Skip the autopilot questions: how to start conversations that go deeper

The Short Version

Small talk stalls because the usual openers (how are you, what do you do, where are you from) have been answered so many times that the other person replies without thinking. Behavioral researcher Vanessa Van Edwards and mentalist Oz Pearlman both name those exact questions as the ones to drop [1][2][4]. Their replacement is a question that asks for a story or a choice: Van Edwards says "Facts are dead ends, conversationally," and Pearlman wants questions that open more doors [1][2]. Charles Duhigg adds that the best communicators ask questions about values, beliefs and experiences, and ask far more of them than other people do [3]. Michael Bungay Stanier opens with "what's on your mind?" so the other person sets the agenda, and insists that what you do with the answer matters more than the question [5]. The protocol that follows from all four is short: skip the scripted opener, ask something specific and open, follow with "tell me more," match the kind of conversation you get back, and deepen in stages [1][2][3][5].

Table of contents

What They Said

Vanessa Van Edwards: break autopilot, ask for stories

Van Edwards calls herself a social overthinker and a recovering awkward person, and says her research began as an attempt to work out what good conversationalists do differently [1]. Two patterns came out of cataloguing their questions. The first: "They are asking first questions that break autopilot." [1] They do not ask how are you, what do you do, or where are you from, because those snap the listener into a script [1]. The second is that they look for stories, not facts [1].

Her objection to factual questions is mechanical. Where are you from, where do you live, how many children do you have: each gets a one-word answer, and then the asker has to think of the next question. She says this puts a burden on the asker and makes them listen less, since they are busy preparing what to say when the short answer ends [1]. The three words that make a person interesting in any room, she says, are "tell me more," and they only work after a question that invites a story [1].

She names two worst questions. The first is whether someone has been busy, which sends the person's mind looking for the negative and has no good answer; she adds that research shows talking about how busy you are makes you look less competent [1]. The second is what do you do, which is so scripted that the brain stays asleep [1]. In an earlier conversation with Mel Robbins she suggests going on a diet from the three standard openers and says that, to talk to anyone with ease, "the only way I think to talk to you with ease and confidence is to break autopilot" [4].

Her replacements are simple. Do you have any fun plans coming up, did you do anything fun this weekend, what are you excited about [1]. In place of how are you she has used a question about what is good, or whether the person is working on anything exciting [4]. She has tested starters in practice: in a speed-networking experiment with 500 people across three events, the highest-rated safe questions were about a personal passion project, the highlight of the week, and fun upcoming plans [4]. One of them, in her words, is "what personal passion project are you working on?" [4]

The same experiment produced a warning. The question about a person's story drew either top or bottom ratings: extroverts loved it, and introverts and ambiverts hated it [4]. She avoids it now, on the grounds that it demands a deep answer from a stranger and sets them up to ramble [1]. She also avoids questions that put people on the defensive, such as why someone is single or what their greatest weakness is [1].

That warning is part of a larger structure she takes from the psychologist Dan McAdams, who describes three levels of knowing a person. Level one is general traits: hometown, family, work. Level two is personal concerns: goals, motivations, values. Level three is self-narrative, the story a person tells about their own life [1]. She says the social brain processes people in that order, so you cannot connect with someone's why before you know their what, and extroverts in particular tend to go too deep too fast [1]. Her answer is to do level one through stories instead of facts [1].

For level two she offers what she calls conversational confetti, a pattern she found in thousands of hours of Howard Stern transcripts: prefaces such as the weirdest thing, the most embarrassing moment, the best or worst advice. They open a gap the listener wants closed, provided the story delivers and is true [1]. She likes guessing games too (let me guess where you are from), which bring play into a factual question [1]. At work, she replaced weather chat at the start of a weekly call with a round of "tell me something good," which gives introverts a predictable turn; one team member told her "Monday is my do-good day," so she would have something to share [1].

Level three belongs to perhaps two or three people in a life, she says, and not to the five minutes before a team call. Questions at that level include what the title of your memoir would be, or the one Lewis Howes asked her about a belief of hers: "what age did that belief start?" [1] If someone jokes such a question away, they are not ready or not your person [1].

