High Quality Conversations: Why Tolerate Anything Less?

By Luis Thiam-Nye on 25 June 2020
You may find it easy to think that beginning a conversation with someone is the kind thing to do — until they start despising you for it!

High-Quality Conversations: Why Tolerate Anything Less?

There are many different types of people in the world: some are more emotional than others, and some are more oriented towards sheer practicality.

Perhaps I am missing something here, but I do not think it makes sense to merely say “Hi!” to someone and let the interaction awkwardly hang there.

Of course, I am not saying that it is wrong to greet someone after a prolonged length of time not having seen them; it’s definitely a positive thing to acknowledge another’s presence, and it certainly makes me feel more real-life (whatever that means). There are also times when people can have highly engaging conversations about common subjects of interest.

However, I’ve found that there can be this gap in the system where it is inappropriate to greet and the conversation has little engagement value. Currently, as I am writing this, I am having difficulty expressing this issue due to the varied forms it can take.

So, let us attack this using examples:

The Feeling That the Silence Needs to Be Fixed

Undoubtedly, we’ve all had those moments in life when we’re all sitting in a car together, travelling to some destination. Our families do not constitute the only passengers, though, since the sure spell of silence comes along for the ride as well.

You know those moments when nobody has talked for such a while that it becomes noticeable, right? In these cases, a creeping level of discomfort can arise which may incentivise some people to attempt to break the silence.

A car journey is a good illustrator of this, seeing that the passengers of the car have no immediate escape from one another. Needless to say, there are plenty of other times where one feels that speaking up is necessary for its own sake. Another such example would be eating around a dining table with your family.

Would you feel the need to fill the silence with a conversation?

Appreciating that we are all unique little snowflakes, not everyone would feel that need. But some would. And that’s fine.

So, for the time being, put yourself in the position of someone wishing to stimulate social engagement. The important part comes when we ask: how would you go about breaking that silence?

Bad Ways to Fill the Silence

If you wanted to initiate a conversation with someone, you might consider these options:

  • A: Talk about the weather.
  • B: Ask an open-ended question like “How are you?” or “What are you doing?”
  • C: Inquire about something specific you know is going on in that person’s life.

Let’s not talk about the weather — it’s probably not a meaningful conversation. That being said, there may be special features of the weather that makes it worth talking about. Has it been long since rain passed? Perhaps the plants need a bit of watering.

Moving swiftly onto option B — where the meat is at. Now, we can start to differentiate between a high-quality and low-quality conversation.

General, Lazy Questions

Think about this: how much effort and thought does it take to ask a general question such as “How’s your day been?”

  • You don’t need to consider any specific interests of that person
  • You don’t need to consider any context relevant to the time or location
  • You don’t need to have anything to contribute to the conversation

Evidently, this strategy of asking an open question about the person’s life is a cheap and lazy way — or, rather, an excuse — to open a conversation; it demonstrates no true interest in that person nor any interest in having a meaningful conversation. It’s a lazy question.

When you ask a question like this, you are essentially asking the other party to do all the work for you; a command for the other person to come up with talking topics on their own.

You object to this conclusion, do you? Do you think I have it wrong?

After all, asking a fellow human being about their day is the considerate thing to do, is it not? Perhaps you view it as a kind act of showing interest in another’s affairs.

Purely innocent.

And then let us not forget the timeless wisdom of successful social skills: always let the other person talk! People love to talk about themselves — it’s human nature. Dale Carnegie and his book How to Win Friends and Influence People would firmly agree.

So, why then would I be against you “taking an interest” in the life of a precious friend or family member?

Well, there’s one problem: often, when I am asked these lazy questions, I do not feel like the other person is truly interested in my activities. Returning to why you would want to ask a lazy question, the underlying intent is to break some sort of silence or absence of connection.

To be clear, the purpose was not to find out what was happening in another person’s life. That came second.

Let’s be honest, you likely don’t go wandering around thinking,

“I really want to know how Jimmy is feeling today and everything that happened in Jimmy’s day!”

But if you do have that independent motive, good for you! You hence have the necessary internal curiosity to hold an authentic, high-quality conversation.

Otherwise, you are forcing a conversation. Nobody likes a forced conversation. I don’t.

For that reason, I only put in as much effort as the other person when I get asked a lazy question. Here are some examples:

Q: “How are you doing?”

“I’m good”

Q: “How has your day been like?”

“It’s okay”

Q: “What are you doing?”

“Nothing much”

Seems harsh? I wouldn’t think so.

If I don’t feel like the inquirer is truly interested in the contents of what I have to say (and that they are just trying to make frivolous conversation), I don’t bother; there’s no point putting much effort into a detailed and thoughtful response if the other person cannot absorb the value in that.

In the exceptional cases, I might have something interesting that I would like to share with that other person, which leads to a fuller conversation. However, I do not first need them to ask me what’s up.

Let’s now turn it around: imagine that you are the person asking about Fredrick’s day, for instance. Do you actually care about what the other person has to say? Or perhaps the question was only asked out of politeness or to build rapport — now we’re losing authenticity.

In most cases, if you were later asked about what Fredrick had responded, you would not remember hardly any of the details. (That is unless you were truly interested in Fredrick’s life or he described his journeys riding magical flying pigs.)

To me, it seems that these general lazy questions are a waste of everybody’s time. After all, what do they seek to achieve? If you really wanted to be nice to someone and light up their day, you would presumably make that extra effort to ask a good quality, engaging question.

