What questions are you asking?

Our daily actions are answers, or attempts at answers, to the questions we ask ourselves. They shape our experience by focusing the energy of our conscious and subconscious thoughts on the search for answers to these questions. They become the lens through which we view reality.

The Simpler Questions

“How can I have more money?”

This is quite simple and practical as money is the universal substitute for anything you want (assuming someone offers it on the market). A common variation of the same question is, how can I save more money. This question very conveniently leads you to marketers offering deals.

Picture abstracted from Amazon Germany home page

Another variation of the same question is – how can I make more money? How can I make a lot more money? This will lead you to another set of marketers, selling skills and strategies. Sales and business advice on how to win friends and influence people. Maybe some on reading ‘lot of’ books – with more advice and inspiring stories.

But we can twist the wording on this question further to lead to very different set of answers.

“How do I make a billion dollars?”

Now this question is rarer and a bit more interesting. People might even laugh at you for asking this. But you will find this more acceptable in the startup world or the world of high finance. Silicon Valley and Wall Street. And the answers you get there will be quite different from getting 30% off on a new phone or learning people’s names during meetings, though probably deals and negotiation will be part of the game.

And if you ask,

“How do I make a trillion dollars?”

This one has answers on the internet ranging from the meaningless to the ridiculous. Apparently, trillionaires, if they exist yet, have little time for giving away their ‘secrets of success’.

But even these questions are not that interesting. They don’t evoke action or interest. They are a bit… bland. And here are some other bland, but devastatingly common questions which have tons on answers on the internet:

How do I get a job at x? How do I make a better resume?

How do I get more people to read my blog?

What are the in-demand skills in the market? How do I improve my skills?

How do I get more likes on instagram?

But you know about these so let’s move on to slightly more interesting things.

Harder to answer, but still commonly asked questions

Then sometimes you will come across more philosophical questions like,

What is the meaning of life?

What makes for healthy relationships?

What things do we regret later in life?

These are harder to answer, and quite incredibly important. People tend to brand them as ‘deep’.

Asking yourself these questions will lead you to more interesting areas. I guess you would feel more satisfied with life if these questions filter your thoughts and feelings, compared to questions about money or likes.

But the internet has answers for these questions too. There are books (talking about fables of alchemists) and blog posts which will offer you insights. There are hardcore philosophy books which address these quite seriously. And of course there are celebrity interviews which do the same.

Amazon’s Jeff Bezos says,

“[I]f I’m 80 years old, looking back on my life and the one thing I have done is make it so that there is this gigantic entrepreneurial explosion in space for the next generation,” says Bezos, “I will be a happy, happy man.”

But while you should investigate these questions, they are still… common. They will only take you so far.

Questions a Google search can’t address

Fresh questions, even if they are about ‘just’ money or business, can be more energizing. Like the zingers by Peter Thiel:

What truth do very few people agree with you on?

What valuable company is no one building?

How can you reach your ten year goal in six months?

These are lovely and rather difficult questions. I have, after quite some time, found inklings to answers of the first two, but am clueless about the third (though I am convinced it has some answers). But the answers are not the point. You want to arrive at novel insights which will happen if you ask these questions. Living with hard questions is way more valuable than living with easy answers.

At AirBnB too, they ask some stimulating questions. For context, we are used to giving 1 to 5 stars to things we like on the internet.

5 Stars
Picture abstracted from Yelp

And seeing those stars, if you offer a service, you might want to ask yourself – how can I get people to rate my service at 5 stars? This is the reflection of Airbnb CEO on 5 stars:

The paradigm with customers today is 5 stars. The problem with 5 stars is you have to be really bad to get 4 stars. Reaching 5 stars is just being nice enough — we wanted to build a product that you loved so much you would tell everyone. Travel has the potential to transform your whole life — I have met people on my own travels who changed my life.

But that’s not exactly the question the CEO of Airbnb asks himself. He asks what about six stars, seven… ten? Thirty?

At Airbnb, we strive to have our customers contact the company and demand a 6th star be added to our 5 star review because the experience was so good. Here’s how we think about service past 5 stars:

  • 5 star service — You leave the airport, go to the Airbnb, your hosts are in the house, they let you in. This is 5 star. Worse than this is if your host is late (4 star) and the worst is if your host never showed up (1 star).
  • 6 star service — All of the above + your host picks you up at the airport.
  • 7 star service — All of the above + there is a limo waiting for you at the airport and inside the limo are your favorite chips and coconut water.
  • 8 star service — There is a giant parade when you arrive at the airport and you are honored for coming.
  • 9 star service — The moment you step off the plane there is 5,000 screaming fans holding signs for your arrive — we call this the Beatles check-in.
  • 10 star — I could go all the way up to 30 stars — I won’t, but 10 stars would be when you arrive and a Tesla with your name on it is waiting for you and in the car the driver is Elon Musk, and instead of your Airbnb, Elon takes you to outer space.

