It’s amazingly hard to ask good questions.

MBWA 7.21.14.png
I’ve been in investigative mode over the last month; trying to understand the root cause of a performance issue and also designing a potential new business model. Both projects mean I’ve had to ask a lot of questions. And they also mean I have had to remind myself how to ask questions.

In my experience, the key to asking a good question is to know why you are asking the question. When people ask questions, they do so for one of three reasons:

  • They want a well-reasoned point of view
  • They want an opinion from an expert
  • They want a factually correct answer

That’s right; people don’t always want a factual answer to their questions.

As a result, asking a well-formed question is incredibly important – especially if the answer is a point of view or an opinion. Unfortunately, people usually ask questions which are unintentionally vague. Vague questions produce vague answers.

I had been looking for a memorable way to make the point about ambiguous questions when I re-watched the movie Die Hard with a Vengeance on a recent plane flight. The villain gives the good guys thirty seconds to telephone him on the number “555 plus the answer” or else a bomb will detonate.

The question is the well-known nursery rhyme:

As I was going to St. Ives,

I met a man with seven wives,

Each wife had seven sacks,

Each sack had seven cats,

Each cat had seven kits:

Kits, cats, sacks, and wives,

How many were there going to St. Ives?

Most people try to multiply the sevens to get to the answer. But, if you look closer, the passage never says the group is travelling to St. Ives. So the answer should be one: the narrator.

But wait. We don’t know if the narrator is traveling alone so perhaps a better answer is at least one.

On the other hand, a plausible answer is zero. The last two lines of the riddle state “kits, cats, sacks, wives … were going to St. Ives?” The narrator isn’t a kits cat, sack, or wife, so shouldn’t count as part of the answer.

Since the nursery rhyme is supposed to be a riddle, it’s intentionally vague. But it makes the point. There is no factually correct answer so you can only have a well-reasoned point of view.

Ask better questions. Or as the French philosopher Voltaire said,

Judge a man by his questions rather than by his answers.

This blog was originally posted on Manage by Walking Around on July 20, 2014.

Please follow me on Twitter, LinkedIn, and Google+.

To report this post you need to login first.


You must be Logged on to comment or reply to a post.

  1. Andy Silvey

    Hi Jonathan,

    nice thought provoking piece as usual.

    I would add,

         never fear to ask a question

    Asking the wrong question in the beginning (qualified as being wrong by not achieving the required answer) can lead to improving the question (as you have shown the different types of question) and achieving required answer. The word required is deliberately used here instead of the word right as we know often there is no right answer.

    In my work as a SAP Basis Architect I ask a lot of questions, and I often tell people, I’d rather ask a stupid question and be wrong, than keep quiet and be right.

    Best regards,


  2. Joao Sousa


    You say there are three reasons, but I think there is another one that is equally important.

    Many times I ask questions to make the other person think. I don’t even want an answer, in fact I already know the answer, what I want is to drive the other person to search for the answer.

    I know this blog is written from an information gathering point of view, but asking good questions is equally important when managing a team.

    Best regards

  3. Sylvia Santelli

    I remember learning that sometimes asking the right questions is more important than hearing the answer.  I’m understanding what that means more and more.  I think it actually reveals the empathy IQ of the asker– what are the true consequences of “this? and what will happen when “this” interacts with “that” or “them”– I believe good questions strive to understand real effects and impacts.

    Great blog, classic scene and classic riddle. +1


Leave a Reply