Useful Questions

Although this will sometimes lead nowhere, occasionally these seemingly obvious questions will lead you to a critical answer. Why? Because they seemed so "obvious" or "dumb" that no one ever asked them before (we're all too scared of looking foolish).

For further reading, in his chapter of Tim Ferriss' book, Tools of Titans, Malcolm Gladwell has a great explanation of why it's so important to ask "dumb" questions.

Similar to the previous point, these are questions that people fail to ask. Often the goofiest questions lead nowhere, but occasionally they uncover fresh, valuable insight.

We all make assumptions all the time, about everything. They're built into the thoughts we think and actions we take. And a lot of them are really valid and sensible. But not always. Stop regularly to check your assumptions and question them.

Ask: why do I assume that? Is that assumption true? What if I'm wrong about it?

This is another question related to assumptions. We often assume that certain things can't be done, because they've never been done before or because it would fly in the face of convention ("no one does it that way, so I shouldn't either"). And sometimes we imagine "rules" or constraints where they don't actually exist. But, by identifying these "rules that don't actually exist" we can sometimes come up with incredibly important solutions to problems. Here are some famous assumed constraints that turned out to be false (credit to Joseph Sugarman's book on ad copywriting for these):

This is a classic Tim Ferriss question. Imagine that you, or someone else, solves a major problem you’ve been working on in your business. And imagine that the solution ends up being extremely easy. Daydream about that for a little while. OK - now in your imaginary daydreaming scenario - how did you solve the problem so easily?

This is a techniques that Peter Thiel recommends using, in which you focus your mind with an impossibly tight deadline and imagine how you would handle it.

In other words, just because you lost $50,000 from your Apple stock going down, doesn’t necessarily mean that Apple needs to be the vehicle you use to make that money back.

Don’t get blinded by “sunk costs.” Instead, position yourself to best capitalize on the future, as opposed to entrenching yourself further in however you’ve done things in the past.

In other words, how would someone with a completely different frame of reference or experience level solve this problem? Or, “if I was completely new to this job or unfamiliar with this field - how would I approach this problem?”

This is a twist on the previous question. MacGyver was a late 1980's TV show about an extremely resourceful intelligence operative, who could solve crazy problems, when his back was against the wall, using everyday objects like duct tape or chewing gum. In this question, consider, "what would an extremely resourceful person do in this situation?"

Daydream about that. Then, consider, whether you or someone else could put your daydreamed solution into practice.

Ask the question and write down the solutions that you’d use if you had an unlimited budget. And then consider whether any of these solutions you come up with could be accomplished somehow within your actual budget.

Be creative – sometimes there’s a low-budget hack that accomplishes most or all of what the expensive solution does.

Sometimes social pressure is a constraint that holds us back. Give yourself the freedom of brainstorming without it for a change.

Look for ways that others have solved the same problems that your company faces – or similar ones. Can you draw from these examples to solve your own problem?