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50 Incredible Life Changing Questions



Questions Life Changing

In this article I interview Warren Berger the author of A More Beautiful Question and The Book of Beautiful Questions about the art and science of asking questions.

Warren is a former journalist turned “questionologist” and writes for Fast Company, Harvard Business Review, and The New York Times. He has appeared on The Today Show, CNN, and National Public Radio.

The questions that follow will help you to analyze, learn, and move forward in the face of uncertainty. They will get you thinking in a new way, outside of the box, from multiple different perspectives. 

In this article:

Let’s begin:

What is a more beautiful question?

Michael Frank: You’ve written A More Beautiful Question and The Book of Beautiful Questions so let’s start there: What is a more beautiful question?

Warren Berger: The title of the book came out of a line from a poem by the poet E. E. Cummings who said:

“Always the beautiful answer who asks a more beautiful question”

I think what Cummings was getting at, and what the point of the book is that, if you’re asking a better question, you’re going to get a better answer.

I think that’s what makes a question a better question. I think the more thoughtful you are in preparing your question, and the more precise your question is, the more beautiful it is.

I also came up with my own definition of what I consider to be a beautiful question.

Now this is very subjective, but I was doing a lot of research on changes and breakthroughs that started with a question. For instance, someone would say: “Why hasn’t someone come up with a better way for people to be able to get movies from the video store?” And the next thing you know that person launches Netflix. And there are all kinds of examples like that of someone starting out by asking a question: “What if you tried this?” or “Why hasn’t someone done that?” and they lead to breakthroughs.

So I think of beautiful questions as something that has the potential to bring about change, a really ambitious question that asks:

“Why aren’t we thinking about this?”


“What if we tried that?”


“How might we do a better job at this thing?”

I really like those ambitious potentially world changing kinds of questions and that’s what I consider beautiful questions.

Michael Frank: Beautiful questions open your mind and get you thinking in a new way, from multiple different perspectives.

Warren Berger: Absolutely.

Michael Frank: Mark Zuckerberg said once in regard to ideas:

“Let me tell you a secret: Ideas don’t come out fully formed, they only become clear as you work on them” – Mark Zuckerberg

I think that great questions don’t come out fully formed either, they can be refined and refined and refined again.

Warren Berger: I agree

Brilliant questions = Banal answers (& vise versa)

Michael Frank: One thing that has surprised me as an interviewer however, and I’m sure that you’re very familiar with this as a journalist, is that a brilliant question can get a banal answer, and a banal question can get a brilliant answer.

Warren Berger: It’s true. I think the reason for that is a lot of times when people are asked a really good question it catches them off guard a little bit, and so they’re not ready with the answer yet. They need time to think it through and process it. However if you follow up and help guide the person to go a little bit deeper and say: “What I mean by that is…” and explain your question a little more they will eventually be able to address it but when they’re first hit with it, they’re sometimes a little off balance.

The 5 W’s + How

Michael Frank: Do you think the five W’s + How are generally a good starting place for asking questions?

  • Who was involved?
  • What happened?
  • Where did it take place?
  • When did it take place?
  • Why did that happen?
  • How did it happen?

Warren Berger: It all depends on what you’re doing with questions. I think the 5 W’s are great for journalists, because if you’re trying to understand or build a story, you need all these facts in place and these questions allow you to get at the facts.

Why? What if…? How?

Warren Berger: On the other hand, if you’re trying to solve a problem or innovate, I found that the most useful sequence of questions was:

  • Why?
  • What if…?
  • How?

I found that innovators often cycle through these three questions in that exact order, and the reason these three questions work in that order is because let’s say you’re facing a problem, the first thing you have to do is figure out why:

  • Why is it a problem?
  • Why do I care?
  • Why do I want to make this my problem?
  • Why is it important to solve it?

So you have to deal with all of the “Why” questions upfront. Then once you get into trying to solve the problem, you need to use your imagination to come up with alternative ideas. And that’s when “What if” questions become important:

  • What if we tried X?
  • What if we tried Y?
  • What if we turned the whole thing upside down?

