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A Guide to The Best Critical Thinking Questions to Improve Your Decisions

Critical Thinking
6 Minutes
Reading Time

Critical thinking questions are the questions we should have asked before deciding. Often, we shy away from asking them, for fearing what they might reveal. Forgetting emotion and feelings for one moment, we know our decisions should be objective ones. It is this quality that good critical thinking questions provide - a means to objectively assess our choices before deciding.

Given the impact critical thinking questions can have, it seems strange that we aren’t more aware of them. But we’re not. There are several reasons behind this knowledge gap in our decision-making.

1. We don’t know how bad we are making decisions.
2. We underestimate the power of systems to think better.
3. We fail to grasp the role of entropy in our decisions and outcomes.

These three points create serious amounts of overconfidence in several areas. There is the quality of our judgements. Our ability to manage our cognitive biases, and then, how serendipity affects us.

In this guide, you will find questions to help you get beyond these three areas of overconfidence. But, before we get to those critical thinking questions, we should understand why overconfidence gets the better of us.


We think we make good decisions, but we have no idea whether we do or not. Some believe a good decision is a good outcome. This shocking statement is a demonstration of our misplaced confidence when deciding.

Even in those who know better, decision-making is an unknown quantity. Few keep a decision journal or keep note of the choices they make and why.
This inevitably leads to the second point; we underestimate the power of systems to think better.

Mental models – the patterns of thought which explain how the world works enable us to make better decisions. And yet, we don't teach them in school. Furthermore, only a handful know of these models and use them to improve their decisions.

We fall back on our learned behaviours when deciding. Guided by our instincts, we act based on times gone by. Sometimes, this is a good way to decide. But complex problems or big decisions which impact others need a deeper inspection. Systems of thought, like mental models, are an ideal step to compensate for the gaps in our intuition.

Lastly, we fail to grasp the role of entropy in our decisions and outcomes. Entropy is a topic covered here, but the point is that uncertainty, serendipity – luck and chance – are always at work. We kid ourselves we are more in control than we are.
So, how do critical thinking questions help overcome our overconfidence when making decisions?

What is critical thinking - and how does it with decisions?

Critical thinking is a fundamental skill when it comes to making better decisions. Firstly, critical thinking can be misunderstood, so let’s be clear about its meaning.

Critical thinking (noun)
The objective analysis and evaluation of an issue to form a judgment.


Asking critical thinking questions when deciding enables you to analyse the choices before you. You can then make a judgement based on your evaluation.
This process can empower you to overcome the three points highlighted earlier. Just applying this form of logical analysis to assessing the quality of your decision-making is likely to lead you towards a decision journal. How else could you answer the question?

Likewise, with using mental models, why wouldn’t you use them given you know they work. Thus removing the need to reinvent the wheel. With every decision, we want to access the best and most relevant information.

Asking better questions inevitably leads to better answers. With every decision, we want to access the best and most relevant information. So, the quality and depth of the questions you ask to undertake your critical thinking matters.

Critical thinking questions

The substance of this article – the critical thinking questions themselves come next. Each question contains a link to an article explaining the question in more detail. The reason; different questions work in different situations. Different questions bring different answers - the context of each question matters. This context is what exists in each article beyond the question itself.

One last thing; this guide isn’t finished; it is a work in progress as I seek to refine and improve the critical thinking questions listed.

Is this a Reversible or Irreversible Decision?

What is The Risk of Doing Nothing?

How Will You Feel About This Decision Six Months from Now?

What Do I Know to Be True?

What is the Best/Worst-Case Scenario?

Where Will This Decision Take Us?

When is the best time to act on your decision?

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