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Art of Asking Questions

Well I don't know I am embarrased or proud to say that this post is over 4400 words, which means reading time of 20 minutes. In case you have a shorter window and keen on certain topics then here are the links for respective sections

“Question everything. Every stripe, every star, every word spoken. Everything.” – Ernest Gaines

People took this quote too seriously. Look at the kind of Google searches we are doing these days –

-       How do I get home? Monthly Searches – 49,500
Well people get answer in the form of box which asks “Where’s home?”

-       Are aliens real? Monthly Searches – 49,500
Common NASA is working on that but some of us are impatient

-       Does farting burns calorie? Monthly Searches – 49,500
There are better ways to burn calories. By the way, the claim that it burns 68 calories is wrong

-       When will I die? Monthly Searches – 49,500
Who knew google will be able to foretell the future

How come we (or rather our questioning ability) reached to this point?
To understand this let’s go few centuries back...or maybe many centuries back

Tibetan Buddhist monks has this daily ritual of debate—where one monk continually questions another monk, often on esoteric points of Buddhist thought. The impressive aspect of this practice is how the monks use this method of questioning/answering to hone their skills in logic and to probe complex questions

Socrates is well known for using questioning to probe the validity of an assumption, analyse the logic of an argument, and explore the unknown. Questions were a means to educate his students by drawing out their understanding of a subject and then leading them to discover a set of logical conclusions instead of lecturing them on what is true or false

Even in the Hindu culture, there is a dedicated Prashna-Upanishad, one of the earliest of the Upanishad texts that serve as a foundation of Hinduism, pupils pose six great questions to a wise teacher

We asked great questions which resulted in brilliant answers and then more amazing follow-up questions. People were proud (in certain cases egoistic) with their question-asking ability.

The trend continues, Genghis Khan, the founder of the Mongol Empire, was able to create a vast empire basis his observational and questioning abilities. As mentioned in some of the texts, the questions he asked were to identify the behaviour of nearby civilizations, understand the topography, borrow the strong points of the defeated nations and always questioning his own administration current effectiveness and measures needed to improve it.

And the trend continues as we questioned the centricity of Earth in the planetary system. Then we questioned the prevalent flat topography of Earth.

The art of questioning was even present in the 1800s where Newton’s question of “Why Apple fell to the ground” lead him to propose gravitation equation.

Then in the 20th century, Bank of America has had a massive win with its “Keep the Change” program that rounds up customers’ debit card purchases to the next highest dollar, sweeping the difference to a personal savings account. The patented program is breathtakingly simple, for both the bank and the customer.
The question which might have kicked off that campaign could have been:
“How can customers save money without thinking, planning, or clearly foregoing consumption?”

And the last I checked, the art of questioning is still there, but it’s getting rare to such an extent that we need to call it an “Art”.

It is so rare that we have to go through a 3500-word post (or 6-short posts series if you prefer) to understand and practice this art of questioning.
You can tell a man is clever by his answer. You can tell a man is wise by his questions

Wouldn’t world be better without questions?

Well none of them is true, barring the first one.

But have you noticed something here? – A pattern of getting rewards, accolades, promotions, prizes, likes for the ANSWERS you provide. Not for the QUESTIONS you ask.

The gap between “That was a thoughtful question” and “That was a great solution” is widening.

We become wonderfully efficient at solving problems, even if they are the wrong ones to solve

So, what’s the need of asking questions?

Well there are certain benefits

  • By enquiring about the projects & processes, we can surface out the lateral problems which could have killed our proposed solution
  • A good question can create an "aha" moment, which can then lead to innovation and growth
  • Questions keep us in learning mode rather than judgment mode
  • Personal questions can help you find your true purpose and passion
  • Questioning can help us survive in the ever-changing world – Which technology should I embrace? Which skill should I learn? How does this new product work?
  • Follow-up questions can help you get deeper, meaningful answers
  • Not questioning means following someone else’s rational, beliefs blindly or maybe even following the history blindly. Imagine how much would have missed if we kept on following the things as they were
  • Questions help us in making connections. Remember those business meetings or networking event or that casual chat with next seat person on the flight? During those times asking questions help us initiate a conversation which can become a possible connection

Now asking questions make some sense? 
But wait I almost forgot to share the real intent of asking questions.

