Finding and eliciting valuable information is one of the most useful skills someone can develop. This is an ongoing list of proxies and heuristics that I’ve found helpful to date.
1. If someone is displaying behavior that so strongly goes against the grain of how they typically act, it’s worth digging deeper. There’s probably some important factor driving that abnormality that’s important to identify and understand.
2. Give people something to react to. This is especially helpful in scenarios where someone is split and/or indifferent to a decision.
Picking a side of the decision and committing to defending it (for the sake of discussion) helps propel the process forward – it elicits the best arguments both for and against that decision. Presenting an “I could go either way” viewpoint is harder to debate and interrogate.
3. One way to spot talent is to pay attention to who within an organization peers are gravitating toward when they need help. If a set of peers are consistently asking someone for help, it reveals that they not only trust and respect that person, but also that they view them as knowledgeable and collaborative.
4. If you put an idea out into the world and many people call it stupid or silly but someone with deep category knowledge thinks it’s interesting, there’s probably something there. This is a tactical way of spotting opportunities that fit the “good ideas that sound like bad ideas” adage.
5. Be extra thoughtful / patient if someone is communicating in a non-native language. It may be more challenging for them to fully communicate the nuance of their ideas.
There’s a scene from the show Modern Family where Sofia Vergara’s character – who is a native Spanish speaker and generally seen as unserious by the other characters – shouts in frustration, “If only you all knew how smart I am in Spanish!” I think about that scene legitimately every week.
6. When trying to solicit a broad set of opinions from a team, try having the junior folks start. It’s easier to forward a viewpoint that may diverge from your superiors if you don’t yet know your bosses’ perspective.
7. Always try inversion. A good question to ask is, “in what ways could we be wrong?”
8. A lot of information is more readily available than many may realize – you just have to ask.
For example, say you want to build a consumer product. Do an audit of where you spend money and time each month (literally: look at your credit card bill and breakdown of screen time). Then ask your friends. Then ask their friends. Then ask yourself where you and they would be willing to spend more money and time, if given the right product or opportunity.
9. It’s powerful when someone voluntarily admits that they were wrong about something. But it’s 10x more powerful when they immediately follow that up with “here’s what I learned…”
10. You can learn from other’s successes (i.e. what to do right), but rarely their failures (you’ll never know the full extent of what went awry).
11. Pay attention if someone refuses to give an opinion because they claim they’re not knowledgeable about the subject (these people aren’t afraid to say “I don’t know”). It means that when they do have an opinion about something, they’re probably quite well-informed and it’s worth paying attention to.
12. Actively solicit the perspective of whomever is closest to the job being done, regardless of their rank. They probably have opinions on how something should be done, but may not normally have a forum to voice those opinions.
13. Very little beats the quality of learning while in person. Same is true for seeing the data points live. A good example is in the Big Short: in the movie, Burry and his colleagues visited some new housing development sites. Many of the homes were either empty or occupied by people who couldn’t sustainably afford them; it made clear there was a bubble waiting to pop.
14. Actively verify / probe data. If the data seems to conflict with reality, the data is probably wrong.
An example: in the early days of Amazon, one of the S-Team gave Bezos a report that stated Amazon’s customer service was great and took under a minute to get a response from an agent. But customers were still complaining. So in the meeting, Bezos called customer service live; it took over 10 minutes to get an agent on the phone. The data was wrong.
15. Develop a set of questions to ask yourself daily. These are mine.
This is fantastic piece of advice. I also wanted to thank you for all of your thought provoking diaries and posts on this substack. I've been a fan for a while and your writing also inspired to start writing about my journey to crypto. For that I am eternally grateful.