The Art of Strategic Questions

How to learn more in less time.

How effective are you at asking thought provoking, compelling questions?

Asking great questions is an art.  Yet how often do we pause to consider our effectiveness in this small leadership skill?  Because in the last few episodes I’ve focused on practices in which asking great questions is essential.

When you consider collaboration, or empowering, delegation or coaching effectively, one of the most valuable communication skills you can demonstrate is asking questions.

When you think about it, questions serve many purposes, they help us to:

  • Gather information
  • Get engagement and cooperation
  • Persuade and influence
  • Garner commitment

All in all they help to connect us with others, to create trust and a meaningful bond.  Because we are deepening our insights into someone’s’ thoughts, their perspectives, their reality, their interpretation of the world, and even their emotions.

So powerful.  How effective are you at asking great questions?  It is an art.  The right question at the right time to the right person can be momentous in their subsequent thinking and actions.

Here are 4 elements of strategic questions, they:

  1.   Are thought provoking and framed in an open manner, i.e., what, how and tell me about. Caution: “Why” questions can evoke defensiveness and imply judgment, e.g., “Why was the report late?” or, “Why didn’t you stay late to finish the report?” Limit closed ended questions and avoid leading questions.
  2. Inspire self-awareness and self-reflection:  Effective questions should prompt others to pause.  Let them.  Increasing awareness & reflections are instrumental to growth and change.
  3. Stretches the individual’s perspective:  They help others to realize their impact on a situation, another person, or the bigger picture.
  4. Can be hindsight or foresight oriented for growth discussions.  Hindsight looks back at strengths, development areas, values, interests, etc.  While foresight questions focus on looking at changes to the future of the industry or company, both internal and external.

Example:  You want to ask an individual to think about their growth and development.

You could ask:  “What are you most interested in doing?”  or,  “What do you really enjoy?”

The answers can potentially be all over the board, with the answers sometimes focused, sometimes not.

A more strategic question could be:  “What changes do you see in our business in the next year and what are you most excited to learn?”

In phrasing the question in this manner, I set an expectation that #1 change is coming, #2 that there is an expectation of growth, and then #3 capturing their thoughts about growth?  (And how aligned is their thinking with my thinking?)

I think the true brilliance of being a great asker of questions is to be a truly mindful listener.  They go hand in hand.  Is your mind cluttered and distracted as someone is talking to you, and sharing their point of view?  Or are you fully engaged in the discussion.  Understanding what is said, and also what is not being said directly.

Because how we continue to dive deeper into someone else’s perspectives, we have to remain committed to the experience.  (See link in EP 13 on Listening Styles; when asking questions use therapeutic or active for best results.)

So as you look within and consider your skills:  How would you rate your effectiveness around asking strategic questions on a scale from 1-5 (1 low)?  When will strategic questioning be most valuable to apply?  When can you do more of it?  How can you increase your focus on asking great questions?