What? You believed all the above reasons are the only benefits of asking questions?

Well, questions are the subtle way of showing an intent. They are those indirect ways to communicate your feelings towards a person or his work.

Intent behind questions

To get the answer –The basic intent of asking a question.

“Where are we on the benchmarking project?”
“It’s completed”
“Fantastic, Thank You”

·      To test you – Most of the How questions fall into this category
“Where are we on the benchmarking project?”
“It’s completed”
“How are you going to relate it with the alternate benchmarking we did last month?”
This will showcase your preparedness, alternate scenarios thinking capability.

·      To accuse you
“Where are we on the benchmarking project?”
“It’s completed”
“What are you going to do to about the extra man-hours we took?”

It sounds like “The late delivery is your fault. I blame you.”
Conversations about who’s to blame are rarely useful, certainly not when there’s work to be done to solve the immediate problem

·      To get you off their back
Questions will be asked to get you more data, more runs, more proofreads in order to delay things

“Where are we on the benchmarking project?”
“It’s completed”
“Thanks, have we run pass the same before securities & legal times? Also, can you check for me what’s the industrial benchmark standings on this project?”

·      To express disapproval
“Where are we on the benchmarking project?”
“It’s completed”
“Thanks, but why have we used Monte-Carlo simulation while running this project?”

Here it’s not a question of the type of simulation. It’s more like – “I disagree with your use of Monte-Carlo simulation”

·      To exert power
“Where are we on the benchmarking project?”
“It’s completed”
“Can you give me a couple of reasons of not following this benchmarking report”

In most of the cases, such questions are meaningless and only used to exert power

·      To make a statement
“Where are we on the benchmarking project?”
“It’s completed”
“Ok, and how many folks are you expecting to tune to our presentation today?”

It’s more kind of statement expressing the concern of thin audience during the presentations

Imagine without questions how would have such subtle cues be delivered?

It looks like we have many good as well as bad reasons to ask the questions.

Why we stopped asking questions?

·     We haven’t done our homework
There are times when we could not prepare ourselves for the upcoming meeting, conference, lecture or interview. Though we won’t be delivering the presentation or driving the conversation but yet we are not comfortable enough to ask the questions. Obviously, if you don’t know the basics then how can you think of meaningful questions spontaneously. So, we act cool, show that we know almost everything, don’t ask questions. In the end, we shout the loudest thanks to the presenter

·     Let someone else asks the question
While sitting in the conference rooms or in seminars, I dread sitting in the last seats. Not that I am studious or want to get noticed but because I don’t want to shout out to ask the questions. In that cases, I would like someone else to ask the question. When was the last time you asked a question from your group? When was it that you asked the question despite being tough (in terms of logistics or seating or subject knowledge) for you?

·     Our question is stupid
How many times it happened that you start raising your hand to ask a question, and immediately stopped after seeing people nearby you? What if it’s a dummy question? What if someone already asked this question couple of meetings ago? Or maybe “My manager is sitting here. What if he judges me the basis on this question?”

·     Who knows what kind of answer we get?
Sometimes we are afraid of the environment and the presenter, especially either he is subject matter expertise or a loud-mouthed or both

A few years back, during one of our group meetings, I asked a senior manager about rumours of dissolving our team. His response was – “Mandhir! You should be standing near the water cooler to get answers to such questions” It took me 3 months to ask any question to him

·      Answer will confirm our fears
 I used to schedule my one-on-ones with my manager on Friday. Why so? I was afraid of asking certain questions to him. I was afraid not because my boss was scary, but it was the answers which were going to be scary. I knew my performance was not good. Our team was going through restructuring. There were client expectations. I also knew the answers to the questions – “How much will be my appraisal?” “How can I grow within the team?” “What skills I should possess?”

I knew answers to all of them, that’s why I was afraid to ask

·     What to do even if we get the answer
Suppose, we got the confidence to ask the question, knowledge to make this question meaningful, an environment which encourages asking the question, then also we don’t ask a question sometimes. Why so? Because the answer would not make sense to us.