I exaggerated this to make a point but the principle is if what you need to do is find 100 people who love you — 5 star is what people expect. For them to love you, you need to do more than what they expect. We play out these scenarios all of the time — once you go up to 10 stars, 6 stars doesn’t seem so crazy anymore.

Apart from questions about money or business, there can be others used to clarify your thinking. Like,

What data point, or piece of information, would convince you to change your opinion on <x>?

This is a simple and powerful one, and ensures your thinking has discipline. That you have arrived at an opinion not through blind preference, but via a deliberate framework. You can try this now. Think of something simple, like iOS and Android, and apply this question to your preference. Enjoy the thoughts which arise.

Another variation on this one,

On what areas do you disagree with, with a thinker you deeply respect, or even respect the most?

I sometimes enjoy thinking about areas where I do not agree with Peter Thiel and Nassim Taleb. It feels like an exercise of the brain in quite a literal sense.

There is even a meta question you can pose about questions.

What question is this person trying to answer through this book or this talk or this product?

One reason I found the book Antifragile deeply enjoyable was that it was an attempt to answer the question,

How do I live happily in a world I don’t understand?

I loved this question because of course we chase happiness and I used to think understanding the world would lead to it. After all, countless philosophical hours have been devoted to this elusive understanding. This was the first time someone came along and said screw it, we won’t ever get it, but we can still be happy, and here is how.


Most of the times one would ask how to have more order in life, and this guy came along saying we could gain from disorder. He never shuts up but I did give him my money.

Questions affect the economy of your country

At this point, I hope the importance of hard and interesting questions is quite stark. But these questions still address individuals and companies. We can go to the level of whole economies.

For example, in this brilliant talk, professor Clayton Christensen outlines how reframing a question led to the multi-decade stagnation in the Japanese economy (check it at around the 50 min mark). The professor blames the world of finance for changing how success was measured. In the 1970s, they were asking,

How much output are we generating?

And then later they started asking,

How much output are we generating compared to the inputs?

and then,

How quickly can I get my money out after I put my money in?

While seemingly similar they are vastly different questions. The first one leads to an absolute number and the others to a ratio. The absolute number may lead to comparison with one’s own past performance, while the ratios will lead to comparison with others, or by focusing on speed, guide effort towards short term projects.

What they realized that if they measured success by ratios, then you could compare two companies that are not comparable… in fractions, it commoditizes everything around the denominator.

… just look at Japan. Because in the 60s, 70s and most of the 80s, Japan’s economy was growing at unprecedented rates. And the reason why they were growing, was because they had companies in that economy that kept investing in disruptive innovations. So Toyota made cars affordable for mankind. Honda made motorcycles affordable for mankind…Sony.. Canon..  because they made these things affordable and accessible, billions of people around the world were able to own and use things that historically had bene beyond their reach. And that forced these companies to make more products… and for 30 years they had no economic recessions.

And in the late 1980s, in Japan, the analysts in Japan started to measure their success as [financial ratios like] gross margins, and net present values and internal rates of return. And since 1990 in Japan, they have not yet generated a single disruptive innovation.

Now the reasons for whatever happened to the Japanese economy might have been more complex, but this exploration shows how questions can influence country scale outcomes.

Questions about your Product

Segueing back to more immediate matters, when you think about your users of your product, you can ask:

What questions are your users asking, to which your product is the answer?

What are your customers buying, when they are buying your product?

Questions also separate the roles and the hence the actions of people in product teams. A product or growth manager probably asks,

What do my users want?

How can I increase the usage of my product?

How can I get more users, faster?

Meanwhile someone focused on the experience will ask,

What do my users feel in their tasks? How can I help them feel better?

What does the product mean for the users?

What is the product like?

And someone focused more on the interface itself might ask,

Is this user interface usable and accessible?

Is this interface beautiful? Does it showcase love for craftsmanship?

Product teams can see debates between two lines of thought – build with a vision, don’t listen too much to users, or – just ask user what they want and build it. The conflict is between ‘what do we love?’, versus ‘what do users love?’

But this question by Prof. Roberto Verganti is interesting and seems to bridge these approaches.

What would we love people to love?

(This question is part of the design process outlined in the book ‘Overcrowded’)

I feel the urge to get back to the more philosophical questions, but I rest the case. The central point is this – it is immensely valuable to think about difficult, carefully, originally articulated questions about your life and work. They will take you places no books and no coaches will.

What questions are you asking?

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