Real questions, useful questions, questions with promising attacks, are always motivated by the specific situation at hand. They are often about situational anomalies and unusual patterns in data that you cannot explain based on your current mental model of the situation, like Poirot’s letter. Real questions frame things in a way that creates a restless tension, by highlighting the potentially important stuff that you don’t know. You cannot frame a painting without knowing its dimensions. You cannot frame a problem without knowing something about it. Frames must contain situational information.

The same dynamic occurs at personal and global levels. Here are terrible personal questions:

How can I be happy? What career do I want? How can I lose weight?

Here are examples of corresponding questions that are useful:

Are people with strong friendships happier than loners? (Answer: yes) What is the top reason people leave jobs? (Answer: they dislike their immediate manager) What causes food addiction? (Answer: carefully-engineered concoctions of salt, sugar and fat)

Here are terrible global questions:

How can we create peace in the Middle East? What can we do about global warming? How can we reform Wall Street?

Here are potentially useful corresponding questions:

Do Israelis and Arabs communicate in different ways (Answer: yes) Why are summers getting warmer and wetter, while winters are getting colder and snowier? (Answer: I don’t know; climatologists might) Is the principle of limited liability a necessary condition for a free market economy? (Answer: I don’t know)

…

The Poirot Method: This is the basic trail-of-clues method of focusing on an anomaly that your current mental model cannot account for. Since my colleague Dave and I often argue about Poirot vs. Holmes, let me throw the Holmes camp a bone (heh!): the classic Holmes’ question of the “dog that didn’t bark in the night” is an excellent insight question. The Jack Welch Method: Also known as the “stretch.” You ask ridiculously extreme versions of ordinary formulaic questions. Instead of asking “How do we grow market share 3% in the next year?” You ask, “How do we grow our market 10x in the next 3 months?” The question so clearly strains and breaks the existing mental model that you are forced to think in weirder ways (the question is situation-driven because numbers like 3%, 1 year, 10x and 3 months will need to come from actual knowledge). The 42 Method: Sometimes the right answer is more easy to find than the right question. Entrepreneurs are often in this boat. They don’t know who will use their product or why, but they just know that their product is the answer to some important question somewhere. They are often wrong, but at least they are productively wrong. If you don’t get the “42″ reference, don’t worry about it.

Link