Critical thinking. That phrase seems to be a mainstay in job descriptions today. Being a critical thinker is in high demand. It would not be an exaggeration to say that the quality of our work output or even the quality of our life depends on the substance of the decisions we make. Learning to master the skills of decision making while using critical thinking can have a profound impact on many aspects of our life and career.

First, let’s make the distinction between critical thinking and conventional thinking. Critical thinkers take a wide-ranging, long-term approach to solving issues. It involves neutral analysis, planning, and competent decision-making. A critical thinker will look at a problem from a 360-degree perspective, while the conventional thinker will follow the same path because it’s the way it’s always been done. A critical thinker is interested in what happens in the future, and a conventional thinker is concerned about today.

Critical thinking goes beyond thinking about what is and envisions what could be. While the concept seems to hold some mystique, it’s not a designation that only a few people can hold. Anyone can be a critical thinker. And, it’s not that hard. All you do is break down any given scenario or issue into manageable concepts. These manageable concepts are surprisingly simple, yet powerful.  There are six magic questions that should be asked: who, what, where, how, when, and the all-important why.

Your Guide to Critical Thinking

The key to critical thinking is asking questions. When we ask the right questions, it kickstarts our brain and allows us to imagine how much better things could be if we were making the best possible decisions, day in and day out.

Here’s a list of questions to help get you started. It’s not an all-inclusive list by any means, but it will get you on the right track. Try this the next time you are trying to solve an issue or when implementing new projects.


  • What is the issue?
  • What is causing the issue?
  • What do you want to do?
  • What are your goals?
  • What’s happening because of this issue?
  • What resources will I need to solve it?
  • What is the best thing that can happen when solved?
  • What is the worst-case scenario if it is not solved?
  • What other perspectives surrounding the issue am I missing, specifically, are there counterpoints of view?
  • What alternatives do I have?
  • What if….?
  • What obstacles are getting in my path of solving the issue?
  • What positive changes will come about by solving this issue?
  • What are the pros and cons of the solutions I am proposing?
  • What assumptions am I making?
  • What am I missing?


  • Why is this a problem?
  • Why has there not been a solution previously?
  • Why it this important to solve?
  • Why is this way to solve it the best way?
  • Why was this allowed to happen?


  • How will this problem be solved?
  • How will this plan be carried out?
  • How do you approach this in a manner to cause the least amount of disruption?
  • Or, if disruption is what you seek, how will this disrupt things?
  • How will this benefit me?
  • How will this benefit others?
  • How will this harm me?
  • How will this harm others?
  • How will this change be used for the good?
  • How might this be interpreted differently?


  • When will this be completed?
  • When should I begin to take action?
  • When will people see a benefit?
  • When should I ask for help if needed?


  • Where can this be improved?
  • Where all is this a problem – ie, is the problem isolated?
  • Where does this problem mainly occur?
  • Where will solving this problem take us?
  • Where else are there similar situations?
  • Where is there the most need for this resolution?
  • Where can you find more information on the topic / issue?


  • Who will be involved in this?
  • Who will benefit from this?
  • Who will be harmed from this?
  • Who will be most directly impacted if solved or not solved?
  • Who will be most directly impacted by the solutions I propose?
  • Who will make the decisions on this?
  • Who are the key people that will carry out the plans?

These questions will get you started on the right track. Start asking questions and see where that takes you. Once you get into the habit of asking powerful questions, your conventional thinking will quickly evolve into critical thinking and you will see more questions flow because of it.

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Jan Johnston Osburn is a Certified Career Coach and Organizational Consultant. Her organizational specialties are Talent Acquisition, Training, and Leadership Development. She holds a Master’s degree from the University of Buckingham, UK, and has certifications in Executive Coaching and Advanced Social Media. Her website is www.YourBestLifeTodayCoaching.Com .