How to get unblocked: Ask yourself some Extreme Questions

Ever feel like you’re stuck in a rut? That brainstorming (especially online) feels like hard work? Or that fresh ideas actually… aren’t? Yep, me too. Miserable, isn't it?

Instead, here’s a more extreme approach we've found to be very effective.

Ask yourself and your team some Extreme Questions.

We stumbled across this wonderful blog post by Jason Cohen that outlines 13 (lucky for some) prompts:

1. What if you had to increase your prices by 10x?
2. If you were never allowed to provide any technical/customer support, what would have to change?
3. What would be the most fun thing to build?
4. If your biggest competitor copied everything we had, how would you still win?
5. What if you only had 2 weeks to ship something?
6. What if you were forced to charge customers in a completely different way?
7. If you had no website, how would you still grow your business?
8. What would you do if you couldn’t have any meetings?
9. If you could never talk to customers again, how would you figure out what to build?
10. What if it didn’t matter how unprofitable you were? What if you could spend 100x more money?
11. What if you could change anything about the company, regardless of what anyone thinks or feels?
12. What external issue could kill the entire company?
13. What if you could only ship one thing this year?

As for what to do with these prompts, here’s how we tackled them:
- Each Wavetable team member individually wrote their responses (limited to a few mins for each)
- I tagged them on anything that was particularly interesting, unclear, or curious
- After a round or two of clarifying/amplifying, we collated everyone’s responses and created a composite ‘highlights’ version
- We ran a shaping session on how each of these possibilities could manifest, with a couple of versions for each
- The most promising ideas went forward into development

A lot of surprises emerged.

One was that I quickly found I had a couple of 'favourite' Extreme Questions (Company Killer, and No Talking to Customers).

How about you?

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