So that’s the brainstorming stage. And “What if” is a really important brainstorming question. And then I found that by the end of the innovation process innovators are starting to get very practical, and “How” is a very practical question:

  • How are we going to do this?
  • How much is it going to cost?
  • How do we make it affordable?
  • How do we get started?

So I found that:

  • Why?
  • What if…?
  • How?

was an interesting sequence for problem solving and I think people can apply it in their lives. For example: If you’re trying to decide whether to move to another city, you start with why:

  • Why would it make sense?
  • Why am I even thinking about this?

And then you start working through what if:

  • What if I could take all the things that I like about where I am, but find a place that has all of those things, plus a bunch of other things?

And then you get to how, okay if I were going to do this:

  • How would it work on a practical level?

So I love that sequence of:

  • Why?
  • What if…?
  • How?

For all kinds of problem solving.

Ask “Why?” 5 times

Michael Frank: I also think it’s good advice to ask why five times to get to the heart of the matter, to find out the real reason for something, the reason behind the reason.

Warren Berger: Yeah the five whys are big, I talk about those a lot. The five whys will help you to get a better understanding of the problem but they don’t begin to solve it. They only help you to understand it. And that’s why I think that sequence:

  • Why?
  • What if…?
  • How?

Is so important. Because understanding is not enough. You have to somehow get from why to what are we going to do about it? We understand why there’s a problem, and we’re starting to understand the dimensions and reasons for the problem, but what are we going to do about it? And that’s when you cycle into those other types of questions.

What is a stupid question?

Michael Frank: In reality, is there such a thing as a stupid question? And if so, what is a stupid question?

Warren Berger: To me a stupid question would be a question that is off topic. Let’s say everyone agrees to have a meeting about solving a problem with a particular product and then a person in the meeting says: “I want to know why I can’t have more vacation time?” So you see there’s no connection between that question and what is going on in the meeting, and that to me would be a stupid question.

But what is not a stupid question, yet is often called a stupid question, is when someone challenges the fundamental assumptions of let’s say the group. So you’re in a meeting and everyone has decided we have to make this product better and then someone says: “Why are we focused on this product in the first place?” “Why is this so important to us?”

When someone asks a question like that in a meeting a lot of times people will say: “That’s a stupid question” but actually those kinds of questions are really important and they need to be asked from time to time, those very naive fundamental questions that step back and say: “Wait a minute, let’s take a look at our assumptions… let’s take a look at the reasons why we’re doing this thing… does it still make sense? Maybe it made sense last year, but it might not make sense now…”

So I love it when people have enough guts to ask those really fundamental and basic questions, even though they might get called stupid if they do.

Leading questions are a no-no

Michael Frank: I agree with you and I think it’s great to question assumptions. One thing I don’t like about a lot of journalists, and I know that you are a former journalist, is that they tend to assume the answer before they’ve even asked the question. So they ask a lot of leading questions: “Yeah, but don’t you think…” “Yeah, but what about…” they have this idea in mind, this assumption, and they just continue to go down that path no matter what.

Warren Berger: Yeah my favorite one is: “Isn’t it true that…” (laughs) and then they ask the question. Talking about a leading question. I think what’s going on there is that they’re using the question to help them write the story that they’ve already decided upon and that’s a bad habit. It’s a lazy form of journalism. They want to do the story they want to do and they don’t want any surprises, nor do they want to have to rethink what they started out with, or to consider that they might have been wrong.

I think that when you ask questions as a journalist, yeah you can definitely come in with certain things you want to find out, but you should also be totally open to things you might be getting wrong or that you might not know about.

A worthless question: “How are you?”

Michael Frank: I think another worthless question is the cliché: “How are you?” Because almost everyone’s going to say: “Fine” “I’m good”. But it doesn’t really reveal any information. And generally the question asker doesn’t even care about the answer anyway.

