Skip the autopilot questions: how to start conversations that go deeper
October 6, 2026 · 17 min read
Vanessa Van Edwards says to ask for stories instead of facts and offers research-based conversation starters, mentalist Oz Pearlman tells people to skip the autopilot questions, Charles Duhigg finds that supercommunicators ask deep questions about values and feelings, and Michael Bungay Stanier opens with a question that hands the agenda to the other person. Their shared claim is that the first question sets the depth of the whole exchange, which makes better questions the simplest fix for small talk that goes nowhere.
The rules, numbers and steps worth keeping in front of you.
- Van Edwards and Pearlman: drop how are you, what do you do and where are you from. People answer them on autopilot.
- Van Edwards: never ask whether someone has been busy. It sends the mind looking for the negative.
- Van Edwards: ask for stories, not facts. Try fun plans coming up, the highlight of the week, or a personal passion project.
- Van Edwards: do not ask strangers for their story. Extroverts loved it, and introverts and ambiverts hated it.
- Van Edwards: go in levels. General traits, then goals and values, then self-narrative for only two or three people.
- Van Edwards: conversational turns typically run 15 to 30 seconds. Past 45 feels self-absorbed.
- Pearlman: notice something, compliment it sincerely, and ask about the choice behind it.
- Pearlman: never ask a yes or no question.
- Pearlman on names: listen, repeat the name at least twice, and attach it to something.
- Duhigg: supercommunicators ask 10 to 20 times as many questions as average.
- Duhigg: if work comes up, ask why they chose it.
- Duhigg: match the conversation, whether practical, emotional or social.
- Duhigg: loop for understanding. Ask, repeat back in your own words, then ask if you got it right.
- Bungay Stanier: start with what is on their mind, then listen without advising or one-upping.
This is the short form. The full insight has every expert's reasoning, their own words and the sources.