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Question
Intensity
Notes
1
If today was your last day, what would you have most regretted not doing yet?
2
If today was your last day, what would you of have been most proud of?
3
What’s something most people see as black or white that you think they should be seeing as gray? Is there something you’re seeing as black and white but think there may be a gray area to consider?
4
if you could only have 3 of your 5 senses, which would they be?
5
What are the two absolute luckiest things that have ever happened to you?
6
Do you have an area of interest that you would likely (95%+ confidence) still be interested in in your old age? (80s, 90s, beyond)
7
What do you want written on your tombstone?
8
If your life was a dashboard what would be the key stat/ measure?
9
Is there something that can’t hurt you and you’re still afraid of?
10
Let’s say we were going to start a village. What would you bring to the table? Why?
11
What’s the biggest commitment you’ve ever made?
12
What's the hardest challenge you’re working on yourself?
13
What’s the best worst thing you’ve ever done?
14
Could you teach me something complicated I don’t know? (Sergey’s fav interview q. Google)
15
What do you know now in a deeper way than you knew it before?
16
What tittle would you give this chapter in your life?
17
Whats an unusual habit you have?
18
What’s something Google doesn’t know about you?
19
What’s the worst advice you hear often in your field?
20
Do you have any favorite failures? Any failures that in hindsight led to incredible things?
21
In what ways has your personality served you in achieving dreams vs. held you back?
22
What are the most worth while investments you’ve ever made? This can be time, energy, money...
23
If you could pick one class that would be mandatory for everyone, what would it teach? At what grade level(s) would it be mandatory?
24
Do you have a hunge of how you’re going to die?
25
What do you really want to do, and how does that differ from what you feel you should do?
26
What were you like as a child? And what do you think the child version of you would think of you you’ve become today?
27
Outside of work, what do you feel like is working in your life right now? What isn’t?
28
If you had to be a drink which and why?
29
If you could have one gigantic billboard anywhere with anything on it—metaphorically speaking, getting a message out to millions or billions—what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)
30
What’s a question I didn’t ask that you wish I’d asked?
31
What lesson did you have to learn "the hard way"? How can you help others avoid your mistake?
32
How do you think of luck? What about luck in correlation with success?
33
Locus of control: what percentage do you think yours in internal vs external? What about for good things that happen? Bad things?
34
Do you think the end or the means are more important?
35
Complete this statement: “I lose track of time when...”
36
What have you done in the past 3 months that makes you feel proud?
37
As you have gotten older, what has become more important and less important to you?
38
What are some challenges that you’ve had to overcome in your life?
39
If you could study with any expert in the world, who would you work with and what would you study?
40
If you could invite 3 people (living or dead) to your home for dinner, who would they be and why?
41
Do you think the future would stay the same if you were told the future? Or would you act differently and it’d change as a result.
42
What’s something you think is truly worth doing, whether you fail or succeed?
43
How would you like things to be different in your life?
44
What’s missing from your life that you could add with effort?
45
If you could go back and tell your 20yr old self ‘this is where you are going to be and this is what it took to get here,’ do you think you’d still do it?
46
What is something you want to remind yourself of in 10 yrs?
47
Can humans be satisfied being taken care of just like a family dog? (When robots/ AI can do everything for us)
48
Suppose that you go to bed tonight and sleep well. Sometime, in the middle of the night, while you are sleeping, a miracle happens and all the troubles you have are resolved. When you wake up in the morning, what’s the __first small sign__ you’d see that would make you think, ‘Well, something must have happened- the problem is gone!’?
49
Prod for more specifics ‘what will you do instead?’It doesn’t ask you to describe the miracle itself; it asks you to identify the tangible signs that the miracle happened.Focus on the first hits of the miracle to avoid answers that are overly grand and unattainable.When was the last time you saw a little bit of the miracle, even just for a short time?
50
Do you think feelings can be false?
51
What song would play anytime you walked into a room?
52
If you were the dean of admissions at the world’s top university, what would be your decision rule?
