9 Provoking Critical Thinking Questions to Ignite Deep Reflective Discourse

Besides radical skepticism. Critical thinking can be defined by these three questions:

  • What is true?
  • Why is it true?
  • What else is true?

Your ability to question a piece of incoming information. Doubt it, so you can come up with the best possible solution is more important than any certificate or diploma you’ll ever receive during your life.

Think about it.

In a typical company. People don’t hire other people to just stare at a screen and click buttons. If the job was to sit behind a monitor all day and tick random boxes. A company wouldn’t require a whole hiring team. Every corporation in need of staff would simply go outside the tall building they reside in and pick the first person passing by willing to sell his soul to the corporate regime.

No. What HRs are really interested in when they conduct interviews is this: They are trying to evaluate how you think.

Can you press the right buttons for the needed tools? Yes, surely they are looking for that, too. But more importantly, can you solve a challenge in an elegant way? Can you find your way out of a situation when things get sideways? Can you properly evaluate difficult cases and find the best possible solution without ruining the established systems and values?

These are the actual skills HR members are after.

Cognitive skills. Not mouse-clicking skills.

And while you can easily teach a smart person how to operate a particular software. What you can’t teach. Or at least will require a substantial amount of effort and nerves. Is to try to teach a dump person how to think properly.

But as I said in my recent post on how to improve critical thinking skills. We are systematically not challenged.

No matter the work you do – unless you work for NASA. Between 2 and 3 years. A job usually starts to feel like a venomous tonic of bitterness.

The repeated mundane tasks not only lead to a lack of drive. But also deteriorate your thinking.

If you happen to be in such an unchallenging and depressive state. Or if you are simply looking for ways to shake the cocktail of thoughts that circle inside your brain.

The following critical thinking questions will resurrect your enthusiasm and remove the rust from your gray matter.

Note: To better engage with the text. I highly recommend grabbing a notebook and answering the questions on paper. No rush. You can tackle them in the order you like. Also, don’t need to answer them all now. Tackle one question now and the rest when you have the time.

9 Provoking Questions to Foster Critical Thinking:

1. What Are We Absolutely Sure Is True?


The standard way we think about a problem or when we face a certain situation is to reason by analogy. We approach a situation looking at what someone else did to solve it. Then, we copy the solution and slightly adjust it to fit our case.

But a more sophisticated way to look at incoming situations is by reasoning based on first principles.

That’s precisely the question above: “What are we absolutely sure is true?”

For example, in an interview where Elon Musk talks about first principles. He explained that Tesla was able to become what it is – one of the largest companies that offers affordable electric cars. Not by doing what everyone else did with batteries – buy the expensive batteries and put them in a car. No, the Tesla team figured out what batteries are made of. What are their core materials? Once the team saw that the spot market value of these core materials is really cheap. They simply had to find a clever, and better way to assemble the pieces in a battery shape.

All of this means that when you are presented with a task. Don’t blindly copy what everyone around you is doing. Think about what is surely true. Then reason from there to find the best solution.

2. What Would My Ideal Life Look Like in X Years?


The second critical thinking question is: “What would my ideal life look like in X years?”

You can replace the X value with the number of years you fancy. But probably the prior question you should ask yourself is this: “What does my ideal life look like – in general?”

We rarely think in that direction. And even if we do. I don’t think we think enough about this.

If you ask yourself this question now. You’ll probably say something general like: Working a meaningful job; Traveling the world, etc., etc.

But what kind of job? Where do you want to travel?

What makes this question great is that it creates a series of sub-questions. Questions that are equally deep and challenging.

Additionally, you can tailor it to a product or for your job.

For example, “How do I imagine the best possible version of this product?” Or, “How do I imagine the perfect day in my day job?”

3. If I Had To Write a Book, What Would It Be About?


What makes this critical thinking question great is that it forces you to think about what you know. And more precisely, to try to package what you know in a volume. Furthermore, it will reveal what you value most.

If you think that you should write a business book. Then probably you value money. Or innovation more than anything else.

If your answer is a psychology book to understand human behavior, for example. Your interests are probably around the spectrum of understanding yourself along with others.

4. What’s The One Thing I Can Do That Will Make Everything Else Easier Or Even Unnecessary?


We are used to having endless to-do lists. We imagine that the more things we do. The more our value will increase.

Looking at the top companies in the world and the most successful athletes will show you otherwise.

The best in the business are not good at everything. They are masters of one specific category.

For instance, a basketball player is superb at playing basketball. Does that mean that he’s good with math? He can be. But probably he is not. Surely, though, he’s doing OK in life.

The point is to figure out what one thing you should focus on that can remove things from your list of tasks and help you achieve better results.

And this question can be applied to everything:

  • Fitness: I can train at home with a set of dumbbells, which will make going to the gym unnecessary. I will save time and money and still be in shape.
  • Business: I can focus on creating a single product. I don’t need a range of products in the same category. This will remove the need for additional machines and staff.
  • Investing: I can focus on investing only in these 3 companies. This will prevent me from trying to learn about the rest of the industry – and stress about the rest of the industry. Plus, increase my return on investment because my cash will be focused on a small portfolio.

5. What Am I Currently Avoiding?


Do you avoid talking about an important topic with your spouse? Do you avoid changing your career? Are you purposely drowning yourself in endless social media posts to avoid thinking about your future? Are you purposefully not starting to work on the current task because you are no longer motivated by the work you do?

There are many things we can avoid.

You can even avoid thinking about avoiding things.

Once you crystallize what you are avoiding. You can then ask yourself why.

Why are you avoiding this? What’s the core reason?