·     Not everyone shares
A classic case of what we see our politicians do to us. At the time of elections, there will be a lot of promises, hope, schemes and assurance of much better future. On asking questions regarding delivery of those promises they would prefer to keep quiet or worse diverge. This non-committed and passive attitude makes us asking fewer questions. And this is not the case with politicians but within organizations as well. In the name of confidentiality, “results will speak soon” people prefer not to share any information which leads to the death of further probing

·     We don’t have an alternate source of information
I see this a lot while making investment decisions, forming political opinions. We are happy to stick to one source of information, especially the one which confirms our biases, our likings, our opinions. Thus, in absence of an alternate source of information we don’t question the opinions or authenticity of our preferred source and thus we stopped asking the questions

Now we know the reasons behind our hesitation of not asking the questions.
Let’s see what are the types of questions

Type of questions

Closed questions invite a short-focused answer- answers to closed questions. They can often be binary type - either right or wrong, either yes or no etc.  
They are usually easy to answer - as the choice of answer is limited - they can be effectively used early in conversations to encourage participation

By contrast, to closed questions, open questions allow for much longer responses and therefore potentially more creativity and information

A leading question, usually subtly, points the respondent’s answer in a certain direction.
Asking an employee, ‘What good you found about the latest benchmarking reports?’
In a very subtle way, it raises the prospect that maybe they are not finding the latest benchmarking report so good

Clarifying questions help us better understand what has been said. In many conversations, people speak past one another. Asking clarifying questions can help uncover the real intent behind what is said. “Can you explain it a bit?” and “Why do you think so?”

Questions can also be categorized by whether they are ‘recall’ – requiring something to be remembered or recalled, or ‘process’ – requiring some deeper thought and/or analysis
‘Which is the deepest ocean?’ 
‘How can we reduce a step from our production assembly line?’ 

Evaluative questions usually require sophisticated levels of cognitive and/or emotional (affective) judgment.
Can you compare the performance of our major competitor in APAC region and EMEA region?

Rhetorical questions are often humorous and don’t require an answer
Two men are having a disagreement in a bar. One says "Do you want me to punch you in the face?" Of course not.
Rhetorical questions are often used by speakers in presentations to get the audience to think – rhetorical questions are, by design, used to promote thought
“If all these architectures are already built then why do we call them building?”

We can use clever questioning to essentially funnel the respondent’s answers – that is ask a series of questions that become more (or less) restrictive at each step, starting with open questions and ending with closed questions or vice-versa
"Tell me about your most recent holiday."
"What did you see while you were there?" "Were there any good restaurants?" "Did you try some local delicacies?"

Adjoining questions are used to explore related aspects of the problem that are ignored in the conversation. Questions such as, “Can you think of alternate ways we can establish our supremacy in the market through this TV Ad?” or “What are the related uses of this technology?” fall into this category.
Our laser-like focus on immediate tasks often inhibits our asking more of these exploratory questions, but taking time to ask them can help us gain a broader understanding of something.

Elevating questions raise broader issues and highlight the bigger picture. They help you zoom out. So, you can ask, “Taking a step back, what are the larger issues?” or “Are we even addressing the right question?”

To make sure we are asking right questions, we can use frameworks. They will guide us, clarify our thought process, keep us on the track and move us in a progressive manner.

Frameworks to ask Questions

5 Why’s

The 5 Whys strategy is a simple, effective tool for uncovering the root of a problem. You can use it in troubleshooting, problem-solving and quality improvement initiatives.

Start with a problem and ask "why" it is occurring. Make sure that your answer is grounded in fact, then ask "why" again. Continue the process until you reach the problem's root cause, and you can identify a counter-measure that prevents it from recurring.

Problem statement - Our conversions on mobile are low for India


People are getting off from our payments page


They are getting the error message while making the payments


Their Payment session is getting timed out


The speed of the internet is slow in India and we are not able to customize our payment experience to make it faster


We copied the payment experience of other markets to India

The 5 Whys uses "counter-measures," rather than solutions. A counter-measure is an action or set of actions that seek to prevent the problem from arising again, while a solution may just seek to deal with the symptom. As such, counter-measures are more robust, and will more likely prevent the problem from recurring.

