How to ask better questions

Unlock big ideas, develop others, scale yourself

TLDR: people and companies start by asking all sorts of questions, but do it less and less over time; to be the best, keep asking questions

Throughout my life, I thought the smartest people had all the answers. Consulting firms take pride in being answer-first. Tech companies take pride in moving fast through iterating on the answer.

While expedient, I’m learning there are real costs to being exclusively answer-first. Starting with an answer instead of a question robs us of the opportunity to develop others, scale ourselves, and imagine a more interesting future.

We’re trained by school and work to come up with convincing answers, but where do we learn how to ask better questions? After all, every big idea can be traced back to a thoughtful question.

Why → what if → how

The book A More Beautiful Question outlines the progression of questions behind a number of big ideas.

Netflix: Why does Blockbuster charge late fees, making most of their margin on upset customers? What if video rental was run like a gym membership?
Polaroid: Why do you have to wait for the picture? What if you could take a picture and instantly print it out?
Airbnb: Why should you be stuck without a bed if I’ve got an extra air mattress? What if you could rent / host a bed in any city?
Gatorade: Why aren’t athletes peeing more? What if you could hydrate athletes properly?
Instagram: Why do people not share more pictures? What if you could make every picture share-worthy?

Game changers come from questioning the way things have always been done. They don’t typically emerge as fully-formed answers because there’s little precedent for them. They don’t start as an exercise in TAM, but rather an exercise in exploring overlooked opportunities.

They start with Why and What if, followed by a long journey in How to work out the details. How is answer-driven, but it comes after open-ended questioning of the problem space.

Imagine this as a bridge between wandering questions and focused execution. If you jump on any bridge, you may end up working on uninspiring answers. But if you never cross the bridge, you become lost. I think the best time to cross is when the What if is something you’re very excited to work on. The devil is always in the details, but picking a promising direction keeps you energized and determines your ceiling.

The other upside of starting with a question is that it attracts people who are similarly curious, and want to partner up in search of the answer. They are excited to cross the bridge with you to yet unknown lands.

Don’t let the questions wither

These questions are not exclusive to starting something new. It can be applied to anything important you’re working on. Companies start by asking all sorts of questions, but once they become the status quo, the questions wither away, along with the ability to create something new.

So many failed projects are the result of jumping into How without thinking about the Why and whether there’s a better What if. Key assumptions are left unquestioned. The more ambiguous and complicated the project, the more important it is to spend time on upfront exploration. Time upfront can save you multiples in effort.

In fact, writing down and sharing questions can even help align people. It’s funny how often disagreements actually stem from being focused on very different questions. Example: the sales team wants a feature in order to sign a specific account next week, whereas the product team wants to make signing all types of accounts easier in 3 months. To untangle disagreements, revisit the questions that drive the work.

The most powerful questions start open-ended. They don’t lead to easy yes or no answers. They challenge and re-examine the status quo. This also applies to people.

Coach through questions

A recent leadership training session made me realize a deep-seated habit. I tend to seed questions with an answer in mind. I say things like: have you thought about {option A}? or should we test {idea B}?

These types of questions are useful when you’re in a crunch and need an immediate answer, especially as an individual contributor. But most of the time, they deprive others of the opportunity to figure things out on their own. When people figure out an answer, they’re more excited to take action.

Having strong opinions (even if weakly held) is a double-edged sword. On one hand, it drives clarity and momentum. On the other, it removes oxygen for competing opinions. When everything’s already determined, there’s little incentive for others to contribute their perspective. People lose an important muscle.

You should still develop your own POV, but start with more open-ended questions.

Closed: Should we do X to move Y?
Open: What are the most important things given goal Y?
Closed (and judgmental): Aren’t you too busy to take on this project?
Open: What are your priorities? How committed are you to doing X?
Closed: Any questions?
Open: What questions do you have?

Open-ended questions help you calibrate people. If they’re lost, you can set the expectations that you will lean in more. If they’re on the right track, you can focus on guiding their direction instead of managing the details.

Follow-up questions are extra special. They nudge you to listen carefully, and help you learn more about others. See here for more examples of closed vs. open questions.

Here’s a rule of thumb I’ve observed: people new to a task tend to learn faster by seeing a model answer; people familiar with a task are more empowered by learning through questions. But everyone benefits from starting with open-ended questions.

Scale yourself

Mastering asking questions also enables you to scale yourself. It feels nice to be the trusted go-to person, but when you’re consistently providing all the answers, you are limited by time and expertise. There are only so many quality answers you can give, and so much scope you can take on. Your impact is unbounded once you learn how to use questions to spark answers in others.

Even better, democratize question-asking. I find this has become easier in a fully-remote environment where everyone takes up the same-sized square block in a video. Encourage live and asynchronous questions, especially at the start of a new roadmap when changing direction is cheap.

People are more engaged when questions belong to everyone. Searching for answers is more interesting than executing an order. But when you also get to ask the question, you make it your mission to find an answer.

Turn periods back to question marks

If asking a flurry of questions seems like a distant memory to you, you’re not alone. The peak age for asking questions is 4 years old, followed by a sad but predictable decline.

As the saying goes, we enter school as question marks and leave as periods.

This would be ok if we lived in a stagnant world. But in an age where computers get exponentially better at coming up with answers, learning how to ask thoughtful questions is the single best investment we can make in each other. To forge ahead, we need to revive our innate curiosity.

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