Learning how to ask compelling questions in a non-threatening manner is one of those unexciting but absolutely critical skills for an emerging leader to develop.  Questions are the leader’s lifeblood of information, and like most skills, learning to ask great questions in the right manner is something best learned through repeated practice. 

I’m not certain if my perspective is widely shared by those that measure intelligence and assess people for leadership potential, but I place a premium on observing an individual’s style and comfort in asking questions.  And while asking questions for clarification is a great habit, and something that every leader must encourage, the type of questions that I am looking for are those that I’ve not thought about before or that show that the individual is looking at a problem from different angles.  For lack of a better phrase, I will call these strategic questions.

Strategic questions tell me a lot about an individual’s and a team’s command of a complex topic.  When assessing new investments or new business directions, there will never be complete certainty for decision-making (and in fact, it may approach near-uncertainty).  In addition to understanding assumptions, I want to understand what it is that is not known…and what questions people wish they could answer with better clarity.  There is a great deal to learn in the unanswered questions as it relates to assessing risks and anticipating success or failure.

I’ve observed the questioning styles of many leaders, and some of them are…well, they are truly questionable.  These include: asking questions in rapid fire fashion, tagging on personal commentary and veiled insults, assuming a prosecutor-like pose where the receiver is certain that he or she is guilty of something, not waiting for an answer and many more.  Unfortunately, people learn from observing their leaders, and these bad habits and styles are passed on from generation to generation. 

The alternative is for you as the leader to develop and exhibit a positive style for asking questions and to reinforce this approach at every opportunity. 

Eight Suggestions for Developing Effective Questioning Skills (for you and your team):

  • Manage your tone and your facial expressions.  Focus on being calm and thoughtful when asking questions and make certain that your face does not betray you.  Any hint of irritation or impatience in your voice and you’ve damaged the communications event.
  • Ask open-ended questions and then be quiet until the answer is complete.  Sometimes it takes people a few seconds to form their thoughts or even to parse through your question to understand your request or intent.  Silence as the questioner is your best friend.
  • Ask clarifying questions to the answers.  This is a great active-listening technique and shows the other party that you are working hard to pay attention.
  • Summarize what you think you heard in the answer.  Another active-listening technique that allows the receiver a chance to clarify their answer.
  • If someone offers “I need to think about it” as an answer, provide them that opportunity, but don’t forget to close the loop.  Your willingness to not embarrass the individual into a spontaneous answer and your accountability in looping back for the follow-up will help strengthen your team’s working environment. 
  • Encourage people to ask you questions…and provide them opportunities to do just that.  This is not the “Any questions?” comment at the end of one of your meetings, but rather you creating opportunities for people to ask you compelling questions on key issues.  Of course, this only works more than once if people see that you are genuine.  Don’t show irritation if you don’t like the question or can’t answer it, and don’t judge the question.  The same rules apply for you…, you can think about a question, but make certain to loop back with an answer.
  • Build on one person’s questions in a group setting.  “Great question, Sarah.  Let’s answer that one first and then I’ve got another that jumped to mind based on your question..”
  • Encourage and reward intellectual curiosity that links to action.  Questions are great, and actions drive performance.  Turn great questions and subsequent ideas or directions into tangible actions as you pursue innovation or experimentation.  This will help fuel an innovation-oriented culture.

The Bottom-line for Now:

The right questions in the hands of a skilled practitioner yield new insights and new ideas.  It behooves you as a leader to develop your skill in this area, and it certainly behooves you to create a culture that encourages and rewards questions and ultimately actions.  We learn by asking, listening and doing, but it often starts with being smart enough to figure out the right questions.  Too many leaders are great talkers and lousy listeners.  How skillful are you at asking and learning from your own questions?