Add a little spice to your questioning!

Spicy questions

A wise person once said:

“He who asks a question is a fool for a moment. 
He that does not ask a question remains a fool forever.”

Harsh words perhaps, but brimming with truth. 

However, as critical as questioning is, to developing a strong understanding of another person’s challenges, priorities and goals, it can also be tiring, wearying even, for both the person being questioned and the person asking the questions.

Consequently, it is important to be able to vary your questioning approach and add interest and surprise to your questioning.  This is where Spicy Questions can be so useful.   

Spicy Questions add a certain piquancy to a conversation.  They are designed to unblock conventional thinking and identify new information and ideas.  Like spices, they should not all be added in to the mix at the same time – use sparingly and add at the right time.  

Spicy Questions come in seven flavors and have different uses:




Encourages the creation of a forward vision.


A longer timeline, aiming to understand what really drives a person at a deep level.

No barriers

Creates an ideal, typically unrealistic, future vision that encourages radical thought. 


Take a current situation and stretch it beyond what is reasonable.

Positive / Negative

Asking for positives cushions questions about negatives.


To jolt someone’s thinking and challenge complacency.


To ask about a sensitive topic without the question appearing as your question.


“What do you think will be different in three years’ time?”

 “How would you like to see things progress over the short, medium and long term?”

“What are the key strategies for the next 1, 3 and 5 years?”

The simplest of Spicy Questions.  Simply ask a question with a future timerame attached.  A simple way of getting someone to map out how they would like to see things progress.


“Your face is on the cover of xxxx magazine.  What does the headline say?”

“You’re retiring after a successful career, what will you say in your leaving speech”

 “What do you want to be remembered for?

A longer timeline question that encourages thinking about what is left behind.  Targets the things that people hold most important.

No barriers

“If cost was not a factor, how would you approach this?”

“If you were given all the time and resources you needed what could you achieve?”

 “If you had your time over again, what would you do differently?”

Useful where the other person cannot see beyond making small improvements to the current situation.  This will help them see that there is potential for a significant improvement in the situation, even if the initial response to the question is unrealistic.  Can also be helpful in uncovering deeper desires.


“Suppose you doubled everyone’s targets, what do you think would happen?”

“Could you achieve five days from order to delivery?”

“What would happen if we cut next year’s budget by 90%?”

Stretch takes an existing situation or target and stretches it – beyond the point of reason, to encourage new perspectives.  Often the other person will resist the full stretch, but, when they disagree with the stretch suggestion, they often back-track to a more realistic position, but one that is still further advanced than the point where the question started.

Positive / Negative

 “I understand business is going well – what do you see as the biggest achievements of the last year?”
 followed by
“and what do you need to do to ensure continued growth?”

“Selecting a partner is a big decision – what do you see as the most important criteria?”
 followed by
“and what sort of things would disqualify someone in your mind?”

This question engages the other person’s by asking them to discuss positive aspects of a topic.  This also builds an environment that facilitates then asking about potential negative aspects.

To add a bit of rigour, ask for three positive and three negative responses.  This encourages the other person to think more deeply, leading to better insights. 

For example:

“What are your three biggest hopes for this project, and your three biggest fears?”


“If the government mandated zero-carbon production, how would you comply?”

“If there was a major flood or other natural disaster, how would you continue operating?”

 “If one of your competitors decided to offer their product totally free – what would that mean for you?”

This is a very useful question type when trying to help someone who is only looks at positives, or who is satisfied with the status quo.  You paint an extreme (and possibly unlikely scenario) that is beyond the other person’s control of the buyer.  If it was to happen though, it would have a major impact – and almost certainly a negative impact.

Note that the key difference between a Stretch question and a Shock question is that in a Stretch question, the goal is set by you.  In a Shock question, you have no control over the trigger event.


“I read an article last week that under-the-table inducements are increasing as the economy tightens.  Is that a feature of this market [industry or territory]?”

“I was at a meeting last week and someone made the comment that artificial intelligence (AI) is the next big thing.  Is AI having an impact in your industry?”

“When I was overseas recently and there was a lot in the press about how new agile entrants are disrupting many previously stable markets. 
Is that trend happening here [in your country]?”

Non-stick is a particularly useful approach when the subject you want to know more about is potentially sensitive.  The idea is to tell a story about something you have read, heard of, or seen elsewhere, and ask the other person their views on the broad topic – as opposed to suggesting that the scenario applies to them. 

The key is to keep the topic broad and not to ask “Does this apply to you?”!