1) Have you guys found a place to put your coats/bags, or are we just holding on to them?
This question plays on the communal confusion that occurs at every event. No one knows what they're doing. And the ones that do will revel at the chance to be the one "in the know."
2) You guys look like you're having the most fun in the room, mind if I join this conversation?
Of course, this group actually has to look like they're having a good time.
3) Have you guys been having any trouble with the Wi-Fi?
Good news: The answer is almost always "yes."
4) That X looks great. What is it?
Whether it's a food or a beverage, this question can offer a few different answers -- whether a description, a comment on the quality, or where they got it.
5) You from Philly?
Or Boston. Or Austin. Or St. Louis. Or whatever city or state their attire and accessories are sporting.
6) Mind if I squeeze in and share this cocktail table?
7) Do you know anyone else here or are you flying solo?
If they know other people, your circle expands. If they don't, you generate some empathy as a fellow lone wolf.
8) Know anywhere I can get some good food or drinks around here?
If they're a local, you'll probably get them rattling off about their favorite spots. If not, you both can bumble about for the recommendations you've each heard through the grapevine.
9) Did you hear X speak?
Being at the same conference, the sessions and speakers are some of the only guaranteed common ground. It's a great starting point that can go in a lot of different conversational directions.
10) Are you here to meet or see anyone in particular?
If you're both interested in meeting the same people or seeing the same sessions, this question will help you establish that common ground. If not, you get to learn more about each others' goals.
11) Did you all come here together, or did you meet here?
This question opens up the conversation to the entire group -- the more people chatting, the better.
12) Since we've got some time to kill, I just wanted to introduce myself.
This works great when you're waiting in line for a keynote, the bathroom, food, etc.
13) How are you guys getting to the next event? Want to share a cab?
Start with the first part of the question -- but offer up a ride share if the group doesn't really have a plan.
14) Are you or anyone at your company speaking at this event?
Be sure to have a quick follow-up if the answer is "no" -- like asking about which sessions they plan on attending.
15) Is this your first time at this event?
Old-timers will be able to share some insider tips, and first-timers can empathize with you.
16) Did you understand X from Y session today?
Ask someone who was in a common session or talk to explain something to you if you want to do a little ego stroking while you network.
17) Alright, I got an awesome marketing joke for you.
This only works if you actually have an awesome marketing joke -- but I wrote a list for you in this blog post, so you're all set.
18) Did you catch any good sessions today?
This question helps reveal people's interests -- way easier to keep a conversation going if you know a little bit about the person.
19) I'm tired of talking to my colleagues -- I see them all the time. What are you guys talking about?
This is a spinoff of a pickup line one of my favorite comedians, Pete Holmes, shared on his podcast. His original version was "I'm tired of talking to my friends, what are you guys talking about?" I like it because it's probably true, and shows an interest in getting to know new people.
20) Hi, I'm X.
It actually works. Provided you have a follow-up so you're not just staring at each other in silence.
The key to all of these conversation starters is that you have to be ready with a follow-up. This is just your "in" to the conversation -- be ready to keep the conversation going, and take it conversation to the next level.
And if all else fails, just ask ...