She adds two things for the receiving end. When you are asked a boring question, treat it as a chance to wake the other person up: answer with humor, or give a short answer with hooks that make a follow-up easy [1]. And prepare. List the questions you are asked most often and have a short and a longer story ready for each [1].

Oz Pearlman: turn a compliment into a question

Pearlman has spent more than 30 years as a mentalist, and says the useful part of his work is not the tricks; it is making other people feel like the star [2]. The person everyone raves about after a party, he says, is rarely the one who talked about themselves. They found a way to bring things out of you [2].

His first rule is to skip the first three questions you want to ask, because they are what everyone else asks. He calls them the dreadful ones: where are you from, what do you do for a living. People have been asked them a thousand times and answer by rote [2].

His method is to notice something, compliment it sincerely, and attach a question about the choice behind it. His example is a pair of unusual glasses: where did you get them, and what made you pick those over another pair? The person gets a compliment and is asked about a decision most people never ask about [2]. Mel Robbins isolates the move. Telling someone you love their socks ends the exchange. Asking "What made you want to put those on this morning?" starts one, and the answer might be that a son gave them for Father's Day [2].

He gives the rule in one line: "Never ask a yes or no question or a question that ends with a period." [2] Those let people close doors. What he wants instead: "I want to open a door that leads to room with more doors." [2]

If you must ask what someone does, he says, put a different spin on it [2]. At a networking event he suggests opening with how you feel, which others often share: admit these events make you nervous, say the person seems friendly, and ask for one funny thing that has happened to them at one of these before [2]. And when you know whom you will meet, do the homework; he does not consider it cheating [2]. He spent months preparing a single opening line for the chance of meeting President Obama, because he knew nearly everyone opens with how honored they are [2].

He also covers the first seconds after the opener. Most forgotten names were never heard in the first place, he says: "the main culprit in forgetting people's names has nothing to do with your memory. It's that you never even knew the name to begin with." [2] His routine is listen, repeat, reply: quiet your mind, say the name back at least twice, and attach it to something [2].

Charles Duhigg: deep questions that sound ordinary

Duhigg studied the people he calls supercommunicators. His definition is homely: a supercommunicator is "the person you call when you're having a bad day who you know will make you feel better." [3] He stresses that it is learned. Most of them say they were not good at it at first [3].

What they do, among other things, is ask. "Super communicators tend to ask 10 to 20 times as many questions as the average person," he says, and many of those are quick ones, like "tell me more," that do not feel like an interrogation [3]. The questions that matter most are what he calls deep questions: questions about someone's values, beliefs or experiences [3].

His important point for small talk is that a deep question can sound ordinary. If someone says they are a lawyer, you can ask whether they love practicing law, or what made them go to law school [3]. The answer shows what kind of person you are talking to and what kind of conversation they want. One lawyer talks about steady work; another talks about watching a father get arrested and wanting to fight for the underdog [3]. So the question that Van Edwards and Pearlman ban, what do you do, becomes usable in his account once the second question asks why.

That matters because of what he calls the matching principle. Every discussion, he says, holds several kinds of conversation, most of them in three buckets: practical (solving problems and making plans), emotional (sharing and hearing feelings) and social (how we see ourselves in relation to others) [3]. If one person is in an emotional conversation and the other in a practical one, neither hears the other [3]. A deep question is how you find out which one you are in. He cites a question schools teach teachers to ask upset students: "do you want to be heard? Do you want to be helped? Or do you want to be hugged?" [3]

He treats the opening of a conversation as a quiet negotiation, in which each person signals how casual it is, whether interrupting is fine and how open to be. The start is for experiments, and he quotes his wife, a scientist: "If every experiment is a success, you're a terrible scientist." [3] Howes adds his own rule as an interviewer, "the pre-show is the show," meaning that the connection made before the cameras roll shapes the whole interview [3].

After the question comes proof of listening. His technique, looping for understanding, has three steps: ask a question, repeat back in your own words what you heard, and then the step people forget: "Ask if you got it right." [3] When someone shares something vulnerable, reciprocity deepens things, as long as you do not take the spotlight: answering news of a father's death with a story about your aunt redirects attention to you [3]. He sums up the aim: "the real point of a conversation is simply to understand the other person." [3]

Michael Bungay Stanier: hand over the agenda, then listen

Bungay Stanier wrote The Coaching Habit, and his definition of the habit is a question in itself: "can you stay curious just a little bit longer" and rush to advice a little more slowly, because "most people are advice giving maniacs" [5].

