A few years ago, I gave an ignite talk at Google I/O about the ways I'm shy and the many ways I've found to work around my shyness. I recently saw a post on overcoming shyness at conferences on HN, and realized I never formally wrote up my own tips.
Before going into my shyness hacks for conferences, let me clarify what I mean when I say that "I'm shy". For me, it means that I'm afraid of approaching and talking to people, especially when its me and a group of strangers. Ultimately, it's because I'm afraid of rejection. As long as I don't approach people, then I don't have to worry that they will ignore me or turn me away. Sometimes I try to just be a hermit and not worry about my fears, but I soon realize I crave human interaction, and always will. If I'm going to go through the effort to go to a conference, then I don't want to waste that opportunity for interaction.
Given that, here are my shyness hacks for conferences:
Be a Speaker
This is my primary hack. I will almost never attend a conference if I'm not a speaker, because I know that if I'm just there as an attendee, I will spend my time getting shyer and shyer until eventually I'm just reading my book in a corner in the bathroom.
After I deliver a talk to a group of people, there will be a whole room of people afterwards who know who I am and even better, who know what conversation topics they can approach me with. Speaking isn't easy- I still get sick to my stomach just before I talk- but for me, its worth it. When I moved to Sydney and didn't know anyone, I gave two talks at their BarCamp my first weekend there, and that's how I met 90% of my Aussie friends. If you're nervous about speaking in front of a big audience, start small - give a lightning talk or lead a BOF session - that's still a group of people that now know who you are!
Whenever I get the choice of when to speak in an event, I always ask for an early slot - - early in the week if it's a multi-day conference or before lunch if it's one day. I want to make sure that people know who I am as soon as possible so that I can spend the rest of the time hopefully getting approached by them with their thoughts on my talk.
Talk to Speakers
Okay, let's say you really don't want to be a speaker, or you didn't have a speaking opportunity at this conference. Now that you've seen that many speakers (okay, at least one of us) become speakers because they want to be approached, an obvious hack is to talk to the speakers.
I will typically keep a running notepad with the questions that come to my mind during a talk, and then I will often ask one during the formal Q&A, so that the speaker's seen my interest, and save the rest for attacking them after with my curiosity. Most of the time, the speaker is more than happy to answer questions, and loves that somebody is interested enough to ask.
Go to Workshops
Traditional presentations are not very conducive to social interactions. It's a bunch of people, watching a speaker, and the only opportunities to talk to each other are before and after. A workshop, however, is inherently more interactive: there's many a time at which you'll be working on an exercise, and that's a time at which you can talk to the people near you about what you're working on. If you want to be very popular, then try to be the one that pays a lot of attention and can help out everyone else. Otherwise, don't be afraid to ask for help, too. (Just not *too* much).
Be a Conversation Piece
This is a hack that works anywhere in life - parties, cafes, dinners. If I make it so that some aspect of my physical presence provokes conversation ideas, then people will have an obvious and immediate excuse to talk to me.
That's typically in the form of a t-shirt, like a geeky one, an awesome band, or some ironic one from Threadless, but it can also be in the form of a crazy hat or accessory, like my often brightly colored hair or super cute animal socks. I actually don't wear geek t-shirts to work anymore, but I've saved up a spectrum of them so I have appropriate ones to wear at each conference I go to.
Hand out Free Shit
This is the hack that I used as a kid. I was shy around my classmates, so I would bring crazy candy to school in a Santa-like bag and offer it to everyone around me. The word would get around fast, and pretty soon, everyone would be approaching me, even the "cool" kids.
This isn't something I've done frequently myself at conferences, but I've seen others do it. Lug around a bag of cool stickers or shirts, and pretty soon, because we all have grade school sticker-mongers deep inside us, you'll have random strangers approaching you for them.
I'll update this as I think of more. Feel free to share your own hacks in the comments!