How to Talk to Anyone

11 techniques that will make you the best conversationalist in any room + I'm coming to SF!

👋 Hey, it’s Andrew.

Quick note: Everyone in NYC tech is talking about this: NY may eliminate QSBS and retroactively tax startup exits for founders, employees, and investors. If passed, it could make New York one of the least attractive places to build and invest in startups.

Tech:NYC has put together an open letter to Albany. Takes two minutes to sign. Deadline is today at noon. Sign here.

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My team and I just got back from Austin, where we had an unforgettable few days meeting dozens of founders and CEOs, and even throwing a 2,000-person tech party.

In a few weeks, we’ll be in San Francisco. If you’re around, I’d love to see you there.

Today’s article is about an increasingly rare skill: the art of conversation.

📅 Upcoming Events

• Mar 31 | 🍽️ Junto Founder Dinner (NYC)

• April 6–9 | 🌉 HumanX (SF) – Join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

• April 7 | 🍽️ Junto Founder Dinner (San Francisco) – Hosted with my friend, Nikunj Kothari, Partner at FPV Ventures, at a Michelin-star Thai restaurant.

• April 8 | 🍽️ Junto Founder Dinner (San Francisco) – Hosted at my favorite steakhouse in SF for Seed–Series B founders!

• Apr 17 | ☕ Founder Breakfast Club (NYC)

• Apr 21 | 💐 spring tech mixer (NYC) – Come meet founders, operators & friends in tech!

• Apr 22 | 🍽️ Junto Founder Dinner (NYC)

• • •

I was terribly awkward until my early twenties.

I found it difficult to talk to service staff, strangers at parties, anyone I didn’t already know. Part of it was cultural. I spent two decades in China, an only child with quiet parents. Part of it was confidence. Either way, conversation didn’t come naturally.

My bible for surviving high school was a little yellow book called “How to Talk to Anyone.” I studied it religiously.

The biggest misconception is that most people think you’re either naturally good at it or you’re not. But it’s not true. Some of the best conversationalists I’ve met weren’t born that way. They learned and developed specific habits and techniques over time.

Today I host fireside chats with prominent entrepreneurs: Sahil Bloom, the founders of Venmo, Foursquare, BarkBox, and many others.

Put me in a room with anyone, and I can get them to reveal their deepest darkest secrets.

Last week in Austin, I spoke to over a hundred people, and it reminded me of where I started from: a clueless, shy introvert. And I’m writing this today to share with all of you who were in my shoes a decade ago that yes, it can’t be changed.

Interviewing Sahil Bloom at our OOO Summit in 2025.

Here’s what I’ve learned from studying the best interviewers, hosts, and conversationalists in the world, and how you can apply it.

• • •

What makes a great conversationalist?

It’s not about being the most interesting person in the room, or even having the most interesting things to say, but about making the other person feel like the most interesting person in the room.

Dale Carnegie wrote about this nearly 90 years ago in “How to Win Friends and Influence People. He tells the story of attending a dinner party where he barely spoke all night. He mostly asked questions and listened. Afterward, the host told others he was “the most interesting conversationalist” at the party. He’d said almost nothing.

The best conversationalists aren’t waiting for their turn to talk. They’re curious, listening, and interested in what the other person will say next. It’s a dance, not a fight. There’s no winning or impressing. But you’re playing with the other person, building something neither of you could create alone.

• • •

How to make conversation

Step 1: Make them the hero

Most people try to be the hero of every conversation. They share accomplishments, one-up stories, and impress others with their knowledge.

But great conversationalists do the opposite. They make the other person the hero.

Dale Carnegie’s most enduring insight: people care most about themselves. The best conversationalists use this for great conversation.

Remember their name. Carnegie called a person’s name “the sweetest sound” to them. Use it and remember it. It shows that you care.

Appeal to their interests, not yours. Before meeting someone important, Theodore Roosevelt would stay up late reading about subjects his guest was passionate about. He knew the way to someone’s heart was through their interests, not his own.

Ask about their wins. Their proudest moments. The obstacles they overcame. Let them be the protagonist of the story.