The "5" in 5 Whys is really just a "rule of thumb

As you work through your chain of questioning, you'll often find that someone has failed to take a necessary action. The great thing about 5 Whys is that it prompts you to go further than just assigning blame and to ask why that happened.

Phoenix checklist
It’s a tool developed by the CIA to define problems and plan solutions. The questions in are known as ‘context-free’ questions and are designed to encourage agents to look at a challenge from many different angles. It is like holding your challenge in your hand. You can turn it, look at it from underneath, see it from one view, hold it up to another position, imagine solutions, and really be in control of it.
Here is how you use it:
-       Write your challenge
-       Ask questions.  Use the checklist to dissect the challenge into a variety of areas
-       Record your answers.
  • Why is it necessary to solve the problem?
  • What benefits will you receive by solving the problem?
  • What is the unknown?
  • What is it you don’t yet understand?
  • What is the information you have?
  • What isn’t the problem?
  • Is the information sufficient? Or is it insufficient? Or redundant? Or contradictory?
  • Should you draw a diagram of the problem? A figure?
  • Where are the boundaries of the problem?
  • Can you separate the various parts of the problem? Can you write them down? What are the relationships of the parts of the problem? What are the constants of the problem?
  • Have you seen this problem before?
  • Have you seen this problem in a slightly different form? Do you know a related problem?
  • Try to think of a familiar problem having the same or a similar unknown
  • Suppose you find a problem related to yours that has already been solved. Can you use it? Can you use its method?
  • Can you restate your problem? How many different ways can you restate it? More general? More specific? Can the rules be changed?
  • What are the best, worst and most probable cases you can imagine?

  • Can you solve the whole problem? Part of the problem?
  • What would you like the resolution to be? Can you picture it?
  • How much of the unknown can you determine?
  • Can you derive something useful from the information you have?
  • Have you used all the information?
  • Have you taken into account all essential notions in the problem?
  • Can you separate the steps in the problem-solving process? Can you determine the correctness of each step?
  • What creative thinking techniques can you use to generate ideas? How many different techniques?
  • Can you see the result? How many different kinds of results can you see?
  • How many different ways have you tried to solve the problem?
  • What have others done?
  • Can you intuit the solution? Can you check the result?
  • What should be done? How should it be done?
  • Where should it be done?
  • When should it be done?
  • Who should do it?
  • What do you need to do at this time?
  • Who will be responsible for what?
  • Can you use this problem to solve some other problem?
  • What is the unique set of qualities that makes this problem what it is and none other?
  • What milestones can best mark your progress?
  • How will you know when you are successful?

Socratic method
The Socratic method is named after Greek philosopher Socrates who taught students by asking question after question. Socrates sought to expose contradictions in the students’ thoughts and ideas to then guide them to solid, tenable conclusions
This technique involves finding holes in their own theories and then patching them up

Generally, the Socratic professor invites a student to attempt a cogent summary of a case assigned for that day's class. Regardless of the accuracy and thoroughness of the student's initial response, he or she is then grilled on details overlooked or issues unresolved. A professor will often manipulate the facts of the actual case at hand into a hypothetical case that may or may not have demanded a different decision by the court

At its best, this approach forces a reasonably well-prepared student to go beyond the immediately apparent issues in a given case to consider its broader implications. The dialogue between the effective Socratic instructor and his victim-of-the-moment will also force non-participating students to question their underlying assumptions of the case under discussion

Include these powerful questions in your life

Areas of our life & Questions to asks 

This phase is related to your day-to-day objectives & how you are spending the time. This can also include questions around your interactions but we will cover them under social section
  • What is the aim of this discussion?
  • What do you want to achieve long-term?
  • What is happening now?
  • What is holding you back?
  • What could you do to change the situation?

