When I was in New York last week, I had the fortune of catching up with one of my favorite people inside the rustic walls of Il Buco. Needless to say, an hour and a half was not enough to contain months of development and change. So, to continue our tea, the next day, after she met up with the one of the heavyweights in her industry, she asked:
“How do you keep your enthusiasm in check but show it to the extent that shows respect to the person and also have a conversation as equals?”
In sum, how do you fangirl/fanboy without losing your composure?
I don’t. It happens less frequently now, but I still do.
In fact, even when I try not to or attempt to convince my conscious self, this is just another human being doing their best to live the life they want, there’s something that my eyes do without fail every single time. Here’s to hoping it’s not painfully obvious to the other person.
In fairness, I actually don’t know what I look like when it happens. I can just feel and SEE it through my eyes every time. In fact, I don’t even know what this phenomenon is called. Or if there’s a word for it. If I were to describe it, it’d be if the thousand-yard stare and diplopia had a baby.
It’s completely involuntary. All my other senses and cognitions work just fine. And when it happens, I start blinking a lot more which usually recalibrates my gaze.
Physiological response aside, over time, I’ve simmered down my ability to respond into two ways, especially when my brain decides to turn off. One for each situation.
- I’m prepared. For instance, this is a scheduled meeting, or I know I will see this person at an upcoming event.
- I’m unprepared. The canonical serendipitous elevator ride. For instance, bumping into them at an event. Or true story, we happened to both be helping to carry A/V equipment backstage post-show.
When I’m prepared…
The goal here is to know the other person better than they know themselves at the point in time. This is the same mentality I carry into both conversations in public and private spaces. The former with interviews, fireside chats, and panel discussions. The latter in the form of coffee chats, dinners, happy hours, and the like.
Depending on the timeframe, I come prepared with a different number of questions. But generally, for every 30 minutes, I come with three questions.
The first question is to establish rapport. And it’s always a personal one. I almost never start the conversation with pure “business.” This sets the tone for the rest of the conversation, as well as how candid they will be with you.
You’ll have to do your research. Some may require more digging than others. That said, don’t take it too far by finding their home address or social security number. Here, I usually look for fun facts. Like they did street dancing back in high school or they love going to stand up comedy shows.
If you’re going to take away one thing with this question, it’s to surprise and delight.
For the second one, which is usually the optional question if we’re short on time, I love understanding people’s inflection points. For example, why did they go from consulting to acting? Or from an art gallerist to a VC?
Not just the fact that they went through a massive delta, but I love understanding what they were thinking before, during and after they made the transition. Was it a decision that was supported by their family and/or peers? Was it a difficult decision to make? What got them over the activation energy to commit to this new lifestyle?
The third question is akin to the one I always advise founders to think about when talking to investors. Why would this investor be the best dollar for your cap table? Similarly, even if you’re not raising money, what kind of question can only the person in front of you answer? Or very few others can? It’s usually a function of their work or life experience, where they end up becoming uniquely positioned to talk about that topic.
As a prelude to this last question, I usually preface why this question means a lot to me. Why do I need this answer? Show that you have spent time in the idea maze. Time thinking deeply about the topic already. Naturally, anything that is googleable is off-limits here.
You have one chance to make a great first impression. Don’t waste it.
Cutting it short
Just as it’s important to start the conversation on a high note, in my opinion, it’s even more important to end the conversation on a higher note. As such, I have a three rules of thumb:
- Never overstay your welcome. It’s always better to cut the conversation short than to end with awkward silence. Be extremely acute to where the clock is compared to how much time you’ve asked of them.
- Have a go-to phrase (or phrases) to end the conversation. One of my favorites is, “As with all great conversations, we ran out of time before we ran out of topics.” (The cat’s out of the bag, so now I need a new one.)
- Follow up within 12 hours of the conversation with notes from the conversation, and action items on your end. For instance, if the other person shared advice with you that you solicited, be sure to act on it. Come back two weeks to a month later and share the results of your findings. As you might suspect, bring a pen and paper for the conversation. People really respect it when you take their thoughts seriously. During, and even more so, after.
If possible, pay it forward, and when that time comes, don’t be afraid to share it with the source of the advice.
When I’m unprepared…
While still worthwhile in the former situation, you need to be able to break the ice quickly and give others a reason to listen to you for just two more minutes. People are naturally busy. And if you disrupt their normal flow of life, their whole goal while you are speaking to them is not how they can talk to you more, but about how they can get back to doing what they were doing.
Just as much as you will be unprepared, they will be too. As such, you need to disrupt their flow even momentarily. Your short 10-second bio needs to generate emotion and curiosity. Oftentimes, that is not your title. For instance, one that I like using with folks who I know to be lighthearted and have no context to the startup world is, “I get paid to be the dumbest person in the room.” Self-deprecating humor really does help for folks who can and have time to take a joke.
Other than your short bio, always have 2-3 questions handy via muscle memory that are good to ask in almost any situation AND would give you immense insight. I’ll share one of mine, and likely many more in the future with my DGQ series on this blog.
In your line of work, what differentiates the great from the good? Not just the good from the bad, but how do I tell the very best from the ones that have yet to get there but are still a cut above the rest?
Practice these again and again. In front of a mirror. In the shower. Or while you’re driving. Until they become second nature.
In closing
The important thing to remember is these people don’t owe you anything. And sometimes, while you can’t give them what they want, you can make that amount of time you have with them amusing. Insight doesn’t just come in the form of answers but also questions that get others to think in ways they didn’t before. Going back to one of my favorite Kurt Vonnegut lines:
“Use the time of a total stranger in such a way that he or she will not feel the time was wasted.“
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.