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Critical Thinking

Critical Thinking Questions?

January 16, 2014 by Dr. Jon Warner in Critical Thinking

Critical Thinking Questions

Critical thinking occurs whenever you review a problem in depth and think about solutions which are most creative, long-lasting, novel or sustainable. This type of thinking is valuable because it enables us to analyze, evaluate, explain and restructure our thinking, thereby decreasing the risk of working with false data and assumptions and/or adopting, acting on or thinking with false premises or beliefs. 

Socrates laid the foundation for Critical Thinking by role-modeling the approach of asking open questions as incisively as possible so as to bring greater discipline to the subsequent debate and create better ultimate solutions. However, by introducing a more systematic and self-aware approach, questions can be more powerfully framed and used to lead to better information. As a result, in every domain of human thought, and within every use of reasoning within any domain, it is consequently possible to question:

  • overall ends and objectives
  • the status and wording of statements, arguments and even other questions
  • the sources of information and fact
  • the method and quality of information collected
  • the mode of judgment and reasoning used
  • the concepts that make that reasoning possible
  • the assumptions that underlie concepts in use
  • the implications that follow from their use
  • the point of view or frame of reference within which reasoning takes place, and
  • the criteria by which choice and decisions are made

In other words, questioning which focuses on these fundamentals of thought and reasoning are very much the baseline in Critical Thinking. We therefore need to focus much of our time in discovering what sort of questions we can ask and try to make these as telling or as insightful as possible in the circumstances.

Although, by its very nature, an insightful question is situation-dependent and will always be framed in the context of the issue being considered, we can usefully generalize about what an insightful question is more likely to look like. To this end, the list below gives some indication of the sort of questions we should be asking in an organizational setting:

  1. Is our data/information sound and accurate (and how do we know for sure)?
  2. Have our assumptions been tested?
  3. What are the possible consequences of a particular course of action?
  4. What’s at the back of our/other people’s minds here?
  5. What would we ideally like to happen (without known constraints)?
  6. How can we make things better/more efficient/more effective?
  7. Where are the greatest time wasters/blockages/bottlenecks in our work systems?
  8. What are we really trying to achieve/do?
  9. What is stopping us from achieving our objectives?
  10. Where are we likely to experience the greatest risk in taking an action?
  11. What might we be able to do overcome blockages/resistance to change for the better?
  12. Who really knows/cares about the problem/issue (at a factual level)?
  13. Who can really do anything about the problem/issue?
  14. Where can we find out more about the problem/issue?
  15. What works/doesn’t work in our current methods/approaches?
  16. What are the hidden/indirect costs in this process?
  17. What might we do differently in our approach in the future?
  18. When, where and why do we perform at our best or worst?
  19. When, where and why do we experience our greatest successes/failures?
  20. What do you think would happen if…?
  21. Are there other alternatives that we could explore?
  22. Where/When is the risk likely to have the most impact/severity?
  23. What are the best/most favorable consequences of our planned actions?
  24. What are the worst/least favorable consequences of our planned actions?
  25. What is the primary goal of the planned change/project?
  26. What system(s) will best assist in controlling/coordinating the change?
  27. Are these the best measures of the system/process?
  28. Is this in line with the overall vision/mission/ strategy/goals of the organization?
  29. Where might we experience implementation problems with the proposed solution?
  30. Will we get a positive return on our time and effort?

The above list is not intended to be exhaustive by any means (as by their nature critical thinking questions should be uniquely framed to the issue or problem under consideration). However the list does act as a starting point for general critical thinking questions of your own to be developed.

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About Dr. Jon Warner

Dr. Jon Warner is a prolific author, management consultant and executive coach with over 25 years experience. He has an MBA and a PhD in Organizational Psychology. Jon can be reached at

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  1. Keith DierkingJanuary 16, 2016 at 2:13 pm

    Dr. Warner,

    Thank you for posting your short overview of critical thinking. Showing a list of critical thinking questions one might use during consulting/counseling situations (rephrased as needed for the specific situation/person) is very helpful.


  2. Roger LaneJanuary 20, 2016 at 9:44 am

    A useful start in listing some questions, but the next step in critical thinking is to exercise judgement in decision-making and the choices I wish to make. For example, in the Balkans, to what extent do people want reconciliation, revenge or restorative justice. Placing these in a triad forces people to make a choice about the intensity of their preferences, which is what we can measure in SenseMaker, providing us with unique insights into what people are really thinking, from which solutions can be be developed.

  3. Jim DugganJanuary 22, 2016 at 5:59 pm

    Thank you for this article! It is a good reminder of critical thinking principles.
    One additional thought regarding questions to pose in order to facilitate critical thinking is simply to also ask “why?”.

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Jon Warner

Jon Warner is an executive coach and management consultant and in the past has been a CEO in three very different companies. Read more

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