A great question stimulates the mind. Consider these 15 Global Challenges from the Millennium Project. They're all framed as questions and it's easy to understand why. Every question immediately makes you think. Let's take Challenge 4 as an example:
How can the global convergence of information and communications technologies work for everyone?
Reading this question, you might think of 5G towers, Elon Musk's Starlink, or the Internet.org partnership between Facebook and big telecom companies. A question like this pushes you to query and search, and that's exactly what the Millennium Project wants.
Unfortunately, people don't ask enough questions. Whether it's overconfidence, apathy, fear, or something else, most people keep their lips tight when questions roam their minds.
This puts those who do ask questions at an advantage, because the right question is a pickaxe that mines the gold in someone's head. But that's not its only benefit. Asking questions will make you more likable in the eyes of your conversation partner too. You'll seem a better listener and, perhaps paradoxically, a more interesting person.
"The important thing is not to stop questioning."
- Albert Einstein
This article will give you a nuanced overview of the most important things to keep in mind so you can start asking better questions.
Ask More Questions First
A large part of getting better at asking questions is simply asking more questions. This is the equivalent of studying versus practicing. There's only so much value in learning how to ask a better question if you don't put that knowledge to use.
Don't fall into the trap of asking fewer questions because you're trying to come up with the perfect one. Firstly, there's no such thing as a perfect question. Secondly, asking more questions is a much faster road to asking better questions. Practice will build the implicit knowledge you need to understand what's a good question in a particular context.
Keep it Simple
In almost all scenarios, it's best to stick to one question and one question only. Instead of asking "Why did you start coding and what do you hope to achieve in your coding career?" ask one of either question and you'll get a better answer.
You might have the urge to squeeze as many questions as possible in one long, rambling question, but the person answering will most likely either be confused or end up answering only one question. So pick the single question that's most important to you and ask that one instead.
Mostly Ask Open-ended Questions
Closed questions, also called yes/no questions, serve a narrow purpose: they can help confirm a specific something and they leave much less wiggle room for someone to give a vague answer. There's a reason journalists often press politicians with closed questions instead of open questions.
However, closed questions easily introduce bias and manipulation. For example, "Was it difficult learning C++?" is a much more biased question than "What was it like learning C++?"
C++ is a notoriously hard language and the first question nudges them to say that it was indeed difficult. While you might still get people to say that it was difficult by asking the second question, it will come from a more honest place. You'll also get a much more informative answer, because it's an open-ended question.
Of course, no one's perfect. If you catch yourself asking a closed question, you can easily follow up on someone's answer with an open-ended question. In our C++ example, you could ask "What was difficult about it?" to a yes answer or "What did you like about it?" to a no answer.
When someone is answering your question, don't think about your next question. That defeats the point of asking questions in the first place. Instead, keep new questions in the back of your mind and focus on what is being said instead.
This is what makes follow-up questions so powerful. They show that you've been listening and your conversation partner will appreciate you more as a result. Follow-up questions give you the opportunity to steer a conversation, something that's particularly true when your conversation partner gives you choices.
For example, imagine you've asked "Which clean code principles have been most important to the quality of your code?" Your partner replies with DRY and YAGNI. Now you have three paths to go down on. Do you ask more about DRY, YAGNI, or do you switch the topic altogether?
Just make sure that any next question is a natural transition from their last answer. Don't jump around from topic to topic with your questions, because the conversation won't flow and your partner will quickly feel uncomfortable.
Create a Safe Environment
People will give much more honest answers when they feel at ease. That's why it's easier to get honest answers in a casual environment. People are more at ease. It helps if you let people know that their answers won't be held against them and if you give them an unembarrassing way out of the conversation.
Some of this can't be replicated. Talking to a friend in a bar will always be more casual than an interview in an office. But one of the ways to make a conversational partner feel safer is by giving them easy questions at first. Gradually escalate by asking deeper questions as the conversation goes on.
One other point is that it's usually best not to leave a conversation on a very deep subject. Before you end a conversation, reintroduce some levity with a few easier questions. It'll make for a better finish of any conversation.
There are many other tips for getting better at asking questions. Get comfortable with silence, go with the flow in a conversation, don't interrupt, etc. But we hope that the above has given you a good start to understand the importance of a good question and how you can get better at asking them.