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Critical Thinking is About Asking Better Questions


As a person specializing in mediation and conflict resolution and as a speaker doing continual research in the area of collaboration, I want to share some insights with you about how to ask better questions. Why? Listening actively is the key to understanding related to both conflict resolution and collaboration. Taking this up a notch, asking even better questions will help you analyze the situation better, gain further insight, and produce better results.


Critical thinking


Critical thinking is the ability to analyze a situation, break it down effectively to gain further insight allowing you to make a better decision. Problem solvers solve a specific question asked. That often is all that is needed. However, solution providers go further and ensure that the problem identified is indeed what needs to be addressed. Often due to timing constraints, resource constraints, or other needs, the appropriate approach is to identify what is perceived as the problem, react appropriately, identify alternatives, and decide. Sometimes biases or short term thinking enters into the defining the problem properly.  When this happens, decisions may be suboptimal.

Critical thinking is when you step back from a perceived problem and explore whether you have defined the problem properly or whether you’re only working on a symptom of the problem.

By exploring the issue further, you may look at the problem differently, dig deeper, and explore questions that may lead in a different direction. As a mediator I often ask questions that help the parties look at their situation differently. This has positive results related to de-escalation, mindset, and openness to other perspectives. Similarly, effective questioning by having a broad perspective in your initial hypothesis goes a long way towards exploration.




By exploring your motives with what you might ask, and seeing if the question may help with understanding with openness, this may curb some questions and encourage others. You must come with an attitude to help rather than attack. You have your initial point of view and perspective. This leads you to a preliminary conclusion and approach. That is fine, but you must be willing to shift your perspective and question your initial assumptions and preliminary conclusions.

It is important when you question yourself to avoid being defensive.

Nothing is gained by blaming yourself or others. Rather the perspective needs to be what are we going to do from here with what we know now? The key is “we” and going “forward.”  It is not about you. It is about focusing on the problem and thinking more broadly approaching the problem jointly.

Your questioning has to focus first on listening actively. That is, take an appropriate amount of time (often at least ten minutes) to really listen to the other party. When they are talking, consider what else should I be asking? To ensure you are understanding summarize key points of what you believe you have heard in your own words. Ask open ended questions to allow the speaker to elaborate on their answers. Be empathetic by putting yourself in their shoes and exploring ways to help. Take your questioning to a deeper level, by exploring reasons behind their perspective. Explore the assumptions by the other party. Help the other party to pause and reflect on why they are oriented towards their perspective. Be open minded in your attitude as you ask these questions.

Consider being counterintuitive to your perspective.

What would others say or how would others respond to what agenda I had thought to bring to this interaction. Be prepared later to move off of your assumptions and look at the problem differently.

That is, what might others ask of your perspective? You want to avoid groupthink.  That is the psychological phenomenon when the desire for cohesiveness of the group overpowers the rational decision making resulting in an irrational or dysfunctional outcome. By stepping back and asking questions like:

  • What information am I missing?
  • Why am I reacting this way?
  • What else am I missing?
  • What else haven’t we thought of?
  • How would someone with the opposite perspective perceive our approach?
  • How might that impact what we have produced?
  • What else should I be asking?
  • What are the other options?
  • What happens if we make that particular decision?

These types of questions may allow you to perceive what you are doing differently and help you “fill the gaps” where you have holes in your thinking or may lead you to a whole different approach that you had not thought of previously.


Take time to reflect


When you are addressing a major concern and you want to make sure you are approaching this appropriately, consider taking a break after a while. Do something else. Go for a walk. Give your mind an opportunity to go in a different direction. Sleep on it. Reach out to others as a sanity check. Reach out to a trusted peer or friend and bounce your ideas off them.

By giving it further thought and putting the question on pause for a moment

 this may give your mind time to clear.

The result may even be an “aha” moment of sudden insight or discovery because you let it go for a period of time. Sometimes an idea can come to you even while you are sleeping. If this happens and you wake up, write it down. It may or may not make sense in the morning, but if nothing else it may make you think differently and that may help you.


Follow up


Finally, before concluding consider going back to the beginning and consider whether you have defined the problem properly. Who else might you ask? What else might you ask? What are the additional questions you might want to ask? Consider how you are reacting and why you are reacting that way. Are there options that you may want to explore? Bring it home by making the best decision you can, having given this problem a thorough review. Let me know what you think. What are your ideas?

About the author

Mike Gregory is a professional speaker, an author, and a mediator. You may contact Mike directly at mg@mikegreg.com and at (651) 633-5311. Mike has written 12 books (and co-authored two others) including his latest book, The Collaboration Effect: Overcoming Your Conflicts, and The Servant Manager, Business Valuations and the IRS, and Peaceful Resolutions that you may find helpful. [Michael Gregory, ASA, CVA, MBA, Qualified Mediator with the Minnesota Supreme Court]