#67 - Twenty Questions You Can Ask to Make Any Conversation Better

Ever wondered how to switch your conversation from surface level to substantial? Ever been unsure of how to make it feel like you're actually connecting with someone? Whether at a work meeting, a date, or a family dinner - it's important to be able to ask HiGH QUALITY questions. 

In this episode I go over 20 proven, level-3 questions that you can use to make any conversation better. Level 3 questions are intended to be after first initiating the convo (hello!) and establishing a conversation (how are you?). 

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Transcript

Welcome to the Communication Mentor Podcast.

This is your host, Chris Miller.

If you have never been here before, this podcast exists to help us become better communicators so that we can live fuller lives and be more resilient to life stress.

We believe that life is better when you talk to people and that one of the most important pursuits of life is to clearly and confidently articulate your thought.

So each episode helps us do that.

Today's episode is all about starting conversations that matter.

I often refer to conversations that matter as three level conversations.

The first level being the actual initiation, saying hi.

The second level being how are you doing or asking a question that goes beyond that first breaking the barrier of silence.

And then the third level is really where you can foray into a substantial and meaningful conversation.

And typically what makes this a meaningful moment is that it deviates from the social script.

We know how to respond whenever someone says, how are you doing?

It's already wired within us.

I'm doing well, how are you?

Or good, or I'm doing all right, thanks for asking.

But then what's the third question?

What's that third level and how can we get there?

And I have a list that I'm going to put in the description of this podcast of 20 different, what I would consider high quality conversation starters.

The goal with this episode is not for you to memorize or be able to know all 20 of these.

Rather, if you listen to this podcast episode, it's going to be less than 20 minutes and you find one or two that resonate with you, then that is a major benefit.

And you are investing in yourself and you're going to be making your future conversations better because you're going to have more in your toolkit.

So listen through these, find one or two that most resonate with you, and then commit to using them within the next seven days.

I'd love to know which ones you picked and which ones you are committing to using.

Remember, these are level three.

Let's get started.

Conversation starter number one.

This is one that you've seen a lot.

What is the best movie you've seen this year, and what about it stood out to you?

People are detailed in what they watch.

One of my favorite questions to ask people is about the media they consume.

In particular, I may even ask a question like, so what TV have you been watching lately?

Have you been watching any TV?

Typically, I start with the simple one.

Have you been watching any TV?

Because then we can go from there, and if they say yes, then it creates more alignment between the conversation.

The more you get the other person to agree, even if it's really simple questions, the more, as Charles Duhigg calls it in the Super Communicators book, he just wrote neural entrainment.

It's where we get to the point our brains are essentially thinking the same thing, and that's the goal with Great Conversation.

The more you can get agreement by asking these simple questions, do you watch media?

Yeah, sure.

Do you watch TV?

What have you been watching lately?

Oh yeah, that's super fun.

I've really been enjoying that too.

We've been watching this, but it's kind of crazy, and I don't know if I'm going to watch another season, right?

Neural entrainment.

Another thing, what's something you'd love to learn about, in particular, a skill and why?

Aspirations and dreams are a really funny thing.

If we can get people thinking ahead into the future, it opens people up, and it gets people away from the current moment, especially if people are stressed, or they feel financially strained, or they're not feeling the best.

If you get them out of the current moment and thinking to the future, it taps into a different brain, and it creates great conversation.

Five, if you could start a charity, what would it be for?

I'm getting mixed up here.

Four, five, what are you passionate about, and why?

Passion is a really scary question.

Oftentimes, passion is overwhelming and intimidating.

Many people don't know what they're passionate about.

I put it here because I wanted to talk about it.

A lot of people jump to this question, something that I may replace passionate with is what are you interested in?

Because many people don't know about passion.

They get like, passion, I don't know, I need to find my passion.

Man, I want to be passionate about something.

But if you ask interest, that seems a lot more casual, obtainable.

And typically, if someone has a high interest in something, you'll be likely to find a passion in it.

Six, if you could start a charity, what would it be for?

This is fun.

It reveals values and social consciousness.

It goes, it surpasses and transcends us beyond maybe finite resources, something we want to do, but we can't.

If you had even more time, what would you do in your life?

If you had a million bucks, how would you spend it?

These are the questions you could tap into there.

It's inspiring.

What's the funniest thing that's happened to you recently?

All these questions, they're all not as casual as I'd like them.

I went through and I found a whole bunch of different questions, and I tried to pick out my favorite.

But as I read them here, rather than saying what's the funniest thing that's happened to you recently, I would say, have you had any big laughs lately?

