Asking Beautiful Questions: A Guide to Billion-Dollar Breakthroughs

Beautiful questions lead to billion-dollar breakthroughs:

- Uber: why do I have to wait for a crappy taxi?
- Amazon AWS: why is our IT a cost center, not a profit center?
- FedEx: what if letters could be delivered overnight?

Here are 12 concepts to ask beautiful questions:

— Michael Girdley (@girdley) June 13, 2023

* Challenger Questions

Experts often get things wrong because expertise cements their perspective.

A famous study on forecasting found that experts perform on par with “dart-throwing chimps.”

Knowing less about a topic lets you question assumptions more easily.

Do this with…

— Michael Girdley (@girdley) June 13, 2023

* Role Play

Ask questions like you’re someone else.

What would Jack Welch ask? Neil Patrick Harris? Elmo? Elmo on drugs?

It’s a forced way to gain new perspectives.

As Peter Drucker did, an excellent way to be “ignorant and ask good questions,” as Peter Drucker did.

— Michael Girdley (@girdley) June 13, 2023

* WWH

Most questioners get stuck in the details and limit themselves to what seems possible.

The “Why, What If, How” framework helps you break through to action.

Ask:

Why? (are we doing it this way?)
What if? (we could do things differently?)
How? (would we make it happen?)

— Michael Girdley (@girdley) June 13, 2023

* Vuja De Lens

Deja Vu is seeing something new, but it’s somehow familiar.

Vuja De is looking at something familiar in a new way.

Step back and pretend you’ve never seen them before.

Use that to generate new perspectives and new questions.

(This is very George Carlin.)

— Michael Girdley (@girdley) June 13, 2023

* 5 Whys Technique

Toyota invented this.

Ask why questions five times in succession of any problem.

Gets to the bottom of the issue.

— Michael Girdley (@girdley) June 13, 2023

* The Sticky Question

We all have questions that we just can’t shake.

If you just can’t seem to let it go,

That’s one to keep probing.

Your subconscious has flagged it as important.

Come back to it from new angles and perspectives.

— Michael Girdley (@girdley) June 13, 2023

* Question Storming

Imagine brainstorming.

But instead of creating ideas, you’re asking more questions.

Try generating 50 questions on a problem with a team before shifting to ideas.

It forces everyone to see new perspectives.

New perspectives get you breakthroughs.

— Michael Girdley (@girdley) June 13, 2023

* School beats questioning out of you

We learn that answers are more valuable than questions.

Good in school.

Bad in life.

Real problems aren’t multiple choice with right/wrong answers.

They involve exploration and questioning.

We have to overcome the way school “broke” us.

— Michael Girdley (@girdley) June 13, 2023

* Killer Questions

Key questions you should have in your inventory:

What if our company didn’t exist?
What if you couldn’t fail?
Why am I the lucky buyer?
How would a child picture this?

Your quiver of arrows.

When you hear a great question, add it to your repertoire.

— Michael Girdley (@girdley) June 13, 2023

* Question Assumptions First

Most analysis fails in the assumptions.

Data is concrete. Logic is easy.

But bad assumptions will lead you wrong.

As a boss/leader, you want to probe assumptions first and foremost.

— Michael Girdley (@girdley) June 13, 2023

* There are Bad Questions

They say, “There are no bad questions.”

That’s wrong.

Bad questions are where the asker didn’t think critically in preparing it.

Notice how those are the ones that piss you off?

As a leader, you want to encourage good questioning as an org.

— Michael Girdley (@girdley) June 13, 2023

I was inspired to spend a week researching world-class questioning by @brentbeshore. (Thanks, BB!)

I learned these by reading two books. pic.twitter.com/yXgIC7uB1V

— Michael Girdley (@girdley) June 13, 2023

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— Michael Girdley (@girdley) June 13, 2023