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What I’ve learned from hosting online trivia, webinars, and events

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Like many businesses, America Josh had to change how it operated due to COVID-19, shifting from an event and in-person based community to an online one. The mission though has stayed the same: to help people settle into their new lives in the United States – so what have I learned from the shift to virtual?

Working from home, social distancing, mask-wearing, and outdoor dining have become staples across the United States (and lots of the world) as the Coronavirus has covered the country. In fact, this is probably the opening sentence to 10,000 other blogs and articles written in the past 8 months.

It's really quite incredible though that I'm writing this in November 2020 and can distinctly remember my last subway ride in New York City on Friday, March 13, when I went uptown to collect what I needed from my office “for a month or so of working from home”. Oh, how much has changed.

Since then, we've converted the second bedroom from a guest room (read: storage room) into a fully-fledged home-office, we've gotten a COVID puppy, and we've adjusted our lives to be, on the most part, lived inside our own four walls. We are a couple who would generally like to be trying to new restaurants or seeing friends, but this year we've shelved all that to keep our family and friends safe.

I, especially, am someone though who thrives on meeting new people, connecting with new friends, and building relationships, so this year has come with some pain points. To overcome that, I have worked to adapt myself into a virtual host for both fun and informative events which required me to re-learn how to interact with people on a screen and without all the normal cues that come with an in-person or group chat.

Not only have I been organizing events for the America Josh community, but I have also been running trivia, Charity, and corporate events for organizations around the world, and while we're all slightly different, I think there are a handful of tips and tricks that apply to every online community.

So here are my most important learnings from this year, hosting online.

Keep it short… really short

An hour is an absolute maximum even if your content is fun, engaging, and everyone likes it. It's a long time to be sitting in one spot and it's a long time to be on a computer. Combine those things and you'll quickly realize that you're no longer helping, you're hurting.

I have no doubt that your participants will cringe when they think about attending another 2.5-hour session with you next time!

This one is absolutely crucial and not debatable.

Big groups don't facilitate… anything

Virtual meetings have made it incredibly easy to get your whole working group, department, or even company into one meeting, party, or event; but that doesn't mean you should.

Before I jump right into this one, I do want to add a small caveat: If the point of the event is simply to present information or answers to as many people as possible (i.e. an information webinar where the subscribers are watching because they have specific interest in the specific topic), then big groups are fine and great. i.e. If you aren't trying to engage a community together with eachother, then you don't need to worry about this.

However, for all of you who are hosting large group meetings online in order to “get everyone on the same page and allow for the whole company to chat and connect”, you're not going to find success in large online groups. You might think that everyone is tuned in and paying attention and that the large group just means more opportunities to connect, when in fact the majority of your team are likely texting a smaller side-group with the real feedback or thoughts they have.

We're social creatures but for the vast majority of us, that doesn't mean we like to be put on the spot and present to a whole organization without proper notice or preparation. It's also true that we don't really work well when placed in a circle of 30 people and told to all have a chat. This is the exact same behavior and response that you would see in a physical event, so it's no big surprise that this is the case for virtual events too.

While the large group part of an event might be required at the beginning and end to set things up and make some introductions or conclusions, it shouldn't be the majority of the event, it should be something that everyone is brought back into when it's completely necessary and appropriate only.

What's my alternative to big groups when hosting virtual events?

Breakout rooms. Honestly, I think my biggest take away from every event I've hosted is that the breakout rooms functionality in Zoom and other tools is possibly the most important.

In online trivia events, for example, we can have anything from 20 to 300 people but we don't want the experience to dramatically change for everyone if the group is larger.

The breakout rooms are always ranked in the top one or two elements of the virtual events that we host and the feedback is normally something along the lines of:

It was really nice to be able to actually chat with my co-workers about something other than work and actually be able to hear everyone when they spoke.


I got to meet some people who I would normally never have spoken to in the breakout rooms!

We see that even when connected with people who attendees have never met, they still have a better experience in the smaller breakout rooms than they would if they were just an attendee in a broader group.

My recommendation is to keep breakout room sizes to around 4 or 5. Anything bigger and you'll see the same users disengage and find it difficult to actually be able to contribute. If you've got a close and connected community, you can go right up to that 5 person limit, but if you've got a community who don't know each other well, or who might be quieter, keep the rooms smaller and be sure to give some structure (keep reading).

You can't just expect everyone to get involved

Don't put people on the spot without preparation and don't expect everyone to create their own fun. Again, this is just like a physical event. When you have everyone over for a party, you don't invite them to an empty warehouse and say “have at it!”, you've setup a mood, music, games, drinks, and more.

Also, going around the virtual room and saying things like “Janine, you haven't said anything for a little while” is awful and it's awkward for everyone watching, not to mention Janine.

The breakout rooms from above are perfect but too often have I seen good use of the breakout room functionality without any mission, or any task. People are left to their own devices and are required to generate topics of discussion or tasks to do all on their own, and that's not what a hosted event should look like.

We're all living stressful lives and there's a good amount of Zoom-fatigue going on internationally right now, so you want to work hard to formulate ideas and direction prior to starting.

The solution to this is structure and direction

You want your attendees and community members to be excited about participating in the event, and you want the event to feel free-flowing and productive, even if you're pushing it in that direction without everyone aware of the planning that went on behind the scenes.

Send out information prior to the event, give the event a specific topic, a specific theme, something that people can grab onto and think directly about before they connect.

During the event, this is just as important as well. Don't ask open-ended questions if you want to keep things running smoothly. Ask very specific questions with short answers, and don't allow much (really any) space for conversation to stagnate and stop, because every time the virtual event goes completely quiet, everyone becomes critically aware that this is online and a little bit strange.