53
What's your biggest failure, and what can I learn from it?
54
If every person on the planet had to listen to you for 5 minutes, what would you say?
55
What are three negative things about ya?
56
If you could give credit or thanks to one person in your life that you don’t give enough credit or thanks to, who would that be?
57
How much is enough?
58
What’s the big burden that is now time to put down?
59
What’s the crossroad you’re at?
60
If you were to die tomorrow and you could only leave your children one paragraph worth of all of the knowledge you’ve accumulated over the years, what would it say?
61
If you were to get kicked out of the company what do you think the new CEO/____ would do? (A more beautiful question book)
62
What if your company didn’t exist? (Think about the industry and your role in it without the luggage or sunk costs) - useful if at any point in the future you see the possibility that the core business might slow down Who would miss us? Help clarify who your most important customers are and what your real purpose is. What should we stop doing?
63
If we were to pop a bottle of Champaign, celebrating you, a year from today. What would we be celebrating?
(After response) in order to achieve that is there anything you need to solve or overcome?
64
Given the choice of anyone in the world, whom would you want as a dinner guest?
65
What would constitute a “perfect” day for you?
66
If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
67
What was the last meaningful “thank you” that you received?
68
What are a few ways in which you express your gratitude?
69
What are you most proud of? / What is your proudest moment? Why?
70
What is something that can instantly turn your bad day into a good one?
71
Complete this sentence “I wish I had someone with whom I could share...”
72
Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
73
What fun topic could you give a short presentation about with no preparation?
74
Think about yourself one year ago. What’s one thing that’s changed since then?
75
What would you consider a defining moment in your life?
76
What do you value most in a friendship?
77
Human memory has been shown to be incredibly unreliable. With that in mind, how do you know which of your memories are genuine and which have been altered or made up?
78
What is your most treasured memory?
79
If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
80
What does friendship mean to you?
81
If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
82
If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
83
Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
84
What do you want to want?
85
If you had to give a TED talk on a subject/ topic you’re not know for, what would it be?
86
When did you last cry in front of another person? By yourself?
87
If there was a movie about your life what would it be called?
88
What’s the greatest lesson you’ve had to UN-learn in the past year?
89
If every day someone was filming everything you did and in the evening you and your loved ones had to watch it all. Would you still do the same things?
90
Do you think everyone is always doing their best?
91
Do you think painful emotions should be ignored?
92
Do you think there’s a right way to feel in every situation?
93
Do you think you can control the way you feel?
94
Can time exists without language?
95
If we all shared the same values/ morals, would we need government?
96
How would you like people to remember you?
97
If people didn’t have to work, because AI and machines are doing everything and there’s so much abundance that everything is free. Universal basic income is going to become a necessity. Then how will people have meaning? a lot of people derive their meaning from their employment, so if you aren’t needed, there’s no need for your labor. What’s the meaning? Do you have meaning? Do you feel useless?
98
If your life was a book, would you read it?
99
If you could live indefinitely, would you?
100
What’s your conversational landmine? (What gets you going)
101
Which item on your bucket list will be the easiest to tackle? The most difficult?
102
What’s your definition of success? What does it look like?
103
If you could spend a day in someone else’s shoes, whose would they be? Why?
104
What's one thing your mother/father taught you that completely changed your life?
105
What's one of your favorite memories?
106
Imagine that a spell of unanimity has been cast on you from now on for the rest of your life no one would know what you do, no one would know how much money you make, how successful you are, you and you alone would know. In such a world of unanimity what would you do?
- What we’re passionate about without worrying about other peoples expectations of you or what they think of you.
107
What's one thing about you that surprises people?
108
If you could instantly become an expert in something, what would it be?
109
If you could wake up tomorrow having gained any one quality or ability, what would it be?
110
For what in your life do you feel most grateful?
111
Name three things you are thankful for at this time in your life.
112
What’s the best piece of advice you’ve ever been given?
113
If you didn’t have to sleep, what would you do with the extra time?
114
What’s your guilty pleasure?
115
Has anything ever happened to you that you could not, and cannot, explain?
