Asking Great Questions

Published: December 11, 2018

Some professions require that you learn how to ask questions to actually do your job. For example, in order for a doctor to prescribe medication or perform the correct procedure, he must ask the patient a series of questions. The more information the patient can give the doctor, the more thorough the prescribed treatment will be. Without asking this series of detailed questions, the doctor would have zero clue how he could help his patient feel better.

As ludicrous as this may sound, this exact same idea applies to your business. To obtain answers about the performance, trajectory, or future of your organization, you have to get good at asking questions. Subsequently, by learning the art of asking great questions, you are able to add incredible value to the organization.

The challenge that is common among many organizations, is that there are not enough leaders, managers, and employees that ask questions. In fact, what keeps most leaders asking questions, is that they are trapped by their ego. Furthermore, many leaders think they must know all the answers, and be the one giving the answers. Instead, you cheat yourself out of learning when you don’t ask questions, and may even cheat someone else of sharing something valuable with you that could benefit both parties and the organization.

As a leader, challenge yourself to change your mindset to have the questions, and seek the answers. Furthermore, instill a culture in your organization that encourages everyone to ask questions. Incorporating a question-based culture into your business, will help spark innovation, build trust among team members, uncover potential risks or business hazards, and will give you clear focus.

In Hal Gregersen’s Harvard Business Review article, Better Brainstorming, he shares an outline on how to implement “question bursts” — a brainstorming process — into your business. We have summarized his outline below:

Step One: Set the Stage

Select a challenge or potential opportunity within your business. Enroll other leaders or team members to help you — inviting others to help will give you access to a wider knowledge base. Take only a couple minutes to share the problem, outlining how things would be better if the problem were solved. Then let the group know that they are only allowed to ask questions, not suggest solutions.

Step Two: Brainstorm the Questions

Set a timer for four minutes and, as a group, list as many questions as possible — remember, don’t give solutions! Aim for about 15 questions in total. For this exercise, put emphasis on quantity.

Step Three: Identify a Quest & Commit to It

Take some time, by yourself, and look over the list of questions. Select a couple that intrigue you, and then expand on them by asking additional related questions that will help you understand why it really matters. Of the couple that stick out to you, choose one that is the most important or most meaningful and pursuing a new pathway from it.


As sales team leaders MUST ask more powerful questions for the reasons discussed above.  One way to do this is through the use of the “Question Triangle”.

Why = the weakest question.  Think about questions that start with the word “why”. Why were you late?  Why did you not lead generate? Why did you hit your sister? What kind of answers do you get to questions that start with “why”?  Likely the answer is an excuse, incomplete, or even a lie!

What = “What” questions are stronger than those starting with “why”.  What can you do to make certain you are on time tomorrow? What stood in your way of lead generating today?  What could you differently (instead of hitting your sister)?

How = “How” questions are some of the most powerful questions one can ask.  How do you believe the highest performers in our industry behave (and what are their habits)?  How will you make certain that you will lead generate for 120 minutes tomorrow? How does a good girl/boy behave?

Who = “Who” questions are the most powerful questions to ask, and if the actions steps generated by the “who” question are followed, you may be able to elicit the greatest, most positive response.  Who can hold you accountable to being on time? Who are you letting down when you fail to lead generate?

NOTE:  I have found that the “Question Triangle” actually applies more at home with my spouse and kids than it does in the office!  Try it out!

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