Add some spice to your conversations

Sometimes conversations get bogged down. Conversation stalls, or continues, but in ever decreasing circles, focused on the immediate problem or task, but failing to take account of broader implications or future trends. Our tendency to focus on the immediate is further reinforced by cognitive biases such as groupthink and confirmation bias.
When this happens, Spicy Questions can help us break away from our current path of discussion and head off in a new direction that yields fresh insights and perspectives.
Spicy Questions come in seven flavors, with different uses:
Type
Use
Type
Timeline
Encourages the creation of a forward vision.
Future positive
Legacy
A longer timeline, aiming to understand what really drives a person at a deep level.
Future positive
No barriers
Creates an ideal, typically unrealistic, future vision that encourages radical thought.
Future positive
Strech
Take a current situation and stretch it beyond what is reasonable.
Future positive
Positive / Negative
Asking for positives cushions questions about negatives.
Future positive /
Current negative
Shock
To jolt someone’s thinking and challenge complacency.
Future negative
Non-stick
To ask about a sensitive topic without the question appearing as your question.
Current negative and sensitive
As with cooking, these spices should be used selectively. Use too much and they lose their impact. Your skill lies in knowing which question to ask at what point in a conversation.
One word of caution – not everyone responds well to searching questions. Before asking some of these types of question, take a moment to reflect on how the other person might react and consider asking permission.
You can evaluate and get feedback on the impact of your own behavioral preferences and consider how you would react to different questions by accessing the free preffr© behavioral questionnaire at prefrr.com. You can also use the prefrr© framework to reflect on the preferences of others and their impact.
Timeline questions are a simple way of encouraging someone to map out how they would like to see things progress. You likely ask similar questions to this already.
- “What do you think will be different in three years’ time?”
- “What would you want to be doing in two years that you’re not able to do now?”
- “How would you like to see things progress over the short, medium and long term?”
You can flex timeline questions for different people. Big picture thinkers prefer longer timeframe; more cautious or detail-oriented people prefer shorter time-frames. For organised people, think in terms of milestones.
Legacy questions are a specific form of timeline question that put forward a longer timeline to encourage thinking about what is left behind. They target the things that people hold most important and the feelings that are attached.
- “Your face is on the cover of xxxx magazine. What does the headline say?”
- “Imagine you’re about to retire after a successful career, what do you want to say in your leaving speech?”
- “Your grandchild is asking you what you did to make the world a better place. What will you say?”
No barriers questions are useful when the other person cannot see beyond making small improvements to the current situation. These questions help them see that there is potential for a significant improvement. They can also be helpful in uncovering deeper desires.
- “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 could choose when and how you work, what would you do?”
Optimists and big picture thinkers enjoy these types of question. They tend not to work well with cautious and detail-oriented people. Their response to such a question is likely to be along the lines of “That’s totally unrealistic” and they may not engage in the discussion any further.
Stretch questions take an existing situation or target and stretch it – beyond the point of reason, to encourage new perspectives.
You paint a picture of an extremely positive outcome, so positive that it is unrealistic. You do this to generate a shift in someone who finds it hard to think beyond their current situation.
- “Suppose you doubled everyone’s targets, what do you think would happen?”
- “How would processes have to change if we cut next year’s budget by 50%?”
- “What would need to change to achieve next-day delivery?”
Often, the stretch option in your question is rejected, but the compromise that follows is beyond where you would have landed, without the initial stretch.
The key here is an initial stretch that may not be credible, but is defensible. Then you choose not to defend the stretch too much.
Positive / Negative questions engage through asking a person to discuss positive aspects of a topic, then asking for negative aspects. Starting positively builds positive sentiment and increases the likelihood of a response to a question that targets negative aspects. This is a particularly helpful question for experts or consultants with a tendency to focus too much on “problems”.
- “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 service provider is a big decision – what do you see as the most important criteria?” followed by “and what sort of things would disqualify a provider in your mind?”
To add more depth, ask for three positive and three negative responses. This encourages the buyer to think more, leading to deeper insights. After each response you may have to gently nudge for the next. Your skill comes in knowing how far to push!
- “What are your three biggest hopes for this project, and your three greatest fears?”
One other consideration, if you are talking to a more cautious person, consider reversing the order and asking a Negative / Positive.
- “What would be the worst-case result?” followed by “and what would be the best-case?”
Shock questions are useful where you are trying to move someone who only looks at positives, or who is satisfied with the status quo.
You describe an extreme and unlikely scenario that is beyond their control – something that is external to them and their organization. If it was to happen though, it would have a major impact – and almost certainly a negative impact.
- “If there was a major pandemic, how would your business adapt?”
“If regulations changed and outlawed cold-calling, what would that mean to your business?” - “If one of your competitors decided to offer their core product totally free – what would that mean for you?”
Shock questions are enjoyed by cautious people who like to plan for disaster, but more powerful with opportunistic people who otherwise often fail to anticipate possible bumps in the road ahead.
- “When I was in the US recently there seemed to be a lot in the press about how less face-to-face interaction is making it difficult to win new customers. Do you see this in your industry?
- “I was at a meeting last week and someone made the comment that younger customers are increasingly questioning the social and environmental impact of how goods are produced and transported. Do you see this happening in your market?”
Non-stick questions have a very specific use. They should be used when the topic you want to introduce is potentially sensitive and may generate a negative response. With a properly constructed Non-stick question, any negative sentiment attached to the question does not attach to you.
Non-stick questions work by introducing the sensitive topic as something that you have read, heard of or seen elsewhere. You then ask the other person’s views on the broad topic – as opposed to suggesting that the scenario applies to them.
- “I read an article last week that talked about the increasing use of snooping software by employers to monitor employees working from home. Do you see this happening in your [industry or territory]?”
- “When I was in the US recently there seemed to be a lot in the press about how less face-to-face interaction is making it difficult to win new customers. Do you see this in your industry?
- “I was at a meeting last week and someone made the comment that younger customers are increasingly questioning the social and environmental impact of how goods are produced and transported. Do you see this happening in your market?”
Be careful not to focus the final part of the question onto the person you’re talking or their organization.
- “I read an article last week that talked about the increasing use of snooping software by employers to monitor employees working from home. What do you think about this?”
- “When I was in the US recently there seemed to be a lot in the press about how less face-to-face interaction is making it difficult to win new customers. Is that something that concerns you?”
- “I was at a meeting last week and someone made the comment that younger customers are increasingly questioning the social and environmental impact of how goods are produced and transported. Is that a problem for you?”