When someone feels like the hero in your presence, they’ll want to keep talking to you.

The legend, Dale Carnegie.

Step 2: Ask better questions

Skip the standard “What do you do?” “Where are you from?” “How’s work?” These questions produce autopilot responses.

Larry King built a legendary career on simple, direct questions. He never asked multi-part questions. He’d ask one thing, then shut up. “Why?” “How so?” “What happened next?” The silence created space for the guest to fill.

Tim Ferriss takes a different approach: unexpected questions that break people out of their rehearsed answers. “What would you put on a billboard?” “What’s a belief you’ve changed your mind on?” “What’s a purchase under $100 that changed your life?” By asking questions guests haven’t heard before, he gets fresh answers even from people who’ve done hundreds of interviews.

Ask open-ended questions that can’t be answered with a single word. Ask questions that make people think. The quality of your questions determines the quality of the conversation.

But don’t ask too many questions. A conversation isn’t an interrogation. If you’re firing question after question, the other person will feel interviewed.

Larry King, radio and talk show host.

Step 3: Use support responses, not shift responses

This is from Kate Murphy’s book “You’re Not Listening,” and it changed how I think about conversation.

A shift response turns the conversation back to you: “That happened to me too, let me tell you about it.” A support response keeps the focus on them: “What did you do next?” “How did that feel?” “Tell me more about that.”

Most people default to shift responses. Someone shares something, and we immediately relate it to our own experience. It feels like connection, but it actually redirects attention away from them.

Great conversationalists use support responses to follow the thread instead of changing it.

The other key: ask follow-up questions, instead of new questions. Amateur conversationalists have a list of questions in their head and move to the next one regardless of the answer. Great conversationalists follow the thread.

Kate Murphy, journalist & best-selling author

Step 4: Say “Yes, and”

After doing improv comedy for a few months, I’ve learned the cardinal rule of “Yes, and.” Accept what your scene partner offers and build on it.

Most people do “No, but” in conversations. They reject, correct, or redirect. “Actually, I think...” “Well, that’s not quite right...” “But have you considered...”

“Yes, and” keeps the conversation flowing and makes the other person feel heard. It doesn’t mean you agree with everything. It means you accept their contribution and add to it.

“Yes, and what happened next?”

“Yes, I see what you mean, and I’d add...”

“Yes, that’s interesting, and it makes me think of...”

When you say “yes, and,” you’re telling the other person: I hear you, I value what you said, and I want to build on it.

Step 5: Match the conversation type

Charles Duhigg’s book “Supercommunicators” explains that every conversation is actually three conversations happening at once:

• Practical (what’s this about?)

• Emotional (how do we feel?)

• Social (who are we to each other?)

[elaborate on each type of conversation]

The mistake most people make is mismatching. Someone is venting about a problem, seeking emotional support. You jump in with practical advice. They feel unheard. You feel confused about why your helpful suggestion landed poorly.

Supercommunicators read which type of conversation is needed and match it. Before responding, ask yourself: What kind of conversation is this person trying to have? Then match it.

CHarles Duhigg, author and reporter for the New York Times.

Step 6: Answer the question behind the question

People rarely ask what they actually want to know. There is always a real question under the service question.

Esther Perel, the renowned therapist, is a master at this. In her podcast “Where Should We Begin?”, she listens for what people aren’t saying and gently brings it to the surface.

When someone asks, “How’s work?” they might really be asking, “Are you happy?”

When someone asks, “What do you think of my idea?” they might really be asking, “Do you believe in me?”

When a friend asks, “Are you busy this weekend?” they might really be asking, “Do you still have time for me?”

The surface question is the iceberg that is 10% above the water. The real question is the 90% below.

Listen for the question behind the question and answer that one, not just the surface question. This is how you make people feel truly understood.

Esthel Perel, psychotherapist, author & podcast host.

Step 7: Go first

Howard Stern has gotten famously guarded celebrities to reveal things they’ve never shared elsewhere. His secret: He goes first.

Stern shares his own insecurities, fears, and embarrassments openly. He talks about his therapy, his failed first marriage, his anxieties. This gives guests permission to do the same.

