How to Ask Better Questions

Guest Post by Mary-Anne Webb

Imagine if you never took time out to ask questions. Nothing would change. Big questions serve to challenge the status quo. When we question we open ourselves to new possibilities. It sounds easy but the art of questioning is a skill that’s best learned young and developed as we grow.

The original TED conference creator Richard Saul Wurman observed that in school we are praised for having good answers, but rarely praised for asking good questions. We have to start with children and encourage them to explore their curiosity and remain inquisitive. We need to give them space to ask questions even when we don’t like what they’re asking. We can teach them to be great questioners.

The role of questions in innovation

Questions help us to challenge convention or unearth new insights. They are the necessary fuel to fire up new innovations. Most of our new ways of doing things from UBER, to AirBNB, to the first iPhone all came from questions that asked why does it have to be so? Why can’t things be different? Often what unites these innovations are questions that come across as naïve, crazy or a bit of both. It’s only natural that when you question long held assumptions you are rattling a cage that maybe others don’t want you to touch because it serves their interests. But what you find by rattling that cage is that these assumptions are not as solid as you first thought. So go ahead and challenge. Researchers at Brigham Young University and the INSEAD business school conducted a study of some 3,000 creative executives and found that what linked them was their curiosity and willingness to question. So the morale of the story is maintain your curiosity and you’ll always have a question to ask.

Great questions are game changing because they get you out of a tired loop of expectation and stretch your imagination to areas/ideas that you couldn’t previously conceive. Today there are many new businesses that didn’t exist a decade ago and I’m confident of many more in the future that you can’t conceive today. Perhaps someone is asking a new question right now.

Know what you want from your question

It helps when you’re asking questions of others to help them understand what type of information you want from them. Do you want the facts; do you want their opinion on a situation or an objective appraisal with no personal bias? Any guide you can give your subject will help them and ultimately help you too.

Professional interviewers, like journalists, are paid to ask questions. They know the better their questions the better the information they’ll receive and maybe even a revelation or two. When it comes to interviewing I like this analogy by John Sawatsky, a leading authority on the art of the interview, as captured in the American Journalism Review: “The best questions are like clean windows. A clean window gives a perfect view. When we ask a question, we want to get a window into the source. When you put values in your questions, it’s like putting dirt on the window. It obscures the view of the lake beyond. People shouldn’t notice the question in an interview, just like they shouldn’t notice the window. They should be looking at the lake.”

John found that we’re asking the wrong questions too often and stressed that the interviewee is the subject not the interviewer. As well as knowing what type of information you want, it’s important to know how to question. The majority of times what leads an interviewer to fresh insight is the quality of questions they ask.

“Judge a man by his questions rather than by his answers.” ― Voltaire

Questioning Techniques and Tips

Even if you’re not Sherlock Holmes, a journalist or budding innovator, developing your questioning technique is a skill that will serve you well. Here is a collection of techniques to help.

1. Ask open-ended questions

This means avoid asking questions that can be answered with a ‘yes’ or ‘no’ simply to draw out a richer answer. Yes/no limits the response and can leave you with an incomplete picture. Questions starting with “would,” “should,” “is,” “are,” and “do you think” have a higher probability of achieving a yes or no. When you start your questions with “who,” “what,” “where,” “when,” “how,” or “why” this leads people to give thought to their answers and provides more detailed, interesting information. Sawatsky suggests the best starters are ‘what’, ‘where’ and ‘how’.

2. Probe further

This involved digging into the answers you’re given to unearth more insight. You can do this by asking follow on questions like “what made you say that?” or “how did that make you feel?”. Your ability to dig deeper will pay off with richer insight and possibly correct any initial assumption you were prone to make. When you keep an open mind your questions will more likely be open too.

3. Know when to shut up

As the interviewer your role isn’t to keep talking but to keep your subject talking. Sometimes it might feel like you need to jump in and fill an uncomfortable silence but these moments may be your subject thinking what they’re going to say next. Give them space to think and don’t fret periods of silence. It means you’re listening skills are being activated and that’s a good thing. Be like an interrogator who knows how to use silence effectively.

4. Listen, don’t interrupt

If you’re truly listening you’re not planning what you are going to say next, instead you are waiting for your turn to speak after the other person has finished. The only exception to the don’t interrupt rule is when the person has significantly deviated from the topic, and then it’s entirely appropriate to interrupt to bring them back on track. You can do this respectfully and direct them back to the topic at hand. Otherwise, keep in mind that interrupting can stop someone’s train of thought and limit the insight that might have come.

5. Start general then go specific

Start with broad topic questions and then, subject to the answers you receive, narrow in on specific topics as they come up. Planning your general questions is always the best approach. Specific natured questions can’t be planned as they arise from the conversation. You just need to be listening for the cues to go down the specific path.

6. Ask one thing at a time

Don’t try and load your questions with double barrel requests. Too many points or topics in the one question will only serve to confuse the other person.

7. Ask only questions you want answered

This will respect the other person’s time and yours too. Keep to the subject matter that’s important and relevant. This will save you time and not create more answers than you know what to do with.

8. Let the conversation flow naturally

If you’re truly actively listening then your next question will relate to what was just said, unless you specifically want to introduce a new topic. When you listen properly and respond in kind your conversation will flow and you allow new insights to reveal themselves that you couldn’t anticipate.

“The scientist is not a person who gives the right answers, he's one who asks the right questions.” ― Claude Lévi-Strauss

Good answers come from asking good questions and take practice.

Mary-Anne Webb


Mary-Anne Webb is S


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