The Kind of Questions Leaders Ask: 7 Characteristics

Leaders not only ask questions – they ask GREAT questions of the people in their lives and on their teams. But, great questions carry certain characteristics. Among the essential skills of effective leaders is the ability to turn a good question into a great one. This involves understanding what makes a great question truly GREAT. The right question asked of the right person at the right time can do much to draw out fresh and meaningful insight, initiative and creativity. The wise leader today will use questions to challenge and inspire his team to greatness.

Asking rather than telling, questions rather than answers, has become the key to leadership excellence and success in the twenty-first century. Peter Drucker, considered the leadership guru of the twentieth century …, notes that the leader of the past may have been a person who knew how to tell, but certainly the leader of the future will be a person who knows how to ask. . . (from Michael Marquardt, Leading With Questions: How Leaders Find The Right Solutions By Knowing What to Ask (San Francisco: Jossey-Bass, 2005, pp. 23-24)

But, what characterizes truly “great” questions.? What sets them apart? Effective leaders recognize that GREAT QUESTIONS ARE:

#1 – Fueled by Genuine Interest. Paul the Apostle said: “Each of you should look not only to your own interests, but also to the interests of others (Phil. 2:3-4).” In other words, it’s time to improve your “interest” rate.

Refreshing your interest in the lives, the thoughts, ideas and opinions of the people around you requires a bit of wonder on your part. By this, I mean taking the time to wonder about other’s thoughts and experiences. Ask yourself:

  • I wonder how their day went today?
  • I wonder what their greatest joys are? Their greatest challenges?
  • I wonder what ideas and dreams they hold?
  • I wonder what they fear or worry about?
  • I wonder what they are hoping for?
  • I wonder what question they most need me to ask?

These questions and others work wonders when it comes to getting us out of ourselves and interested in others. They enliven our sensitivities and create an intrigue that inspires great questions and motivates great question asking. They inform our topics and inspire our tone.

#2 – Not Answered Merely with a “Yes” or “No”. Nothing will slow down a conversation much more than a pastor or leader that asks questions which can be answered with one word. Such questions are not just simple, they are simplistic. They merely search out facts while failing to engage the personalities, minds or opinions of another. The best questions are open-ended ones that inspire sentences of response.

#3 – Razor-Sharp. Great questions are those which effectively illicit a response. Vagueness will shut down openness and cut off responsiveness in communication. The best questions are those which do more than seek information, they seek specific information. If you were a youth pastor, for example, which of the following questions would you most want your senior pastor to ask you:

“So, what’s your vision for this new outreach anyhow?”


“If you and your team could do one thing to serve this community and be guaranteed it would succeed, what would you like to do?” (Notice how this question removes any concern of fear or failure that may hinder thinking?)

Few things are duller than a dull question. Keep them sharp by being specific.

#4 – Usually Not Begun with the word “Why”. Too often we tend to ask “why” questions much too early in a conversation. (I think it is one of the first ones we ask our parents as toddlers – “Why???”) Like a submarine suddenly electing to dive straight to the ocean’s floor without adjusting the cabin pressure, “why” questions tend to go for too much too quickly. They tend to suddenly overwhelm instead of carefully inquire. They storm into places where angels fear to tread, without thought or consideration of the readiness or responsiveness of the individual being asked.

For example, a husband may abruptly ask his wife, “Why are you so uptight?”

However, if he is wise, he may ask it this way: “You seem to have a lot on your mind. Would you like to sit down, have a cup of coffee and talk about it?”

It is clear which of these would garner the best response, is it not?

#5 – Sometimes Followed by a Pause. Don’t be afraid if your question is initially met by a little silence. Sometimes the most honest answers are preceded by a pause. (Some sociologists call this the “pregnant pause”). Instead of hurriedly interpreting quietness as non-responsiveness, give the question a chance to sink in a bit. The pause may mean they need a moment to think before responding. Perhaps your question is a penetrating one.

To hurriedly or nervously interject follow-up questions may short-circuit the genuine initial responses that need to be heard. Ask, and then wait. You may just be surprised at what you hear.

#6 – Drawn From Great Motives. Before you ask a team member a question, it helps to first ask yourself one: “What’s my motive? What is motivating me to ask this question of this person right now?” More often than not, the tone of a question is even more important than the topic. What is fueling the question? Is it curiosity? Boredom? Anger? Interest? Suspicion? Hope? Concern? Frustration? The motive behind a question colors the tone in which it is asked.

“A word aptly spoken is like apples of gold in settings of silver (Prov. 25:11).” In other words, asking the right question of the right person and the right moment with the right tone for the right reasons can produce something amazing.

#7 – Provocative. Great questions provoke us to think and to action. The story is told of a young CEO, Steve Jobs, who was trying to build his executive team in the early days at Apple Computer. When he met with one executive he had his eye on at PepsiCo he found himself struggling to find a way to convince the well-paid corporate leader to make a mid-life career change. As a last ditch effort and a little desperate, Jobs asked the question a bit differently: “John, do you want to spend the rest of your life making sugared water, or do you want to change the world.”

Wow! What a question; specific, provocative and challenging. Jobs did the work of turning his good questions into a great one. As a result, he found himself with a new team member.

What kinds of questions are you asking? Make them sharp and purposeful.


ROBERT and PAMELA CROSBY are the Co-founders of Teaming Life, investing their lives in men and women who desire to live as Teaming Couples, Teaming Families and equipping leaders to build strong Teams in the Church and Marketplace. Robert’s works include The Teaming Church: Ministry in the Age of Collaboration and The One Jesus Loves. Together they have written, The Will of a Man and the Way of a Woman, recently released.