How to Approach Someone at an Event
It’s the second week of September.
The memories of summer are already starting to fade away. The annual ritual of “back to school”, a glorious event celebrated by parents across the northern hemisphere, has come and gone. Burning Man is over. So is the After Burn. And the After After Burn.
For most of the world, that means back to the humdrum of office life. But for residents of Startupland™, the second week of September marks the start of fall event season. YC officially kicked things off yesterday with with their S25 Demo Day in San Francisco. In startup ecosystems around the world, the coming weeks will be filled with happy hours and hackathons, receptions and retreats, soirees and cinq à septs. (All while founders try their best to make actual progress on their business and VCs fight over the hottest deals.)
Packed room to hear the Mayor of San Francisco speak
It’s a busy time of year, but also one filled with opportunities…provided you play your cards right.
Knowing how to get the most out of an event is an underrated and unpracticed skill for many founders. I’ve previously shared tips for how to pitch a VC at a party. In this post, I’ll pop up a level and discuss more broadly how to make the most out of any work-related event.
1. Define Your “Why”
The best founders don’t go to events for the sake of going. At least, not after the initial buzz of being invited to “exclusive” events for the first time wears off (we’ve all been there). There has to be a reason for high achievers to take time away from work, friends, family and other priorities to attend a professional event. What’s yours?
There are plenty of reasons to attend an event, including:
Prospecting for customers
Prospecting for investors
Prospecting for employees
Getting feedback on an idea
Meeting other high-achieving founders (for inspiration, to build your network, etc.)
Showing support for someone or their company
Being seen and/or catching up with people you already know
Just getting out of the office (that’s okay too!)
Before you go to an event, take a moment to really think about your objective. What is your “why” for attending the event?
2. Quantity or Quality?
The second question to answer is “quantity or quality?”
Do you want to have deep conversations with a small number of people or are you hoping to connect with as many individuals as possible who fit your target persona?
Think about this question carefully. Would you be happy if you spent the entire night speaking to only one person? What if you already knew them? Are there specific people you absolutely have to speak to (if only so they know that “you were there”) or is your primary objective to meet new people?
Even if your reason for going to the event is simply “to get out of the office,” thinking about the types of conversations you hope to have and/or the types of people you hope to meet will help you to navigate the event with more intentionality.
3. Target List
Who are the people you absolutely, positively need to see at this event?
Write down those names or personas and what your objective is with each person (Is it simply to say hello and be seen? Do you want discuss a particular topic with them? Do you hope to get their contact information?) If you have access to the invite list, spend 5 minutes to review it and highlight anyone you specifically want to talk to. Think about the types of conversations you hope to have with each person and how much time you want to spend with each of them.
“At 7:35pm, the Series A VC will arrive…”
4. The Approach
Despite the title of this post, I’m not actually going to tell you how to approach a stranger at an event. There are plenty of books, posts and podcasts that have been made on the topic, so I’ll leave that as an exercise for the reader. But I will encourage you to be thoughtful about it. There isn’t necessarily a perfect approach, but there are plenty of ways that are guaranteed to fail.
Here are some actual approaches I’ve had from people at events:
A self-proclaimed “ecosystem leader” who rudely interrupted an obvious conversation that I was having with a young founder, positioned his back to the founder, and then proceeded to declare how influential he was in the ecosystem and that we should find time for a conversation
A founder who physically blocked me from walking onto a stage (while I was holding a microphone) and insisted on trying to pitch me despite my saying multiple times, “I have to go on stage”
A founder who followed me into a bathroom, stood beside me and attempted to pitch me while I was doing my business (that really does happen…)
In general, people who attend networking and other startup events are there to meet and talk to others. So if you’re patient, polite and just the right amount of assertive, chances are you can talk to almost anyone at an event. If only for a few minutes…
5. Make Your Move
You’ve patiently waited and finally have the opportunity to talk to the person you’ve had your eye on. What’s next?
If you’re doing any sort of prospecting, your goal is actually not to pitch the person on the spot. Rather, it’s to get their contact information so that you can have a proper 1-1 conversation later. Events are loud (at least, the good ones are). It’s hard to hear people and you frequently get interrupted. As such, it’s essential that you are concise.
Make your elevator pitch and see where the conversation goes. If the person shows interest, ask if you can get their contact information to follow-up later. By preempting your own pitch with an early ask, you signal respect for the person’s time and, in doing so, are more likely to get a ‘yes’ than if you gave them an extended pitch. At this point, they might happily give you their contact info or they might ask more questions (in which case, you can dig in deeper if you choose).
The other benefit of making the ask early is that you can be more efficient with your time. The faster you make the ask, the sooner you’ll close the “sale”. And the sooner you close the sale, the sooner you can move on to your next prospect.
(On the other hand, if your goal is quality over quantity, then by all means engage the person in a deep, lengthy conversation about whatever topic you have in mind.)
6. Watch for Yes
If someone offers you the close — i.e. they offer to share their contact information with you — take it. Even if you’re not ready.
It’s not uncommon for someone to interrupt your pitch during an event in order to preemptively offer you their contact information. I do it all the time. It usually goes something like this,
“This sounds great. Why don’t you send me an email and we can find time to continue the conversation later.”
Many times, founders are so focused on their pitch that they fail to recognize that the person they’re talking to just said yes and they continue pitching. By not watching for yes, they miss the signal in the response.
When someone interrupts you to preemptively offer their contact information, they’re not only saying “yes”, they’re also saying, “I want to end this conversation.” There could be any manner of reasons why they want to move on, but the critical piece is that they gave you a yes. If you fail to catch the double-meaning — and graciously cut off the conversation while taking their contact information — it’s possible they won’t offer it a second time. And you might ultimately lose the opportunity.
Also be prepared for the yes to come in a form you weren’t expecting. For example, you might ask for an email address and they might instead offer you their phone number or a LinkedIn QR code. Whatever form they offer, you should take it. Here’s an actual conversation I had with a founder recently:
Founder: “Can I have your email address?”
Me: “You already have it. The invite for tonight’s event came from my actual email…just hit reply and email me there.”
Founder (pulling out phone): “Ok, but can I have your email address?”
Me: “You already have it. The invite for tonight came from my actual email…just email me there.”
After the founder asked for a third time, I shrugged and said no.
That might seem harsh, but if someone has to repeat themself more than once, it’s generally a signal that you’re not listening (and as an investor, it’s not a great signal). So always remember, if you want people to say yes, you have to listen to them.
I’m sure that more than a few of you have made it to this point and are thinking “wow, Chris really overthinks things,” or “this all seems a bit over-calculated.”
You certainly don’t have to meticulously plan out each and every event you attend. By all means, show up to some events and just have fun. But if you take a few minutes to consciously set a goal for each work-related event you attend and then “debrief” with yourself afterwards (did you meet the goal? why or why not?), you’ll soon discover that you’re navigating events with far more intentionality and effectiveness than you were before.
And as a founder, every little bit helps.
