59 thought starters to crack your big idea

Sometimes all you need is just the right question to kick your idea back on track. This is less a guide and more just a litany of questions if you get stuck. I recommend going through each of them and letting your mind wander on the answer.
If you to go hardcore, come up with five answers to each one. Just a few lines might do. It might take you a few sessions, but at the end you’ll have over 250 ideas. Whenever that seems daunting, I always think of how nice that would be to start with in the morning.

Experience

  • What is it like to use the product?
  • How can you convey the experience without using it?
  • How can you share someone's experience using it?
  • Do you need to challenge people to use it?
  • What happens if you challenge people to not use it?
  • What is a shocking demonstration of its benefit?

Value

  • Does the product give a lot of something good?
  • Does the product take away a lot of something bad?
  • How is the product the unique in what it does?
  • In what situation is your product the hero?
  • Why is it okay to not be better than competitors?
  • What is the unexpected alternative of your product?

Feeling

  • What is the emotional benefit of the main feature?
  • What is the emotional state before using the product?
  • What is the emotional state after using the product?
  • What emotional weight remains from not using it?
  • What is the emotional weight that's lifted from using it?

Spokespeople

  • What character could embody your core message?
  • How can you share an influential person's experience?
  • Who is the most interesting person to support it?
  • Who is the most unexpected person to support it?
  • What is interesting about a normal person using it?
  • What's uninteresting about someone special using it?

Customers

  • Who are the most diehard users of your product?
  • Who should be the most diehard users of your product?
  • Who needs your product that doesn't care about it?
  • Who inspires you to make your product better?
  • Who inspires your customers to make themselves better?

Mission

  • How does this product embody the brand's mission?
  • How does this represent the core values of the brand?
  • What did it take to arrive at this product?

Entertainment

  • How can you adopt another category's look and feel?
  • How can you turn it into a parody?
  • How can you make it the hero of a short film?
  • How can it be in the background of a short film?
  • Can you make your audience part of the story?

Humor

  • What's funny about your serious product?
  • What's serious about your funny product?’
  • What is the most ridiculous way to convey the benefit?
  • What ludicrous scene makes your benefit memorable?

Appearance

  • Why is the product unexpectedly beautiful?
  • What happens if you make the product ugly?
  • How would your product be presented in a museum?
  • What would we learn if we looked really close?
  • What is something obvious we're missing?

Society

  • What would a world look like based on your product?
  • How would our world change if everyone used it?
  • How would our world change if nobody used it?
  • What needs to change for your product to be ubiquitous?
  • What would happen if this product existed 500 years ago?

Support

  • Whose achievements can you authentically praise?
  • Who can you authentically support to improve the world?
  • What cause does your brand have a right to stand for?
  • What can your brand no longer stand for?

Honesty

  • What does your product not apologize for?
  • What is the unfiltered truth of your product?
  • What did your haters get right about the product?
  • What do your fans love that nobody else understand?

If All Else Fails

  • What is the clearest description of what your product does?