You need to prepare, listen and engage.
Charlie Rose

I’ve met a lot of incredibly successful, accomplished and well-known people. In some cases, I’ve even worked with them. This is one of the huge perks of working with Ron Conway, who I put in this bucket. (Incidentally, this sounds like a nested humblebrag but just because I met these folks obviously doesn’t put me in that bucket.)

For me, one skill that really stands out among some of these folks is their ability and willingness to listen. I’m not just talking about the level of listening where you remember what the other person said. And not the pollyannish notion of “I feel your pain.” I’m talking about the deeper level of listening that requires a mastery of body language, a genuine level of empathy and most important, a genuine interest and curiousity in the speaker or subject matter, or both. They are curious in either the person or the material, regardless of the person or material.

I’ve tried to become a better listener. About fifteen years ago, I bought this book and even highlighted portions of it. I got through about a quarter of it and threw it into my “Books Aborted” pile, which is a very large pile by the way.

I don’t want to sound too obsequious, but Ron is one of the best listeners I have ever seen. People like him lock into the other person a la Bill Clinton, who is probably the Mozart when it comes to this. For every meeting that Ron does, he brings a huge pile of notes related to the other person (i.e., he prepares) and completely locks into that person. His signature move is to furiously jot notes to record and remember what the other person is saying. I’ve asked him why he does this and he said, “Because I forget shit.” But the signal it sends to the speaker is immeasurable. It’s charisma in a nutshell.

When I first met Ron in 2005, we would talk about online video, his then-current interest. He would scribble notes furiously, sometimes on cocktail napkins. I thought I was the smartest person in the world on video. When I realized a few years later that he did that with virtually everyone on every topic, I was a bit crestfallen to say the least.

I wish I were a better listener. I’m subpar. Ask my wife. And to her chagrin, I want to improve not necessarily because I want to be a better and more empathic person. it’s because I think it’s an incredibly valuable skill to have as an investor, particularly in the startup world.

Regardless of your approach or business model, a huge part of startup investing (and in some cases, the only part) is human talent evaluation. “We invest in people” is probably the most common refrain for startup investors. And if you’re investing in people, you need to understand not only their skill, aptitude and potential but also their insight, drive, motivation and toughness – the immeasurables.

And that’s where listening comes in. One difference between a good investor and a great investor is that the great investor asks the right questions. And just as importantly, they’re able to process and synthesize the answers. They ask the incisive ones that cut through the noise. And identifying the right question is a function of great listening. Listening increases the throughput of data and also filters out the noise. If you watch Charlie Rose or watch great interviewers, they ask the great follow-up, unscripted questions that reveal the most important and telling details. This can unearth the people who have the missionary and authentic drive to do something great – and just as importantly, weed out the people who say the right things but don’t actually mean it.

The other person who comes to mind for me ont his topic is Michael Moritz, the legendary investor at Sequoia Capital. We’ve co-invested a lot with Sequoia, but I’ve never really worked with him personally. But his path to investing is not necessarilyt the conventional one. Before his investing career, he was a journalist and writer. And without speaking to him about this or knowing if this is bullshit, it kind of makes sense. Without knowing anything about the profession, a great journalist has to ask the right questions and synthesize the answers (among other things). And that’s a dynamic exercise that’s a direct function of getting the right information and inputs – i.e., being a great listener.

Clayton Christensen said that questions are places in your mind where answers fit. The relevant facts are there for everyone but you need to be able to ask the right questions to unearth them. The great investors can get to the most insightful answers and meaningful insights faster than the rest of us. In the startup world, where data is scarce but potential is abundant, that is an elite skill.