And maybe laughs or what's been the craziest thing?

Yeah, what's been the best joke you've told lately?

Or when was the last time you had a really good sneeze, right?

Goofy questions, but it makes people pop out of their mind, like the typical space that they're in.

Here's one.

What book has influenced you the most?

I love this question.

Books are great.

Books are pages and pages of thought, and the beauty of a book as an author has compiled a whole bunch of thought in a certain sequence, and we get to read it, and we deduct new paradigms.

We deduct a completely new way to live life from a really impactful book, and it's a doorway into someone's intellectual and emotional landscape, saying, hey, this is the book.

Also a really good way to get into ideologies.

If someone says, oh, the best book that I read was, you know, Crazy Love by Francis Chan, you're like, oh, okay, like you're a Christian.

Or if they're like, the best book I've read is, um, who's that person?

I got to get back to my grad school days and think of all my critical theory stuff.

Oh, like Foucault, right?

Like power.

Okay, hey, you think a lot.

You are, you've taken a couple of seminars.

Dream job as a child.

I like this one a lot.

I like questions as kids.

What was your favorite thing to do whenever you were growing up after school?

That's a great one.

Dream job as a child is fun because it taps into the wonder and the energy, and it's guaranteed to make you laugh.

What's the most challenging project you've worked on?

This seems a bit too formal for me.

I would say, have you had to work on anything in work that, or has there been anything in work that's made you want to pull your hair out lately, or made your eyeballs want to pop out of your head because it was too much?

The most challenging project you worked on sounds more like an interview question.

And use it at your peril.

Who in your life has inspired you the most?

Let's think of a better way to ask that question.

Who do you find most inspirational?

It could even be better whenever you ask it with a subset, like who do you find most inspirational when it comes to business, or when it comes to family, or when it comes to creativity, or when it comes to faith or discipline.

But I think discussing admiration is cool, because heroes and role models have so much influence.

And if someone really does have inspiring people in their life, it can be a great way.

It leads to some awesome conversations.

You get me talking about my mom, very inspired by my mom.

You get me talking about my dad.

You get me talking about a lot of the people in my family.

I find them very inspiring.

So I think that's a really good question.

It's like, where do you find that...

Who's provided you the most inspiration throughout all this?

What's something you've always wanted to try but haven't gotten around to?

I like that question.

What's something you've always wanted to try?

I remember I used to ask this question on my podcast to everybody, and it was, what's something you wish more people knew about you?

Most of the time, people would always say, oh, I'm an open book.

Uh-huh, sure.

And then they would say, but there's this thing.

Yeah, there we go.

And that's the beauty of questions, is that there will be this thing, but it may not pop up after that first question.

Typically, the best way to get there is silence.

The other way to get there is through probing questions.

Follow up, oh, you're an open book.

Well, let's give it a shot, right?

Prompting, but silence.

So, what's something you wish more people knew about you?

What's something you've always tried, but haven't gotten around to?

Okay, if you could instantly become an expert in anything, what would it be?

This is fun.

Expertise is a funny thing.

I asked this question to somebody this weekend.

I said, if you could be the best in the world at any sport, which sport would you choose and why?

I think we both settled on NBA.

I think I settled on soccer, but then I reneged NBA.

I forget.

I think living in the United States, growing up in the United States, we probably have a bit more respect for NBA, even though I'm a big soccer guy.

What's the most unusual conversation you've had?

That's a fun question.

I think that I can think back of a conversation I had in graduate school where I was sitting in a graduate seminar room by myself.

It was late.

No, I wasn't by myself.

I was with a friend.

And we were studying, and this person climbed through the window.

And the conversation that ensued was one of the most bizarre and memorable conversations that I've had.

You can also ask this question a lot of different ways.

For instance, what's the most memorable conversation you've had?

What's been the biggest conversation in your life?

One of the questions I used to ask in the podcast was we can look at life through days, through weeks, through months, through years, but we can also look at it through conversations.

Me having the conversation with my mom, first learning about her cancer, I think about that.

Me having a conversation with my brother whenever he was having a really hard time with schizophrenia, I think back about that.

I remember going to his door and him opening the door and looking like a skeleton with sunken in eyes.

I was off at university and just, I remember standing on that porch and seeing him and really seeing the lack of life in his eyes.

I remember talking with Annie at Winston Salem Dash baseball game before graduate school started, where she told me I should write a book.

I remember sitting down with her dad feeling nervous, eating breakfast, having the ring in my pocket, asking for his blessing.