Warren Berger: I refer to those as rote questions. And if you ask someone a rote question such as: “What’s up?” “How are you?” you’re going to get a rote answer. I always suggest people put a little variation in that. Instead of asking: “How are you?” or “How’s it going?” make it a little more specific and say something like: “How is your morning going?” That’s a little bit better. Now if you really want to get deeper into it, instead of asking: “How’s it going?” or “What are you up to these days?” you shift the question to something like: “What are you really excited about these days?” or “What are you passionate about right now?” Give people something they can grab onto. And that will be more of a conversation starter than just those really vague general questions.

Mistakes people make when asking questions

Michael Frank: In addition to asking leading questions, and assuming the answer before you’ve even asked the question, what are some mistakes that people typically make in their questioning?

Mistake 1: Not listening

Warren Berger: I think one of the biggest mistakes people make is not listening. So they ask a question, but instead of listening to the response they’re getting, they’re thinking about something else, and by doing that they miss out on the opportunity to ask follow up questions and to go deeper on whatever the person is saying. And journalists are very guilty of this by the way. They’re always thinking about the next question on their list. So that’s one mistake.

Mistake 2: Watch your tonality

Another mistake people make with their questioning involves tonality. If you use the wrong tone when you ask a question it can become uncomfortable to people. It can seem like you’re challenging or criticizing them. Tone is very important. Imagine a boss walking around his company and when he sees someone working on something he says: “What are you doing?” or “Why are you doing that?” All of a sudden the person gets very defensive and they think they’re being attacked. But if the tone was slightly different and the boss said: “I’m curious to know what you’re working on there?” or “I’m wondering why you’re doing that particular approach?” it would be different. So you want to soften your tone and make sure that your curiosity comes through when asking questions. You want questions to feel like there’s curiosity driving them and not criticism.

What would you attempt to do if you knew you couldn’t fail?

Michael Frank: What’s your favorite question overall, on any subject, on any topic?

Warren Berger: One of my favorite questions is:

“What would you attempt to do if you knew you couldn’t fail?”

I love that question because it allows you to think about the question without the fear of failure limiting your thoughts. That’s why it’s used a lot now by tech companies in Silicon Valley. So again:

“What would you attempt to do if you knew you couldn’t fail?”

Now of course there is a chance you could fail, right? So in a way it’s an artificial question, but that doesn’t matter because it’s very powerful and it allows you to use your imagination in a very courageous way.

And then when you’re done with that you can go back to reality, and in reality of course there is a chance you could fail, but you want to set that aside briefly so you can think, and that’s one of the things you can do with questions, you can use questions in interesting ways to speculate:

“What if the world were a little bit different?”

“What if the situation were different?”

“What if money were no object?”

“What if I had five days to live?”

“What would I do then?”

So you can use questions to create an alternate reality that allows your imagination to run wild.

What if we did the opposite?

Warren Berger: Another one of my favorite questions has to do with opposites. So the idea is to ask yourself:

“What if the opposite were true?”

“What would be the opposite way of thinking about this situation?”

“What would be the opposite of what I would normally do in this situation?”

There is an episode of Seinfeld where George Costanza decides that his judgment is so bad, that whenever he has a decision to make instead of doing what he would normally do, he will do the opposite. This is actually a really interesting thing for people to do, but the difference is you shouldn’t just think of the opposite and then do it.

You should think of the opposite just so you can consider it. That’s all. It doesn’t mean that you should do the opposite of what you were inclined to do, but you should definitely think about what the opposite would be because it may open up new possibilities for you that you hadn’t thought of.

Michael Frank: That’s my favorite episode. I love that episode!

My favorite question

Michael Frank: One of my favorite questions is:

“What one thing, if you were to take action on it, would produce the greatest difference in your life?”

I love that question and I find that it helps you to immediately identify and prioritize the most important next step.

Warren Berger: Yeah, I think of that as a focusing question that is designed to get you to cut right to the core of what matters most.

Questions to check beliefs and biases

Michael Frank: One of the things I love most about The Book of Beautiful Questions is that it has a good amount of focus on critical thinking so let’s start there. What are some good questions that we can ask to check our beliefs and biases?

