An Introvert’s Secrets To Creating Great Conversations Without Saying Much
By: May Pang
Tags: Self Improvement, Personal Development, Life Lessons, Introvert, Conversations

An Introvert’s Secrets To Creating Great Conversations Without Saying Much

With examples on how to expertly insert them into almost any conversation May Pang Jun 25·9 min read

Something that surprises literally everyone I meet is the fact that I used to be painfully shy. The most common response I get when I share this fact about myself is, “But making friends is your superpower!”

What people don’t realize is that this superpower came from years of experimentation — including lots of awkward and uncomfortable encounters. For example, when I first arrived in the US and was endowed with a hefty work travel allowance, I made it a goal to take Lyfts everywhere so I could challenge myself to have an intimate conversation with every Lyft driver that I met.

Unlike meeting someone at a mutual friend’s party or a frisbee social game, you pretty much have no common ground to initiate a conversation with a Lyft driver, so it was definitely challenging. The driver could be 18 or 70, an aspiring actor, or a single mom — so, it was impossible to plan what to say.

One of the most valuable skills I learned from that experiment is how to create engaging conversations even when I was feeling low on energy or especially introverted. I discovered that there are ways you can say very little and still leave the other person feeling like they had a great conversation.

These conversational “shortcuts” have served me well over the years on days when I’ve had to interact with others for work or in social situations but really didn’t feel like it. Fortunately for you, you can skip the years of awkward social experimentation and enjoy the fruits of my discomfort.

The secret to having a great conversation without saying much is two-fold. First, ask the right kind of questions that allow people to open up. Second, say things that encourage the conversations to flow towards feelings and not facts. The first part allows them to do most of the talking and the second part will result in them enjoying it.

Part 1 — The Questions

Most people assume that the biggest skill required for making friends is knowing what to say, when it is, in fact, knowing how to ask questions. Questions contain no judgment, make no assumptions, and require no knowledge from you. They shift the focus from you to the other person.

“The art of proposing a question must be held of higher value than solving it.” — Georg Cantor

The best kinds of questions are those that ignite an emotion (preferably a positive one) that cause the other person to open up and want to talk. Here are some that I found especially effective with specific examples on when to use them. The examples presented are actual conversations I’ve had over the years.

1. If you had a magic wand, what would you wish for?

When to use this: This line can be used anytime someone expresses frustration or displeasure of any kind.

Examples of how to use this:

You: “How are you?”

Person: “My work has been so stressful lately; I’ve been getting slammed.” or “You know, just grinding. Gotta pay the bills, right?”

You: “Hmm… if you had a magic wand, what would you do for work instead?”

Person: “Man, I have this novel I’ve been working on forever.”

You: “That’s interesting! Tell me more.”

Why it works: It invites the other person to reframe their deepest pain points into something positive. Focusing on what they want instead of what they don’t want will help them shift their mood. This question will also naturally cause the person to reveal something they are passionate about. You then simply have to follow their lead and simply ask more about it.

2. I was listening to a podcast where they were talking about “x”…

When to use this: This line can be used anytime someone gives you a super generic response and doesn’t give you much to go on. Pick topics that anyone can relate to, preferably ones that relate to passions. The sentence can also be replaced with, “I was reading a book that talks about…”

Examples of how to use this:

You: How are you?

Person: “Good. Good. What about you?”

You: “Good! I’ve been pondering something since I listened to this fascinating podcast that said that most people don’t know what their dream job is. Do you think that’s true? Do you know what yours is?”

Why this works: It allows you to guide a conversation away from small talk and into an area with a bit more depth.

3. I’m having such a hard time doing “x.” Any recommendations?

When to use this: This is another opener that can be used when the person doesn’t give you a lot to go on. As with the question above, pick a simple dilemma that most people are likely to have encountered at some point in their lives. Best combined with asking for a recommendation.

Examples of how to use this:

You: How are you?

Person: “Good. Good. What about you?”

You: “I’m having the hardest time finding good restaurants in this city to take a date. Do you have any favorite restaurants around here?”

Person: “Ooo, there’s a Creole restaurant around the corner that is a cozy little hole-in-the-wall. It reminds me of my grandmother’s cooking. She was the most amazing woman.”

You: “Ahh, sounds like you have a special bond with your grandmother. Tell me more about her.”

Why this works: Asking someone for recommendations gives them the feeling that their thoughts and opinions have value. They will generally follow it up by explaining why they like that one thing so much which gives you an opportunity for follow-up questions. Since they will be describing something that they like a lot, it will also put them in a good mood.

4. If you could only solve your problem by removing things, what would you take away?

When to use this: Best used when someone expresses that they feel overwhelmed or that there is too much going on.

Examples of how to use this:

You: “How are you?”

Person: “Life has been so hectic! Feels like there is just too much going on all the time, and I can never catch up.”

You: “Hmm… If you could only solve your problem by removing things, what would you take away?”

Person: “Maybe I don’t need to bake my daughter’s birthday cake and can just buy it instead.”