Use quiet background music, set the mood, and when setting up breakout rooms be sure to give specific instructions, even if it's something simple like telling everyone to “Introduce yourself and what room of the house you're in”. Any topic at all that doesn't instinctively make you cringe (ice-breakers can be awful) will help push things through and keep the conversation lively.

It's also important to set expectations for how long sections of the event will be going for and when people will have a chance for breaks. We've come to think that because everyone is at home, they must be comfortable to sit for a long period of time but I would argue the inverse is actually true. Give regular breaks, make sessions as short as possible, and divide it into as many sections as you can. Don't rely on “30 minutes for discussion” amongst your team because if it doesn't take off immediately, you've set the tone for future events.

Virtual events lack proximity and closeness

One of the most difficult elements of online events is the fact that we're lacking the intimacy and proximity of having friends and family close-by. It makes everything feel a little surreal, and it makes it more difficult to get excited and engaged when connecting to “another” online event.

This can be overcome by experiencing the same thing locally, while virtual

If you're hosting a special event, send out goodie bags or hampers, or at least something that physically represents the virtual event that someone is attending. This won't work for every single online meeting, but for the events you want people to really enjoy, it's important that they have something that they can use or touch at the same time as everyone else.

A lot of the events I've hosted have included a “Cheers” at the beginning of the event where we toast a particular group or person, which has meant that everyone prepares themselves a drink before the event starts. While I don't think alcohol is the key to every meeting (or… maybe) it does act as an icebreaker and does give everyone something to hold in common with everyone else. Importantly it's not just your bottle of water you have on your desk at every meeting.

Businesses have really embraced this concept by sending little bottles of wine, or cocktail kits out to teams or communities before events in order to add a physical task before the virtual event. It sets the mood, it sets the tone, and it imitates (in at least a small part) the idea of being in the same space as each other.

Other groups I've worked with have decided on costume themes or sent out apparel to their team members, some have required that everyone collect a prop for the event from around their home, and in general, this has worked tremendously effectively to lighten the mood right from the start.

There's no feedback loop

We've all been on a call with a delay where people start speaking and then get interrupted, only then to have the other person say “you first” resulting in an endless loop of “Haha sorry, no you go”. It's torture.

We've also all become pretty savvy with how our virtual tools work and can mute ourselves for long periods of time so we can talk with our puppy while on a call, but this has meant that the feedback loop is broken. When you make a little passing joke, you don't hear a handful of people chuckle quietly, and when you make a good point you don't hear the “mmhmm”s, which makes being a part of these events especially difficult.

This can hurt your confidence in these events and even without knowing it you can start to withdraw from the conversation or leave yourself on mute for longer, which perpetuates the cycle.

It's completely understandable, but there are ways to manage this and try and push through.

Your job as a host is to limit how often this happens and to push through the awkward moments that might occur.

For the hosts out there, the solution is to just keep swimming

It's like stand-up and you think everyone's having a great time, but you've got earplugs in and can't tell for sure.

The key to everything hosting is confidence and moving forward. You can make your quiet audience jokes if you breeze through them, and you can confidently announce that you know it was funny, but just know that you're setting the tone and people will follow you.

If you're running the event with a team, or even a co-worker, then you can ask that they always remain un-muted and therefore the whole group can hear their reactions. I also like to make liberal use of telling everyone to un-mute themselves in certain sections and while it's absolute chaos in some groups, for many, the noise generated really helps give the event a feel of being something more real.

You can also allow for chat functionality and a lot of people will be more comfortable giving their feedback in writing. Read out the feedback as it comes in, chat with the people writing as if you're having a conversation, but carry both sides of it. If the person you're chatting to is comfortable, they may un-mute and engage, which will further the group's volume and the overall engagement of the event. Every little bit helps.

Feedback. Is. Important.

Every single one of my events, virtual and in-person have opportunities for feedback, and it has shaped everything I've done.

It's important to understand what a group thought of an event so you can grow your own skills, but it's also important for the impression of the event itself. Having everyone give their feedback makes participants feel heard, and that can improve their overall impression of the event.

This will mean that future events can include elements that might have been contributed but it also means that participants at the first event will feel more inclined to get involved because they were heard the first time.

Listen to feedback (but ignore some of it)

One note I will make though is that especially in bigger events, you are going to get all sorts of feedback and suggestions. While I think you should read and digest all of it, I don't think you should adjust your events based on every piece of feedback you receive.

Some of it will be fantastic, maybe telling you that one section was too long or short, or that something didn't work well with their members, but you will also inevitably receive suggestions about things you can add to the event, or ideas they've had, and they won't always be conducive to good online events.

So take in everything, digest, and pick your battles one at a time!

They can be fun!

Honestly, they can. You can actually run events that people don't talk about mockingly if you put the time and effort into them that they require.

If you had a budget for a physical event normally, then make use of it for the virtual event, don't think that because it's virtual everyone can fend for themselves, because that message is especially evident when you're sitting alone on your laptop in kitchen.

How to have Josh host an event

I'd love to host an event for you, how about some trivia or some games?

You can email me at [email protected].

Josh Pugh

Josh Pugh

Josh is a business founding, digital marketing focused, charity driving, community builder from South Australia, living in New York City. After moving in 2017, Josh realized that there was an opportunity to curate and help the community of expats who moved to the United States – and launched America Josh. Josh is also the President of Variety – the Children's Charity of New York, Secretary at The Mateship Foundation, and Founder & CEO at Fortnight Digital.View Author posts

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