Extreme questions to trigger new, better ideas - Deepstash
Extreme questions to trigger new, better ideas

Extreme questions to trigger new, better ideas

Curated from: longform.asmartbear.com

Ideas, facts & insights covering these topics:

15 ideas


537 reads


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Brainstorming is hard

Brainstorming is hard

We’re blinded by our daily work. We see the trees, not the forest. We focus on an idea that we've had for a year, the familiarity of repetition undeservedly increasing its importance. We find it difficult to think past the last seven customer interviews or sales calls and while these are great for generating usable ideas, they only lead to small increments.

Extreme ideas can help you out of tiny thinking. Some ideas are so extreme that they border on nonsense, but the different perspectives can reveal distinctly new ideas.


83 reads

10x prices

If you were forced to increase your prices by 10x, what would you do to justify it?

  • What type of brand looks and feels like something that is expensive? How would the design of both the website and the product need to change?
  • What part of your market would you have to target? Do they have different problems or needs?
  • What expensive services might you need to supply?


64 reads

New customers

If you had to earn your growth and brand from scratch, what would you do? We often become complacent with our marketing, or we never get around to having a truly compelling unique positioning statement.

  • How would you distinguish yourself with a unique compelling message? Would you use a different pricing model?
  • Would you throw out some features? Would you build some new features that would make you more competitive?


51 reads

No tech support

If you were never allowed to provide tech support in any form, what would you have to change?

  • How would onboarding need to improve?
  • Where would the product need to provide the user with more control, since they can’t ask?


52 reads

Maximize fun

Maximize fun

What would be the most fun thing to build? What feature do you think would be cool for customers to use? What technology would be fun to work on?

It has to be something that makes your product better, not random or unrelated.


45 reads

Complete rip-off

Complete rip-off

If your biggest competitor copied every feature you have, how do you still win? Creating a bigger and more emotional distinction is a powerful way to win.

  • Is the answer inside your product, in something other than the utility of the features? What is it, and how could you make more of that?
  • If the answer is outside of our product, where is it? Is it a higher purpose or brand promise that your customers buy into?


40 reads

No time

What if you had to have a new feature in just two weeks that would delight and surprise a fraction of your customer? Every bit of complexity has to be stripped out, the scope needs to be reduced to a minimum.

A 1000-page book can be summarized in a 40-page Cliff’s Notes. The key lessons of Cliff’s Notes can be summarized in a 1-page blog post. The main theme and one unique perspective of the book can be summarized in one sentence. If we trade things off, It can always be smaller.


31 reads

Flipped business model

What if you were forced to charge customers in a completely different manner? If you’re usage-based, you’re forced to charge a flat monthly rate; if monthly with tiers, you’re forced to measure and charge daily with some formula.

Business models force you into certain thinking structures about how to monetize the value that you create. Shaking up the business model shakes up the value/cost equation. Sometimes a different business model is actually better for everyone.

  • How would you change how you position the value you deliver?
  • How would costs change?
  • Are there features that you’d need to build?


31 reads

No website

If you were not allowed to have a website, how would you still grow your business?

  • Could you grow by word-of-mouth?
  • Could you create advocacy, as in channel partners or ambassadors?
  • Could your product be marketing?

Your advocates are already using your product, the product is already a platform for growth. What if “in-product marketing” is more impactful on growth than any useful feature?


24 reads

No meetings

No meetings

What if you don't have synchronous meetings ever again?

  • What if you had to onboard new employees without meetings, operate the software, or find where things are located? What systems would need to exist, and what materials would you need?
  • What if you had to make decisions without meetings. Is it possible that brainstormed ideas could be even better without meetings?
  • How would you create social ties and inside jokes and 1:1 as well as group relationships if you’re never in the same space at the same time?


19 reads

No customer contact

If you could never talk to your customers again, how would you figure out what to build?

  • Could you measure their behaviour so well that you could quickly measure whether any change was positive or negative? Are there clear signs of value or happiness that you could use?
  • Could you be even faster at testing new ideas?
  • What could you use online in what customers or competitors are saying, that would inform your strategy or product?


16 reads

Cost is irrelevant

What if it didn’t matter how unprofitable you were? How much value could you deliver if you thought of the product as an exercise in philanthropy?

It can be surprisingly difficult to convert money to real customer or business value, If there is a way, it might lead to a new pricing tier.


19 reads

Sociopathic CEO

What if you could change anything, regardless of what anyone thinks?

  • Terminating an entire product line would shake the organisation and possibly cause layoffs. What if it’s the best thing to do, regardless of that?
  • Pivoting the entire company could break the organisation, destroy trust in leadership, and cause people to leave. But what if that’s what's required to fix the strategy?


18 reads

Mortal wound

What externality has the potential to kill the entire company?

  • Can you think of a security breach that is so significant?
  • Or what if most of the customer base leaves within a year?
  • How could the economy change so that no one would buy your software?

Is there something you could do to mitigate the effects? Or something that pivots the company such that it is no longer a threat?


20 reads

Only one thing a year

Only one thing a year

What if you could only ship one thing this year?

  • What single initiative would make the most difference? 
  • What would generate the most revenue?
  • What would be so exciting that customers would stay even if other things are missing?

When you look back over years of a business, often the whole trajectory comes down to 1-2 big decisions per year.


24 reads



Clinical molecular geneticist


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