Are You Asking the Right Questions?

The least appreciated and most valuable skill is asking the right questions. Without this skill, you will waste your time solving the wrong problems.

Unfortunately, Question Askers are often viewed with derision. You schedule a quick 20-minute meeting to verify the budget numbers for next quarter, and some annoying Question Asker asks, "How much longer can our business survive by shipping outdated, overpriced products?"

What an idiot, you think. Except he is asking precisely the question you should be asking. You are annoyed because you set aside twenty minutes to preserve the status quo, rather than an extended period to set your business up for ten years of profitable growth.

When we worked together, my friend Don Peppers used to sometimes say that I reminded him of George Ball, President Lyndon Baines Johnson’s under secretary of state in the 1960's. Ball was always asking questions about the policy of escalation in Vietnam. Johnson usually listened carefully to Ball, appreciated his questions, 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 - will lead you into a box. They are the reason why seemingly successful companies fade into obscurity, and why 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 give you a simple rule of thumb that will lead you in the right direction:

Ask why, three times in a row.

I still remember when our kids were at that amusing stage in which they asked, "Why?" incessantly. First it seemed cute, then it grew annoying.

Over the long run, I learned that asking "why?" three times in a row often led to a deeper understanding of whatever you are considering.

There is a similar 5 Whys approach that comes out of the manufacturing industry, but five times is probably too much for daily use. If you ask "why" five times in a meeting, you are likely to end up with a Coke poured over your head. Stick with three, at least for now.

Bruce Kasanoff is a ghostwriter for entrepreneurs. 

He is the author of GIVERS DELIVER: Grow Your Career by Helping Others and also How to Self-Promote without Being a Jerk.