The art of asking better questions

When writing this post I set out to determine what a good question looks like. What I found is that it’s very much dependent on the situation and context, and who’s asking. But there are broad characteristics that make up a good question. And a few principles that ensure a question is delivered well.

As a strategist, questions are central to everything I do. One of the most important parts of my role is gathering information from various people. I might need to understand goals and objectives (e.g. to write briefs and build proposals), to collect feedback (e.g. when presenting a strategy or discussing recommendations), or to talk to prospective customers (e.g. testing a product or message). Whatever my goal, the quality of information I get is heavily dependent on the questions I ask (and how I ask them).

I’ve interviewed many different people, from FBI agents to someone who’d gamed the screener questions and shouldn’t have been taking part in my research! Gathering good information is about asking better questions. From briefs to customer interviews, even working with colleagues – the better the information you have the better results you’re likely to get.

Characteristics of a good question

If you google ‘what is a good question?’ a lot of the results focus on open-ended questions that further a conversation. In an educational setting, a good question might challenge students to think critically about a topic. In a journalistic context, it might elicit information that is of interest and value to readers. In a personal conversation, it might lead to deeper understanding and connection between individuals. The nature of a "good question" can also be influenced by cultural, societal, and individual preferences. What's considered a valuable or respectful question in one culture or setting might not be seen the same way in another.

Regardless of the context or situation, or who is asking, there are a few things that contribute to making a better question.

Clear and concise

The question itself should be easy to understand. Avoid jargon and complex words. Keep your questions as short as possible. The longer your question the more chance you have to confuse things and miss the mark. This is something I’ve had to work on especially in workshops - it can be easy to keep talking to try to add more context but in reality most of the time you end up complicating things.

Relevant

It should be obvious to the person you’re asking why you’re asking them the question. It should be focused on the topic being discussed and be well-timed so not to disrupt the flow of thinking or conversation. A better question is crafted with a clear purpose, whether that's to gather specific information or spark a discussion.

Constructive

Of course, there may be occasions where you have to ask questions about negative or difficult subjects. However, as much as possible better questions should be constructive – aiming to build knowledge or understanding rather than diminish or destruct.

(Generally) Open-ended

It’s important to know when to use different types of question. Open ended questions are good for exploring a topic and getting people to open up. But when you need to clarify certain points or distill a concept into simpler terms – a closed question to gather a yes/no answer can be valuable.

Principles for asking better questions:

The difference between a good question and a game-changing one often boils down to its delivery. Whether you're navigating a workshop, steering an interview, or sparking a casual conversation, the following principles will elevate your question-asking game:

1. Prepare with Purpose

Always have an agenda. While spontaneity has its place, having go-to questions for recurring situations—like a briefing template or rapport-building icebreakers—arms you with confidence and direction.

2. Set the Stage

Context is king. Ensure that your question lands within the right framework, clearing any ambiguities. This not only sharpens the accuracy of the answer but also deepens the insights received.

3. Don’t interrupt the flow

Interrupting can derail a speaker's train of thought. Let them complete their point; the information they provide might be just what you need.

4. Use silence to your advantage

After posing a question, staying silent can create a subtle pressure for the other party to fill the void. This tactic often compels them to speak first and can be a useful way to get people to start talking more, especially if they’ve been keeping their answers short or not opening up.

5. Know when to put people on the spot

Reading the room is crucial. Know when to gently push someone for deeper answers, especially in group settings where reticence can be a barrier. Being tactful about when you challenge someone can determine whether you get an open response or a defensive one. You may need to be direct in group settings where people aren’t forthcoming with answers. This often happens in remote workshops and you may be left with no choice. It’s best to give a warning first but if people stay silent, start working your way down the list of names asking for a response.

6. Script as a guideline, not gospel

During research or interviews, remain fluid. Instead of robotically ticking off questions, use them as a conversation foundation. Dive deep, seeking the hidden layers beneath initial responses.

7. Dig deeper with the '5 Whys' model

I love a good mental model to frame my thinking. The ‘5 Whys’ is a well-established model that helps dig deeper with the aim of finding the root of a topic or challenge. A gift from Toyota's problem-solving handbook, it prompts one to ask "why" five times, drilling down to the root of any challenge. There’s also a Miro template! (Explore it here: Miro - 5 Whys template)

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Mastering the art of asking better questions is an ongoing journey, one that adapts and evolves with each conversation, interview, or workshop. What's apparent is that the quality of our questions directly impacts the richness of the information we gather. By understanding the key characteristics of a good question and by honing our delivery methods, we not only facilitate deeper conversations but also foster connections, gather invaluable insights, and drive forward-thinking solutions.

Whether you're a strategist, a researcher, or simply someone looking to communicate more effectively, remember: it's not just about asking questions, but about asking the right ones in the right way.