116
If forensic analysts confiscated your calendar and email records and web browsing history for the past 6 months, what would they conclude are your priorities?
117
If we weren’t to talk for the next 3yrs and I called you and asked for a life update and you’ve achieved everything you could have wished for, what would you tell me? “Holly shit! You won’t believe what just happened...” (Dom)
118
What would you do if you received two life changing phone calls. In the first call, you’d learn that you’d inherited $20m, no strings attached. The second call would inform you that, due to a rare and incurable disease, you had only 10 yrs left to live. What would you differently, and, in particular, what would you stop doing?
119
Do you feel lucky in life?
120
If you repeat the actions (/ habits) that you performed today for the next 10 years, would you be pleased with the results?
121
What’s the most unbelievable-but-true thing that’s ever happened to you?
122
If money were not an issue, what would you be doing right now?
123
What's something you wish you had done years earlier?
124
What words of advice would you give your younger self?
125
How do you clear your mind after a long day?
126
If you had a free round-trip airplane ticket to anywhere in the world, where would you go?
127
Who has been the greatest influence in your life? How?
128
What's the most creative thing you've ever done?
129
Which founders or startups do you most admire?
130
What's your super power? or If you could have any superpower, what would you pick?
131
What’s your favorite quote? / Your motto?
132
What aspects of your work are you most passionate about?
133
What was the most impactful class you took in school?
134
If you could know what someone was thinking, how do you think it’d be presented to you?
135
Tell me the story of your life and the decisions you made along the way and why you made them.
136
Video games are becoming so real that in the future it will be hard to tell the difference between being in the game and in real life. Who’s to say this hasn’t already happened in the past and that we aren’t in one of those games now. How would you know?
137
What’s the quirkiest thing about the town where you grew up?
138
What’s the craziest way you’ve ever traveled? Hot-air balloon, camel, blimp… ?
139
If you could change one thing about yourself, what would it be?
140
Do you take any classes or practice a particular hobby? Would you like to?
141
In a world without death/ heaven/ hell/ reincarnation- what will happen to religions?
142
If people were to live to 160yrs old easily. How do you think it will impact family structures/ relationships? What about careers?
143
If you could win an olympic medal for any sport, real or fake, what would it be?
144
Have you had a near death experience? How did it affect the direction of your life?
145
If you could change your name, what would it be?
146
What movie or TV show tittle best describes your week?
147
If you had to eat one thing for every meal going forward, what would you eat?
148
Who, or what, was your biggest teacher?
149
What’s something you’ve done that made you feel extreme happiness?
150
How can someone win a gold star with you?
151
What culture, other than your own, do you find most fascinating?
152
What qualities do you value in the people with whom you spend time?
153
Would you like to be famous? In what way?
154
For what would you be famous?
155
What does your dream day look like?
156
If you had to choose only 3 adjectives to describe yourself, which would you choose?
157
How many jelly beans could fit into this room right now?
158
If your significant other died and was reincarnated into another body. How would you know it was them? What question would you ask to know?
159
Who have I been over the last few weeks / months? (give 3 adjectives)
Follow up with: Who do I need to be in order to get to where I want to get? (Give one adjective)
160
What are the 3 things you want to achieve on a personal /business level that would give you a tremendous feeling of success?
161
What are the relationships you want to have?
162
What are 3 genie/magic goals you wish (wherefore you have nothing to do for /to have it/ to keep it)?
163
What are the experiences you want to have before you leave the planet,
164
What are your 3 naughty goals (goals you should't have)?
165
What goals SHOULD you do by the end of the year (SHOULD GOALS)?
166
What are your top 3 OTHER PEOPLE's goals?
167
What are your growth goals - How do you want to grow?
168
What do you want to contribute to the planet?
169
Significance Goals - What to you want to be known/be remembered for?
170
What are your ANTI-GOALS - What do you never want do EVER again?
171
What's your IMPOSSIBLE Goal?
172
What do you need to simplify (instead of what should you do) - Less but better?
