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The Attention Span. "Great Question!"

“Computers are useless- they can give us only answers”- Picasso

The age of information abundance has helped us find the answer for almost any imaginable query on demand. But computers are much more limited in helping us find the right questions to ask in the first place. Formulating a great question is the foundational tool for benefitting from the wisdom and experience of others. It is the filter for the ocean of noise we’re swimming in.

“Great Question!”

[8 minute read]

Pip Coburn from Coburn Ventures recently produced an update to his “Questions for Management” series. His rationale strikes at the very heart of any investment process: how do you obtain uncommon insights?

Here are five questions he suggests. They should be equally useful for business owners and investors.

1. “What is something in the past 3-4 months that you sense people really aren’t appreciating about your business, that is very, very important when thinking about the next 3-5 years? In other words, most of the investment world is somewhat focused on what you think is the wrong stuff, and in the process, they are missing 1-2 extremely vital elements?” – Pip thinks this is likely to produce both uncommon and highly relevant insights.

2. “If I was told that I had to take over as CEO of your company in just three weeks, what would you HAVE TO teach me?”

3. “What is your working definition of culture, and when was the last time you saw something inside your company that had you just wonder a bit if the culture was strong enough in key ways that you want to support success during the next 5-10 years?”

4. “What will be the greatest adaptations your organization will need to accomplish to be successful out 4-5 years from now?”“How do you use customer complaints SPECIFICALLY to create a better business?”

5. “How do you use customer complaints SPECIFICALLY to create a better business?”

6. A suggestion from me “If you had just one bullet in a figurative pistol, whom among your many competitors would you save it for?”- via Andy Grove in Only the Paranoid Survive. This is a question for business leaders to ask themselves and their employees to make sure their understanding of the competitive landscape is current. “When the answer to this question stops being as crystal clear as it used to be and some of your people direct the silver bullet to competitors who didn’t merit this kind of attention previously, it’s time to sit up and pay special attention.”


As a follow-up: here are eight of my favourite questions from other great thinkers and investors:

1. “What have you experienced that makes you believe what you do?”- via Morgan Housel. The longer I think about this one, the more spectacular it becomes. For any debate, especially a political or tribal one, this question helps people relate back to emotions rather than cold facts. It opens the conversation and delightfully exposes those who get their opinions second-hand. Then when somebody asked it back to me, I realized it burns off a lot of dead wood. It made me question many of the opinions I held without any real foundation. It was a necessary but extremely uncomfortable exercise.

2. “What probability would you put on that outcome?”- via Michael Mauboussin. The question forces someone offering a binary forecast to focus more granularly on outcomes. This is consistent with Philip Tetlock’s work on forecasting that found a critical component of success was the ability to finely calibrate probabilistic forecasts to adjust to new information.

3. “What have you changed your mind about recently?”- inspired by Jeff Bezos. Related to the above question, lives lived online often mean conflating our public opinions with our personal identity. Once an opinion has made it into our very sense of self, it becomes exceedingly difficult to dislodge, especially publicly. Remarkably few public intellectuals readily broadcast their cognitive flexibility. Yet belief-updating is proven to be a critical variable of forecasting success: 3x as important as intelligence. “Anybody who doesn’t change their mind a lot is dramatically underestimating the complexity of the world that we live in.”- Jeff Bezos.

4. “What important truth do very few people agree with you on?”- via Peter Thiel. Why does he ask it? It’s a way to identify differentiated thoughts and thinkers. “This question sounds easy because it’s straightforward. Actually, it’s very hard to answer. It’s intellectually difficult because the knowledge that everyone is taught in school is by definition agreed upon. And it’s psychologically difficult because anyone trying to answer must say something she knows to be unpopular. Brilliant thinking is rare, but courage is in even shorter supply than genius.” A similar question posed by Paul Graham in the absolutely magnificent essay “What You Can’t Say” is “Do you have any opinions that you would be reluctant to express in front of a group of your peers?” Why is this question good? “If the answer is no, you might want to stop and think about that. If everything you believe is something you’re supposed to believe, could that possibly be a coincidence? Odds are it isn’t. Odds are you just think what you’re told.” See more on this, as well as the original fantastic essay, below.

5. “Can you explain this to me like I’m twelve?”- inspired by Richard Feynman. Not only helps you understand something from first principles, but quickly reveals whether the other person does too. See more below.

6. “If you could have a gigantic billboard anywhere with anything on it, what would it say and why?”- via Tim Ferriss in his excellent book Tools of Titans. Distills and communicates what you think is most important in life.

7. “What pain do you want in your life?”- via Mark Manson in The Most Important Question of Your Life. We can all easily tell ourselves what we want, but we don’t always consider the price of that desire. Manson asks “What are you willing to struggle for? Because that seems to be a greater determinant of how our lives turn out.” More on this below.

8. “This is the main question, with what activity one’s leisure is filled.”-  via Aristotle. I have come to agree that this is the most important question of all, but not necessarily for immediately intuitive reasons. I will explain this in a piece around Memorial Day Weekend.


Other follow-up reading:


  • Read. The Most Important Question of Your Life by Mark Manson (9 minute read)
  • Why Read. This article won’t be for everyone. It contains profanity. I’ll confess I’m not a massive Manson fan generally, but this article is very provocative in a good way. It reminds me of the quote from Chris Nolan’s wonderful movie Interstellar: “Newton’s third law – the only way humans have ever figured out of getting somewhere is to leave something behind.” Progress requires sacrifice.
  • Sometimes I ask people, “How do you choose to suffer?” These people tilt their heads and look at me like I have twelve noses. But I ask because that tells me far more about you than your desires and fantasies. Because you have to choose something. You can’t have a pain-free life. It can’t all be roses and unicorns. And ultimately that’s the hard question that matters. Pleasure is an easy question. And pretty much all of us have similar answers. The more interesting question is the pain. What is the pain that you want to sustain?


  • Read. What You Can’t Say by Paul Graham (40 minute read).
  • Why Read. As I noted above, this is an absolutely foundational essay for me. It’s an uncomfortable examination of the view that every human culture regards its moral and ideological foundations as totally settled, only to look absurd to future generations.
    • “It seems to be a constant throughout history: In every period, people believed things that were just ridiculous, and believed them so strongly that you would have gotten in terrible trouble for saying otherwise.”


  • Read. The Feynman Learning Technique by Farnham Street (23 minute read)
  • Why Read. It’s a cliché that we learn by teaching and explaining, but I adamantly believe it’s also true. In an age when it is stunningly easy to absorb an opinion without foundations, this helps build them first.
    • “There are four steps to the Feynman Learning Technique, based on the method Richard Feynman originally used. We have adapted it slightly after reflecting on our own experiences using this process to learn. The steps are as follows:
  1. Pretend to teach a concept you want to learn about to a student in the sixth grade.
  2. Identify gaps in your explanation. Go back to the source material to better understand it.
  3. Organize and simplify.
  4. Transmit (optional).”

Have a great weekend!


Tom


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