How to ask the best questions?

How to ask the best questions?

In a world of freely available and instantly accessible information, a hidden yet valuable skill, is being able to ask the very best questions in conversations, meetings or interviews.

Such questions enable you to generate answers laden with valuable information and often build rapport and relationships more quickly.

In my experience active listening is important as it helps you generate a much higher quality of question, access richer information and develop a stronger rapport .

However , one of the leading authorities on the subject is Harvard psychologist and author Steven Pinker and he suggests five practical strategies to asking the best questions ;

1)  Ask the questions that other people are not asking. 

Whilst this is perhaps obvious its much easier said than done. However, if you can step outside what is known, and probe gaps that exist, then you can generate questions that will provide answers to fill them. For example, a question to ponder yourself before asking ‘the’ question might be ‘What are we not considering? ‘ 

2)  Keep asking open questions like ‘Why?”

This is a derivation of the ‘5 Whys’ technique developed by Sakichi Toyoda, the Japanese industrialist, inventor, and founder of Toyota Industries, in the 1930s. The 5 Why’s method is remarkably simple to use when a problem occurs because you drill down to its root cause by asking "Why?" five times. Then, when a countermeasure becomes apparent, you follow it through to prevent the issue from recurring.

Similarly, in a question without an obvious problem you may pursue more information and it is in this quest that you may find the edge of what is known and, therefore, as per above find a question to ask, for which an answer is not known.

3)   Follow up with follow-up questions.

Research conducted at Harvard University suggests that in any given conversation the most powerful type of questions are follow-up questions, since they show a genuine interest in what the other person has to say. As a result people feel more respected and heard, which will improve your relationship and most likely the quality of answer.

The good news is follow-up questions don’t require much thought or preparation, since they are situational , based very much on the conversation at hand . However , it certainly helps if you can focus on listening rather than trying to anticipate the answer ,as listening gives you clues as to the best follow up questions to use.

4)   Ask questions in the right tone 

The tone of your voice when asking a question is important in generating rapport and trust more quickly . If you can ask questions in a casual rather than officious uptight manner you are likely to have a richer conversation where the other person is more likely to reveal more of themselves than they might otherwise do.

5)    Pay attention to the order of your questions and whether or not they are open ended 

Interestingly there are two distinct approaches on the order you ask questions depending on the outcome you are seeking. 

If you’re seeking information ask the tougher questions first . Although it may temporarily feel awkward, studies show people are more likely to open up if you ask questions in decreasing intrusiveness. This may be due to the unexpected shock of the question that causes an answer to be given.

In contrast If you’re looking to build relationships the opposite is true and you should start with innocuous questions and slowly progress to more difficult or sensitive ones . Studies have shown that by following this simple structure, relationships became stronger than those that asked sensitive questions right away.

The distinction between open and closed questions can be important too.

Asking open questions (using why, what , where , when , how ) can provide broader deeper answers helping you to uncover information, form relationships or learn something new.

If you ask closed questions it can seem more like an interrogation than a conversation although closed questions can be helpful in some situations, such as negotiations or reporting as they restrict the opportunity for evading the question with a broader answer .


Paul Lyons is an experienced CEO who coaches leaders to improve their performance and wellbeing by developing their mental toughness and emotional intelligence. To learn more contact Paulor Mental Toughness Partners

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Thanks to Sammie Vasquez for the photo 


Emanuele Mazzanti

Turning leadership talk into real impact—through facilitation, development, and coaching. I bring energy and curiosity to foster connections & growth. 2h57′ marathon runner.

4 年

More Yoda moments are needed. Love the breve question: ”What are we not considering?” ”What is not being addressed here that should?” thanks Paul!

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Paul Lyons

Mental Toughness Expert | Helping athletes, coaches, leaders and their teams effectively measure, and develop mental toughness for a stronger, consistent performance

4 年

Thanks for your comment here Nita N.

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Nita N.

Freelancer IT Project Manager Digital, Application & Infrastructure at Not for Profit Org

4 年

Great share Paul

Andrew Lawrence

Clear Calm Growth&Flow (GLOW) | CEO TAB Gordon | Founder Corporate Intraprenuer, PresentNow & SME Genius | Co Founder Group Fit Training & Danolyte ANZ | Director Youth Impact Foundation | Sustainability |

4 年

Inspiring ideas! These are really useful.

Art Patrick Yare

HR Manager at LinkedVA

4 年

Truly helpful! It's great to know how to ask the best question to generate valuable answer. Worth the share!

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