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Extreme questions to trigger new, better ideas

Extreme questions to trigger new, better ideas



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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 fo...

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...

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...

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?

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.

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...

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 le...

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 stru...

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 al...

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 decis...

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?

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 pri...

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 organisat...

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?

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 b...

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