173
What are you prepared to struggle for?
174
Focus question : what's the one thing you should do that would make all the other goals easier/unnecessary?
175
What have you accomplished that you're proud of, but would be unimpressive to anyone else?
176
What’s your communication style? How does it affect the people around you?
177
In the future, which one of these things do you think we’ll look back on and think was the most barbaric? manual driving, labeling based on gender, governing with a two-party system, poor health care, factory-style education, destroying the environment, war and eating meat
178
Describe your “average” day. What are your rituals/routines?
179
Complete this statement: My favourite time of the day is...
180
What are three things you believe you need in order to be happy?
181
How would you spend 6 hours with your best friend?
182
What do you daydream about?
183
If you could "stop the clock" and live forever at a particular age, what age would it be and why?
184
If you could outsource one of your daily tasks, what would it be and why?
185
What would you say is your greatest strength?
186
What is one word your best friend would use to describe you?
187
How would your best friend describe you in 2 words?
188
What is something you would like to learn to do?
189
Imagine that tonight there is a party honoring you on your 80th birthday. What are five brief things you would like family and close friends to say about you?
190
What are 3 things you would like to be doing in three years?
191
What do you look forward to every night? Why?
192
If you had to move and could only take 3 things with you, what would they be?
193
Describe the most unpleasant job you ever had to do.
194
What did you want to be when you were growing up?
195
What has been one of your happiest moments?
196
If your closest friend wrote a book about your life, what would the title be?
197
What are you excited about right now?
198
Share an interesting fact about yourself that not many people would know.
199
What are you working on?
200
What are some ways that you reconnect with yourself?
201
Who is the first person that comes to mind when you hear the word "successful"? Why?
202
What is one thing you couldn't live without?
203
If you could start a charitable organization, what would you name it and what would the cause be?
204
Where would you like to retire, and why?
205
What was your first job?
206
What is one of your top business/ career achievements?
207
What is often your first thought upon waking?
208
What are 3 things you really value?
209
What's the most exciting thing you have ever done?
210
Any upcoming travel plans?
211
Are you a night owl or an early bird? Does it hurt or help you?
212
What brought you here?
213
How do you two know each other?
214
When you’re not working, how you like to spend your time?
215
What are you reading currently?
216
What is your favourite movie/documentary? Why?
217
What do you most hope to visit?
218
What is your most used emoji?
219
What’s the one thing you’re excited about that’s coming up in 2019?
220
What’s your favorite word?
221
What’s your favorite book?
222
What do you do to “reboot” so that the busyness and tech overload in your life does not result in burnout?
223
What’s your dream job?
224
Can you see yourself being stimulated and fulfilled on your current career path for the next five years?
225
What’s been on your mind lately?
226
Where is your happy place?
227
What energizes you/ brings you excitement?
228
What would you tell your future self?
229
What is the true measure of wealth / success?
230
What’s your favorite / most memorable child book / fable / story? how has that shaped you?
231
Think about the price and value you currently deliver. if you were to 10x that price, what would you deliver? what would you add?
232
If right now you couldn’t get new customers other than from your existing customers, how would your current customer experience change?
233
If you needed to provide more value than you currently are for 1/10th the price, what would you have to build that is free to replicate to deliver that value?
234
In as much precise detail as you see fit, how does your mind work?
235
What important truth do very few people agree with you on? - Zero to One
236
What, and who, is worth suffering for?
237
What would you stand for if you knew that nobody would judge you?
238
What would you do if you knew that nobody would judge you?
239
Do you think my name suits me? If so, why? If not, what name could I pull off?
240
If your life were a story, what would be the biggest plot twist?
241
When you were young did you imagine you would be where you are today?
- Share one prediction that came true and one that was way off
242
Tell me about a time you felt invincible
243
What is a lesson in your life that keeps repeating itself?
244
Has a compliment ever changed the way you think about yourself?
245
What is something so far out of your comfort zone that you wouldn't even consider trying it?
246
Are there any strangers you still remember?
