Having a vibrant, local Less Wrong or EA community is really valuable, but at least in my experience, it tends to end up falling to the same couple people, and if one of or all of those people get burned out or get interested in another project, the meetup can fall apart. Meanwhile, there are often people who are interested in contributing but feel intimidated by the idea.
In the words of Zvi: You're good enough, you're smart enough and people would like you. (Or more explicitly, "assume you are one level higher than you think you are.")
This is an email I sent to the local NYC mailing list trying to break down some of the soft-skills and rules-of-thumb that I'd acquired over the years, to make running a meetup less intimidating. I acquired these gradually over several years. You don't need all the skills / concepts at once to run a meetup but having at least some of them will help a lot.
These are arranged roughly in order of "How much public speaking or 'interact with strangers' skill they require."
Look for opportunities to help in any fashion
First, if public speaking stuff is intimidating, there're many things you can do that don't require much at all. Some examples:
- Sending a email reminder to the group for people to pick a meetup topic each week (otherwise people may forget until the last minute)
- Bringing food, or interesting toys to add some fun things to do before or after the official meetup starts.
- Helping out with tech (i.e. setting up projectors, printing out things in advance that need printing out in advance)
- Take notes during interesting discussions (i.e. start up a google doc, announce that you're taking notes so people can specify if particular things should be off the record, and then post that google doc to whatever mailing list or internet group your community uses to organize)
Having an explicit activity can take some of the edge off of "talking in public."
A short lightning talk about the beginning of a meetup can spark interesting conversation. A meetup description like "So and so will be giving a short talk on X, followed by freeform discussion" can go a long way. I've heard reports that even a thoroughly mediocre lightning talk can still add a lot of value over "generic meet and greet."
(note: experimentation has apparently revealed that 3.5 minute talks are far superior to 5 minute talks, which tend to end up floundering slightly)
Facilitate OTHER people giving lightning talks
Don't have things to say yourself at all? That's okay! One of the surprisingly simple and effective forms of meetups is a mini-unconference where people just share thoughts on a particular topic, followed by some questions and discussions.
In this case, the main skill you need to acquire is the skill of "being able to cut people off when they've talked too much."
The goal is just exposure therapy for "OMG I'm talking to a person and don't know what to say", until it no longer feels scary. If the very idea of thinking about that fills you with anxiety, you can start with extremely tame goals like "smile at one stranger on your way home".
I did this for several years, sometimes in a "learn to talk to girls" sense and sometimes in a general "talk to strangers" sense, and it was really valuable.
Once you're comfortable talking at all, start paying attention to higher level stuff like "don't talk too fast, make eye contact, etc."
Think about things until you have some interesting ideas worth chatting about
The trick is to not just think about interesting concepts, but to:
Help other people talk
- you will probably need to "prime the pump" of discussion, starting with an explanation for why the idea seems important to think about in the first place, building up some excitement for the idea and giving people a chance to mull it over.
- if you see someone who looks like they've been thinking, and maybe want to talk but are shy, explicitly say "hey, looks like you maybe had an idea - did you have anything you wanted to share?" (don't put too much pressure on them if the answer is "no not really.")
- if someone is going on too long and you notice your attention or anyone else's face start to wander...
Knowing when to interrupt
- "Hey, sorry to interrupt but this sounds like a tangent, maybe we can come back to this later during the followup conversation?"
- "Hey, just wanted to make sure some others got a chance to share their thoughts."
Have an Agenda
If you're doing a presentation, this can be a series of things you want to remember to get to. If you're teaching a skill, it can be a few different exercises relating to the skill. If you're facilitating a discussion, a series of questions to ask.
Welcome Newcomers
Then I had a year where I was just like "meh, screw it, I don't care", didn't run meetups much at all.
Then I came back and approached it from a "I just want to have meetups as often as I can, do as good a job as I can, and if it ends up just being a somewhat awkward hangout, whatever it'll be fine." This helped tremendously.
I don't know if it's possible to skip to that part (probably not). But it's the end-goal.
(Some people may not trust me if I don't acknowledge it's at least possible that people actually just don't like you. It is. But I think it is way more likely that you didn't pitch the idea well, or build enough excitement beforehand, or that this particular idea just didn't work)
If you have an idea that is only worth doing if some critical mass of people attend, I recommend putting an explicit request "I will only do this meetup if X people enthusiastically say 'I really want to come to this and will make sure to attend.'"
It may be helpful to visualize in advance how you'll respond if 20+ people come and how you'll respond if 1-2 people come. (With the latter, aiming to have more personalized conversations rather than an "event" in the same fashion)
Sometimes, people naturally think an idea is cool. A lot of the time, though, especially for weird/novel ideas, you will have to make them excited. Almost all of my offbeat ideas have required me to rally people, email them individually to check if they were coming, and talk about it in person a few times to get my own excitement to spread infectiously.
(For frame of reference, when I first pitched Solstice to the group, they were like "...really? Okay, I guess." And then I kept talking about it excitedly each week, sharing pieces of songs after the end of the formal meetup, demonstrating that I cared enough to put in a lot of work. I did similar things with the Hufflepuff Unconference)
This is especially important if you'll be putting a lot of effort into an experiment and you want to make sure it succeeds.
Step 1 - Be excited yourself. Find the kernel of an idea that seems high potential, even if it's hard to explain.
Step 2 - Put in a lot of work making sure you understand your idea and have things to say/do with it.
Step 3 - Share pieces of it in the aftermath of a previous meetup to see if people respond to it. If they don't respond at all, you may need to drop it. If at least 1 or 2 people respond with interest you can probably make it work but:
Step 4 - Email people individually. If you're comfortable enough with some people at the meetup, send them a private messaging saying "hey, would you be interested in this thing?" (People respond way more reliably to private messages than to generic "hey guys what do you think" to the group?)
Step 5 - If people are waffling on whether the idea is exciting enough to come, say straightforwardly: I will do this if and only if X people respond enthusiastically about it. (And then if they don't, alas, let the event go)
Further Reading
I wrote this out, and then remembered that Kaj Sotala has written a really comprehensive guide to running meetups (37 pages long). If you want a lot more ideas and advice, I recommend checking it out.
Is awkward actually something that happened?
I have the feeling for our meetups the failure isn't awkward which mostly never happens but "wasn't as fun or insightful as the attendees were looking for".
Basically I meant the latter, and it might just be a thing about me that I parse that as awkward (in particular when I'm afraid other people aren't having fun/insight)