The subtle art of asking questions


There is more to asking questions than get the information we seek. This is something I learnt several years ago.

Here is an example from my days in the advertising business. We used to have a set of questions to be answered to get a proper advertising brief.  I often shared that with my clients before we met and then run through those during the meeting. It seldom worked.

I shared my frustration with our managing director, when we were going together to meet a client. “He speaks in mono-syllables” I complained to him, about the client we were going to meet - the Managing Director of a client organisation.

I then watched my MD get answers to every question in my list by having a fascinating conversation. My ‘mono syllable’ client was articulate, interesting and most forth coming. I was initially tempted to dismiss it - he opened up as MD to MD. But I knew that was not true.

That is when I really understood the power of using questions to steer a conversation, open people’s minds and help people get clarity.

Over the years I have been working on ‘the art of asking questions’ (as opposed to questioning ability). When a manager graduates from a prescriptive style to a facilitative style, ‘the art of asking questions’ becomes an asset.

I am sharing here a set of questions that work for me.  This is by no means a laundry list of questions. Each question serves a different purpose.

What else?

When to use this:

- When you are presented with an option/solution for a problem

- When you want to stretch the person’s thinking

- When you are presented with an option/solution for a problem

- When you want to stretch the person’s thinking

So.... (or So What?)

When to use

- Early stages of discussion

- Bringing clarity into the thinking about what the idea does,

what are its benefits, potential etc

- Provoke the other person to think deeper

- Shake off complacency

What do  you want from me?

When to use

- Preferably every time someone wants to meet you

- Forces them to think about the purpose of the meeting and

how to get the best out of it

What questions do you have for me on this?

When to use

- Beginning of the meeting

- Some times at the close of the meeting - What other questions  do you have for me?

- To force people to understand how to get the best out of you as their resource

What decisions  do you want from this meeting?

When to use

- In the beginning of the meeting

- Sometimes when people are asking for time from you for a meeting

What is the most important thing we should be

discussing about this idea?

When to use

- Ask at the beginning of the meeting

- To force the person to be focused on the outcome of the

meeting

- To bring clarity into the discussion

- To inculcate the habit of thinking about this before they

approach you next

What do you think is happening now?

When to use

- When you want to get an assessment of the current situation

- Additional probe: What do you think is really happening?

Tell me more...

When to use

- When you think the person has an idea with potential

- When you want to unearth a possible story to explore

relevance

- When you want bring more clarity/specificity to the idea

- When you want to help the other person understand his own

idea better (its plus points and limitations)

How did you start? (What exactly did you do?)

When to use

- When you want to understand if the person had followed due

process

- When you suspect that the person could have taken a few

short-cuts/skipped steps

- When you want to identify why something is not working as it should

- Follow-up question: If you were to start all over again, what

would you do differently?

What do you think?

When to use this

- Discussing a dilemma, when we need to make a tough choice

  • After you have shared your views on a particular issue
  • Before you share your views, to understand the other person’s perspective first

- When some one comes to you with a problem

How will this help you achieve what you want?

When to use

- When your manager is deciding to invest considerable time/

resources on something

- When you suspect the other person has not done his/her homework thoroughly

How do you think I can help?

When to use

- When you find the person is struggling on his own and might benefit from some help

- When you think he needs help but does not know who talk to

- Sometimes, when you think he is feeling stuck

Who do you think might be able to give us some new perspectives on this?

When to use

- When you think the person is stuck or having a mental block

- When you believe he could benefit by talking to an expert to

make his idea more powerful

How to state an opinion as a question

Instead of: “Your idea seems a bit vague”

try “How would you explain the benefits of your idea to a 10 year old kid ?”

Instead of: “This idea is dumb” try

“How would you convince a  VC to put money on this idea?”

Instead of telling ask thought provoking questions

Instead of playing expert invite/ask others to contribute their expertise

Instead of giving your expert views ask others to share their

experience

Instead of assuming meaning ask for what the other person

means

What is in  it for the user?

When to use

- When you find the person has thought of it as a technical

problem to solve but has not thought about its impact

- When you find the person has thought of it as a technical

problem to solve but has not thought about its impact

“Why do people do, what they do?”

Asking why(five times)

When to use

- When you want to understand the real reason behind

somebody’s action or decisions

- When you want to get to the root cause

- When you want to understand, what about the idea,

is driving/motivating the person

- When you want to understand the real reason behind

somebody’s action or decisions

- When you want to get to the root cause

- When you want to understand, what about the idea,

is driving/motivating the person

Follow-up questions

What will make this even more powerful?

Why are you in love with this idea?

What might come in the way of making this idea happen?

What will make this even more powerful?

Why are you in love with this idea?

What might come in the way of making this idea happen?

Is this the best we can do?

When to use

- When you think an idea is mediocre and we can do far better

- When you think the other person has not stretched himself

- When you think the other person is too easily satisfied and

has settled for something inadequate

Alternative ways

Do you think there is room for further improvement on this?

In what ways do you think this could be better?

Follow up Questions:

What stops us?

What is the best part? What can be better?

Would you put your signature on this? (Would you be proud of this?)

What does your heart tell you?

When to use

- When it is decision time

- When it is tie between two close options

- We have exhausted all logical arguments

- When you want to understand what the person is passionate about

What do you wish you had, so that you can make youridea fly?

When to use

- When the idea needs improvement

- When you want to open the person’s mind to newer/bigger

possibilities

What question have I not asked?

When to use

- Closing part of the discussion

- Make sure everything is covered

- Provoke the other person to start thinking in this manner

What do you think should be our next steps?

When to use

- Closure time

—Person is not clear on how to move forward


“My greatest strength as a consultant is to be ignorant and ask a few questions”

- Peter Drucker

This is a strength all of us can develop. It is not easy, needs practice but once you know how to do it - your questions become your passwords to new insights.

Something every business leader and manager is looking for all the time.



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