Good Leaders Ask Great Questions

Here is a common set of questions in everyday conversation:

Person 1: Hey! How are you?
Person 2: Good…you?
Person 1: Fine…awkward silence..
and end of conversation.

How often do we get asked questions that shorten a conversation rather than generate genuine engagement? Imagine if that question was being asked differently. “Hey! Good to see you. What have you been doing at work that is challenging you?” It may sound a bit stilted in this example, but do you see the difference in how that conversation could go?

Eighteenth century French philosopher and poet, Voltaire is noted to have said, “Do not judge a man on the answers he gives, but on the questions he asks”.  Leaders often feel it is their job to have all the answers and help people by being the “go to” person. Often, it is easy to mistake management  for leadership in this regard.

Leaders, especially those who lead other leaders, strive to gain understanding and knowledge that informs before offering advice, direction, or  offering “what if” solutions. Good leaders use questions that explore and ignite conversation, creating safety from intimidation and generate healthy dialogue. Great leaders master the art of when to ask powerful questions and when to use direct communication. Thus, leaving their people with clear expectations, challenging objectives, empowered leadership, and inspired motivation to move forward.

If the best way to connect with your team and be most effective as a communicator is through asking questions, then they must be the right questions. Whether you are a high level executive or just trying to be a good friend or parent, ensure that your questions have P.O.W.E.R.

Five Ways To Improve Question Asking

P – Purposeful – Ask the question with intent to understand the situation with 360 degrees of clarity. Then ask good follow up or clarifying questions to gain different perspectives on the situation. Leading question: “What was the ultimate outcome of the event?”  Follow up: In what ways did you see your goals reached? Follow up two: How did the team respond to the outcome of the event? Follow Up three: “What environmental factors did you face that affected the outcome?” Follow up four: “What would you like to improve upon next time?” Each question should dive in closer to action steps that are constructive and helpful.

O – Open – Open questions are the type that bring insight into reasons not just facts. The opposite of open questions are closed. For example: “Did you do that task that I assigned you?”  An open version of that question could be, “What progress did you make on that task we discussed last week?” One question yields a yes or no answer, while the other promotes dialogue. Closed questions are not invalid, but they do not promote discussion the same as open questions.

Also, be open to receiving an answer; if you enter a conversation expecting a certain result, you’re likely to shut down the most clear and insightful communication. Remain open-minded; to ask productive questions, not based on opinion but facts. Even if your position will not change on the issue, be open to hearing all sides of the discussion.

W – Winning  – Winning questions are those that promote inspiration and motivation. This is not fluff, but is a method to encourage the person and empower the goal that the topic is designed to reach. “What were you thinking when you did this?” Is both open and powerful but it is a discouraging, and draining. It likely will not gain influence even though it is powerful.  Alternately, “What circumstances were present that impacted this decision?” This could achieve the same goal while still valuing the person, promoting healthy relationship, and giving the leader great understanding without jeopardizing the concern.

E – Empathetic – Healthy communication is founded on empathy, and a strong question is formulated through the lens of it. If you’re able to relate to, and understand someone, you can dive deeper and be productive while maintaining relationship. Start off asking things that gain understanding of circumstances and personal viewpoint on issues. These can assist the leader in guiding self evaluation and discovery which is more likely to produce change. Which is more effective; “That’s three days in a row! Why were you late?” or “What circumstances have caused your lateness the last 3 days?”  A simple semantic can bring empathy without compromise of position.

R – Reflective – Great questions are not known for the complexity by which they are asked but by the amount of reflection they create. In the interest of expediency it is tempting to simply recite or answer these questions for them based on limited information. Reflective questioning takes time to get to the heart of an issue rather than dealing with the surface problem only. For example: “What long-term effect did you desire from this decision?”  “What people were positively affected in the process of making this decision?”  The end result is self education and correction without humiliation and defensiveness. Listen to gain understanding. Ask powerful questions to gain reflection, discovery and change in direction.

Take your leadership to the next level. Ask powerful questions that empower your team and give you the insight you need to reach your goals.


These 5 improvements are not comprehensive, but they can be the catalyst toward reigniting relationships and having powerful leadership tools at your disposal. For this type of learning contact our ShiftAgent coaching program for individual or group training. If you need further or deeper assistance, let us help you find the right professional to help you in your current situation. We are here for you, contact us and we will be glad to assist.