Questions. I love them.

Questions have the power to reveal information about people. Even if they don’t give you an answer, silence is an answer in and of itself. A carefully crafted question reveals empathy and insight on behalf of the question asker and for the question answerer, it may be liberating for them to answer and to craft their story. I love how questions are a way to draw out the hidden parts of people. The parts of people that make them uniquely them. The parts I find the most beautiful and love celebrating with—no matter how odd. Every person is interesting, and if you don’t believe so, try asking better questions—you’ll find something there. Questions keep you curious, and being curious keeps you creative.

Here’s a list of some of my favorite questions I’ve collected so far to use in informational interviews or just to chat with people I find fascinating. 
 

(Some of the questions are repeated in the different sections)

  • For Anyone

  • For Better Learning

  • For Creatives (General, Advertisers, Photographers, Podcasters, Film)

  • For Entrepreneurs

  • For Professors


For Anyone

  • What’s the biggest misperception of you?

    • What’s the difference between misperception and perception?

  • If you could have a billboard anywhere where would it be and what would it say?

  • How would you describe yourself?

  • What was an unexpected struggle you learned from [insert whatever]

  • Who are your mentors?

    • What do you learn from them?

    • What 3 qualities make them great?

  • On a scale from 1-10 how weird are you and why?

    • What’s your weirdest quirk?

    • What is something absurd that you love doing?

  • Do you have a morning routine?

  • What are some underrated documentaries that you love?

  • What animal would call you their spirit human?

  • Who do you think is successful and what 5 traits do you admire from them?

    • Or what are 5 characteristics you admire in a friend?

    • Or what are 5 characteristics that describe who you are when you’re successful?

  • How do you ask questions?

  • Do you notice a pattern in your own curiosity?

    • Or pattern in your own questions?

  • What are 4 books that you gift the most often?

  • What do you want me to know about you?

  • What do people never ask you, that you wish they did?

  • What is something you learned about yourself in the past [insert amount of time]?

  • What are you learning right now?

  • What is something you wish you did differently in [college/time rn]/something you regret not doing?

  • What is a purchase that’s $100 or less that has positively impacted your life?

  • What are things people come to you for expertise in? What do you think you are an expertise in?

  • What’s a criticism you’ve gotten that you’ve found helpful

  • How do you self care?

  • How do you know when to say no?

  • If the old you could see the new you, what would the new you say?

  • What did you come in thinking doing [insert role] would be and how did your perception on it change after being in it?

  • When you do X [or when Y happened to you], what does your internal self-talk sound like? What do you say to yourself?

  • After [insert experience], did it affect how you see people in the real world/real life?

  • What are the Man vs Man, Man vs Self, Man vs Society struggle in your life?

  • Are there any questions you wish I asked you?

  • What are some misperceptions I might have of you from our conversations?

  • What is the mold of a [their occupation] and why do you fill it well?

  • Who do you spend most of your time with?

  • What do you spend most of your time thinking about?

  • What has given you joy this past week?


For Better Learning

  • If you were [your age], how would you get to where you are now?

  • Who else would be good to talk to, to learn more about [insert whatever]?

  • Who is good at [insert whatever] who shouldn’t be?

  • Who are the most controversial/unorthodox [insert whatever]? Why? What do you think of them?

    • “Who are the most controversial, or unorthodox runners/trainers? why? What do you think of them?”

  • Who are the most impressive lesser known teachers?

  • What makes you different? Who trained you or influenced you?

  • Have you trained others to do this, and have they replicated your results?

  • What are the biggest mistakes and myths you’ve seen in [insert whatever]?

    • Even at the pro level, what are the common mistakes?

  • What are your favorite instructional books/resources on this subject?

  • If people had to teach themselves, what would you suggest they use?

  • If you were to train me for 4 weeks or a [fill in the blank] competition and had a million dollars on the line, what would the training look like? What if I got to train with you for 8 weeks?

  • What are your key principles for better/more consistent [fill in the blank]?

  • What does the progress of these exercises look like?


For Creatives

General

  • Do you think it’s fair or wrong to evaluate an artist’s work based on their personal life choices?

  • Where is the industry going, and how is that affecting [whatever]?

  • How do you approach struggles and obstacles in the creative process?

