Writing at the Harvard Business Review website, Dan Pontefract, head of learning and collaboration at the Canadian telecommunications firm TELUS, delivers an important if familiar message about how leaders need to develop a reflex for asking questions. “Perhaps the first step toward a better future for your organization is to acknowledge that you don’t necessarily know the way there — and, just as important, to understand that by asking questions, you not only awaken and engage people, you stand to collect more valuable perspective and ideas than you would by starting from a position of authority.”

OK, great. But what questions do you ask, and how do you ask them?

There’s no such thing as a dumb question. But I think we can agree that some questions are smarter than others. Reporters like myself struggle with this: Depending on the context, you sometimes ask head-on, sometimes you approach indirectly, sometimes you ask a “dumb question” on purpose. Sometimes you shut up and let people fill in the gaps. Whatever works.

But there are more structured ways to go about it. In their new book, Decisive, Chip and Dan Heath (the latter the Closing General Session speaker at ASAE’s Annual Meeting) spend a little time discussing the fine points of asking questions. They break questions down into two types: probing and open-ended. A probing question is designed to extract specific answers about specific problems from people who are in a position to provide detailed information. As an example, the Heath brothers discuss a study to find what question would help people learn about a defect with an iPod while shopping. “What can you tell me about it?” was a clunker. “What problems does it have?” got sellers talking.

An open-ended question, by contrast, is meant to get answers when the nature of a problem isn’t quite known and—this is important for leaders—to avoid questions that only serve to confirm the biases of the person who’s asking. The example here is a doctor who asks a patient “What was the pain like?” instead of assuming a peptic ulcer and then poking abdomenward.

When do you ask which type of question? The Heaths write: “A good rule of thumb is to ask yourself, ‘What’s the most likely way I could fail to get the right information in this situation?'” For a leader who’s trying to learn something from their staffs and their members, I think specificity is the path to failure here. Pontefract details TELUS’ experience launching an initiative to improve its customer relations. The company management asked rank-and-file staff to share what they were hearing from customers. That resulted in 1,000 responses, which management whittled down to four “Customer Commitments.” The post doesn’t detail what specific questions were asked, but that level of response doesn’t happen unless the question is both relevant and open-ended. I’m betting it was something along the lines of “What are you hearing?”

I’ve written before here about how leaders are prone to working in bubbles. A good first step to avoiding that problem is to mix up the people who you meet and draw on for insight and information. A good second step is to think about what you ask. Are you looking for the facts, or just reassurance?

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