For startups
- What if we could only ship one thing this year?
- What if we could change anything about the product, regardless of what anyone thinks or feels?
- If we simply decided to increase our prices by 10x, what would we have to do to justify it?
- What would we build if it didn’t matter how unprofitable we were? (Perceptive readers will notice that this question leads to the same answer if you were to ask, “What would we have the most fun building?”)
- If all our customers vanished, and we had to earn our growth and brand from scratch, what would we do?
- If we were never allowed to provide tech support, customer support or guidance, in any form, what would we have to change?
- If we could never talk to our customers again, how would we figure out what to build?
- If we decided to not have any synchronous meetings ever again, what about our work would need to change?
- If we were forced to shut down our top two marketing channels, how would we still grow the business?
- What if we were forced to ship a finished product in just two weeks? Knowing what we know now, what would change in our MVP?
- What if we were forced to charge customers in a completely different manner?
- If our biggest competitor copied every single feature we have, how would we still win?
- What changes in the market could kill the entire company?
For Careers
- If you could only work on one product or service for the rest of your life, what would it look like?
- If you were allowed an indefinite timeline, capital, and resources to work on a creative project within your company, what problem would you take up?
- If you were forced to never manage your employees again, what about your hiring process would change?
- If you had no stakeholder buy-ins to worry about, what feature would you ship?
- If you had all the money in the world and weren’t worried about getting paid, what would you work on?
- If you could only work with two other professionals to ship a project, what would their skillsets be? (You can ask this question for any new project you undertake.)
- If you could only learn one new skill for the remainder of your life, what would it be?
- If salary hikes were not a thing while switching jobs, would you still switch?
- If you had no manager managing you, how would your work change?
- If the depth and breadth of learning was your only goal, what job would you take up?
- If promotions didn’t exist and you could only get a different role by switching jobs, in what ways would it change the way you think about your career?
There are no wrong answers, only surprising realisations. Life is not binary or black and white, but takes a multitude of shades and approaches based on your unique context.
What part of your context are you missing currently? Try answering these questions and they may shock you out of your blindspots.
I’ll see you tomorrow.