Warren Berger: Yeah we have a lot of biases that we’re not aware of. And we tend to think we know more than we do.

What am I inclined to believe?

Ask yourself the question:

“What am I inclined to believe on this particular issue?”

It could be a political issue, or it could have to do with changing jobs and moving to another city.

“Am I the kind of person who’s a little shy or leery about doing that kind of thing?”

“Am I the kind of person who believes in staying in one place?”

Think about what your tendencies are. That’s an important question to ask right up front.

Why do I believe what I believe?

Another important question to ask is:

“Why do I believe what I believe?”

We don’t ask ourselves that question very often. Arno Penzias the Nobel Prize winning physicist called that “The Jugular Question”. He said he asked himself that question all the time.

“Why do I believe what I believe?”

Because oftentimes we just accept our beliefs, but we don’t challenge or question them.

What would I like to be true?

Another interesting question to ask whenever you’re facing a decision is:

“What would I like to be true?”

This is to try to get at something called the desirability bias. Because often we make decisions based on what we want to be true, but that doesn’t mean that it is true, or that it’s going to happen. So you have to challenge yourself to distinguish between what you would like to be true, and what is true.

What if the opposite of what I believe is actually true?

Another good one is:

“What if the opposite of what I believe is actually true?”

You need to consider that as one of the questions that will help you to check your biases and preconceived notions.

Questions to test your intellectual humility

Warren Berger: When it comes to critical thinking you also need intellectual humility and the ability to open up and not be locked into your current way of thinking. So you can use questions to do that.

Do I tend to think more like a soldier or a scout?

Here’s a great question that I borrowed from Julia Galef from The Center for Applied Rationality and that’s:

“Do I tend to think more like a soldier or a scout?”

If you’re thinking like a soldier, you’re defending your beliefs and what you already know.

If you’re thinking like a scout, you’re curious and open to explore new ideas.

You want to be thinking like a scout instead of a soldier as much as possible, because too often we get into that defensive mode of trying to defend our beliefs, and the way we think and what we already know, and that keeps us from being open to new ideas and possibilities and from exploring, and it can keep us from learning. So I think that’s a really important question.

Would I rather be right? Or would I rather understand?

Related to that you should also ask another question I love:

“Would I rather be right, or would I rather understand?”

A lot of us are very concerned with being right. That’s the most important thing. So when we get into an argument or a discussion or there is any kind of disagreement with people all we care about is being right, and when it comes to politics, we end up wanting to be proven right: “See I said that all along!” “I supported that guy and look I’m right!”

So we end up being way too concerned about being right, and when we get that way it locks us into our positions and causes us to always try to skew everything to make us look right, but that keeps us from being flexible and from learning and changing our positions.

So it’s important to use questioning to make sure you’re not too locked into one way of thinking.

Do I seek out and solicit opposing views?

Michael Frank: I also like your question:

“Do I seek out and solicit opposing views?”

And the answer for most people is no you do not.

Warren Berger: Most people don’t seek out and solicit opposing views because it makes them uncomfortable, and it’s the same phenomenon as wanting to be right. It forces you to have to realize that there’s another way of looking at this and now you have to contend with that.

I think it’s just a matter of getting used to that discomfort or allowing yourself to deal with that discomfort. It’s actually not as bad as we think it’s going to be when we do it, but we’re a little leery of doing it.

Questions to detect BS

Michael Frank: Let’s continue down this critical thinking path. What kind of questions should we ask to detect BS?

Warren Berger: I have about four or five go to critical thinking questions that you can ask whenever you encounter new information or ideas. And we want to be evidence based when we’re evaluating and deciding on things, because if we don’t go on evidence, then we’re going to end up going on emotions and feelings, and when there’s too much emotions and feelings involved that’s when we get into trouble and our biases get the best of us, and that’s when we often make some bad judgements.

What’s the evidence?

So start with evidence. You should always be asking:

“What’s the evidence behind what this person is telling me?”

There are several sub-questions you can ask too:

“How strong is the evidence?”

