Learning & Knowledge-Based
Questions for authors, experts, academics, and knowledge-sharing conversations.
Best Questions to Ask an Entrepreneur
For the twenty minutes you get with a founder who has told their story many times before. These are the questions that have no rehearsed answer, aimed at the month the money ran short, the hires and failures they do not put in the talk, and what they would do differently. If you are meeting for the first time and want something easier to answer, the good questions set is gentler ground.
20 questions
Good Questions to Ask an Entrepreneur
For a first proper conversation with someone who runs their own business, at an event, an introduction or a coffee you asked for. Every question here is one a founder can answer comfortably in front of strangers, so there is nothing about pay, cash reserves or regrets. Once you know each other well enough for that, the past the pitch set goes considerably harder.
20 questions
20 Questions to Ask an Immigrant
Twenty questions for a genuine conversation with someone who moved countries, starting with practical ground like the first week and paperwork before reaching what they left behind and what home means now. The guide covers what not to ask, including anything about status or papers.
20 questions
Good Questions to Ask Artists
Questions to ask an artist at a studio visit, an opening or an interview. They cover where a piece starts, how a recognizable style settles over years, what a working day actually involves, how the money works, and how they decide a thing is done.
20 questions
Questions to Ask Artists
Twenty questions about the working life of an artist rather than the work itself, for a student weighing the path, a writer or interviewer, or anyone curious how a practice is sustained. They cover income, training, galleries, contracts, dry spells, and what artists would not repeat.
20 questions
Questions to Ask Astronauts
Twenty questions for an astronaut talk or panel, aimed at what only someone who has flown can tell you: what launch feels like, how crews live and work in orbit, and what coming home is like.
20 questions
Questions to Ask at a Book Club
Twenty discussion questions for a book club, ordered from easy openers to the arguments worth having, with notes on facilitating a group where not everyone finished the book.
20 questions
Questions to Ask at Orientation
Questions for a first-day or first-week orientation, whether you are starting a job or joining a program: system access, logistics, early expectations, and the local rules nobody writes down.
20 questions
Fun Questions to Ask Authors
Twenty questions for a book club night, an event queue or an interview: who they would cast, which character is closest to them, the research that went strange, and the ending they wrote and then dropped.
20 questions
Good Questions to Ask Authors
Questions to ask a writer at a signing, a festival panel, a book club visit or a recorded interview. They cover where the book started, what got cut, how the drafting and editing actually went, what the publishing side looks like from inside, and what readers get wrong.
20 questions
Questions to Ask Authors About Their Book
For writers asking other writers, at a craft panel, a workshop visit, or an interview aimed at people trying to finish something of their own. The questions stay on process: the working day, what had to be learned along the way, how the drafts moved, which edit notes were worth arguing with, and what to do when a draft stops working. If you want to talk about the story rather than how it was built, ask about the book itself instead.
20 questions
Questions to Ask Authors About Their Books
Questions for a writer who has published more than one book, for book club visits, festival panels, and interviews that look across a body of work rather than a single title.
20 questions
Questions to Ask Baseball Players
Twenty questions for talking with baseball players about the parts of the game that never reach a box score: routines, slumps, coaching that stuck, and what a full season costs. Written for reporters, coaches, parents and fans who get a few minutes with a player, at any level from high school to the majors.
20 questions
Basic Questions to Ask in Spanish
Twenty basic Spanish questions you can use on day one, with English translations and notes on when each one fits. Written for beginners, travelers, and anyone who freezes up halfway through a conversation.
20 questions
Questions to Ask Basketball Players
Twenty questions for talking to basketball players about the work behind the game: gym habits, what they read before a pass arrives, guarding someone quicker than them, and what an injury changed. Written for fans, young players, coaches and anyone with a few minutes in a gym.
20 questions
Questions to Ask Before Reading a Book
Twenty questions to run through before you commit to a book: why you are picking it up now, who wrote it and when, what the contents page actually promises, how much attention it will demand, who argues the other side, and what would make you put it down. Most can be answered in ten minutes with the book in your hands.
20 questions
Questions to Ask Beta Readers
Questions for a writer sending a manuscript out to beta readers, designed to get reactions rather than edits: where attention slipped, what was confusing, who they cared about, and whether the ending landed.
20 questions
Questions to Ask Billionaires
Questions for the rare conversation with someone at the far end of the wealth curve, aimed past the origin story: what the decisions actually were, who is allowed to disagree with them, and what money has and has not changed.
