Three Questions That Have Never Failed To Generate Creative Ideas for Me at Work

Making it easy, considering the opposite, and roleplaying through your idols

Photo by Brett Jordan on Unsplash

I love questions. One of my favourite books that I read last year was Warren Berger’s The Book of Beautiful Questions. In it, Warren identifies hundreds of questions, spanning different topics such as “what are the best questions for breakthrough ideas” or “what are the best questions for when you’re giving advice”. I wanted to share three questions that have helped me generate creative ideas at work.

What would this look like if it were easy?

This is a question I learned from Tim Ferriss and is similar to another question “if I had a genie who could magically make this happen, what would they do”. It’s a question that asks you to eliminate all barriers, obstacles and challenges and to picture yourself at the finish line.

What happens when you ask yourself this question is you start to get ideas of how things could work. And when you imagine how things could work, your brain goes into overdrive thinking about how it can make what you imagine into a reality.

What if the opposite were true?

Another great question I learned from Tim Ferriss but it is applicable to many situations.

For example:

  • What would it take for people to hate to leave work?
  • What things don’t I like doing? What if I didn’t do them?
  • What would happen if I did this in an opposite way?

To that last question, Tim Ferriss worked a sales job where he competed with other sales representatives to contact executives to sell them products and services. He asked himself the last question, and instead of competing with other sales representatives, he decided he would call between 6–8 in the morning and 6–8 at night. He found that the gatekeepers (secretaries) wouldn’t be working during those times and he could speak with the CEOs and CFOs directly. This meant he was getting much better results getting through to the key decision-makers while working fewer hours (4 hours compared to the normal 8 hours).

How might I approach this if I was Jerry Seinfeld? Steve Jobs? Elon Musk?

Sometimes it helps to imagine a problem or situation from the perspective of someone you admire.

  • Jerry Seinfeld has a way of looking at things where he points out the absurdity of the situation. For example, one of his jokes is that dogs would be rich if only they had pockets. Why? Because they walk around, they see all this change on the ground, but they don’t have any pockets to keep them in.
  • Steve Jobs has a deep understanding of what customers want, even if they can’t express it themselves. Although the iPod was incredibly successful, he saw that customers had an iPod, a phone, a notebook and other things they would carry with them, and Steve asked himself why he couldn’t combine all of those things together to make it easier on the customer.
  • Elon Musk looks at things from the first principles approach (i.e., looking at the fundamentals and building from the fundamentals). Looking at the insane costs of NASA rockets, he looked at the different materials comprising the rockets and found that there was a significant gap between the two. And when he looked at the NASA rockets, he couldn’t figure out why they were so much more expensive. In other words, there was an opportunity for a competitor to make cheaper rockets: enter SpaceX.

This post was created with Typeshare

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