This post has been adapted from Circle's event on How to run engaging events that took place on 11/29/2021. Thanks to Jillian from Smart Passive Income and Megan from Fresh Exchange for sharing incredible tips as my co-panelists, and to Mathilde from Circle for moderating and asking thought-provoking questions.

Level-up your community skills - get these guides delivered straight to your inbox!

How to run engaging community events

1. Pay attention to what people are asking The greatest gift of being a community steward is having a direct line to your people. Host events based on your members' pain points. If your triathlon group is curious about nutrition, maybe you replace your monthly triathlete happy hour with nutrition coaching sessions with Coach Superfood. (Fake name, but if you know a Coach Superfood, please tell me ASAP.) Jillian from SPI Pro talks about how this shapes their meetups and office hours — for example, one big pain point in their community is automating various technologies, so they have a specific automations meetup to work on this.
2. Identify your event's purpose: education, action, or connection? Mathilde, who manages the Circle community, shares her categorization of events. Are they going to learn something? Do something? Do someone Meet someone? You don't want to show up to a monster truck rally with a 30-minute PowerPoint on monster trucks. Purpose is important. 🛻
3. Set clear expectations Until I started attending more events in the corporate world, I realized this "set expectations" thing, which sounds like a given, is actually unclear to many hosts. If you're going to put people through a cheesy icebreaker, send an email beforehand that participation is expected. If it's a webinar, don't call it an interactive workshop. Whether it's in the beginning of your event or in the communications leading up to it, be very clear of what is expected of attendees. I like to give people an opportunity to say/ask what's expected of me too — in our signup forms, I'll ask what questions people have, and I also include a field for them to privately share accommodations they need, like live captioning, etc.
4. Create an intentional, comfortable space The thing I said above about live captioning — it is SO important to create an inclusive space. Your members will tell you what they need if you show them you're listening. One thing I've borrowed from Carrie Melissa Jones is to tell people to get 10% more comfortable — turn off devices, be present, get a glass of water, etc. The beginning of an event is a threshold into the world you're building for your attendees, and this is one of the biggest things I'm trying to improve on in 2022, because it's so easy to just "wait for people to trickle in" and then "let's get started".
5. Make sure your venue reflects the tone Your venue is your greatest opportunity. I may not have said this in early 2020 when the best option out there was Zoom, but now we have SO MANY GATHERING PLATFORMS! It's amazing! I use Mixily for our casual gatherings since it's playful and not stodgy like Zoom (sry). I've loved Topia.io and Gather.Town for conference-y style things that feel personal. And I recently heard of Looped Live for webinars that can feel like TED stages or concerts! I've also gotten a bunch of recs for WorkFrom.co for coworking together virtually without getting Zoom fatigue. People will react a certain way based on the space you provide them, whether or not it's conscious.

6. Think asynchronous Jillian talks about how SPI Pro has a "Pat's Corner" space (Pat is the founder of SPI). He has dedicated 2-hour AMAs, and one thing that makes it special is that anyone in the world can participate. Instead of going all-in on a live Zoom call, when you think about "posts" as "asynchronous events", it can change the way your members engage with each other. One potential pitfall: asynchronous events aren't always treated like "real" events. If you don't treat them that way (i.e. if you don't promote them, share widely, make the post author feel valued, etc.), they will not add value to your members in the same way a live event will.
7. Anchor your community in seasons Megan Gilger's Fresh Exchange community is around gardening, so this makes perfect sense for her members. It gives the community a way to root themselves (haha get it) in a common timeframe regardless of where in the world they live. If you can't see the seasonality in your own community, think more deeply. It's there. Let's say you run a mastermind for women founders, which is notedly less seasonal than gardening — you'll notice different types of questions being asked depending on the time of year. Many investors take vacations in the summer and towards the end of December, and that affects what the founders in your community are thinking about. The great thing about seasonality is it can give people a push to get re-engaged! After the holidays, for example, people are too busy being stuffed to think about their online communities... unless you send them a nudge. If Santa were to run a membership community for his elves, maybe he would do a "design the 2022 toy of the year" contest for them when they get back from their post-Christmas stress relief!
8. Try trivia This is an EASY event to host. I won't even say anything more about it because you have to do SOME homework, come on. Every single community in the world can host a trivia event, because you're all loosely bonded by some topic.
9. Do a Q&A We do Q&As in the form of fireside chats. Imagine this: instead of listening to a podcast on the bus with some fascinating activist leader, you get to pop in for 30 minutes during the day and ask questions. Or, if that's not your thing, you can just listen in! I've also seen this done successfully with member hot seats. Q&As can be done as live events, asynchronous posts, pre-recorded videos, or an elaborate game of charades. Especially if you're just starting your community, Q&As are easy wins as long as you ask the right questions. (Hint: do NOT stick to the script.)
10. Host a demo day or a showcase You may have seen "show and tell" or "ask and offer" channels within the communities you've joined. These are great when they're active. It's also a cool way to provide members with recognition by inviting them to show off their accomplishments. Again, this can take any format you wish, but for the sake of example: In your Side Hustlers Community "show and tell" channel, there's 8 people who consistently share what they're working on, encourage others, and answer questions. You reach out to them to see if they want to present their projects to the entire community, et voila, your community now has an annual demo day.
11. Play games If you're hosting a social gathering, you still need it to have structure unless your community members really do know each other enough to be comfortable shooting the breeze. Codenames.game and Skribbl.io are some fun group games to give you something to do while you get to know each other better.

12. Empower your community members Give people opportunities to be involved in events. Every community manager's dream is to have people step up and lead, but this doesn't magically happen. For Soapbox, when a member reaches out with a speaker suggestion for a fireside chat, the first thing I do is ask them if they want to host the session. I can still handle all the logistics, but they're in charge of the questions. Separately, when a member makes a post with an event suggestion, I work with them to put them in the driver's seat. Empowering your community members is hard work, because it's ongoing and requires a lot more puppeteering than you might think. But it's SO WORTH IT — the hard part is identifying the baby steps and starting earlier than you might be comfortable with. And really trusting your members. P.S. A smaller way to do this is to let members submit their own events that are external to your community. This can be good, but in many groups I'm part of, this "external events" is more spammy and less value-add. I will venture a guess that these forums aren't explicitly showing event-posters how to step up as community leaders.
13. Collect feedback and use it.

Megan says, "We sent a Typeform at the end of the season for our members. This helped us get ideas and clear steps for how to adjust our events to what our members want. It is anonymous too so they can feel they can be very honest with us." Remember the "pay attention to what people are asking" thing from the beginning? Well, here you go!

Chime in on the discussion thread below if you have any input — what's been your favorite community event so far?

Level-up your community skills - get these guides delivered straight to your inbox!