Workplace comprises of you, your manager, directs, your team, leadership, organization and working environment.
One should be asking meaningful questions about each of them
·      Yourself –
o   Am I feeling motivated?
o   Am I being valued?
o   Am I being productive off late?
o   Which areas I need to work on?
o   What 3 things I can immediately change?
·      Working environment
o   Does my team have all the resources to be successful?
o   Does my working environment encourages inclusion?
o   Does my working environment celebrate diversity?
o   Can I voice out my honest opinions?
·      Team
o   Is my team co-operative?
o   Can I trust my teammates?
o   How can I help the growth of my team?
o   How can I make working easier for my peers?
·      Manager –
o   Is my manager supportive of my long-term objectives?
o   Is she/he promoting my work efficiently?
o   Is she/he challenges my thought process?
o   Are my concerns being heard and handled well?
·      Organization
o   Why do we do things this way?
o   Is there a better approach?
o   Does my organization has principles or values?
o   Is my Organization’s vision being in the interest of larger humanity or profitability?

These are the questions which, if powerful, will make you upset, feel vulnerable and think hard. These should be deep ones to add value and meaning to your life. Can be from the futuristic perspective or present state or even reflection from the past
  •       Where do I want to be in five years’ time?
  •       What is my story?
  • -       What bad habits do I need to stop?
  • -       What am I grateful for in life?
  • -       Have I taken an alternate road, where would I have been?
  • -       What lies have I told myself?
  • -       Who are my heroes? What qualities of their I aspire?
  • -       Where did I spend time today? Will this matter 1 year from now? 3 years? 5 years?
  • -       What limiting beliefs am I holding on to?


  • -     What kind of personality I have? – Introvert, Extrovert, Ambivert?
  • -     How do I feel while attending Social gatherings? – If good then what makes me feel good? If bad then what do I hate the most?
  • -     What kind of people, talk, environment I don’t like?
  • -     Does being socially popular affect my self-image?

  • -       Am I physically fit?
  • -       Do I rate physical quotient as an essential element of human personality? Why / Why not?
  • -       How can I become physically attractive?
  • -       What should be my exercise regime?
  • -       Am I eating a healthy meal?

  • -       What virtues should I be having?
  • -       What sins should I avoid?
  • -       Was I rational today?
  • -       What harsh truths do I prefer to ignore?
  • -       What does it mean to live a good life?
  • -       How long will you be remembered after you die?

  • -       What do I eat for breakfast? Is it considered healthy?
  • -       If I have 1 million dollars, what will I do with it?
  • -       What is my ideal home like? What should I do to achieve it?
  • -       What are the most important things to you in life?
  • -       For every experience, you get: What are the biggest things you have learned?

Tips to ask meaningful Questions

  • Learn different type of questions (open-ended, rhetorical, leading etc.) and basis the need uses them
  • Explain Why You Are Asking and Make Sure You Are Asking the Right Person
  • Ask Politely and Don’t Put Them in Uncomfortable Position
  • Ask for the Reasoning behind the Answer – It’s always the logic which does the magic as you can replicate the logic in different scenarios. For instance, the solution to low conversion in India can be offering discount coupons. But the logic behind it is to increase consumer count on our website. Now solution might not work for other countries but logic will work irrespective of geography
  • Never ask “Don’t you think” type of questions – This will show that you are already opinionated about the solution and you are merely confirming your thoughts by asking the question
“Don’t you think that weather in South India is better than that of North India?”
Instead, you can ask “What do you think of North & South India weather?”

  • Ask Neutral Questions and Don’t Impose Answers – Leading questions can be good from the hint perspective but in case of enquiry, they will create bias. The matter will become worse if you are in authoritative position as your direction will influence the direction of the probe
  • Provide people tool & space to give visual answers – All answers won’t be in a conversational form. Some of them require visualization, some require flowchart. Keep white space & markers handy. Encourage them to provide visual answers
  • Allow answers to come in form of a story – Many people prefer relating problem to their personal story. This can be bit verbose but it will bring empathy to the solution. So, answers like “Well this reminds me of…” can be valuable and thus should be encouraged
  • Don’t get lost in those stories – The common problem with storyline based solutions is them being wayward which means getting lost in the narration and missing out the context
  • Ask for Clarification – Fact or Opinion? – This can be a good follow-up question because if the answer is a fact then being a universal truth it would be easier for us to be on the page. However, if it’s an opinion then one should understand the reasoning behind that opinion

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