How to ask better questions

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I first learned the power of questions when I was hired into a software engineering company as one of the first, and few, non-engineers.  Most of what was discussed was over my head. I had three options: pretend I understood, remain silent in the hope I “didn’t get called on,” or ask a question. It quickly became apparent that I would learn nothing from options one or two and if I was to swim rather than sink I had to learn and learn fast. I soon determined that there was great power in being the most ignorant person in the world just so long as I asked smart questions. These questions often clarified the discussion and even surfaced hidden assumptions. Thus questions became my most powerful tool as they helped me learn and helped focus discussions.

After being exposed to the Socratic Method I learned that asking the right question of the right person at the right time was extremely powerful. I also learned that making statements can make people defensive, whereas if you phrased the statement as a question it made people think.

The Wall Street Journal article The Secret to Asking Better Questions by Hal Gregersen, sub-titled Most bosses think they have all the answers. But the best bosses know what to ask to encourage fresh thinking. Here are six ways to build that skill drew my attention. Here are the six ways to ask better questions, annotated from my own experience.

1. Understand what kinds of questions spark creative thinking. There are five ways a question can break down barriers to creative thinking: It reframes the problem. It intrigues the imagination. It invites others’ thinking. It opens up space for different answers. And it’s nonaggressive—not posed to embarrass, humiliate or assert power over the other party. What I’ve found is that the newspaper reporters six questions can often be the right ones to spark creative thinking: who? what? where? when? why? and how? Of these the question I ask the most is why? as it will reveal intentions and goals.

2. Create the habit of asking questions.

I find the sample questions in the article far too generic. The more specific the question the more specific the answer. Generic questions like “What more can we do to delight the customer at the point of purchase?” are far from penetrating. Better to ask, “what are we doing now at the point of purchase to better engage customers? Then a series of follow up questions: “What are our competitors doing?” “What do our POP programs cost us?” “Should we be evaluating these programs on a strict ROI basis or are the more long term strategic initiatives?” “How do POP programs relate to customer satisfaction at the point of consumption?” “How are we measuring customer satisfaction and when do we take these measurements?”

3. Fuel that habit by making yourself generate new questions.

Better yet lead your team into a question generating mode by setting an example for them and positively reinforcing the asking of questions. Keep in mind, “There are no dumb questions, only dumb answers.” Staff need to feel safe in questioning senior managements thinking and assumptions, otherwise they will suppress their questioning.

4. Respond with the power of the pause.

Silence is a very powerful tool. It can slow down a rush to judgement as well as stimulate more discussion. By the way, this is a technique interrogators use, as people naturally dislike silence and may talk when they should have held their piece!

5. Brainstorm for questions.

This can be an effective technique when a team is stuck. Rather than trying to brainstorm answers brainstorm questions. That may enable you to zero in on the real problem.

6. Reward your questioners.

If there’s one constant theme here, it’s the idea that bosses should reconceive what their primary job is. They aren’t there to come up with today’s best answers, or even just to get their teams to come up with them. Their job is to build their organization’s capacity for constant innovation.

So whether you are a mentor, a manager, or an individual contributor, learning to ask more and better questions will help you and your team improve.

Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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