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

May 31, 2021
• Updated
December 2, 2023
Read time —
6 Minutes
The eyes of this man expose the thought he might be thinking critically.

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In this Article

Critical thinking questions are the questions we should ask before deciding.

Often, we shy away from asking them, fearing what they might reveal. Forgetting emotion and feelings for one moment, we know decisions are better when built on open-mindedness. Good critical thinking questions give us a shot at finding clarity amongst the chaos.

Considering the impact critical thinking questions offer, it seems strange that we aren’t more aware of them.

But we’re not, and 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 help us think better.
  3. We fail to grasp the role of luck and randomness (entropy) in our decisions and outcomes.

These three points create real problems for decision-makers.

We become over-confident and certain in our ability to make effective judgements.

Low-lying clouds hang around the hilltops where I live and drive, blinding my senses. My judgement of the road changes as I lose the perspective of the landscape.

Overconfidence does the same, helping us ignore the effect of our biases. Then there is the way of serendipity on outcomes.

In this guide, you will find questions to help you get beyond these areas of overconfidence. Before we get to those critical thinking questions, we should first 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 notes 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, and 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 help 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.—Wikipedia

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?

When is the best time to act on your decision?

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