Specific Questions Are a Nuisance Too

“Okay then,” you may think to yourself, “if I should be putting more effort into my questions, then I need to ask about specific things in the person’s life!”



It may seem like I am contradicting myself here, but you need to be careful when you open a conversation using a topic you know is particularly relevant in the other person’s life. I will illustrate with an example.

Let us say that you know Peter is a software developer extraordinaire. Meanwhile, you know nothing about programming. However, you happen to be aware that Peter is having problems getting his software to work.

You ask: “Hey Peter, did you get your program working?”

While you are indeed demonstrating knowledge of the current affairs in Peter’s life, this question is problematic for two reasons.

Firstly, if Peter has not fixed the problem, you have reminded him of his problems; he subsequently throws a tantrum and turns over the desk.

Secondly, if Peter has fixed the problem, Peter gets annoyed that you are asking such a useless question about trivial, routine matters. Remember, you’re stepping onto Peter’s territory — coming across bugs and fixing them is routine and nothing unusual. When questioned about these routine matters, Peter can feel like you are obsessively monitoring him with every breath he takes.

To clarify, this is still a lazy question because it would never elicit a meaningful response; it’s a yes-or-no answer.

Another mistake you could make is asking the wrong questions based on a lack of

knowledge. If you lack knowledge but are curious to learn more, that is fine. However, it gets quite bad when you ask a question which rests on flawed assumptions. A lack of knowledge could cause you to come out with some questions that blatantly fail to make any sort of sense whatsoever.

For instance:

“Hey Peter, did you the JSON header file?”

But there is never was a “JSON header file” — that itself makes no sense. In fact, the issue had always been that the website response headers specify the wrong content security policy.

Peter sees that, clearly, a mere mortal like yourself has a very shallow understanding of his craft. Thus, he is insulted by your pathetic attempt to “join the club”. You’ll never be like peter.

Evidently, inquiring about specific details can counterintuitively produce the opposite effect to what you intended.

Instead, you could have asked more generally about the issue, with a learning attitude. If Peter sees that you acknowledge your own flaws in your understanding and that you have a true interest in learning, then perhaps he can educate you.

Although, he could equally consider you as lacking true dedication if you came to him for help before you consulted other resources like the Internet.

The Ultimate Energy Drain: Forming Judgements

Meet yet another virtual actor: Kevin.

Kevin has just completed his entry exam to the University of Irresponsible Magicians. After months of immense preparation, it is fair to say Kevin has given out all the blood, sweat and tears he has to give. Now, he is exhausted, albeit relieved that at last the exam is over and done with.

Next thing he knows, you come walking into the scene and think the time is ripe for a healthy dose of social interaction:

“How did you find your exam?”


Do you want to end lives with that sharp hook of the question mark that pierces deep into the flesh?

Anyway, you run the risk of Kevin not enjoying this question.

Firstly, you are requesting Kevin to form an opinion — in this case, about how his exam went. This can be mentally taxing, and certainly not “computationally kind”. Realise that people don’t always have pre-defined opinions about everything; sometimes people choose to not spare the time to think about certain things.

In this case, Kevin has not given much thought to how he would describe the exam experience. Of course, there is always the reliable, uninformative fallback of “It went okay.”

That’s when you know you’ve stumbled across a topic that the other person does not want to talk about.

Secondly, if that did not annoy Kevin enough, your question appears to ask for information Kevin does not have access to. After all, how can you judge how well an exam went if you have not actually gotten any results back?

Yes, Kevin could guess based on how easy he found it, but that is a difficult thing to judge. Once again, you are straining Kevin’s fragile little brain. He has already put so much mental energy into the exam, and now you are requesting that more juice be squeezed out of a withered, dry lemon.

It’s okay for it to be as it is: the exam was neither good nor bad.

Often in life, we have that temptation to constantly making sense of things and forming opinions. Although, the real truth is that we do not need to have opinions on everything we come across; it’s okay to focus solely on the aspects of life that are most meaningful to us as individuals.


In conclusion, your attempts to promote healthy social interaction could unintentionally bring unwanted inconvenience to the other person.

This is merely something to be mindful of. Unfortunately, I have no recipe for starting engaging conversations. So, my message is this: at least try and put in the effort to make a conversation worth everyone’s time.

Remember these key points:

  • Having conversations take energy.
  • Acts of recall, judgement, assessment, and evaluation can drain someone’s precious energy.
  • Base your interactions on authenticity and genuine interest.
  • Make an effort to understand things before you ask about them — your effort will show.
  • Be careful not to ask about something that is not relevant to the other person.

Of course, as I mentioned early on in the article, sometimes silence is bliss; be aware of the times when conversations are unnecessary.

Some topics may not be what the other person enjoys talking or thinking about. For instance, you are probably best refraining from heavily inquiring about a recent death of a relative. In some cases, the other person could feel like you are stepping on business that is none of yours.

Another little tip: reduce the assumptions in your questions, since these assumptions can make your lack of knowledge about the other person stand out like a stubborn wart.

To exemplify, if you do not know for sure whether someone participated in a sports game, avoid this:

“How highly you score in The Darts Tournament?”

Instead, begin with a quick initial stage-setting query such as:

“Did you play The Darts Tournament?”


“Oh nice, what was your score?”

Lastly, this article was inspired by times when I would get annoyed by people asking me what I thought to be pointless questions. However, I have absolutely zero credible expertise with regard to the art of successful conversations.

So, don’t take my word for anything.

Don’t tell anyone, but I rarely know what I am talking about!

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About the author

My name is Luis Thiam-Nye and I own this place.