Ask Great Questions

The Basic Idea: Many would-be social media “influencers” employ the same ineffective strategy: they publish an unending stream of “smart things that I said.” No one likes a know-it-all.

Explanation: As a ghostwriter, I have learned that the least appreciated—but most valuable—skill is asking the right questions. Without this skill, you may waste your time solving the wrong problems, or running hard in the wrong direction.

For this reason, one of the most helpful things you can often do for another person is to suggest the right question when they need it the most.

“Have you ever thought about doing the opposite of what you’ve been doing?” is a lot easier to hear than, “My research says you are all wrong and you should employ my proven strategy instead.”

Every interesting book starts with a problem. After all, we need a bit of conflict to keep things interesting, right?

When we worked together, my friend Don Peppers used to sometimes say that I reminded him of George Ball, Under Secretary of State to President Lyndon Baines Johnson in the 1960s. Ball was always asking questions about the policy of escalation in Vietnam. Johnson usually listened carefully to Ball, appreciated his questions, and then ignored him.

I took this as a compliment, with full knowledge that it was not entirely intended that way.

Asking the right questions is never easy, because most people ask the wrong questions. This is not because they are dumb or naive. It is because the right questions often lead to more time, energy, and resources than seem to be available.

For this reason, the “most logical” short-term course of action is often to stick with the wrong questions. But such easy questions—and answers—often lead people into a box. They are the reason why seemingly successful companies fade into obscurity, and successful professionals “suddenly” find themselves out of a job.

For example, it is probably unwise to decide whether or not to take a new job on the basis of how much money you will make next year. A better question might be, “Which opportunity will most benefit me three years from now?”

Asking questions is both an art and a science, and I can’t claim to be an expert at this—but I can tell you it’s easier to help people by posing provocative and worthwhile questions than by sharing a constant stream of your own “wise” soundbites.

Example: Technically, this Guy Kawasaki tweet promoting his episode with the late Sir Ken Robinson isn’t a question, but by implication it is a truly profound one: are you playing it too safe?