Crossposting this from my LP specific Substack…
I met a family office last week and she asked me a really interesting question. Probably the question a lot of us are asking ourselves. Whether you’re a VC or an LP or someone looking to hire team members.
How does one really understand another person?
The short answer is I’m still looking for the answer to that question myself. And probably will continue to do so till the day I die. Kinda like one of those questions… What is the purpose of life? Is there other sentient life in the universe besides us and what are they like? What happens to all the memories we forget? But I digress, though you can probably guess I’m writing this piece in a good mood 🙂
And so I responded.
Doubt I or anyone really has the answer to that. But there’s that Charlie Munger line: “Show me the incentives, and I’ll show you the outcome.”
My first step in every investment conversation is understanding why someone does what they do. Are they trying to prove someone wrong (ie a parent, an ex, their kids, former boss, etc.)? What is their chip on shoulder if they have any? What gives them joy? What gives them pride? How do they identify themselves? Who do they see themselves as? Is there something they’re unwilling to tell me? Why? What’s stopping them?
And some permutation of the questions below is what usually comes up in conversation. While I don’t have a checklist of questions I have to ask, as long as I’m not sure what my sparring partner’s motivation is, I keep trying to figure out. Hopefully, the below questions serve as inspiration for you. Or are just more questions to your arsenal.
- What is your selfless motivation—the one that goes in the Forbes interview? What is your selfish motivation—the one you tell yourself when you’re struggling? Your selfless motivation will inspire you on your best days. Your selfish one will keep you going on your worst.
- What do you want to have written on your epitaph? Do you have adjectives or words you particularly like?
- What is the greatest regret you’ve had? Why?
- What’s the greatest thing you’ve ever done that no one around you knows about? Proudest?
- What’s the proudest sacrifice you’ve made that no one knows about?
- Is there a question no one has ever asked you but you would like to give the answer to?
- What is a question you feel uncomfortable asking me?
- Is there a set of questions you would feel uncomfortable if I asked you?
- Why did your spouse first fall in love with you?
- Why do you think each of your former bosses hired you? Would you say they all hired you for the same reason?
- What’s the closest you came to breaking?
Photo by Doncoombez on Unsplash
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.