Ask Good Questions: Deep Dive

Questions as part of the toolkit of our social skills

At some point on my path to becoming a designer, the weight of “good questions” started bearing down on me. This is part two of my two-part series about what I think constitutes the art of asking questions.

Last time I talked about the importance of situations in determining the quality of a question. This time, I will look at the nature of questions, and what to watch out for before you bring a question to the table.

What are questions?

Questions are powerful. They are not just static ideas we chance by. They do things, they actively seek to engage our mind. Think of it this way: You step into a bar. There are sixty other people, densely packed, humming their tunes, laughing, and drinking. You are in the middle of it all. Sure, it’s pleasant. But then, there is that one group of people that actually notices you, says “hi”, and makes room for you.

Although nobody in the group knows how the night may unfold, they take you in to be part of what determines how the night shapes up. Questions are not that different. They engage a piece of our mind to help complete an inquisitive thought. They invite us to participate, to abandon our role as an observer, and collaborate.

Questions are open invitations…What was that? Not the type of questions your boss asks you? Those usually shut your brain off?

Good catch. And that brings us to the heart of question-asking as a tool of everyday social encounters, or in our case, board-meetings, client-meetings, etc.

Different ways we think of questions

How question-asking is used and perceived is tightly entangled with the mindsets of the people involved. And I can see two prominent mindsets: Authoritative and collaborative.

Authoritative Mindset
Questions are there to help you critique, analyze, dissect, drill down, and get to the bottom of something. In this mindset, a question is a rallying cry to hunt down flaws and failures. There is a right answer to an inquisitive thought. So, question-asking takes on a confrontational flavor, because it puts a great burden on whoever attempts a response

Collaborative Mindset
In contrast, collaborative mindset is like going on an excursion on a virgin island. Every question is like a pair of eyes. The more eyes there are, the more of the landscape you can take in. Everybody has something to contribute. When operating in this mindset, questions seek to increase the stock of knowledge, and add perspective. Truth is not your practical goal, you are instead looking to reduce uncertainty.

As a designer, I have found that more often than not good questions rise out of the collaborative mindset, because people feel welcome and safe to chip in with their own thoughts and questions.

Asking good questions is not just about you

No matter how you craft a question_ say, you pick the right mindset, adjust it to the situation_ it can still fall short of being a good question, if you haven’t given a thought about who you are approaching with your question. What’s their thinking style? Do they take a deep dive with every question? Are they impatient? How do they fare with abstract questions? Like every other social encounter, question-asking requires that we consider our audience.

Let me take you back to that night at the bar. Why were you approached? The group probably saw something in you that made them think you would be a good addition to their crowd.

So, if your questions are invitations for people to join you in finding answers, then be mindful of who you invite. As designers, even when we have the vaguest questions at the start of a project, we still have an idea of the type of conversations we hope they will provoke: Concrete bullet points v.s abstract philosophical debates; More information v.s less but specific information; etc. Make sure that the person you are inviting to think along with you is a good match for the type of “mental bar”, where you will be taking them.

At Last!

That’s as far as I have come on my quest to become more deft at asking questions. Three points that I hope you take away from this series are:

  • Understanding a situation that has occasioned a question is half of the battle in coming up with a good question ( find out more about the different types of situations in my first post ).
  • Approach question-asking with a collaborative mindset to give space to others to participate.
  • Know who you are posing a question to, and whether they are a good match for what you hope your question should achieve.