All of these are big conversations that we can look back at life on.

That's a great question to ask.

What are some of the biggest conversations you've ever been a part of?

What's something you're proud of but never had the excuse to talk about it?

How would I answer this question?

I have some things in mind.

I think that being proud of giving myself organization when no one is telling me to do that, being proud of researching just a little bit more about a podcast topic or about content, being proud of exercising, being proud of there's a whole bunch of stuff.

Maybe I'll talk more about them later.

That's something I struggle with.

What's a habit you recently adopted and made a significant difference in your life?

Everybody's on habits right now.

If you ever read the book Atomic Habits, habits is a buzzword.

Habits is a buzzword.

Can a single word be a buzzword?

Habits, everybody wants good habits.

There's so many newsletters and videos out there about establishing award-winning habits, habits that will change your life.

But we do love habits.

What's a habit you've adopted that made a significant difference in your life?

If you're really open, maybe what's an addiction you have that's debilitating to you?

What's something you wish you'd stop?

There's a whole bunch of stuff going on right now.

People are losing a lot of money gambling, you know, smoking, alcohol.

A lot of people want to quit watching porn.

A lot of people want to make changes in their life.

What is that for you?

And the more open, the better.

I think that could be a really good conversation.

What's your favorite quote or saying and why does it resonate with you?

Quotes.

There's quote people out there who know a ton of quotes, but most of us have a sequence of words that somebody else has said or written that resounds with us unusually.

It resounds to us much more than all the other words we read.

I remember someone told me whenever I was a freshman in college, they looked at me and they said, you will thrive.

Three words, you will thrive.

I still think about that to this day.

I have on my whiteboard over there, as I'm navigating a lot of different vocational uncertainty and knowing what to do here, what to do there, you will thrive is on my whiteboard.

Psalm 100, make a joyful noise to the Lord all the earth, serve the Lord with gladness, come into his presence with singing, know that the Lord, he is God.

It is he who made us and we are his.

We are his people and the sheep of his pasture.

Enter his gates with thanksgiving and his courts with praise.

Give thanks to him, bless his name, for the Lord is good, his steadfast love endures forever, and his faithfulness to all generations.

I need to know that.

The Lord is good, his steadfast love endures forever.

That's encouraging to me.

If you were hosting the president for dinner, what would you cook for him?

What would you cook for Joe Biden?

What would you cook for Barack Obama, George Bush, Bill Clinton?

I love this question because you better bring out the best.

Hey, you may be a Republican and you're like, I'm gonna cook grits for Joe Biden.

Well, that says something about you and we can learn more.

Or maybe you're like, I'm gonna cook something really nasty for Trump.

It's like, okay, well, we can talk more about that.

What would you do if you won the lottery tomorrow?

Ha!

This is an awesome question, Zach Harris, a good friend.

Hopefully, I may do a guest podcast episode with him soon.

He has a 20-step process for what he's gonna do when he wins the lottery.

He's going to make sure he has contact this one money man, contact these few attorneys, go to this one place and get this one room and claim it via proxy and immediately establish or look into establishing a 501C3 and have this LLC that it goes and goes and goes.

But it creates such a fun conversation.

If you just know a few questions to ask to back that up, what would you do if you won the lottery tomorrow?

What would you spend it on?

How would you spend it?

And then you get more specific.

The more specific, the better when it comes to hypotheticals.

If you know me, you're getting to know me now.

Maybe this is your first time listening.

Know that I love hypotheticals.

Never have I ever not loved hypotheticals.

Lately, I've even been making hypotheticals more extreme by saying, if you won the lottery tomorrow and you had to make a decision on how you're going to spend it, what would you do?

And then if they're having a hard time, I say, and there's a gun to your head.

It may be morbid, but it helps people answer, even though it's not real.

It's just more immediate.

Those are some great questions that you can inject in your conversation to make it much more substantial, to allow yourself to unplug from the social script, get into territory that is unseen, unheard, really what could be seen as dangerous for some.

If you are supposed to speak on a teleprompter and not get off script, these questions aren't for you.

But if you want to know more about the people around you, and you want to spark up the conversations you're having at work, on a date, or anywhere in between, ideally don't date at work, but hey, I know some really good love stories happening from that.

So it works for some, you just gotta cover your bases.

Alright folks, if you like this podcast, if it's giving you any value, share it with one person, leave a review and a rating.

The more the podcast grows, the more people are able to see it.

And I'll be back next Monday with a brand new episode.

I'm excited to see you soon.