I’ve worked with some highly creative people during my career. I’ve also worked with very insightful thinkers, both in business and in academia. Oftentimes, the two skills overlap: creative people are also insightful thinkers and vice-versa. I’ve often wondered if creativity leads to insight or if insight leads to creativity. Lately, I’ve been thinking that there’s a third factor that produces both — the ability to ask useful questions.

Indeed, the title of today’s post is a quote from Pablo Picasso, who seemed both creative and insightful. His point — computers don’t help you ask questions … and questions are much more valuable than answers.

So, how do you ask good questions? Here are some tips from my experience augmented with suggestions by Shane Snow, Gary Lockwood, Penelope Trunk, and Peter Wood.

It’s not about you — too often, we ask long-winded questions designed to show our own knowledge and erudition. The point of asking a question is to gather information and insight. Be brief and don’t lead the witness.

You can contribute to a better answer — even if you ask a great question, you may not get a great answer. The response may wander both in time and logic, looping forward and backward. You can help the respondent by asking brief, clarifying questions. Don’t worry too much about interrupting; your respondent will likely appreciate your help.

Remember your who, what, where, when, how … and sometimes why — these words introduce open-ended questions that often result in more information and deeper insights. Be careful with why. Your respondent may become defensive.

Don’t go too narrow too soon — decision theory has a concept called premature commitment. We see a potential solution and start to pursue it while ignoring equally valid alternatives. It can happen in your questions as well. Start with broad questions to uncover all the alternatives. Then decide which one(s) to pursue.

Dumb questions are often the best — asking an (open-ended) question whose answer may seem obvious often uncovers unexpected insights. Even if you’re well versed in a subject, don’t assume you know the answer from the respondent’s perspective. He or she may have insights you know nothing about.

Be aware of your ambiguities — even simple, seemingly straightforward questions can be ambiguous. Your respondent may answer one question when you intended another. Here’s a simple example: what’s the tallest mountain in the world? There are two “correct” answers: Mt. Everest (if you measure from sea level) or Chimborazo (if you measure from the center of the earth). Which question is your respondent answering?

Think of parallel questions — I’m reading a Kinsey Millhone detective novel (U is for Undertow). One of the important questions Kinsey asks herself is, “why were the teenage boys burying a dog?” It gets her nowhere. But a slight tweak to the question — “Why were the boys burying a dog there?” — provides the insight that solves the mystery. (Reading detective novels is a good way to learn questioning techniques).

Clarify your terms — my sister is an entomologist. She knows that there’s a difference between a bug and an insect. I use the terms more or less interchangeably. If I ask her a question about bugs, she’ll answer it in the technical sense even though I mean it in the colloquial sense. We’re using the same word with two different meanings. It’s a good idea to ask, “When you talk about bugs, what do you mean?”

Think about how you answer questions — when you respond to questions, observe which ones are annoying and which ones lead to interesting insights. Stockpile the interesting ones for your own use.

Silence is golden — when speaking on the radio, I might say “over” to indicate that I’m finished speaking and it’s your turn. In normal conversation, we use body language and tone-of-voice to make the same transfer. Breaking the expected etiquette can lead to interesting insights. You ask a question. The respondent answers and turns it back to you. You remain silent. There’s an awkward pause and, often, the respondent continues the answer … in a less rehearsed and less controlled manner. Interesting tidbits may just spill out.

Don’t be too clever — Peter Wood probably says it best, “A few people have a gift for witty, memorable questions. You probably aren’t one of them. It doesn’t matter.  A concise, clear question is an important contribution in its own right”.