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John Candeto
John Candeto
/Great Questions
Great Questions
Great Questions

Great Questions

This is my intentional effort to learn and craft outstanding questions. The most effective people often ask the best questions. The most recently added questions are at the top. ”It’s a great thing to be rich in unanswered questions.” - Paul Graham
Do you believe people can change?

Apr 9, 2026 8:16 PM
What was the last big thing you changed your mind about?

Apr 9, 2026 8:16 PM
What will you never learn if you only use the tools of language and logic?

Jan 27, 2026 7:40 PM
What are you becoming?

Sep 29, 2025 12:40 PM
If someone watched you for a week, would they believe you are serious about your goals?

Aug 10, 2025 6:41 PM
What do you want to be doing in the last decade of your life?

Peter Attia

Jul 8, 2025 7:48 AM
What increases in value as wealth approaches infinity?

May 22, 2025 12:03 AM
What increases in value as information approaches infinity?

May 5, 2025 8:48 PM
Are your best days ahead of you, or behind you?

Apr 16, 2025 7:05 PM
Are you treating life like the dress rehearsal or the show?

Mar 26, 2025 1:41 AM
Where is it wise to compress complexity?

Mar 18, 2025 7:01 PM
What is the most obvious thing to do right now?

Mar 18, 2025 1:31 PM
What experiences would I need to have to believe what you believe?

Mar 17, 2025 11:28 AM
What would you do if you could hire a tireless genius for $20 per month?

Feb 28, 2025 6:49 PM
What would you do if you had 10x the agency you have?

Jan 30, 2025 6:42 PM
What’s the best way to think about being helpful to you?

Nov 20, 2024 3:19 AM
How can I serve you well?

Nov 20, 2024 3:19 AM
What have you recently subtracted from your life?

Jun 20, 2024 3:52 PM
Why did we mock religion, only to mimic it?

Freya India

Jun 6, 2024 4:04 PM
What knowledge work can be converted into tokens?

May 15, 2024 10:31 AM
What led you to take this meeting?

Jesse Pujji

May 6, 2024 12:27 PM
Take a few minutes and think about something you are an expert in…then explain it to me.

Apr 28, 2024 11:48 AM
When you’re told that something is impossible, is that the end of the conversation, or does that start a second dialogue in your mind?

Eric Weinstein

Jan 29, 2024 1:43 PM
If you could have the answer to any one question, what question would you want the answer to?

Max Grev

Dec 14, 2023 3:03 AM
If you could take a year off to work on something that probably wouldn't be important but would be really interesting, what would it be?

Max Grev

Dec 14, 2023 3:03 AM
What's the last thing you crossed off your bucket list?

Max Grev

Dec 14, 2023 3:02 AM
What have you been thinking about lately?

Daniel Rhodes

Dec 14, 2023 3:01 AM
Did anything happen last week that you're still thinking about?

Varadh Jain

Dec 14, 2023 3:00 AM
What are you getting most excited about right now?

Sahil Bloom

Dec 14, 2023 3:00 AM
What gifts will I leave for unborn generations to come?

Patrick O’Shaughnessy

x.com
Dec 3, 2023 3:13 PM
What do you consider to be your finest hour?

Oct 31, 2023 12:10 AM
It’s impossible to please everyone. The question is: are you disappointing the right people?

Adam Grant

Oct 16, 2023 9:01 PM
Who has deceived thee so oft as thyself?

Oct 2, 2023 2:46 PM
If someone talked to you the way you talk to yourself, would you be friends with them?

Sep 10, 2023 2:44 AM
What do you spend an unreasonable amount of time doing?

David Perell

twitter.com
Aug 12, 2023 2:35 PM
Who is good at <skill> despite being poorly built for it?

Aug 11, 2023 6:16 PM
If you were required to dispose of all but one asset, what would you keep?

Aug 11, 2023 5:45 PM
For someone who is outside your field, what would they find most surprising about your field?

Jul 29, 2023 3:22 PM
How have you evolved? Show me.

Sam Hinkie

Jul 20, 2023 3:19 PM
Regardless of what they do or produce, who do you know that has the highest quality bar?

Patrick O’Shaugnessy

Jul 20, 2023 2:33 PM
What is the return on time for <item>?

Jul 19, 2023 6:17 PM
What is the outlook AND what is the predictability of the outlook?

Jul 19, 2023 6:15 PM
What has surprised you about <topic>?

Peter Kaufman

Jul 19, 2023 6:15 PM
How do you measure yourself?

Jul 19, 2023 6:15 PM
What is most alive in you right now?

Jul 19, 2023 6:15 PM
What is calling you right now?

Jul 19, 2023 6:14 PM
DO NOT ask “what do you do?” INSTEAD ask “what are you working on?”

Jul 19, 2023 6:13 PM
Who / what are you becoming?

Mark Canlis

Jul 13, 2023 10:20 PM
What do you excel at that is unrelated to your occupation?

Jun 23, 2023 9:25 PM
What course could you teach?

Jun 23, 2023 9:24 PM
If you had to give a TED talk on something that isn’t your profession, what would it be about?

Tim Ferris

Apr 29, 2023 2:35 AM
What do you know more about than most people?

Kevin Kelly

Apr 29, 2023 2:34 AM
Would I think about the world like you do if I experienced what you have?

Apr 27, 2023 1:25 AM
What have you experienced that I haven’t that makes you believe what you do?

Apr 27, 2023 1:24 AM
Who has influenced you the most?

Feb 21, 2023 1:32 PM
Are you a lucky person?

Feb 21, 2023 1:32 PM
Have I earned my gift?

Ric Elias

overcast.fm
Feb 14, 2023 3:21 AM
What does it mean to be healthily adapted to the Internet?

thekcpgroup.com
Jan 4, 2023 9:44 PM
What have you had to unlearn? What have you unlearned recently?

Nov 4, 2022 1:31 AM
If the world were ending in 12 months, how would you spend your remaining time?

Nov 4, 2022 1:30 AM
How am I complicit in creating the conditions I say I don’t want?

Jerry Colonna
Oct 4, 2022 1:59 AM
How was your time in the desert? (as a metaphor: eg time of silence and solitude as precursors to wisdom; time of uncertainty, confusion, doubt, and loss as precursors to success)

Sep 30, 2022 3:50 PM
How do you identify quality before there is a track record?

Sep 15, 2022 2:01 PM
Ideas are networks…novel configurations of nodes in your brain. How do you get your brain into environments where new networks are more likely to form?

www.ted.com
Sep 14, 2022 8:24 PM
If you were CEO of _ tomorrow, what is the first thing you would change?

Sep 12, 2022 8:04 PM
Where are time horizons expanding?

Paul Higgins
Sep 7, 2022 6:19 PM
What needs to be done to become a wonderful ancestor?

Mike Podolsky
Sep 6, 2022 9:11 PM
What’s the view from your favorite window?

Aug 22, 2022 4:38 PM
How can I be your best customer?

Aug 12, 2022 6:46 PM
What is the hardest problem you are working on right now?

Jul 25, 2022 7:25 PM
If I don’t choose you, who would you go with?

Jul 10, 2022 1:11 PM
Favorite Manager questions from First Round (follow link)

review.firstround.com
Jun 9, 2022 12:14 AM
What are you willing to struggle for?

Mar 16, 2022 12:20 AM
What pain do you want in your life?

Mar 16, 2022 12:20 AM
What makes your best employee stand out?

Mar 6, 2022 6:01 PM
Can you be rational when you’re wrong?

Jan 31, 2022 1:28 PM
What do you wish you had told your younger self — that your younger self would have actually listened to?

Dec 31, 2021 4:38 PM
If I could somehow communicate with my future self, what would I want to know now to make the right decision today?

Nov 15, 2021 7:06 PM
What areas are under-invested due to incongruity between market size vs. the number of entrepreneurs that have experienced the problem? (Eg fewer entrepreneurs have kids vs education TAM)

Nov 14, 2021 10:43 PM
What problem would you pay the most to solve?

Nov 13, 2021 11:36 PM
What are the ingredients in having new ideas?

paulgraham.com
Nov 10, 2021 7:38 PM
If a friend came to me with the exact problems I'm facing now, what advice would I give them?

Oct 14, 2021 3:06 PM
What is one of your favorite books that has only ever been recommended by one person?

Oct 5, 2021 12:12 AM
What have you experienced that I haven't that would make me believe what you do?

Sep 25, 2021 9:52 PM
What do you know that most people (or competitors) haven't figured out, yet?

Sep 24, 2021 2:16 AM
Why won't capitalist forces erode your margins?

Aug 17, 2021 8:59 PM
Who do you want your customers to become?

Jul 22, 2021 2:47 PM
What are you an expert in that is not related to your work?

Jun 25, 2021 10:14 PM
What important thing have you put in the "too hard" pile?

Apr 8, 2021 6:35 PM
What important thing have you recently struggled to understand?

Apr 8, 2021 6:34 PM
What do you love to spend time on?

Mar 20, 2021 10:31 PM
What do you love to spend money on?

Mar 20, 2021 10:30 PM
What strongly held belief do you have that most people disagree with?

Mar 18, 2021 1:39 PM
What do you know that most people do not? (often about something uncommon or unusual)

Feb 28, 2021 1:26 PM
What question would you ask to understand how someone thinks?

twitter.com
Dec 2, 2020 12:41 AM
Inspiration from Patrick Collison (follow link)

patrickcollison.com
Nov 21, 2020 1:29 PM
What is the return by security type/area? Are higher returns found in specific types of companies or situations?

Nov 21, 2020 12:40 PM
Does trading in/out of the same positions add to or subtract from returns (after-tax) over time?

Nov 21, 2020 12:36 PM
What is the return by position size? Did larger positions produce higher returns (i.e. does high conviction pay?)

Nov 21, 2020 12:34 PM
What proportion of returns are attributable to management of gross and net exposure?

Nov 21, 2020 12:25 PM
Favorite interview questions from First Round (follow link)

firstround.com
Nov 16, 2020 5:13 PM
What have you had to un-learn? What made you do it? How did you do it?

Nov 16, 2020 4:57 PM
What feedback have colleagues given about you? Do you agree/disagree? Why?

Nov 16, 2020 4:55 PM
What is the best customer service experience you've ever had?

Nov 16, 2020 4:54 PM
What do you worry about?

Nov 16, 2020 4:54 PM
What are you doing right now whose benefits will only be seen years/decades from now?

Nov 16, 2020 4:53 PM
What is your most strongly held belief?

Nov 16, 2020 4:52 PM
What hypotheses are you testing right now?

Nov 16, 2020 4:52 PM
Give me an example of a time you failed.

Nov 16, 2020 4:52 PM
What is the worst thing that has happened in your career?

Nov 16, 2020 4:52 PM
What things do you think are important to do every day?

Nov 16, 2020 4:51 PM
What feedback have clients given you about your work? Do you agree/disagree? Why?

Nov 16, 2020 4:51 PM
What are you most proud of?

Nov 16, 2020 4:44 PM