“Does it seem to be fair?”

“Does it seem to be biased?”

“Does it have an agenda behind it?”

So when you’re thinking about evidence, think about the quality of the evidence.

Michael Frank: I couldn’t agree more. It’s about the quality of the evidence, not the quantity of evidence.

Warren Berger: Exactly right. You want to be asking yourself:

“Who is the evidence coming from?”

“What is their agenda if they have one?”

I think that’s really important.

What are they not telling me?

So ask questions about the evidence, and then you also want to ask:

“What’s missing?”

“What’s being left out?”

“What are they not telling me?”

If someone’s presenting something to me, what’s being left out? There’s usually something being left out. If an advertiser is trying to sell you something, they’re leaving some things out. If a politician is promising you something, they’re probably not telling you the downside of what it is they’re proposing.

So you always want to be ask yourself: What are they not telling me?

What would an opponent of this say?

You also want to consider the opposite point of view:

“What is the opposite way of thinking about this?”

“What is the opposing view of what is being presented to me?”

“What would someone on the other side of this issue say?”

“What would an opponent of this say?”

Questions for creative thinking

Michael Frank: Let’s look at creative thinking.

Watch out for black and white thinking

Warren Berger: I think one of the biggest mistakes we make is limiting ourselves with closed binary either/or type thinking when we’re making decisions, as if there were only two choices and we had to choose between them.

You can open up the question to be decided. So for example, if you’re having some difficulty at work instead of asking a closed binary question:

“Should I quit my job? Yes or no?”

You can take that closed question and figure out how to open it up. Instead of making it a yes/no question, should I quit my job or not, ask a more open-ended question like:

“How could I improve the situation enough that it would be worth staying at my job?”


“What kind of changes would have to happen for me to stay here?”

These are very open-ended questions that don’t have a yes or no answer, and what these questions will do is open up options and give you more possibilities to choose from, and they’ll allow you to make a better decision in the end then that basic yes or no question.

Michael Frank: So try to avoid Black and White Thinking also known as all or nothing thinking or binary thinking, because there are many more possibilities than either/or, this/that etc.

The vanishing options question

Warren Berger: Another thing you can do is to ask the vanishing options question. So let’s say you’re trying to decide between a bunch of different job offers: Should I take this job offer? Should I take that job offer? Should I do this? Should I do that?

The vanishing options question is:

“If none of the current options were available, what would I do then?”

And the reason you ask that question is because you’re trying to add even more options and possibilities into the mix. So you take the two or three existing options that you’re trying to decide on and temporarily move them off the table and say:

“If none of these options were on the table, then what would I do?”

This forces you to come up with a fourth or fifth option that isn’t in that original mix, and now all of a sudden you’ve got one more thing to consider.

And by the way, I know this can sound like we’re making decision making harder because we’re bringing in more options and more things to think about, and in a way that’s true, but when you’re making important decisions and you have the luxury of time, you should make the decision a little harder. You have a brain – use it. You have lots of information available to you on the internet – use it. All of these things will help you to make a more informed decision. And they’ll help to open up more options for you to choose from.

I also think that in terms of creativity, the questions we ask can allow us to see more possibilities all around us and I think that’s really important.

Poor creative questions

I think that people commonly ask some poor creative questions:

“How can I find an original idea?”

“Hasn’t everything already been thought of already?”

“Where am I going to find that big idea to work on?”

The truth of the matter is there are ideas all around you, so all you need to do is ask yourself questions to help you recognize them.

What stirs me?

So ask yourself questions like:

“What stirs me?”

“What am I seeing day to day that I find really interesting?”

“What bugs me?”

“What really bothers me?”

I’ve talked to innovators and they say that if you pay attention to the things that bother you, you will find ideas that you can work on and take ownership of.

So ask yourself questions like:

“What do I keep coming back to?”

“What’s important to me?”

What would a 5-year-old child find interesting about this situation?

If you want to see the world around you differently, if you want to be a little more creative, then you want to get into that sort of beginner’s mind.

