Asking The Right Questions

A Critical Doer attacks problems from the inside out

 In general, the farther you advance in your career or mature your business…the more general and less specialized you become.  In the beginning, you’re expected to be the technical expert that has all the answers to the questions.  Later, your role transitions to managerial or leadership duties to guide others who are now the most current technical experts.  At this point, your greatest value is likely not in providing answers…it’s asking the right questions.  The premise is if you ask the right questions, your people will give you the right answers.

Dr. Stefan Eisen, a gifted lecturer in critical thinking and negotiation at Air University at Maxwell Air Force Base, teaches a course in critical thinking that is based upon the power of questions.  A good deal of what I’m going to share with you in this post…I learned from him.

One of the teaching methods he employs is posting a newspaper headline and giving the class a short amount of time to come up with 10 questions that will essentially recreate the entire story.  At first the drill seems daunting, but as you learn to ask better questions it’s still difficult…but not impossible to do.

In a scenario where you are trying to piece together an accurate picture of a situation, with information coming from various sources, and each has a bias based upon individual circumstances, there is a framework you can follow in asking questions to bring the story to light.  You should ask:

  1. Questions that establish fact. It’s nearly impossible to accurately piece together a complex story if the basic information is incorrect.  Quantifiable questions expressed as adjectives rather than numbers, speculation of intent rather than events, feelings rather than data, and illogical sequence of events are examples of areas where questions to refine the basic facts will help you begin navigating through the maze.
  2. Questions that establish relationships. Figuring out what one thing has to do with another is crucial in unraveling a complex scenario.  Questions that address process dependencies (one entity needs something from another to make progress), past history, consequences of certain actions (second order effects and beyond) are examples of relationship questions that can help you get to ground truth.
  3. Questions that establish context. These questions get to the heart of culture…both corporate and the traditional sense of what defines a group of people.  Something that may be trivial to you could strike at the heart of what makes another group who they are.  Questions that illuminate these sensitivities can help you develop solutions where everyone wins.

Critical Doers, as much as it gives us a source of pride to be the one with all the answers, the natural progression of our professional lives makes it challenging to have all the technical answers as well as develop breadth to accurately figure out what it all means.  As a leader/manager/supervisor/, questions are the compass that guides the effort of your people.  If you ask the right questions, you will get the right answers.

I challenge you to continuously refine your critical thinking skills through education (formal or self-taught) to develop breadth in your knowledge base and increase your capacity to reason.  The more effectively you think, the greater your capacity to do.  Make the investment in yourself that will pay dividends for your organization.  It’s what a critical doer would…do!


Note:  there will be follow up posts about asking questions in a broader problem solving context that will guide your work and maximize creative potential



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Updated: January 27, 2015 — 1:33 am


  1. Learning to ask the right questions is vital.
    So is making up your mind what you “think” is right.

    Quite frankly, as the leader — you should have an expectation of yourself to be correct and others should have an expectation of you to be correct.

    But equally important is the willingness to be convinced that you might be wrong.

    All the times you are correct is important — how much more important is when the one critical thinker convinces you that you aren’t??? Don’t discount the single person courageous enough to disagree with you regardless of the multitudes that agree. It isn’t the number that is important. It is the quality of the thought and argument that is.

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