247
If your closest friend wrote a book about your life, what would the title be?
248
What are 3 things you would like to be doing in three years?
249
Have you had a near death experience? How did it affect the direction of your life?
250
In order to take your company/life to the next level, what is one problem you need to solve?
251
If you could study with any expert in the world, who would you work with and what would you study?
252
How do you externalize your thoughts?
253
If you could know the absolute true answer to one question... what would the question be?
254
What’s your favorite saying?
255
Can there be thinking/creativity without language?
256
What is your serial killer trait?
257
What habits do you have that you hope you don’t pass on to your children?
258
What question do you rarely get, even though you’re thinking about the answer a lot?
259
What's a sacrifice you've made that i haven't acknowledged?
260
What are you hesitant to tell me?
261
Who is the most interesting person you've ever met?
262
Would you rather do what the best ____ does or the opposite of the 3 worse ______s you know?
263
What's the most surprising fun fact you've ever heard?
264
If you were able to ask an alien some questions, what would they be? 👽
265
What was the darkest time in your life and what was your road to recovery?
266
What do you think will be the greatest conversation you'll ever have? What's the greatest conversation you've ever had?
267
If you had to do a guest episode on a podcast with 1m+ listeners, who do you feel is the person you'd be most equipped to interview?
268
Who is someone who makes you nervous?
269
Which activities in your life are you minimizing that should be eliminated? Which activities do you need to savor and how can you best savor them?
271
What personality characteristics do you find most important in people?
272
When you think of the word “successful,” who’s the first person who comes to mind and why?
273
What is something you believe that other people think is insane?
274
What purchase of $100 or less has most positively impacted your life in the last 6 months?
275
What are your morning rituals? What do the first 60 mins of your day look like?
276
What obsessions do you explore on the evenings or weekends?
277
Do you have a quote you live your life by or think of often?
278
What is the worst advice you see or hear being dispensed in your world?
279
If you could have one gigantic billboard anywhere with anything on it, what would it say?
280
What advice would you give to your 20-, 25-, or 30-year old self? And please place where you were at the time, and what you were doing.
281
How has a failure, or apparent failure, set you up for later success? Or, do you have a favorite failure of yours?
282
What is something really weird or unsettling that happens to you on a regular basis?
283
What have you changed your mind about in the last few years? Why?
284
What do you believe is true, even though you can’t prove it?
285
Who is good at [skill or topic] despite being poorly built for it? Who’s good at this who shouldn’t be?
286
Who are the most controversial or unorthodox athletes or trainers in [skill or topic]? Why? What do you think of them?
287
Who are the most impressive lesser-known teachers?
288
What makes you different? Who trained you or influenced you?
289
Have you trained others to do this? Have they replicated your results?
290
What are the biggest mistakes and myths you see in [skill or topic] training? What are the biggest wastes of time?
291
What are your favorite instructional books or resources on the subject? If people had to teach themselves, what would you suggest they use?
292
If you were to train me for 12 weeks for a [skill or topic] competition and had a million dollars on the line, what would the training look like? What if I trained for 8 weeks?
293
How old would you be if you didn't know how old you are?
294
What old picture of yourself would be your album cover?
295
What do you know to be true today that you didn't know a year ago?
296
What are your biggest distractions that hinder your productivity?
297
If someone else described you, what do you think they'd say? Why?
298
If you could have any three things in the world, what would they be?
299
How can you feel more fulfilled in your life?
300
What's the best compliment you've received?
301
What are your best qualities?
302
If you couldn't fail, what would you do?
303
How do you show someone you love them?
304
What is one thing you want to overcome/conquer?
305
How would you behave if you were the best in the world at what you do?
306
When was the last time you did something for the first time?
307
On a scale of 1–10, how happy are you with your life today?
If <10: If your first answer was [answer + one], what would be different?
308
What’s keeping you busy?
309
What is the conventional wisdom that you disagree with?
310
Finish this sentence: "If you really knew me, you would know that I _ _ _ _ _ _”
311
What's something you feel guilty buying but love?