So ask yourself questions like:

“What might I notice if I were encountering this situation for the first time?”

If it’s a route you travel on to work everyday ask yourself:

“If I were traveling this route for the first time, what would I notice about it?”

And that can help you to see things with a fresh point of view.

You can look at a situation and say:

“What would someone very different from me notice in this situation?”

“What would a 5-year-old child find interesting about this situation?”

“What would a 90-year-old person find interesting?”

“What would a comedian think about this situation?”

“How might a comedian have fun with it?”

So you can use questions to almost force yourself to adopt different perspectives and different mindsets.

What would an outsider do?

Michael Frank: I also love your question:

“What would an outsider do?”

What would LeBron James or Warren Buffett or Steve Jobs or Elon Musk do?

Warren Berger: That’s a big deal. I keep coming back to that idea of outside perspectives and opposites, and that’s a lot of what The Book of Beautiful Questions is about. That’s a theme that keeps coming up over and over again. We need to get outside of our own way of looking at things and it’s not that easy to do, but you can use little tricks.

What would I advise my best friend to do?

Another great question in the book that is one of my favorites, it’s so simple, and so powerful. Let’s say you have a major decision to make and you can’t decide what to do. Ask yourself:

“What would I advise my best friend to do?”

Research done by decision making experts shows that we give better advice to our friends than we give to ourselves. And the reason for that is not because we’re masochistic or something, but it’s just because we’re too close to things.

So one little trick you can do is to step back and say:

“If this were not my decision, but my best friend had the exact same situation and were trying to decide, what would I advise they do?”

And the chances are that the advice that you would give to your best friend, you should also listen to yourself.

Questions to test the soundness of a decision

Warren Berger: I also advise you to ask questions like:

“How would I defend this decision to somebody else?”

And you can do that at the time you’re making the decision. You can project yourself into the future and imagine yourself having to defend the decision to someone else. What would be the case that you would make? That can help you to get some kind of advance judgment on the soundness of that decision.

What’s going to be important to me 5-10 years from now?

And although most of us have a bias toward short term thinking:

“What do I care about right now?”

“What’s most important to me right now?”

It’s important to ask questions to project yourself into the future:

“What would future me care about?”

“What’s going to be important to me 5-10 years from now?”

And you can use questioning to speculate on that and then use that as part of what informs your decision.

Michael Frank: I love that one. Be a friend to future you. That’s great.

Warren Berger: Yeah I think it’s really important to project yourself into the future but we tend to be so focused on what matters to us right now. For example: Let’s say you’re thinking about taking a job offer, you tend to be focused on your immediate concerns, the salary, that sort of thing, when in fact what’s most important is:

“How are you going to fit within this organization over the long term?”

“Does it look like a place where you’ll be able to rise?”

“Does it seem like the kind of work that you won’t get bored doing?”

These are all things that matter, but we tend to focus on the more immediate stuff and not ask about that stuff. So really think about these things and ask questions like:

“What’s going to matter over time?”

“What’s going to allow me to evolve and grow and become a better person over time?”

A year from now, what will you wish you had started today?

Michael Frank: Yeah and another good question I like to ask:

“A year from now, what will you wish you had started today?”

Warren Berger: Yeah I call these crystal ball questions and they’re about projecting yourself into the future.

Questions to overcome the fear of failure

Michael Frank: One of the things that often holds a lot of people back from making the right decision is a fear of failure. Instead of asking will this open up possibilities? Will it change the direction of my life? Will it improve my life? People tend to let the fear of failure hold them back a lot of the time. Let’s look at some good courageous questions to overcome the fear of failure and you mentioned your favorite one to kick off the conversation:

“What would I do if I knew I couldn’t fail?”

Warren Berger: Yeah that’s a good question to start with because it allows you to come up with some bold possibilities.

What’s the worst that could happen? 

Another question I like, and this is probably going to strike people as a very familiar question because it’s something I know my mother used to say to me:

“What’s the worst that could happen?”