His opening question, which he calls the kickstart question, is "what's on your mind?" [5] He explains what it leaves out. It is not what is on the agenda, not what we always talk about, and not what I want to talk about. It hands authority and autonomy to the other person [5].

His second question digs. "What's the real challenge here for you?" does two things, he says. It looks for the real problem, since the first thing people say is rarely it. And the last two words turn attention from the situation to the person [5]. A follow-up of what else peels back more [5].

He is clear that the question is the smaller half. Asked which question makes someone magnetic, he says there are many, and "I think the secret is listening to the answer" [5]. That means not interrupting, not adding value, and not one-upping a holiday story with a better one of your own [5]. Jumping in with a solution, he argues, quietly lowers the other person's standing and creates resistance, even when your heart is in the right place [5].

He keeps a range of questions for different depths. A light one he asks himself each evening and offers to others is "what was the best thing about today?" which invites a story [5]. At dinners he hosts for two guests, he brings five deep questions, among them "What's the burden you've been carrying that it's finally time to put down?" [5] He adjusts for company: at an ordinary dinner party, a neighbor asked that question may only have come for chat about the weekend and the weather [5].

He scales the same idea to a room. He opens talks by having people rate how active they plan to be and then pairs them to share the high point of their week, giving up 10 to 15 minutes before he teaches anything [5]. His summary, prompted by a story from Howes about being introduced as the most interesting guest at an event where he had only asked questions: "The most interested person in the room becomes the most interesting." [5]

Where They Agree, and Where They Don't

The standard openers are the problem. Van Edwards and Pearlman independently name the same questions and give the same reason: people answer them on autopilot [1][2][4].

Good first questions are open and specific. A story about the weekend, the reason behind a pair of socks, why someone went to law school, what is on your mind: none can be answered in a word, and each lets the other person choose what to reveal [1][2][3][5].

The follow-up carries the conversation. Van Edwards's three words, Duhigg's quick questions and looping, and Bungay Stanier's what else are the same instruction [1][3][5].

The asker's job is attention, not performance. Pearlman says to make the other person the star [2]. Van Edwards says her old awkwardness came from trying to dazzle [1]. Bungay Stanier warns against one-upping [5]. Duhigg warns against stealing the spotlight [3].

It can be learned. All four describe starting out bad at this [1][2][3][5].

Their differences are mostly about pace and proportion.

How deep, how fast. Van Edwards insists on levels and has data that a deep opener splits a room by temperament [1][4]. Bungay Stanier will put a heavy question to dinner guests [5]. The settings differ: his guests have been invited to a dinner built around such questions, while her finding comes from strangers at networking events. He also says he backs off when someone only wants small talk [5]. Duhigg's version avoids the conflict by making the deep question sound like a normal one [3].

Whether to ask what someone does. Van Edwards calls it one of the two worst questions; Pearlman says to avoid it or give it a twist; Duhigg uses the answer as a springboard to a question about motive [1][2][3]. The practical upshot is the same. If the job comes up, the next question should be about the why.

How much to ask. Duhigg reports that supercommunicators ask many times more questions than average [3]. Van Edwards cautions that some people, whom she calls appreciators, would like to be entertained, and that asking question after question of a boss who talks all day can backfire [1]. She cites a benchmark from a large conversation database that turns typically run 15 to 30 seconds, and says past 45 it begins to feel self-absorbed [1]. Duhigg's own point about reciprocity agrees that a conversation needs sharing as well as asking [3].

Question or listening. The planned claim for this piece was that the first question sets the depth of the exchange. The sources support a slightly different statement: the first question sets the opportunity, and the listening decides whether it is taken. Bungay Stanier says so outright, and Duhigg's looping exists because a good question followed by no evidence of hearing goes nowhere [3][5].

Why It Works

Scripts run without attention. Pearlman describes a shortcut in the brain that answers familiar questions automatically, and Van Edwards says a scripted question leaves the other person's brain asleep [1][2]. A question they have not been asked before requires them to think, which is what wakes the exchange up.

