Asking Questions – A Fundamental Leadership Skill

A common view of leadership involves an omniscient guru sitting at the top of a mountain, dispensing answers to the questions brought by admiring supplicants.

However, many leaders view their function to be asking questions instead of dispensing answers.

Questions force people out of their limbic trance state and into their conscious thinking mind. Questions stimulate creativity. Questions often result in new information.

The trick is to know what questions to ask and how to ask them.

For example, the questions I ask of strategic planning clients and the standard I apply when reviewing grant applications flow like this:

  • What is the external problem you are addressing? How bad is it? What are the trends?
  • What will the world look like when you solve the problem? This is your vision.
  • What is your mission? It had better be to achieve the vision.
  • What are the contributing factors (needs) that lead to the problem? These become your points of intervention.
  • What are the underlying contradictions, the obstacles to achieving the vision.
  • How will you go about overcoming the obstacles, addressing the needs, and achieving the vision? These are the strategies.
  • What will you do to achieve these strategies? These are the activities that make up your Operating Plan.
  • How will you ensure these strategies and activities effectively move you toward the vision?
  • How will you measure and manage the strategies and activities?

Notice that these questions are how and what questions. They are not why questions. The clients must think to answer. Most nonprofits are unable to answer the first question because they have not thought about it. They have been entirely focused on efficiently executing the activities, without examining their strategic effectiveness.

You can check out some prior blog posts with lists of questions here, here, here, here, here, and here.

Generate Ideas with a 4-minute Question Storm

Hal Gregerson, in his book Questions are the Answer, suggests a 4-minute Question Storm. This storm is a certain type of brainstorm generating questions instead of ideas.

I recently used this during a strategy session with a nonprofit. One of the directors had come forward to the committee asking about the viability of a certain long-term activity. I asked the committee members to each spend four minutes writing down questions about this issue, without talking to the other participants. I wanted them to examine our underlying assumptions. I wanted them to think about the information they would need to decide on this matter. I wanted them to express their feelings.

After the 4 minutes, each generated 5 to 7 questions. We went around the room and discussed each of the questions, trying not to spend time looking for the answers. We had an amazing set of questions and considerable discussion. We directed the staff to research several key points before the next meeting. Once the staff answered the questions, we did not have to hold the next meeting. The answer was obvious, which we took directly to the board for approval.

Calibrated Questions

Chris Voss, in his book Never Split the Difference, puts forward the use of Calibrated Questions. Calibrated questions are a specific type of open-ended question, designed to elicit information. Again, calibrated questions always begin with “What” or “How”. These questions are always aimed at the other person, not at “we”. For example:

  • What about this is important to you?
  • How can I help to make this better for you?
  • How would you like me to proceed?
  • How can we solve this problem?
  • What are we trying to achieve here?
  • How can we look at this in a completely different light? What if we could put in a hedge instead of a fence?, and the classic
  • How am I supposed to do that?

Then pause. Absolute silence, paying full attention to the others. Bite your tonque if you must.

Calibrated questions work well with labelling, mirroring, and the late-night DJ voice. If you don’t know what those are check out his website at the Black Swan Group.

Einstein once said, “If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask…for once I know the proper question, I could solve the problem in less than five minutes.”