20 questions
Biology Questions to Ask
Twenty biology questions for a classroom, a study group, or a conversation with a working scientist. They move from how life is organized and how cells copy and signal, through evolution, photosynthesis and food webs, to immunity, the microbiome and what is still unsettled.
20 questions
Questions to Ask Book Authors
Questions for interviewing an author about a specific book, at a bookstore event, on a podcast, or in a classroom. They cover how the book got written, what was cut, and how the publishing side actually worked.
20 questions
Questions to Ask CFO in Roundtable
Questions for a roundtable or panel with finance leaders, written for an attendee who wants specifics rather than platitudes: forecasting, planning cycles, what order costs get cut in, capital decisions, and what boards are asking about now.
20 questions
ChatGPT Questions to Ask
Twenty prompts to try with ChatGPT when you are not sure how to phrase what you want, covering explaining a topic, editing a draft, checking a calculation, comparing options, debugging code and verifying what it tells you.
20 questions
Questions to Ask Christopher Columbus
An imagined interview for a classroom, a debate club or your own reading. Each question is anchored to something Columbus wrote, signed or was accused of, so the answers can be checked against the documentary record afterwards.
20 questions
Questions to Ask College Golf Coaches
Questions for junior golfers evaluating college programs: how the lineup is decided, home course access, winter practice, outside instruction, aid, and summer amateur schedules.
20 questions
Good Questions to Ask College Recruiter
Questions for a high school student talking with a college admissions representative at a fair, a school visit, or a campus information session. They cover academics, cost, housing, support, and the things a brochure leaves out.
20 questions
Questions to Ask College Softball Coaches
For softball recruits and their families on a call, a campus visit, or a showcase. Twenty questions about position and innings, fall ball, missed class days, scholarship terms, and how the staff handles injuries and lost starting spots.
20 questions
Questions to Ask Cops
Questions for a career day, a ride-along, or a community meeting where you get real time with a police officer. They cover training, shift work, discretion, and the parts of the job most people outside it guess wrong about.
20 questions
Questions to Ask Cyber Security Expert
Questions for a small business owner, office manager or team lead sitting down with a security consultant. They are aimed at getting a short list of things to fix in priority order, a plan for the first hour of an incident, and an honest view of what you can do yourselves.
20 questions
Deep Questions to Ask a Musician
For interviewers, podcasters, students and anyone curious about how music actually gets made. Twenty questions on how a song starts, what practice looks like on a normal day, dry spells, bad gigs, criticism that turned out to be right, and what playing has cost.
20 questions
Deep Questions to Ask About a Book
For book clubs, classrooms and readers who want more from a book than a star rating. Twenty questions on what stayed with you, where the book lost you, the character you recognised, the effect of the ending, what the author left out, and who you would not recommend it to.
20 questions
Deep Questions to Ask an Artist
Twenty questions for interviewers, collectors, students and friends who want more from an artist than a statement about their practice. They start with the work in front of you and move toward money, abandoned pieces, and what the artist thinks people get wrong.
20 questions
Fun Questions to Ask Designers
Twenty questions for a studio chat or a portfolio review that has run out of steam: the trend they want gone, the strangest client request, the font they defend, and the work they are proud of that never shipped.
20 questions
Questions to Ask Doctors About Their Career
For a student, career changer or curious visitor who has a doctor's attention for half an hour. These 20 questions get past the recruitment version of medicine to what the training cost, what the day actually contains, and what the job takes out of a person.
20 questions
Don't Be Afraid to Ask Questions
Twenty prompts for anyone who sits on a question in meetings, classrooms, or a doctor's office. They work through what the fear is actually about, what the silence has already cost, who the cheapest person to ask is, and how to word the question so it gets answered.
20 questions
Economic Questions to Ask
Twenty questions on how economies work and who they work for: inflation, inequality, tax policy, interest rates, minimum wage, monopolies, automation, trade and debt. Written for classrooms, reading groups, and anyone arguing about policy in good faith.
20 questions
Questions to Ask Elie Wiesel
Questions framed as an interview with Elie Wiesel, for readers and students working through Night and his later writing on memory, silence, faith, indifference, and the duty of a witness. He died in 2016, so these work as prompts for discussion, essays, and close reading rather than as an actual interview.
20 questions