How Powerful Questions Can Enhance Your Leadership

As a leader, you are expected to have answers. Whether it’s a team member asking how to get a project back on track, a customer asking for more service, or a boss demanding better results, there is pressure to provide quick, definitive responses. 

The drive to find the “right answer” and to do so expeditiously may be well intentioned but comes with considerable risk. What if your response fails to address the issue you are trying to solve? Or more importantly, what if you are spending all of your time and energy finding an answer to the wrong question?

Taking a step back from a problem and further assessing it through questioning can provide powerful insight. In addition to helping re-frame a problem and sharpen focus, asking powerful questions can foster breakthrough thinking and yield many critical benefits such as:

  • generating curiosity
  • surfacing underlying assumptions
  • inviting engagement and creativity
  • encouraging forward movement
  • eliciting more questions

If asking questions is so important, why don’t we invest more time and energy developing them? 

Judge a man by his questions rather than his answers.
— Voltair

One reason is that we are incentivized to come up with quick fixes. Taking a step back to further explore an issue from a strategic view is often perceived as a waste of time. Another reason is a desire to be decisive and to address a problem with clear black/white answers. Finally, some may feel that asking questions is a sign of weakness; an admission of a lack of knowledge or inability to tackle a challenge. 

The unfortunate consequence of each of these is that we end up attached to answers that are unoriginal, narrowly focused, and fail to foster breakthrough thinking.

Constructing Powerful Questions

How can we become better at asking powerful questions? The first step is to look at how we construct a question and the words we select to frame it. Consider the following words and how they can impact a question:

  • Questions that start with Which, Yes/No will tend to generate closed, short responses.
  • Questions starting with Who/When/Where are still relatively narrow in focus and will typically elicit a specific response.
  • Questions beginning with Why/How/What are more open ended and have the potential to evoke more thinking

To further illustrate the impact of the words that are used to construct questions, review the following progression:

  • Are we doing a good job?
  • Where did we do our best work?
  • How can we provide the highest quality of service?

Which of these questions is most likely to generate discussion, reflection, and learning? While there will always be a place for simple yes/no questions, Why/How/What questions have the best chance of provoking creativity and exploration

Scope and Assumptions

There are two other important factors to consider when building a question; scope and assumptions. 

Scope defines the breadth of the question and the potential magnitude of answers. The goal as you develop a question is to pick a scope that appropriately fits your problem or opportunity. For example, the question “How can we improve our community?” is one that that that we can begin to wrap our arms around.  In contrast, “How can we improve the world?” may be interesting to consider but likely exceeds our ability to develop meaningful answers. 

Assumptions, whether expressly noted or implied, are built into almost every question. It is important to be aware of the assumptions we incorporate into our questions because they will have a significant effect on the types of responses. 

For example, questions like “what happened?" or "who dropped the ball?” assume someone made a mistake. A question like this will usually elicit a defensive response. In comparison, asking “what can we learn from this?” will foster an open and collaborative discussion about how to best move forward from the experience. 

Imagine This

Now that we’ve explored the importance of questions and how to construct them, let’s put this all together in a scenario. 

Imagine that you are in charge of a series of technology projects for a large company. One of your project managers comes to you with a pressing issue – “We’re behind on a task and are going to miss the upcoming deadline. What should we do?” Consider the following three responses:

Response 1 – I’ll pull some resources from another team and get them working on this right away. If that doesn’t work, I’ll try to renegotiate the deadline. 

Response 2 – Who messed up? Is there any chance left to make it? When can we get back on track?

Response 3 – What is holding us back from meeting the deadline? What options have we not yet explored? How can we still be successful? 

In Response 1, the leader takes quick action but misses an opportunity to explore the true root of the problem. Will adding resources or changing the deadline truly solve the issue? 

In Response 2, the leader asks questions but chooses ones that may result in defensive and limited responses. 

In Response 3, the leader demonstrates a willingness to step back and consider the broader implications of the challenge. What are the pros and cons of each of these responses? Which is mostly likely to have the greatest impact? 

The important thing is not to stop questioning. Curiosity has its own reason for existing
— Einstein

Enhance Your Leadership with Powerful Questions

Here are a few concrete steps you can take to improve your leadership through the use of questions:

1. Lead by Example

Show your employees, colleagues, and bosses that you are not afraid to ask questions to further explore challenges or opportunities as they arise.

2. Slow Down, Be Curious

Resist the urge to fire off quick answers the next time you are directly presented with a question.  Try to construct a few additional questions using the guidelines above and see what you learn.

3. Change Your Process

Look for opportunities to adjust the structure of your meetings and other collaborative processes to build in time for questions and reflection.

4. Engage Others

Bring in your team and use powerful questions to guide a discussion. Asking questions instead of providing answers will foster creativity and shift ownership to others.

Examples of Powerful Questions

  • What is most fulfilling for you?
  • What is possible?
  • What would success look like?
  • How can we be successful?
  • What have we not yet explored?
  • If there were no constraints, what would we do?
  • What might we think about this five years from now?

Post your thoughts and experiences with powerful questions in the comments below.  How have they improved your performance as a leader?