.

A few years back I was at one of those events with lots of speakers. Imagine TED Talks, but with less science and self-help and lots more gormless self-promotion.

Seated next to me was a well-known designer. I could sense that during one talk he was getting quite irate. The speaker had done one of these “discovering human nature” kind of projects, going out into the world with a set of questions and then documenting, in a stylishly artful way, people’s responses. The problem was, the responses were trite, in a cheap greeting card kind of way.

Under his breath my designer friend blurted out,

“You are getting shit answers because you are asking stupid questions.”

The Quality Of Our Questions Matters

In childhood and at school we are often told, “There’s no such thing as a bad question.” At this stage of life, it’s helpful advice, since many kids are worried about speaking up and afraid of looking stupid in front of their peers. If this worry solidifies it can become a crippling fear of asking for help.

But as we get older, the quality of our questions starts to matter.

My friend the designer was becoming frustrated because a designer’s job involves asking hard, probing questions. The right combination of if, how and why can lead to breakthroughs and new ideas. Doctors are also masters at posing the smart question, working down from a vast range of possible diagnoses to something that can be treated.

Think of all the surveys you take. There’s an art to the way those questions are written, so they create data that can be useful. Or the difference between when an app or device asks you a question that makes sense, that you can easily act on, to when you get a request that seems to make life harder for no reason.

And every time you walk down the aisles of your supermarket, everything you see, from the design of the packages to the way they are laid out on the shelves, is the product of thousands and thousands of questions, little pieces of consumer research, which plays a part in this box being red instead of blue, or how big it is, or where it sits on a shelf.

The Worst Question We Can Ask

Imagine you have the opportunity to ask a question of someone who’s just completed some kind of major creative project. Maybe they’ve written a book, recorded an album, directed a film, staged a dance or play, or put some art on exhibit.

With this chance, what’s the worst question you could ask? I would suggest it’s this one we’ve all heard before:

“Given what you know now, what would you have done differently?”

The question seems to be a kind of summary, a way of getting at what you’ve learnt, since many of us learn from self-reflection, from asking how we could have avoided mistakes or taken different decisions.

But this is pure speculation. You don’t know if the “done differently” stuff would’ve worked, whereas you do know the thing this person actually made did work. So, by asking “What would you have done differently?” you’re saying the hypothetical thing has more value to you than the real thing.

Which is kind of weird, and not a little disrespectful as well. After all, you could ask this question without knowing anything at all about the work or the person who made it.

Any major piece of work has involved thousands of decisions that you could explore, decisions with evidence and data which you could explore, or the values which drove the decisions, and the process which kept them moving along towards completion.

Maybe it’s no wonder that so many answers to the “What would you have done differently?” question end up sounding trite – trust myself more, do more market research, hire more people. It’s the same problem as that of our ineffective speaker who asked the superficial questions and was given nothing but superficial answers.

Some Better Questions

If you wanted to actively explore someone’s regret and self-reflection, then asking about how they felt about a project will probably lead to a more vulnerable and emotional answer. Or you could ask at what point they doubted themselves and how they overcame those doubts.

Good questions will reveal habits and practices you can try to emulate. Asking about everyday habits, essential routines, the use of goals, plans, milestones, and ways of tracking progress are all things you can try to incorporate into your own work.

The best questions require us to do a little work first, a little introspection, enough to reveal what we want from ourselves and the universe around us.