In today’s New York Times. this is Tony Tjan, of Cue Ball, and his wonderful framework on mentoring and giving criticism:
One [mentor] was Jay Chiat, one of the founders of the Chiat/Day ad agency. He had this incredible capacity for optimism, particularly optimism during mentorship. He had this amazing ability to think of every reason why an idea might work before criticizing it and thinking why it might not work. When you’re a mentor, you’ve got to realize that people are often sharing their dreams, and I think it’s human nature to be a critic. We’re skeptics. As you get older and more experienced, wisdom is great, but you also have to be careful not to automatically impose your mental framework and your lessons.
I’ve translated it into a rule that I try to get people to follow, and I’m still working on this. When someone gives you an idea, try to wait just 24 seconds before criticizing it. If you can do that, wait 24 minutes. Then if you become a Zen master of optimism, you could wait a day, and spend that time thinking about why something actually might work. In venture capital, you’re at the intersection of human capital and their big ideas, their dreams. My favorite quote is from Eleanor Roosevelt: “The future belongs to those who believe in the beauty of their dreams.”
This ties in nicely with Bill Gurley’s thesis that the one career-making investment might break the rules and pattern-recognition honed through years of long experience. If so, it is worth spending some time thinking about why an idea might work before dismissing it.