The more you ask why, the more terrain from your puzzled unconsciousness you’ll uncover.

Probably you don’t want to bring a certain topic for discussion with your spouse because you’re afraid of her answer. Or, you avoid taking a leap to another career because you are afraid that you’ll suck.

Fortunately, the more you discover. The more you unclothe your inner thoughts. The better you’ll understand yourself and what you need to focus on next.

6. What Kind of Problems Do I Want In My Life?


Life is basically a series of problems. The good news is, that we get to choose some of our problems.

I know, it sounds a bit absurd. But you’ll see why in a minute…

When you purchase a car, for example. While you surely solve most of your transportation-related issues – i.e., you won’t have to rely on public transportation. Another set of problems comes attached to the ownership of a car. In particular, you’ll now have to handle all the car-related problems – gas bills, changing tires, repairs, etc. And the magnitude of some of the issues will depend on the car you got. For instance, a heavy truck will require more gas and a lot more cash for maintenance than an ordinary sedan.

A similar way of thinking can be observed in every other area of life.

If you don’t want the frustrating experience of the daily commute. You can find a remote job or start your own online business. By doing so, however, your life doesn’t become issue-free. You’ll now have remote job problems – feeling isolated, lonely, etc. – or business problems – need to hire people, figure out how to grow your business, etc.

A subset of questions arises from the “What kind of problems do I want in my life?” Probably the most interesting one is the following: “What kind of problems am I willing to deal with?”

Owning a pet can be observed from the problem lens.

Surely having a dog is an extremely joyful experience. But it’s definitely not a walk in the park. You have to devote a substantial amount of time to care for the animal – feed him, take him out, etc. Yet, people get pets all the time because they are willing to deal with the challenges that come with the ownership of a pet.

What I want to say is that at times, the world might seem totally fucked. Like everyone is against us, and like someone ordered a horde of problems to come our way. This is not entirely true. We choose most of the issues that eventually occur. And we have the power to reduce the number of problems with critical thinking.

7. What Can I Learn From This Person (or Situation)?


Negative feedback makes us uncomfortable. Something that turned out to be not so pleasant is purposefully avoided by the brain. But whether we like it or not. Feedback and trying, failing, and then improving are two of the best ways to grow, become an adaptive thinker, and hammer critical thinking barriers.

There is one extra option, though. A harm-free way to get better.

It’s: To safely observe life from the side bench and take notes while other people do stuff.

If a colleague is doing better than you in your day job. Calling him names won’t do you any good. A much better alternative will be to see what you can learn from this person.

The same concept applies even if someone is underperforming or simply acting like a jerk. There’s a lot of gold not only in “what to do”, but also in “what not to do”.

If you’re struggling to find people to mimic in your physical life. Simply read books written by smart folks.

Reading is probably the best way to expand your thinking skills and outsmart the competition.

My favorite ones in relation to thinking are:

8. Would Could Be?


Thinking only considering what’s already available is not original thinking. You’re simply browsing the catalog of what’s already been made.

The question “What could be?” encourages critical thinking. Furthermore, it ignites creativity and passing the ordinary.

With this question, you break apart from the everydayness and press break from the mundane. You create space to think and to dream.

“What could be” is a mindset.

Just because something is the way it is, doesn’t mean it has to be like this forever. Also, it certainly doesn’t mean it’s the right thing.

So, when the time comes. When something requires a change. Or if you are thinking about solving a problem. Don’t only rely on what’s already been made by others. Ask “What could be?”

9. What Do I Want To Want?


With a question. This question: “What do we want to want?” Is how the ground-breaking book Sapiens: A Brief History of Humankind by Yuval Noah Harari ends. Arguably the most difficult critical question of all.

Because we copy what others want – called mimetic desire. We usually want things everyone around us is longing for. A big house. A stable job. A social media profile with a lot of followers. A wardrobe full of clothes you only wear once.

A dramatically better way to look at life – and essentially at what you want. Is not to preoccupy your mind with what others have and thus copy their desires. But to ask yourself: “What do I want to want?”

Then, further questioning your answer with: “Do I want this because it aligns with my personal values, or do I want it because others are craving it?”

Our goals and our habits are based on our wants.

To ensure that you’ll end up in a place you like – not just land in a random job you’ll regret, for example. The best way to approach your life is by first figuring out what you want.

By far, “what do I want to want?” is the best question I have found that can help you determine the proper direction of your life.

Some Closing Thoughts

There are numerous articles online that aim to improve the way we think. How to approach critical thinking and thinking in general.

I’ve personally covered a lot on the subject in the following entries:

And while there are many good articles and books on the topic. They give you a false sense of knowledge. As if the mere possession of a book or simply reading an article about critical thinking can improve your ability to reason.

Essentially, these are all words on a page – a printed page or a web page, it doesn’t matter.

Reading the words won’t make you superiorly smarter. Using the words will.

And the first step toward using the words we digest is asking yourself questions. Hard questions. Critical questions.

A unique feature of our brain is that if you feed it questions. It will do its best to answer them. Even if nothing initially comes to mind.

So, don’t just scroll through what I’ve labeled above as critical thinking questions. Go to a quiet place. Undust your old desk – the one you used to study when you were a student. Then, take some time to think about the questions above.

Are the answers start to make you feel uncomfortable?

Good. You’re in the right direction.

Trouble Saying No to Temptations?

Join Farview: A newsletter fostering long-term thinking in a world driven by impatience. Trusted by over 4,300 thinkers, Farview is a concise, thoughtfully organized newsletter helping you handle the self-sabotaging thoughts trying to corrupt you.

Share with others: