Context

We often know the answers to questions that can help us dramatically improve our impact/productivity/happiness/health/etc.

This became particularly salient to us after we learned techniques and saw how helpful they were. Examples include:

Resolve Cycles (think of a problem in your life, set a five minute timer, and solve your problem, or set a five minute timer to think of a plan to solve your problem, and then set another five minute timer and pick a harder problem)
Murphyjitsu (ask yourself “How surprised would I be if my current plan were unsuccessful after the deadline passed?”, and “How can I make myself more surprised?”, and then repeatedly iterating).
Hamming Questions (asking “what are the most important problems in your field? Why aren’t you working on them?”)

We (Akash and Kuhan) also often ask questions to try to improve others’ impact/productivity/happiness/health, form close relationships, and produce valuable conversations. Questions can help us understand new concepts and paradigms, generate novel ideas and connections, notice our confusion and holes in our understanding, and make friends.

We wanted to compile a list of the best questions to ask in different scenarios—one-off questions, questions that should be asked regularly, both to ourselves and others, questions to make meetings better, and more. We’d be excited for readers to also suggest questions they’ve gotten mileage out of/have enjoyed asking and answering in the comments.

The NYT published a list of questions that lead to love. Here’s a list of questions that (often) lead to impactful conversations.

List of Questions

Life Optimization Call Questions

*credit to Neel Nanda for bringing many of these questions to our attention

What do you think are the most important problems? Why aren’t you working on them? (Hamming questions)
What is most holding you back? What are your biggest bottlenecks?
Suppose that this meeting increases your lifetime productivity/impact/happiness/motivation by 2x. What happened?
What are the projects you’ve spent >=10 hours on in the last month? Rate each out of 10 for impact, and write a brief theory of impact. Do you endorse this?
What is your personal theory of impact? How do your actions concretely reduce existential risk?
Do you consistently feel motivated about what you work on? What goes wrong? Give a concrete example? How frequently do you use obligations to motivate yourself? Do you feel guilty and anxious all of the time?
What probability would you put that you have any of insomnia, ADHD, depression, anxiety, bipolar? How are your physical health, sleep, exercise, diet, hydration? What niggling health issues are you ignoring? Are there other important health issues I’m missing? Have you spent at least a full-time week solving this? Why not?
Please fill out this depression questionnaire and anxiety questionnaire and consider next steps depending on the results.
What is the biggest mistake you’ve made in the last 6 months? Have you successfully changed the default path of the world such that such a mistake is very unlikely to happen again?
Suppose you leave this conversation feeling super inspired and confident your life has changed, and in practice nothing changes. How surprised are you?
- Bonus: Has this happened before? What went wrong?
Suppose you leave this conversation with some concrete action points that are obviously good ideas that will majorly improve your life. What are they? Make them concrete and give deadlines.
What are the biggest and sharpest trade-offs in your life right now? What are the costs and benefits of each option? Set a 5 minute timer and brainstorm third alternatives, that capture some of the benefits of each and fewer of the costs
What are your ugh fields? Spend 5 minutes brainstorming about this
(Only ask in appropriate setting): Suppose you die before the age of 60. What probability do you put that AI is the reason why?

Career/Impact Plan Questions

What do you think is the most important problem in the world, and what are you doing to work on it?
Imagine a (realistic) plan 10x more impactful than your current plan? What is it and why aren’t you doing that instead?
What do you think is the most important problem in your life, and what are you doing to work on it?
How are you currently thinking about your career?
What are your biggest uncertainties regarding your next steps? How are you currently planning to resolve them?
What skills and aptitudes do you currently have, and which ones do you want to develop? What are some things that you could become world-class in?
If your current plan for impact was missing something really important, what would it be?
When was the last time you experienced burnout? How likely do you think it is that you will experience burnout in the future? What are some steps you can take to reduce that likelihood?
If you had a magic fairy following you around and trying to make you more productive, what would they do?
Are there any ways funding can improve your ability to improve the world (e.g. by making you more impactful/productive/happy/healthy). Would you like to make a plan to apply for funding?

General EA 1:1 Questions

How did you first get involved with EA/rationality/etc? What was most influential in getting you more involved?
What is your favorite thing about the EA community? What is your least favorite thing?
What’s a topic or problem that you’ve been thinking about recently?
What’s something you worked on recently that you’re proud of?
Do you know anyone who could help me with X?
Here’s my current plan for doing the most good. How would you improve it?
What’s something interesting that you’ve been thinking about recently?
What’s something you changed your mind about or became more confused about recently?

Conversation Prep Questions:

If this conversation ended up being one of the most valuable meetings I ever had, why and how might that have happened? What was discussed?
What’s something I’m afraid to ask where doing so could be really valuable (e.g. asking for a favor, or about a topic you feel you should know more about)
What’s my biggest bottleneck/what’s holding me back most from achieving my goals (that I’m willing to share). How might my conversation partner be able to help?
What are my biggest uncertainties with respect to how I can do the most good? How can I resolve these uncertainties?
What are some ways I can provide lots of value to my conversation partner? What are my strengths and areas of expertise? Who in my network might be good to connect them with?
What are some questions/topics my conversation partner would be particularly well-suited to answer?
What intrigues me most about the person or people I’m going to talk to?
What are the biggest gaps in my understanding of them?
What are the biggest ways I might be able to help them? (Check their asks, but feel free to have different ideas)
What are the biggest ways they might be able to help me?
Do I have access to something that they don’t? (Information? People? Projects? Concepts? Resources/Funding?)
If I change your mind about something significant after talking, what might it be?
What else seems useful to discuss?

Problem Solving/Debugging Questions

What are the biggest problems in your life right now?
Imagine all of those problems were solved. Now say, “Everything is fine, and my life is perfect.” What feels wrong? What additional problems do you notice?
Would you prefer that I be in problem solving mode, active listening mode, or a mix of both?
Suppose you leave this conversation feeling super inspired and confident your life has changed, and in practice nothing changes. How surprised are you? How can you be more surprised?
Have you considered applying for funding/using money to solve your problem? Bonus: Has this happened before? What went wrong?
Do you want to set a 5-minute timer and see if you can make progress on that?
What are the situations, contexts, and environments in which you feel the most productive and make the most progress? How can you be in those contexts more often?

Accountability Questions

Can we make your plan more concrete and likely to happen?
Are there ways to increase the likelihood that you follow through with your plan?
Would you like for me to check in with you at X date/every Y days? (Schedule send an email if yes)
Would you like to pay a friend (or me) money if you don’t accomplish your goal by a certain deadline? What deadline, how much, and to whom?
What systems can we implement to make sure you revisit this problem regularly by default if needed?

Obvious Man Questions

*credit to Jake McKinnon for explaining the concept of Obvious Man. The man who follows you around all day, asking you obvious questions that dramatically improve your life.

What are your most important goals? Are you spending your time on them?
Is there anyone you can reach out to who could help you achieve your goals? Why haven’t you reached out?
Is there anyone you can reach out to for mentorship? Why haven’t you reached out?
Did you wake up when you wanted to today? How long did it take you to get out of bed?
When was the last time you exercised?
When was the last time you drank water?
When was the last time you called a friend from home?
When was the last time you met someone new?
Is there any problem you’re experiencing that your friends don’t know about?
When was the last time you had a chance to write or reflect on your life?
What’s the next Google Doc or journal entry you want to write up?
What’s an open-ended question about yourself that you could ask a friend?
Are you procrastinating on anything?
Are you procrastinating on sending an email?
Are you procrastinating on scheduling a meeting?
What’s a project that really excites you when you think about it?
What’s something you’re excited to work on once you have time?
What’s an experience that you want to share with a friend?
When was the last time you expressed gratitude to someone you care about?
When was the last time you had a meaningful 1:1 with someone?
When was the last time you used a dating app?
Imagine that one of your closest friends could see you go through your whole day. What’s something constructive they would tell you?
Is there something you should tell someone else, such that they can help you or this piece of information helps them?

Emotional Intimacy Questions

*some are taken from this list

What is the best and worst thing in your life right now?
What’s an emotional or personal problem that you’ve been thinking about recently?
Would you describe yourself as a happy person? Would you describe yourself as an anxious person?
Are there any situations in which you feel like an imposter?
During what period of your life were you happiest? During what period of your life were you least happy?
What are some of your favorite things about me?
What are some of your least favorite things about me?
What are some of your favorite things about yourself?
What are some of your least favorite things about yourself?
What is the best and worst thing that happened to you in the last day?
What’s something you’re good at that you don’t think people know/recognize?
What’s something that you wish more people knew about you?
Who are your closest friends? What are they like? (Describing one person at a time)
What do you want to make sure you do, achieve, or experience in life?
What meaningful or important thing should you tell a particular person, that you haven’t said to this person yet?
What would constitute a “perfect” day for you?
Name three things you and your partner appear to have in common.
If you could change anything about the way you were raised, what would it be?
What do you value most in a friendship?
What is your most terrible memory?
Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
Make three true “we” statements each. For instance, “We are both in this room feeling … “
Complete this sentence: “I wish I had someone with whom I could share …“
If you were going to become a close friend with your partner, please share what would be important for him or her to know.
When did you last cry in front of another person? By yourself?
Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

Miscellaneous

We recommend that you experiment with asking people these questions and try to notice the ones that reliably produce conversations that you find valuable.
If you want to strengthen your friendships, here’s one simple heuristic. Every few days, message a few people one of these questions. Akash thinks this is one of the most straightforward ways to have stronger connections.
Many of these questions serve not only as conversational prompts but also as solo reflection prompts. You may find it valuable to pull up a Google Doc and answer some of these by yourself.
It can be useful to make sure that your conversation partner can opt-out of answering questions that might be personal or uncomfortable. Setting this expectation can be helpful. Additionally, saying things like “No worries if you want to pass on this one” or “Only answer this if you want to; feel free to change the topic if not” can serve as in-the-moment reminders.
The best Obvious Man Questions vary person-to-person. We recommend that you make a Google Doc with your personal “Obvious Man” questions and sending this to friends/accountability partners.
We offer additional thoughts on how to make the most out of 1:1 conversations in Doing 1-on-1s Better—EAG Tips Part II.
If you have questions that often lead to impactful conversations, please share them in the comments!

Questions That Lead to Impactful Conversations