When writing some guidelines for how I want to approach life, I included, "The important thing is not to stop questioning. Curiosity has its own reason for existing."

Questioning is very useful -- it forces us to face and correct our assumptions, opens the doors to discussions that can improve things around us, and allows us to learn more than we already know. But it is a skill we need to train intentionally by firstly doing more of it, and because it requires a change to our default frame of mind, it can be pretty challenging to get into. So let's talk about asking questions.

Like anything else, we don't begin as masters of it. But we never start from absolutely nothing -- we draw from experience in other fields when we learn new things all the time. The same goes for questioning.

The first hurdle is our internal regulation that tries to keep our thoughts in check, whether to not feel too different or "crazy", help us sound intelligent, or not accidentally upset others. But the problem is that avoiding such moments often hurts our ability to think differently.

Furthermore, in western culture, a lot of questioning comes off as impolite, or we feel it might make us appear unintelligent in the eyes of others. This is partly because our society presumes that individuals always know what they're doing. But we need to stop assuming that we know the answers to help us ask the questions that can help us in the first place. It also helps us deal with having something that we take for granted suddenly questioned, as that often comes as a shock to the system. Realising that it's something we haven't thought about before and not having an answer ready is a difficult position to be in.

Personally, it took quite a few years for me to become comfortable asking questions, but there wasn't a moment I was conscious of where it all clicked, and I suddenly gained enough confidence to do so. Perhaps it helped that I accepted that I don't know everything, so if someone had the patience to answer my questions in-depth, it didn't feel like a negative outcome.

However, discussions have felt problematic when the answer involved how "obvious" or "simple" the answer was, yet the questions I had regarding what I saw as flaws around the concept were never answered. Or when the topic was reduced to differing opinions, shutting down any further potential debate.

But ultimately, answering "obvious" questions is still worth it because we often solidify our knowledge through teaching, a new concept might click in our minds as we do so, or we realise the entire idea was rubbish to begin with.

This brings me to my next point: certain lines of questioning can also sound like the beginning of the usual disingenuous conservative talking points. An example one might face is someone asking a slew of questions that seem somewhat legitimate at face value, backed up by, "I'm just asking questions." But that's because they often rely on the subject not having in-depth knowledge of the topic to answer quickly.

We know we're witnessing such an occurrence when the concepts used to question others depend on vague notions, such as what is considered "natural". But once we start noticing the red flags of disingenuous argument, their hypocrisy is really easy to spot. Furthermore, if we really want to go in-depth, a lot of research reveals that reality isn't as clear-cut as the black and white view of many topics we're taught. For example, many of the terms used in natural sciences are closer to the abstractions from reality we create when coding. But naturally, we can't do that while in the middle of a conversation -- it's something for the time afterwards.

So the challenge is to learn to and become more comfortable questioning everything around us but doing so in a manner that doesn't come off as aggressive, condescending, or disingenuous. We can do two things to work towards a solution here: one, we must also learn to listen better, and two, we must cultivate environments where people feel safe to question and debate.

Learning to listen is important because, besides being the minimum amount of respect we can show for another, it allows us to focus on the here and now more intentionally. It also helps us turn off our internal translators, that can often accidentally turn someone else's ideas into something different that's more acceptable to what our brains are used to. We become more open to seeing how others understand our language and adjust if we find we're misunderstood by many sources. Then finally, because we've processed information through listening, it becomes easier to think of questions to ask. Everyone benefits.

But what can we do to improve our listening skills? 

The trick is then to find the time and space to do so. In a work setting, it can be tricky because sometimes we end up in a team that doesn't want to deal with questions -- they'd prefer to go with assumptions and just get started doing whatever they do. If we find ourselves in a position where we keep redoing the same thing in different ways because we didn't stop to think before doing, someone needs to strongly support an increase in early discussion.

Similarly, sometimes a complex question warrants agreeing to write it down and address it in another meeting that focuses on the question with the relevant parties. Of course, no one likes creating more meetings and being the person asking the difficult questions isn't a glamorous role. However, discussions regarding the hows and whys can prevent extra tedious work down the line.

However, in our personal lives, things are often trickier. We're increasingly compelled by consumerism to engross ourselves in activities when we spend time with friends, family, and loved ones. While highly engaging activities allow for fun, they often make it difficult for actual discussion, so finding time for a healthy amount of simply hanging out and talking can often be beneficial. Make it somewhere that isn't too noisy and give it a decent amount of time; eventually, the level of comfort with questions will increase.

Now we still have one remaining dilemma: how do we learn to ask questions?

An easy one to start with is "why?" To take a quote straight from the mouth of Jurassic Park's Ian Malcolm, "Your scientists were so preoccupied with whether or not they could, they didn't stop to think if they should."

But we can take something from examining the question "why?" that might help us. It's an open-ended question, allowing room for more discussion and requesting more explanation. Answers beyond a simple yes or no are valuable as they help us build follow-up questions, allowing us to delve deeper into any topic. So rather than having a set of planned questions, we can start with something as simple as "why?" and follow where the conversation or train of thought takes us.

There's nothing wrong with veering off the original topic and heading into other territories. So if we set out to discover why something works the way it does and ultimately learn about something completely different, we still learnt something and gave our brain some exercise. Of course, not getting strung along on content binges and what we do with our newfound knowledge are other matters to contend with. But generally, having an open mind and being less strictly results-focused in our lives benefits our mental wellbeing. This means focusing on the process rather than working to achieve an outcome because where we're trying to reach becoming more open-minded and well-rounded intellectually, not meeting direct objectives and key results.

One last thing I'll mention is that if we use a search engine to look for answers, we need to be careful to ensure we don't ask loaded questions. For example, rather than looking for an already assumed opinion, such as "why XYZ is bad?" we should be looking for other, more open terms, such as "history of XYZ". This is because search engines such as Google are trained to give us what we want, so if we infuse the search with an assumption, it will try to provide us with things that match that assumption.

And that's as far as my thoughts have gotten me with this. This more casual approach where I work through a problem as I write was my first experiment in exercising my brain by just writing, and not only did it seem to help, but it was also fun. So I think I'll do it more.

Stay dialectical.