It may seem like a negative question, but it’s really a very powerful question because it forces you to confront your fears about the worst case scenario about a decision you’re making or a risk you’re taking, and to think about them in a very specific way. And when you do that it usually makes them less scary. We tend to be afraid of things that we haven’t thought about.

How would I recover?

So if you force yourself to think about the worst case scenario usually it tends to lessen the fear a little bit and it also opens up the possibility for you to ask another question:

“How would I recover from that failure?”

So it’s sort of a two part question:

“What’s the worst that can happen?”

And then if it did happen:

“How would I recover?”

“What would I do?”

The bottom line is that imagining the worst case scenario usually makes you realize that the fear is not as bad as you might have thought, and there’s always a way back. So all of this serves to take this vague, scary, fear of failure that you have, and makes it a little bit more manageable, a little more specific, and that sometimes enables you to then move forward with a little bit more courage.

If I did fail: What would be the likely causes?

Warren Berger: Another question you can ask:

“If I did fail: What would be the likely causes?

This is a valuable question. It’s a premortem question. A postmortem happens when you analyse the cause of death after someone or something dies, but in a premortem you’re anticipating every kind of potential pitfall and problem before they occur so that you can avoid them.

Michael Frank: I think the premortem is great. I first heard about it from Guy Kawasaki and it’s when you imagine that 6-12 months from now in the future, your business or your project or whatever, has failed, and you’re thinking of all the possible reasons it could happen so that you can develop contingency plans to deal with each one of those things.

Warren Berger: Absolutely.

What if I succeed?

It’s also a good idea to ask yourself:

“What if I succeed?”

What would that look like? Because visualizing success is really important. It’s going breed confidence and it’s going to help you, and it just reinforces the reason why you’re doing this in the first place, and why you might want to take this risk. So be sure to think in very clear terms and to visualize what success would look like.

And then the last questions I would advise in terms of overcoming the fear of failure is:

“How I can take one small step?”

“Is there anything I can do to get started on this thing that I’m fearful of?”

Think about the person who wants to overcome their fear of heights. You don’t have to go to the top of the highest building in the world. You can start by climbing a small hill first before you climb the mountain. So think about whether there are ways you can begin to expose yourself to this fear in a small way, in a limited way.

Michael Frank: I’m a big believer too when it comes to achieving a big goal, you don’t need to know all of the steps, you only need to know the next step, and then have the courage to take it.

Warren Berger: Yeah. That first step is what’s going to give you a lot of momentum to go forward.

Questions to identify your passion

Michael Frank: Let’s look at finding your passion. I remember a book titled: “I could do anything in the world if I only knew what it was” and I think a lot of people struggle with identifying their passion and purpose in life. What are some questions that we should ask in order to identify our passion?

Warren Berger: Well I’m a big believer in using questions to find your passion, but I also want to say that the idea that there is only one passion, or only one thing that we’re meant to do, is not always true. It’s not always as simple as that.

Sometimes there are a number of things that we were meant to do. Sometimes something might be right for you right now, but at another time it might be something else. So the one thing I would say about finding your passion is to be flexible about it, don’t have this idea that there is only one thing that you’re meant to do and that’s all you should do. Be more open and flexible on that concept.

What is my tennis ball?

Now having said that, one of the questions I like comes from Drew Houston the founder of Dropbox, he thinks that people should ask:

“What is my tennis ball?”

So the analogy he uses is: Think about a dog chasing a tennis ball. The dog doesn’t care about anything else except for that tennis ball. That’s the only thing that matters to it. And so similarly you need to think about: What is the thing that pulls you that way? What is the thing that has that effect on you, that when you think about that thing you become totally focused on it, like a dog focuses on a tennis ball?

What did I enjoy doing when I was 10 years old?

How do you find that thing? You might think about:

“What did I enjoy doing when I was 10 years old?”

Because a lot of us had something that we really liked in the past that we moved away from. A lot of us were more creative and courageous when we were kids than we are now. We explored more. We tried more things. And if you think about what you really loved back then, it may be that that thing is still important to you now. It may be that you need to adapt whatever it was then, because maybe what you loved at age 10 isn’t gonna work for you right now as an adult. But there may be something in there, there may be a passion within you that you can adapt to your current life.

