Most teams do not struggle to generate ideas. They struggle to escape the assumptions that shape their everyday work.
In a typical workshop, people bring existing priorities, known constraints, familiar customer feedback, and previous decisions. That is useful—but it can also make thinking narrow. The same safe questions tend to produce the same safe answers.
Extreme questions are a practical way to disrupt this pattern. By changing one condition dramatically, facilitators give participants permission to explore possibilities they might otherwise dismiss too early.
The point is not to implement the hypothetical literally. The point is to identify what it reveals—and turn that insight into a practical experiment, decision, or improvement.
Below are 15 questions to use when your team needs a new perspective.
1. What if we had to charge ten times more?
Imagine that your price, budget request, or perceived value had to increase tenfold.
What would need to be exceptional? Which audience would see that higher price as worthwhile? Would the experience, quality, relationship, or outcome need to change?
For public-sector and internal teams, reframe the question: What would make this service so valuable that people would actively choose it over every alternative?
This prompt helps a group identify its strongest sources of value—and distinguish “nice to have” work from what truly matters.
2. What if we had no existing users or customers?
Imagine you were starting from zero, with all the knowledge you have today but none of the old commitments.
What would you build? What would you stop doing? How would you explain your offer clearly to the people you want to reach?
This is useful when a team is held back by legacy systems, old policies, or features that no longer earn their place. It creates space to ask: If we were not already doing this, would we choose to begin now?
3. What if no support was available?
Suppose no one could answer questions, solve problems, or guide someone through the process.
Could people still succeed? Where would they get stuck? What information, choices, or actions should be clearer or easier?
This question shifts the focus from fixing individual mistakes to improving the system itself. It is particularly helpful for service design, onboarding, self-service, and internal processes.
4. What would be the most fun thing to create?
Ask the team to name something that would genuinely excite them to build—provided it still serves the wider purpose.
Fun is not a substitute for strategy. But it is often a signal of energy, curiosity, and latent expertise. A playful idea might point to a better user experience, a simpler process, or a valuable capability the team has not yet prioritised.
Try following this question with: What could we prototype in one week?
5. What if a competitor copied everything we do?
Imagine another organisation can duplicate every feature, process, or visible offering.
Why would people still choose you?
The answer may lie in trust, ease of use, community, relationships, quality, speed, purpose, or the way you respond when things go wrong. This question helps teams look beyond a feature checklist and articulate their real differentiation.
6. What if we had only two weeks?
Assume that in two weeks, you must deliver a small but complete version of something that would delight a specific group of users.
What is the simplest useful version? What can be manual at first? What detail, polish, or scale can wait until you have learned whether the idea works?
This is a powerful antidote to over-scoping. It invites teams to focus on learning quickly rather than trying to perfect everything before sharing it.
7. What if we had to use a completely different business model?
For a business, this might mean moving from subscription to usage-based pricing, or from paid access to a different value exchange.
For other organisations, it could mean changing how resources, responsibilities, access, or outcomes are structured.
Ask: If the current model disappeared, how else could we create and sustain value?
This prompt exposes assumptions about who benefits, who pays, what costs are necessary, and what people truly value.
8. What if we were not allowed to have a website?
If your usual communication channel vanished, how would people find, understand, and trust what you offer?
Would they hear about it through peers? Partners? Communities? The product or service itself? Could the experience generate advocacy naturally?
This question helps teams move beyond treating communication as a separate activity. Every interaction can either build understanding and trust—or create friction.
9. What if meetings were no longer allowed?
Imagine that synchronous meetings disappear.
How would people make decisions, share context, onboard colleagues, resolve questions, and maintain relationships? What documentation or routines would become essential?
This exercise often reveals knowledge that is trapped in conversations and decisions that lack a visible rationale. It can lead to more inclusive collaboration by giving people time to reflect and contribute in different ways.
The goal is not necessarily fewer meetings. It is better use of meetings—and better systems for the work that does not require one.
10. What if we could never speak to users or customers again?
This is an intentionally uncomfortable question. Without interviews, calls, or direct feedback, how would you know whether you were helping?
What behaviours could you observe? Which outcomes would show that the service is useful? What lightweight tests could help you learn before investing heavily?
The exercise encourages teams to define meaningful evidence of value. It also highlights that stated preferences and real behaviour are not always the same thing.
11. What if cost were no object?
Imagine you could spend whatever it took to create an outstanding experience.
Would you offer a personal guide, faster access, tailored support, a seamless end-to-end journey, or something entirely different?
Once the group has described the ideal, ask: Which part of that experience could we deliver in a sustainable way?
Often, a seemingly extravagant idea contains a simple principle that can be implemented affordably.
12. What if leadership could make any decision without resistance?
This question must be handled with care. Its purpose is not to ignore the human impact of change, but to surface decisions the team may be avoiding because they feel difficult, unpopular, or disruptive.
What would you stop, start, merge, simplify, or redesign? Are there projects, products, or habits that no longer support the strategy?
Then bring the conversation back to responsible practice: How could we pursue the useful part of this idea while protecting people, trust, and fairness?
13. What could cause a mortal wound?
What external event, shift in behaviour, security issue, policy change, competitor move, or loss of trust could seriously damage the organisation?
Do not use this prompt to create panic. Use it to identify a small number of credible risks and consider whether any actions would be wise regardless.
Sometimes resilience work is not only defensive. It can create a better service, a clearer strategy, or stronger relationships with the people who depend on you.
14. What if our only goal was to do the greatest good for the people we serve?
Set aside revenue, targets, and internal convenience for a moment.
How could you help people achieve their broader goals—not merely complete a transaction or use a feature? What would meaningful positive impact look like in their lives, work, or community?
This question reconnects a team with purpose. It can reveal opportunities that conventional metrics miss and give the group a stronger basis for making difficult trade-offs.
15. What if we could achieve only one thing this year?
If every other initiative had to pause, what single outcome would be worth the focus?
What would make the greatest difference? What would strengthen the organisation’s future? What would users remember?
This is one of the clearest prioritisation questions a facilitator can ask. It does not mean there is only one legitimate priority, but it forces the group to identify what it believes is most consequential.
How to run the exercise
Choose one to three questions that fit the challenge. Give participants five minutes of silent, individual reflection before opening discussion; this reduces groupthink and gives quieter voices time to develop ideas.
Capture all responses without evaluating them at first. Then ask the group:
What assumption did this question expose?
What idea surprised us?
What is the smallest real-world version we could test?
What should we stop, start, or investigate next?
Extreme questions work because they make the familiar strange. A facilitator does not need to have the answer. They need to create the conditions in which the group can see new answers together.
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