Andy Capaloff
October 17, 2023

The Art of Asking Questions [Interactive]

The Art Of Asking Questions

We’ve all grown up asking and being asked questions. But there is an art to asking incisive questions. It’s a state of mind.

We’ve all grown up asking and being asked questions. But there is an art to asking incisive questions. It’s a state of mind.

This article will examine styles and attitudes, as well as the psychology of a good question. And it will ask you, the reader, to chime in with your thoughts. Although not specifically business-oriented, it should be clear how to apply the advice that follows to a business context.

The penultimate section will be, to my mind, the most important.

What Makes A Question Bad?

The common wisdom that there’s no such thing as a bad question is absolute garbage! Of course there are bad questions!! There are atrocious, waste of time and breath questions!!!

But I’m not talking about those. I’m talking about questions that are supposed to drill down to facts, but are worded wrong, or at best, ambiguously.

You May also want to read: Question ‘Common Wisdom’: It Isn’t Always Right

I’ve written at length about the importance of crafting the perfect question. Society’s emphasis is all on answering questions. But what if the question, as worded, can’t produce the right answer? What if it means different things to different people or simply takes people in a wrong direction? I delve into this more in the article The Best Possible Answer To An Imperfect Question Is Still Wrong and I’ve talked about forming question circles in search of the perfect question, here.

Beware The Experiential Question!

I’ve never tried to categorize questions before, but the concept of experiential questions came into my head, so I thought I’d put together a very short list of question types. They’re listed in the order that came into my head, not importance:

  • Experiential
  • Factual
  • Opinion

This list effectively splits experiential from non-experiential opinions. My reason for doing that is that if you actually experience something, you do so against a backcloth of your life’s experiences, including cultural and geographical. Doesn’t that make these questions a potential minefield?

Ask a question that is reasonable in your culture, to someone from a background where, for very good reasons that you’re apparently unaware of, the question becomes touchy, or worse, very annoying, and you could end up with an ostrich-sized egg on your face!

You May also want to read: Don’t Just Question Answers. Question Questions

Look For The Uncommon Questions

Common questions can be inane. They rarely get people thinking deeply in order to respond. They were surely expected. Yes, I’m guilty of asking them sometimes. But I’m far more likely to step outside of the normal. I’ll delve more into that in the following section.

As a part of my career as a Quality Assurance Analyst and Tester, I had many people tell me where to look for questions. I always ignored their advice. I believe that a lot of software issues that you, the reader, will have encountered over the years, have been caused by QA people taking (maybe being forced to take) advice from Business Analysts or developers on exactly what to test. What they have, in essence, done, is to rubber-stamp the work of those who created or implemented the software. Earlier in my career, as a programmer, I always tested. When I was done, I would always give my programs to my colleague and friend Yung Ken Wu, with the simple instructions “Try to break it”, or, “Have fun”. He broke it every time, lol!

You can look for the uncommon, thought-provoking questions in just about any aspect of life. The answers to these questions will teach you far more than the answers to the questions that most other people will ask. They will also spur the person you’re asking to think a little more deeply before responding. And one perhaps not so simple question can open the most interesting discussions.

You May also want to read: Context Broadens Audience. Questions Broaden Discussion

Question Asking Styles

  1. Have you ever been interviewed by one of those people whose sole criterion is to catch you out with a gotcha question? Don’t be that asshole. They wouldn’t be your friend. You wouldn’t want them as a colleague. They’ve completely missed the point of why they’re interviewing you. Actually, they made the interview about themselves, not you.
  2. Another style to avoid in most, but not all instances, is the confrontational style favoured by many of my fellow Brits. I grew up with this style and certainly adhered to it for many years. It has its place – in a BBC political interview, for example. I’d venture to suggest it’s also an appropriate style to confront the hostile interviewer with, before you walk out telling them you’d never work with people like them!
  3. Asking questions to corroborate what you already know. Whereas this is certainly important – especially if one of your preconceived notions is challenged by the answer, these can’t be the only questions that you ask. Which brings me to the very best type of question…
  4. Try asking questions with a truly open mind and/or from pure inquisitiveness, and with utmost respect. You’ll be happily surprised with the answers you receive. You may be surprised with what you can ask and who you can ask, if you employ this method. These go beyond the uncommon questions mentioned in the previous section that they are a subset of.

Two Examples Of Purely Inquisitive Recent Questions

When you find yourself in unexpected company, try asking that question you’ve long wondered about.

I recently found myself in the company of a recovering meth addict and a drag racer (not at the same time!).

Q1. I see meth heads making jerky movements and moving their arms wildly. Did you do that, and, if so, what were you thinking at the time?

A1. “I always felt that I was in a sitcom. Wherever I went, I’d be announced by name, so I’d play to my audience.”

I confess this answer was as surprising as it was believable.

Q2. What is it about the noise that your cars make that makes you enjoy so much? Is it the camaraderie?

A2. “When the car is making its noise, I really like the vibration. It’s addictive. And yes, there is also a camaraderie.”

What questions would you love to ask someone, whether in your business or personal life? Can you ask them in a way that will elicit an open, honest, and illuminating answer?

It’s not only what you ask, it’s also the way you ask it.

Questions are fun! Enjoy yourselves! And please tell us your tips on asking good questions. What style has brought you the best answers or discussions?

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Andy Capaloff

Andy Capaloff is the COO of Curatti. Prior to moving into the world of Content Marketing, Social Media Management and the day-to-day running of a Digital Marketing company, Andy spent over 3 decades in various aspects of IT. It is here that he honed his writing and technical skills, and his ability to ask uncommon questions.