Andy Weissman’s blog has the tagline “Maximizing the serendipity around you.” It’s a good philosophy. I think one of the simplest ways to do this is to ask people lots of questions when you meet them. I’m surprised how often people fail to do this. Besides being good manners, it’s also an efficient way to learn about the world and sometimes make important discoveries and connections.
About 6 years ago, when I was working at Bessemer as junior investor, I was at a dinner with a group of friends and acquaintances. The guy sitting next to me was a business school student who spent most of the dinner talking about how he was trying to get a job in venture capital. He never bothered to ask me what I did for a living and I never mentioned it.
Now, I wasn’t a particularly important venture capitalist, but getting a job in the industry is all about meeting as many people who work in it as you can. The fact that he happened to be sitting next to one was potentially serendipitous – had he only bothered to ask questions.
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Why didn't you mention you worked in VC?
+1 I'm really disappointed with how little most of my friends know about the people they spend their time with… and also how out of the ordinary people seem to think it is when I ask questions about why they do what they do, how their job works, etc.
1) i find talking about myself kind of boring
2) i kept expecting him to ask me what I did and at some point it because kind of interesting to see if he could really fill up 2 hrs talking about himself. besides, at that point I wasn't really in the mood to help the guy out.
Agree. I think if you leave, say, a lunch meeting not knowing basics about what the person does for a living, what they did in the past, where they live, a bit about their personal life, where they grew up, what they think is interesting, etc you didn't ask enough questions.
asking people questions about themselves gives them the opportunity to talk about their favorite subject…
asking people questions about themselves gives them the opportunity to talk about their favorite subject…
If possible I like to do my homework too. If I know in advance who I'm meeting I'll try to research what they do and what their interests are. It improves the quality of the questions I ask when we subsequently meet.
Absolutely. I'm always surprised when people haven't even done a basic Google search. If you are meeting someone with a startup, it's also nice to learn about it and maybe even try to give some feedback / say something insightful.
I guess I err at the other extreme–I would have looked you up on Google / LinkedIn when you weren't looking and then asked you leading questions. Perhaps there's a happy medium between narcissism and cyber-stalking.
Much better to err on your extreme versus the other.
Cultural tolerance for asking people questions varies .. In the UK it is almost always acceptable to open a conversation with a remark about the weather, current or anticipated. Though an acquaintance once said to me “You'd talk to people on trains !”
Very true. This is often a signal when I meet new people about how much I will like them; are they are curious about other people? Always surprising to me how many people don't really do this when meeting new people…
Great point, Chris. So important. My co-founders sometimes roll their eyes when I start to play the “name game” or make small talk about hometowns when meeting people, but once I do make a connection, it proves invaluable in furthering the conversation/relationship.
This was essentially the main theme I took away from Taleb's “The Black Swan,” which is seek out serendipity in both business and social circles, because the random outcomes can roll in your favor. I can think of a few instances where the questions I've asked to strangers have allowed me to progress in some fashion.
“In Black Swan terms, this means that you are exposed to the improbable only if you let it control you. You always control what you do; so make this your end.”
I find it's always better to listen the most & speak minimally. Unless I'm asked a question I don't tend to speak up. It's always more interesting to hear from others who may/not be the foremost expert on whatever. It's also a great way to weed out the BS'ers.
Very wise words. I met my current CEO this way (questions via encounter at a ski resort), who introduced me to Andy W, who enlightened me with these words as well. Funny the way it all works.
Also goes along these lines..“You cannot plan innovation. You cannot plan invention. All you can do is try very hard to be at the right place and be ready” -Eric Schmidt’s Keynote Speech, Carnegie Mellon Graduation 2009
I'm often surprised as well.
I think Andy Weismann's quote is meant to be very Black Swan.
Yes, I think it's best to speak just enough to introduce yourself etc but after that you gain more by listening than talking.
I find out all sorts of useful information this way. (Such as there are still a lot of people out there made nervous by the idea of their cell phone making random calls). I tend to like listening and asking questions. It helps to feel like you have a prepared script.
Oddly, something I find out with myself and others- you tend to talk more when you are nervous. Get a list of things you want to talk about, and ask questions about it- it makes both you and the other person feel good. And it makes you feel less nervous too. It really could be anything. Just ask some questions. Even if it is about something you think could be boring. I'm sure your dinner party partner could turn it into something interesting.
(And you learn stuff along the way)
Re: your #2, I often find myself playing this game. Thinking, “At some point, he/she has to take a breath and ask me a question, right?” Never ceases to amazing.
And the people who really kill me: “I've gotta get going. I feel bad we didn't have a chance to catch up on what you're up to. Next time for sure.” But “next time” is never any different—still all about them.
It's a real shame. People miss out on so much!
Yup lifted directly from the Black Swan serendipity concept
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Sir: Agreed–although one arguably has a significantly greater probability of connecting with Bruce Kovner, for example, by discussing his interest in rare books (Caxton the printer) rather than interest rates (Caxton the hedge fund)–
For those not opportunely sitting next to you (or others similarly well established in their respective fields) at dinner, how do you prefer for an interaction with you to be initiated (particularly when the questioner does not yet have the wherewithal to add value to your endeavors, whether professional or personal)? Thanks!
Sir: Agreed–although one arguably has a significantly greater probability of connecting with Bruce Kovner, for example, by discussing his interest in rare books (Caxton the printer) rather than interest rates (Caxton the hedge fund)–
For those not opportunely sitting next to you (or others similarly well established in their respective fields) at dinner, how do you prefer for an interaction with you to be initiated (particularly when the questioner does not yet have the wherewithal to add value to your endeavors, whether professional or personal)? Thanks!