When am I at my best?

You can also look at the different parts of your life. Look for where you’ve been really happy. Look for when you’ve been at your best.

Ask yourself:

“When have I been at my best?”

“When in my life have I felt beautiful?”

“When have I felt like everything was coming together for me?”

And think about what was going on at that time, and what you were doing when that was happening, and there maybe clues in there about what really turns you on.

What are my superpowers?

Ask yourself the question:

“What are my super powers?”

“What are the personality traits, the aptitudes, that just seem to come naturally to me?”

“What are the things that I’m naturally good at?”

Take stock of that stuff because it really matters. You know we all have these things that we’re just naturally good at, but we don’t always pay enough attention to it. So take stock of your super powers.

In what way do I wish the world were different?

Ask yourself:

“In what way do I wish the world were different?”

This is a good question to ask if you believe that you might want to bring about change in the world. Not all of us have those kinds of grand ambitions, but you might, and so that question might help you to figure out how you can serve other people, how you can contribute, what you might be able to, what role you might be able to play in somehow making things better.

What is my sentence?

And the last question I’ll share with you on passion and purpose is:

“What is my sentence?”

If you had to boil your life and yourself down to a single sentence, what would that sentence be?

Think about formulating a single sentence that sums up who you are, and what you’re trying to do as a person, and that will help you to find your passion.

Questions to make someone like, or even love you

Michael Frank: Let’s wrap up this interview with questions to make someone like, or even love you. I thought some of these questions were great and they’re definitely better than the typical “How are you” type questions.

Warren Berger: Yeah these questions come out of research done by a scientist named Arthur Aron in New York, and he’s been doing studies for years about how to build intimacy between people, and how people can make someone else really like them, really quickly.

What he does is he brings two people together, and his goal is that within a couple of hours he wants them to really like each other, and possibly even love each other, which is pretty crazy, right? But anyway, he’s been working all these years on how to make that happen and what he has people do when they come to together is to ask each other a set of 36 questions that are designed to build rapport and empathy and caring between the two people. So person A will ask person B the question, and then person B will ask person A the same question, and they’ll go through this series of questions. And by the end the idea is that they will have built up a tremendous understanding of each other and have a real feeling for each other.

If tomorrow you could have any quality or ability, what would it be?

Some of the 36 questions are:

“Given the choice of anyone in the world, who would you want as a dinner guest?”

“What would constitute a perfect day for you?”

“If you could change anything about the way you were raised, what would it be?”

“If tomorrow you could have any quality or ability, what would it be?”

“How do you feel about your relationship with your mother?”

“When did you last cry in front of another person?”

“What, if anything, is too serious to be joked about?”

“Your house containing everything you own catches fire… after saving your loved ones and pets, you have time to safely make a final dash for one last item. What would it be and why?”

How would you complete this sentence:

“I wish I had someone with whom I could share…”

So I think what he discovered is that intimacy builds as you gradually reveal more and more about yourself to another person.

Michael Frank: Warren Berger that’s a wrap, it’s been an absolute pleasure.

Warren Berger: Thank you very much Michael. This was great. I really enjoyed it.

This interview has been edited and condensed for clarity.

Warren Berger A more beautiful question the book of beautiful questions

Warren Berger believes questions are more important than answers.

He is the author of the international best-selling book of A More Beautiful Question and The Book of Beautiful Questions  

Berger also writes for Fast Company, Harvard Business Review, and The New York Times. He has appeared on The Today Show, CNN, and National Public Radio.

In his work, Warren has interviewed and studied hundreds of the world’s leading innovators and creative thinkers, to analyze how they ask fundamental questions, solve problems, and create new possibilities.

He has conducted questioning workshops at the NASA space program, and has brought questioning ideas and exercises into companies such as Microsoft, Pepsi, and Starbucks. He also visits schools and education conferences, urging teachers to try to encourage more questioning in the classroom.

His website is


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