If you want someone to open up, you have to open up first. Share something vulnerable about yourself before asking others to do the same.

But tease information; don’t give it all at once. Share something personal, then pause. Let them respond. If you dump everything immediately, there’s nowhere to go.

The dance of conversation is gradual revelation on both sides.

Howard Stern, celebrity radio talk show host.

Step 8: Let silence do the work

Most people rush to fill the silence because it feels awkward. So they jump in the moment someone stops talking.

But when you let silence sit, people gather their thoughts and often say something more interesting.

Larry King was a master of this. He’d ask a short question, then wait. The guest would answer. He’d keep waiting. Often they’d continue, going deeper than they initially intended.

The next time someone finishes speaking, count to two before responding. Often they’ll continue. And what they say next is usually more interesting than what they said first.

Step 9: Be genuinely curious

Brandon Stanton, the creator of Humans of New York, has had thousands of conversations with strangers on the street. His photos are famous, but it’s the conversations that make them powerful. People share their deepest fears, losses, and hopes with a stranger on a sidewalk.

His secret is that he has genuine curiosity. He approaches every person believing they have an interesting story. And because he believes it, he asks questions that uncover it.

Here’s the curiosity razor: If you’re bored in a conversation, you’re not asking good enough questions. Every person has something interesting about them. If you haven’t found it, you haven’t looked hard enough. When a conversation feels flat, it’s not because the other person is boring. It’s because you haven’t found the right thread yet.

Brandon Stanton, author and photographer behind Humans of New York.

Step 10: Be fully present

Here’s a razor that cuts through distraction: Talk to people as if it’s the last time you’ll ever see them.

This sounds morbid, but it shifts your attention completely. You stop thinking about what you’ll say next. You stop checking your phone. You stop scanning the room for someone more important.

What if you never saw this person again? Would you be satisfied with how this conversation went? Did you really listen? Did you really connect?

Most people are only half-present in conversations. They’re thinking about work, checking notifications, planning their next sentence. Full presence is rare but people can feel it when you give it to them.

Step 11: Exit gracefully

Great conversations have good endings.

The worst is when a conversation slowly dies, both people looking around the room, unsure how to leave. Or when someone abruptly walks away mid-sentence.

The greatest conversationalists know how to close warmly and clearly. “I’ve really enjoyed this. I’m going to grab another drink, but let’s continue this soon.” “This has been great. I should say hello to a few other people, but I’d love to pick this up another time.”

Direct, warm, and clear with no ambiguity. No awkward lingering. A graceful exit is a gift to both people.

• • •

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

You are no longer the smartest type of thing on Earth by Noah Smith – For most of history, humans were the smartest thing around. That’s no longer true. AI can now outperform us in more and more things. But Noah’s point isn’t that we become useless; it’s that our role changes.

How Social Media Shortens Your Life by Gurwinder – Social media changes how we experience time. Because the content is fast, shallow, and forgettable, our brains form fewer memories.

Why Does Everyone Hate AI? by Rex Woodbury – The backlash against AI isn’t about the tech, but about the timing. AI arrived right when trust in tech was already low, the economy feels unstable, and people are more sensitive to anything that threatens their identity or job.

Three Modes of Cognition by Kevin Kelly – A great tread about the three types of intelligence and what AI vs humans are incredible at.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

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• What other perks should I include? Let me know.

• • •

🖼️ Behind the Scenes

We just threw our biggest party yet with over 2,000 people.

Together with our friends at The Hustle & Agree.com

Every year during SXSW, we host the Secret Austin Garden Party. Thousands of founders, investors, creators, and tech professionals from all over the world come together for one night.

This year was something else...

Live music. A live performance from the Venmo founder, Taco trucks. Cocktails. Cotton candy. A rooftop with one of the best sunsets I've ever seen in Austin.

But the most meaningful part of all this is the people

I watch strangers become friends and founders pitch investors on the patio. I saw creators meet their heroes. Someone flew in from London just for this.

On stage together with Iqram, Venmo co-founder

It was like a music festival!