Top 4 Questions

What would you need to see/hear to change your mind?

Originally from a few Tim Ferriss podcasts. By asking this question, the conversation switches to binary. It’s either a conversation in which we are willing to change our minds (1), or one in which nothing would change our minds (0).

Both are useful conversations, but I find this is a great baseline. If neither of us are changing our minds, let’s just understand the other side for fun. No convincing needed.

What’s the inverse of this?

From Farnum Street & probably a few other mental model books. Oddly enough, I’ve found the most by applying this to people rather than problems. If I hear, “James is a strong manager.” Often unintentionally, I’ve found that something leaks out in the inverse of statements of people. If I’m told repeatedly I’m a strong manager, the inverse could be that I’m not a empathetic manager.

Great leaders know how to communicate using these some of these inverse undertones: “Roger is a creative problem solver.” = Roger doesn’t know how to follow rules or a standard plan.

“Bob is an incredibly focused worker.” = Bob isn’t ready to manage, and struggles with team cohesion/teamwork.

Obviously these are guesses, but after starting to look for the inverse of complements (what wasn’t being said), a lot was revealed.

Also…I want to be clear: None of the above are bad things. They are just more creative ways to highlight bad/good personality traits for role fits. Some companies & leaders highlight strengths/weaknesses openly. I feel this can sometimes encourage employees to work on their weaknesses, rather than be .

How does this look +100 years and -100 years in the past & future?

How does this look in another country?

A friend and I spoke recently about open releationships and the topic of flirting came up. I was emphasising that if 2 people from different countries date, their definitions of flirting can be very different. For example, I have a friend who defines cheating as showing more skin than a long skirt + long sleeve shirt. On the opposite side, I have a monogomous friend who defines cheating as only things below the waist.