Working on my conversational skills: do you like being asked these sorts of questions?

[Anonymous]

I've been actively working to improve my conversational skills as a way to get over social anxiety. I've been reading a lot about tips for improving conversation, and of course the top recommendations are "ask more questions" and "listen more." I think I'm a naturally good listener but I struggle with asking questions so I've specifically been looking for ideas on the kinds of questions to ask people that will help get conversation going and give me a chance to listen without feeling so much pressure to talk (long silences or feeling like the person I'm talking to is bored are big anxiety triggers for me).

Some experts suggest asking more probing questions about people's thought process and feelings, to get people to be more expansive in their answers and to show them you are interested in them. Stuff like "what made you decide to do that?" after they tell you about a hobby they have, or "how are you feeling about it?" when they tell you they just sold their house.

This is throwing me though because I would HATE being asked questions like this. It feels very invasive! If I don't know someone quite well, I would feel so awkward to be asked about my thought process or feelings about something personal.

But maybe I'm an outlier. If you were asked questions like this by someone you met for the first time at a party, would you feel flattered and enthusiastic to answer, or would it feel invasive and off-putting?

[Anonymous]

That’s not conversational skills. Find a new book.

[Anonymous]

I think your instincts are correct but the advice books are being dramatic so you remember their tips.

People really like people who project positivity, friendliness, and interest in them.

It will be okay if you soften the techniques suggested and aren't so extreme.

You can try offering your own thoughts as a starter. And then ask for their reactions. Then go deeper.

You can also ask for advice, even if you don't need it.

[Anonymous]

I don't want to be interviewed. You need to include tidbits about yourself because a real conversation is give and take.

You: What are you up to this summer?
Me: I'm taking sailing classes for the first time!
You: Wow, what made you decide to do that?
Me: I've always loved boats and find the water really calming. What are you doing this summer?
You: I'm aiming to read a book each week.
Me: Cool, what are you reading this week?

You see? Give and take.

[Anonymous]

Anonymous wrote:I don't want to be interviewed. You need to include tidbits about yourself because a real conversation is give and take.

You: What are you up to this summer?
Me: I'm taking sailing classes for the first time!
You: Wow, what made you decide to do that?
Me: I've always loved boats and find the water really calming. What are you doing this summer?
You: I'm aiming to read a book each week.
Me: Cool, what are you reading this week?

You see? Give and take.

This is good advice. I have a difficult time with small talk and also not great at these things.

No, I would not like those probing questions. If there are uncomfortable dead silence and no one is talking it is usually safe to ask if anyone has any upcoming trip planned and then also you can talk about summer plans you have too. Another idea is ask if they have any pets and you can say if you have any. A lot of people like to talk about their pets.

[Anonymous]

“How’s it going?” is a more open question that lets people answer either with feelings or logistics.

PP is right about give and take. The opposite end of the continuum is the person who responds to every comment by turning the conversation back to themselves and keeping it there. Those people are tiresome.

Them: I just sold my house.
You: Wow, that’s big news. I know that can be stressful! Where are you moving to?
Them: We bought a place in X.
You: [something about X or else something general like “How’s it all going?”]

It’s like tennis. Keep lobbing it back and forth. If that thread of conversation peters out, you can always start a new thread asking about summer plans, work, where they’re from, ask for a book or show recommendation (“I’m asking people for book recommendations. What’s a good book you’ve read recently?” or something along those lines.)

[Anonymous]

I understand the idea behind those questions, but they seem a little iffy to me.

"How are you feeling about it?"
If I'm upset about something, it's probably not somewhere I want to go in small talk with someone I don't know. And if the person does tell you they're sad or stressed or whatever, now you're in an awkward, unpleasant conversation.

"What made you decide to do that?"
This one is terrible wording because it can easily be read as judgy if the tone is wrong. I'd preface it with something clearly positive like "Wow, that sounds fun. How did you decide to do that?" or reframe to something more like "How did you get into Hobby X?" or "How long have you been doing Hobby X?"

Your questions should give them an opening to talk, not feel like they're getting grilled. (Though I wouldn't read the second one as asking about my thought process.)

[Anonymous]

Your instincts are right OP.

I think the most important thing is to know your audience. I would HATE those questions and feel incredibly awkward and put on the spot and probably stutter "um, it's fine I guess?" Oversharers might love them, but you need to get to know them first to know that.

More open-ended questions or statements might be better. So if you ask about a hobby and they say kayaking, you can say "Oh, really?" and a shy person can say "Yeah, and what about you?" or an oversharer can open up and tell you a long story about it. If they bought a house you can "Wow, that sounds like a lot going on" and then they can say "Yeah but we're managing" or go into a whole soliloquy about their renovations.

[Anonymous]

Don't ask personally invasive questions. If they mention a hobby, ask a question about it, like what are the basics, or how do you learn the skill, or what is your current project.

They can volunteer their personal feelings if they want. It naturally comes out when they start talking about what they are doing and react to their own thoughts.

[Anonymous]

Don't turn this into something hard, Op. The questions you mentioned are within the realm of normal questions. It the overthinking ahead of time of what you're going to say - that's going to trip you up.

[Anonymous]

I honestly don't know how people get to know each other. Usually people barely give away any info about themselves and if you try to get to know them, it seems like prying and leads nowhere. I think you have to talk about stupid small talk to establish a comfort level. The deep prying questions should come after you already have rapport.

[Anonymous]

Read the book by Dale Carnegie had to win friends and influence people.

Ask people about their lives, their kids, their hobbies, etc.

Now it seems like or ask them.

[Anonymous]

I would answer enthusiastically, and I think those are great ways to get the conversation a little deeper.

[Anonymous]

Too many questions is very annoying and off-putting.

Rather learn to hold a conversation on a topic without asking questions.