Why this works: Most people try to solve problems by doing more. By asking them this question, you are guiding them to approach their problems a little differently, and they are likely to walk away feeling calmer.

5. What would you do if you knew you couldn't fail?

When to use this: This question is great for when someone tells you that they feel lost, in limbo, or are unsure about what to do next in life.

Examples of how to use this:

You: “What’s been happening in your life?”

Person: “I’ve been seriously thinking about quitting my job, but I can’t decide what to do instead. I could go into coding which has better job opportunities or I could go into academic writing.”

You: “What would you do if you knew you couldn’t fail?”

Person: “You know, I’ve always wanted to write children’s books.”

You: “What’s stopping you?”

Why this works: Many people struggle to know what they really desire because their inner critic is so strong and constantly reminds them of all the things that can’t be done. So much so that they won’t even allow themselves to voice their real dreams out loud. By asking them this question, you are creating that space for them to really be honest with themselves.

6. Would this be a loved-based decision or a fear-based decision?

When to use this: When the person you are talking to is trying to make a single decision (e.g., break up with their partner, move to a different country, start a new career).

Examples of how to use this:

Person: I’ve been trying to decide if I should quit my job.

You: Would you be quitting your job to run away from something you dislike (fear-based) or to run towards something you love (love-based). Is this a love-based decision or a fear-based decision?

Why this works: Love and fear are equally strong motivators in life. While both may lead to the same decision, fear-based decisions tend to make us miserable while love-based decisions tend to be more fulfilling. You can provide an incredible amount of clarity to someone by asking them this question even if you knew nothing about them at all.

7. What was your favorite part of your day/that experience?

When to use this: When the person has just told you about a specific experience. It can also be used for future activities for which the person is about to do. A variation of this is, “What do you love about ‘x’?”

Examples of how to use this:

You: What have you been up to this weekend?

Person: “I skied all weekend in perfect conditions!” or “I just chilled out and read a good book.”

You: “That sounds exciting/relaxing! What was your favorite part of your ski session/book?”

Why this works: You’re getting them to relive a positive experience. They will naturally feel positive emotions while describing that experience.

Part 2 — Keeping the Conversation Flowing

Once the person starts opening up, your only job is to stay curious and encourage them to keep going. Here are some easy and highly effective responses and reasons why they work well:

“Wow, that sounds cool. I’d love to hear more about it!” — Expressing wonder by saying “wow” tells the person that something they are doing is unique or special. Everyone likes to feel special.

— Expressing wonder by saying “wow” tells the person that something they are doing is unique or special. Everyone likes to feel special. “That really resonates with me. Tell me more.” — This statement is bonding because you are highlighting that you share something in common with that person. It’s a reminder of the core human elements we all experience no matter how different our lives are.

— This statement is bonding because you are highlighting that you share something in common with that person. It’s a reminder of the core human elements we all experience no matter how different our lives are. “I never thought about it that way. Please continue!” — By saying this, you are expressing to the other person that their thoughts have an impact on you. Everyone likes to know that their thoughts are valuable to someone else. It also demonstrates that you have been actively listening to them.

— By saying this, you are expressing to the other person that their thoughts have an impact on you. Everyone likes to know that their thoughts are valuable to someone else. It also demonstrates that you have been actively listening to them. “How did that make you feel? — This is the classic question of psychiatrists and is perenially powerful. It’s encouraging the other person to continue to tap into how they feel (as opposed to the facts of the story).

Of course, the real secret sauce to all this is genuine curiosity and full presence. We are all born with an in-built lie detector and people can often sense right away when you are not sincere in your interactions.

Takeaway

When Jia Jiang was 14 years old, he heard a talk from Bill Gates and decided that he was going to be even bigger than Bill Gates. That night, he wrote a letter to his family telling them: “By age 25, I will build the biggest company in the world, and that company will buy Microsoft.”

Fast forward to age 30, Jiang had moved to the US and started his own company. He was turned down for an investment opportunity. The rejection triggered a childhood wound and hurt so bad that he wanted to quit on the spot. He then realized that he could build the best product and company in the world, but it wouldn’t matter if he couldn’t get over the fear of rejection.

So, he started a hilarious self-imposed treatment on himself called “100 days of rejection.” For 100 days, he actively sought out rejection so he could be desensitized to it. His experiment went viral and launched his entrepreneurial journey. Today, he is a highly sought-after speaker.

I share this story because as I got to the end of writing this article, I realized that most people will read this, think it was interesting but never take the most important step — actually actioning it.

We often tell ourselves that we don’t do things because we lack the knowledge of how to do it. The reality is that the real reason we don’t do things is that we don’t feel like it.

But here’s the important part — like Jiang, no amount of knowledge will help you live up to your full potential if you never get over your fear of rejection or your inner resistance of not wanting to do something.

I can give you the knowledge, but I can’t make you take that step. I can only tell you what life on the other side of that step looks like. It looks like crazy adventures around the globe, unique experiences with incredible people, unusual job opportunities, and deeply fulfilling communities — all because I took that step to learn to talk to people.

I hope you do, too.