Stories give the next question for free. A fact ends; a story contains details to ask about. That is why Van Edwards says factual questions leave the asker scrambling, and why Pearlman talks of doors leading to more doors [1][2].

People are the experts on themselves. Duhigg says that when you ask about someone's values, beliefs or experiences, you put them where their knowledge cannot be questioned, and they relax and become more willing to listen in return [3].

Deep questions reveal which conversation this is. Matching practical with practical and emotional with emotional is what lets people hear each other [3].

Being understood has a physical side. Duhigg describes neural entrainment: as people connect, their breathing and brain activity begin to match, and he says we are wired to find that rewarding [3]. Van Edwards says live conversation produces oxytocin and dopamine, and that underneath every conversation people are asking, "Do you understand me? Do you choose me and do you love me?" [1]

Giving away the agenda raises the other person. Bungay Stanier's argument is about status: answering for someone lowers them a little, and asking returns the authority [5].

Conversation now competes with the phone. Van Edwards's line is "I think our conversations have to compete with the feed." [1] A dull opener loses that contest.

Where It Applies, and Where It Doesn't

Match depth to the relationship and the moment. Level three is for a few people and is out of place before a meeting [1]. Sharing something personal where it is not safe leads to what she calls vulnerability regrets [1].

Read temperament. Introverts and ambiverts disliked the big open question about their story; guessing games and predictable, time-limited turns suit them better [1][4].

Not everyone wants to be interviewed. Some want to be entertained, and some days, Van Edwards grants, are simply for getting things done [1]. Bungay Stanier's neighbor at dinner may only want chat [5].

A compliment has to be real. Pearlman says it should be genuine, and he also says opening the door only earns a chance; you still have to deliver [2]. Bungay Stanier notes that such tools can be used to manipulate, so intention matters [5].

A question does not replace having something to say. Van Edwards wants people to prepare their own answers and stories, and Duhigg's reciprocity requires giving as well as asking [1][3].

The evidence is uneven. Van Edwards cites her own speed-networking test and a conversation database; Duhigg cites research he reported on; Pearlman and Bungay Stanier speak from practice [1][2][3][4][5]. None of it shows that one question works with everyone.

In conflict, the same tools apply with more care. Duhigg recommends a nonjudgmental question about why something matters to the person, and admitting up front that the conversation will be awkward [3].

What To Do With It

1. Retire three openers for a week. No how are you, what do you do, or where are you from, and never been busy [1][2][4].

2. Keep three replacements ready. Any fun plans coming up? What was the best thing about today? Working on anything exciting? [1][4][5]

3. Notice, compliment, ask about the choice. Pick one real detail and ask what made them choose it [2].

4. End every opener with a question mark that cannot be answered yes or no. [2]

5. If work comes up, ask why. What made you go into that? Do you love it? [3]

6. Say "tell me more." Then keep quiet until they finish. Do not top their story [1][5].

7. Loop. Say back what you heard in your own words and ask if you got it right [3].

8. Find out which conversation it is. If someone is upset, ask whether they want to be heard, helped or hugged [3].

9. In a meeting or with someone you manage, start with what is on their mind. Follow with what the real challenge is for them, and hold your advice [5].

10. Go up a level only when the last one is solid. Facts through stories first, then goals, and self-narrative only with people close to you [1].

11. Prepare your own answers. Have a short and a long version for the questions you are always asked, with a hook in each, so that a boring question put to you becomes a good exchange [1].

12. Learn the name. Listen, say it twice, and tie it to something [2].

Sources

1. Vanessa Van Edwards on Loneliness in the Age of AI and the Three Levels of Real Connection · The School of Greatness
2. Mentalist Oz Pearlman on Reading People, Memorable First Impressions and Beating the Fear of Rejection · The Mel Robbins Podcast
3. Charles Duhigg on How Supercommunicators Make People Feel Understood · The School of Greatness
4. Vanessa Van Edwards on Body Language, Likability, and the ABCD Exercise for Confidence and Energy · The Mel Robbins Podcast
5. Michael Bungay Stanier on Staying Curious, Taming Advice, and the Habits of Magnetic Communicators · The School of Greatness