What small talk questions can I ask when I'm mostly interested in the motivations of people?

Question

I'm not very good at small talk, even though I have improved quite a bit. My mother once said it's because I'm not interested in most of the topics that small talk brings up. But then I guess many small talk topics are politeness and not true interest. Anyways, I sat down and wondered what I am interested in regarding people. I'm an artist and storyteller so I noticed I usually hope the other person has a story to tell when I ask them a question. I'm also a lot more interested in why people do things rather than what they do.

One tactic I've come up with is asking what job someone has, and then following up that question with "How did it come to that?" which in 50% of the cases results in a story. (However, there are many people who chose their path randomly and seem to be without real aspiration and then I'm kind of lost.)

Do you have any suggestions for other small talk questions that are not too personal but still focus on motivations and aspirations?

(Note that I won't be able to check this post until tomorrow, so I won't be able to answer questions immediately)

Update:

I'm talking about one time encounters with longer talks, for example in Germany you can share a group ticket for the train with strangers to save money and you'll end up conversing for an hour. Uber driving might be similar. Or at events such as weddings where you talk to aquaintances of the couple that you will likely not see in years, so essentially also a one-time encounter with extended smalltalk.

Update 2:

I'm also considering a case where a conversation has been established where my example question works.

Answer 1

For small talk, there are some steps you need to go through in my personal experience. (I am not saying you must. These just work for me).

A. They must be genuinely interested in small talk.

If someone is having their headsets on or sitting in a corner reading a book. It is generally a sign they don't wanna interact with anyone or they are just more on the introverted side. If this is just one-time thing it's generally not worth it to disturb them.

B. You got to get a common ground for you to start a conversation with them.

Talking with a random stranger can be an uncomfortable thing for most people. So a random question out of nowhere is gonna be awkward.

C. Give a little, take a little.

You tell them a little about you and they will feel obliged to tell you something back. Humans generally don't like owing anything so this might work. And think about it why should they tell you something when there is nothing in it for them?

D. Introduce yourself.

If you feel after two or more exchanges, they are chatty, introduce yourself. They might do the same and you can pick up from there.

So how do you do these things then? How to identify the common questions? Very simple: on the train, tell them where are you heading and why.

You have to give them topics to talk about. Subtle hints.

Hi heading to xxx? Me too. I am going to meet my friend; real arsenal (Sports club) fan that one.

In the above, since you told them why you are going somewhere, people's natural reaction is to tell you why they are going somewhere too. And this is also subtly telling them "these topics I wanna talk about, are you interested?"

Most people are into some sort of club or sports. Gave them hints about the club you liked. If you are lucky, they might join in or at least you will know they are not a sports fan.

You can ask an open ended question. If they reply then well and good. Continue from there.

With this traffic we are gonna get nowhere, I wonder what the trouble is?

You can ask about the place you are in.

Beautiful place xxx we are heading to. Do you feel the same? I love it there. You are going there?

If they reply then well and good. Continue from there.

You have to build a rapport and get over the barrier of being a stranger. If you sense they are really not into small talk and are just not open about answering any of these then you need to accept it.

Answer 2

Small bit about me

I do love to spend some of my time in conversation even though I consider myself as introvert. Saying that I try to be as polite as possible and keep on smiling as it allows people to feel more calm and brings up the mood for both sides.

My advice

I often start the conversation by politely greeting and then talk about weather. The weather outside and eg. I say "I love weather. Here in Czech Rep we do have all sorts of. What (weather/stuff) do you like?" and you hear what people like.. Good starter is place where other person lives or is from.

If something interests you or you feel good talking about something mentioned you have found common ground. If not you can push the side you like in manner "and do you like any sports?" and can push it further with "I love football and panoramas so I love running where you can see the mountains, sea or forest or even some amazing buildings like our famous dancing house in Prague". Often common ground is other countries, travelling and stuff.. When you know enough story you can interact to find out more. :)

You can talk as long as you both are interested and enjoy the company.

Wish you a lot of pleasant small talks on your travels and weddings. :)

Answer 3

My favorite small talk opener is to make a statement with which my conversation partner will absolutely agree. Then to say something that's hit-or-miss... and which ever way it goes, there will be something interesting to talk about. For example:

"Nice weather last week", you might say... "not in Duesseldorf," he might reply. "When were you in Duesseldorf?" Now you have something to talk about!

Answer 4

There was a TEDx talk about this exact topic back in 2016 by Kalina Silverman. Her story was wanting to make meaningful conversation with anyone. She started working out questions that elicited more than just mundane discussion and instead lead to people discussing themselves and their more inner thoughts and motivations. She calls it "Making Big Talk" and I would highly recommend it.