  • What’s your favorite project? Why?

  • What are some questions you ask yourself to trim your idea? When you review your ideas, what do you ask yourself to figure out what works and doesn’t work?

  • How do you ask questions?

  • Do you notice a pattern in your own curiosity, or pattern in your own questions?

Advertising

  • When you critique ads what do you look for?

  • What's a good example of an ad that shows this, other than your own company?

  • Is there a specific style to the way you make your ads?

  • Is it a goal for people to see a pattern in the way your ads are produced?

  • For example they watch an ad, and they're able to recognize that your agency made it.

  • What are other elements you include besides human truths and keeping your target audience in mind when making your ads?

  • In terms of crowdsourcing, when does letting go become too risky?

  • What content formats work best and what platforms?

  • What is [insert whatever] doing right that is letting them not be part of the system, and allow them to be where they are today?

  • In a world that is constantly saturated with ads, how do you make yours stand out?

  • What is the new digital strategy for your clients and why?

  • When you don’t know the right answer/don’t know where your ethical stance is, what are questions you ask yourself or the client to help them process it?

Photographers

  • How do you go about finding and story, and what are some questions you ask to discover them?

  • Talk about identifying and approaching people during the event

  • How do you use social media for your career?

  • What’s a story you would love to do/get funded for/do it regardless?

  • How do you get your subject comfortable when it’s a sensitive moment?

  • What can you say you’ve learned about other people from doing photojournalism?

  • Have all those experiences lead you to any general insights about human beings?

Podcasters

  • Maybe this is hard to discuss concretely, but can you describe the different tracks you’re going down in your mind as you’re doing an interview?

  • What can you say you’ve learned about other people from doing [insert whatever]? Have all those thousands of interviews led to any general insights about human beings?

  • What’s a question you regret asking a guest?

  • Is there a question you wish you could ask to someone in your life?

  • There was a New York Times Magazine that did a profile on Terry Gross that said that radio listeners create the identity of the person they’re listening to. Who is [insert the name of the podcaster] in the mind of [the show name] listeners?

  • How to you redirect the course if an interviewee is going down a rabbit hole?/How do you make a person stop talking if they’re going over 7 minutes without a breath?

  • How do you get them to talk with you and not at you?

  • Have you learned any reliable tricks over the years for how to salvage an interview that’s tanking?

  • Is there an interview that stands out for you as an example of your being able to take the conversation to an especially revealing place?

  • What’s an interview that felt like a breakthrough for you?

  • How does your work spill over into your personal life? And I mean more from a psychical rather than practical perspective. How does having deep conversations day after day affect you?

Film

  • What is the ratio of pleasure and pain between making this movie?


For Entrepreneurs

  • If you could say something to your 20 year old self what would that be?

  • What is a book that you give out most often?

  • What is something unexpected that you learned?

  • When was that moment in your life that you decided, this is it? I'm going to do this?

  • What is the biggest lesson to give to any entrepreneur?

  • What qualities make the best entrepreneur?

  • How do you convince others it’s a good idea?

  • If you could double a part of yourself, what would it be?

  • What keeps you up at night?

  • If you had to charge 2 times as much for your product and couldn’t do any paid advertising, what would you do instead?

  • If you could only work 2 hours a weeks on your business what would you do?

  • How is success defined in your company?

  • How do you choose the winning idea?

  • You seem very confident now. Was that always the case?

  • How did you get that idea?

  • Was [insert company name] your first company/idea that you’ve made?

  • How did you land on the idea you have now?

  • How did you get the confidence to try this?

  • So you open up [insert company name], and what happens? Do people start buying in from day one?

  • What was your pitch?

  • How much do you think was talent, how much was luck?

  • What do you think when you’re walking through an airport, or some city and you see someone using something you’ve made?

  • Is there ever a point you wanted to give up?


For Professors

  • How do you self care?

  • What do you want us to take away from this class/college career?

  • What does your work-life balance look like? Do they blend?

  • When you don’t know the right answer/don’t know where your ethical stance is, what are questions you ask yourself or the client to help them process it?

  • What do you think is a student’s perspective on your course, and how do you want it to change?

  • How do you keep up networking connections?

  • How do you know when to say no?