Season 1, episode 9, “Hide and Q”
Lesson: games can be effective tools for quickly understanding people
This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each.
Q plays a game with some of the bridge crew, particularly Riker, to continue learning about humanity. Q doesn’t say what the rules of the game are, but he imbues Riker with the power of the Q and tempts him to use it. This power starts corrupting Riker, eroding his respect for the chain of command and tarnishing his judgment of the rest of the crew.
In the final scene of the episode, Picard supports Riker using the Q’s power to gift the crew with whatever gifts they’ve always wanted. Riker does so (instant adulthood for Wesley, normal sight for La Forge, a female mate for Worf, humanity for Data), and despite their allure, all of the crew refuse the gifts. They don’t want to change the fundamental nature of what makes them who they are. Picard anticipated that this would happen, but neither Q or Riker did (Q because he doesn’t understand human nature yet; Riker because power skewed his view of how normal people act).
Q loses at his own game because he misjudges humanity. Picard wins because he’s so in tune with his crew’s motivations, desires, and personalities.
Q’s game is a pretext to delve deeply and quickly into what drives humanity. Games and other seemingly “fun” tasks can be good for that. In early-stage investing, for example, we need to get effective reads on the founders we’re considering backing very quickly. We’re certainly not always right, but I’d say the best VCs are better at this art than most.
I just met a founder who told me that he met and got to know his cofounder after accidentally joining an Australian World of Warcraft server and spending two years raiding together. That’s commitment. When it came time to build a company, they already knew that they worked great together in high-stress situations. It doesn’t matter that a game generated those situations, versus the real world.
Here are some of the more game-like questions I sometimes ask people in first meetings, along with why I ask them. Some are mine; others came from people I respect:
How would your arch nemesis describe you?
This is a spin on the overused “What are your biggest flaws” interview question. For whatever reason, people seem more honest when describing themselves through the view of a hypothetical third party than in their own words.
Name your top 3 favorite movies in no particular order (r if they say they aren’t a movie person, switch to books).
Obviously there is no “right” answer to this question in terms of movie titles. It’s a softball that’s designed to give the speaker a chance to go on a tangent about something they love. I’m more interested in how they describe the movies, what their impact was on their life, and how they speak and react off the cuff. I want to see you geek out on something. The “wrong” answer here is a lifeless one: either reciting safe movies that everyone likes and that doesn’t require any thought, or not being able to recall a single movie you’ve liked. If I had a dollar for every time someone says “The Shawshank Redemption,” I’d be loaded. Sure, everyone likes that movie. It’s an extremely likeable movie. But for god’s sake, have some creativity. You KNOW that everyone likes that movie. Thus you’re not telling me anything about yourself by giving me that answer. You’re basically saying “I’m a person who likes popular things.” And for the people who “can’t think of anything,” I’m sorry but you need to have seen and liked at least one movie in your life or I’m going to hold that against you.
If you could have both a major and a minor superpower, what would they be and why?
Major = something “magical” that greatly surpasses what humans can do today; minor = something that rare and exceptional humans can do today but that you can’t, like being a chess savant or having perfect pitch. A person’s answer to this question tends to show what they value most and how they’d spend their time in a perfect world.
What do you like to do outside of work?
Another softball question. All I want here is a human answer about something the person is passionate about. What it is doesn’t really matter; it’s how they describe it. My favorite answers are those that reveal the person has unexpected expertise that they’ve cultivated, like “I volunteer every Saturday with a lab that teaches parrots English” or “I’m a top-ranked Magic the Gathering player.” My least favorite answers are the boring ones: “I like hanging out” or “I watch sports.” That tells me nothing about you.
If you were on death row, what would your last meal be? You can have anything you want, and as many courses as you want.
I’m just looking for someone to go crazy and get into details here. Again, this isn’t about the food they pick; it’s about their enthusiasm and description of it.
What’s on your bucket list? Share at least one thing.
I like to know what drives a person and what they’d like to accomplish in the future. These goals can be illuminating.
Describe your parents and/or your siblings, if you have any.
The way they talk about their parents, including nonverbals, can say a lot about the person and their relationship with authority figures. Same goes for siblings, especially depending on birth order; sibling relationships can be like co-founder relationships. I don’t expect families or their history to be perfect. I’m more interested in the person’s description and perception of these relationships. Do they seem content? Anxious or upset?
Teach me something right here in five minutes that I don’t already know.
I love this question because A, I get to learn something new if they’re good at it; and B, it’s a real-time demonstration of both their communication skills and their ability to think on the spot. I also put a lot of value on life-long learning and curiosity, especially in founders.
Tell me a story about a time you…[failed] [won] [figured something out] [had a disagreement with a manger] [had a disagreement with a co-worker] [had a great experience with a co-worker].
I’m interested in how you view your past co-workers and jobs. Were they positive? Are you bitter about anything? I’m also trying to get at how action-oriented you are: are you in charge of the things you’ve done? Or do you try to take credit for other people’s work? Do you take ownership of yourself, faults and all?
Do you have any go-to fun, soul-revealing interview questions like these? And for the record, my top three movies are Dumb and Dumber, A Clockwork Orange, and The Matrix; my death row meal would be a cheese pizza from Pepe’s in New Haven, Connecticut, the Omakase menu from O Ya sushi in Boston, and a brownie sundae with peanut butter sauce; and my major/minor superpowers would be controlling the flow of time and having perfect comprehension/memory for everything I read.