How To Host Engaging Online Events, Conferences, And Meetups

how to host online events

Online events offer a way to get what we just can’t have right now: in-person happy hours, team meetings, retreats, conferences, and even coffee dates. 

Luckily, we have the technology to recreate these experiences online, but as anyone who stopped through a never-ending online meeting knows there’s more to it than firing up a digital conference room,

It is possible to engineer meaningful and valuable events online but you have to have a plan and a strategy.

Whether you’re looking to recreate an in-person conference experience in a digital environment or get creative with ways to bring people together for the first time, this article will guide you through creating the purpose, structure, schedule, content, schedule, communication, and technology setup that will work best for your event. 

You’ll also learn about the role you play in an event, how to keep from overwhelming your audience with too much information, and why there’s no such thing as too much communication around your event.

Before we get into plan and strategy, though…

Learning how to host online events is really about learning a new tool for leadership. 

What we’re all realizing as we make big adjustments to our lives and our communities is that we are in a unique position of leadership—especially those of us who are willing to step up and do things differently than we’ve done before.

So with that in mind, let’s get into it. First, your online event needs a clear purpose.

State the purpose of your online event

Stating a clear purpose for an online event does several things. 

First, it helps create a sense of grounding at the beginning of an event. 

Second, it helps us state clearly why we are there and why it’s important to the people who are gathered. 

Third, it helps create structure and meaning. That structure is what we can come back to throughout the event so that people feel that it’s cohesive and consistent. 

Having a purpose also helps you see a broader context for the experience that you’re creating. Consider what the experience should look like, what it should feel like, and how it should be structured and then build a format that works for the purpose and experience rather than a one-size-fits-all format.

As you create your online event, ask yourself:

  • Why are we gathering?
  • Why are people taking time out of their day for this event?
  • What are we accomplishing together? 

With online events, it can be very easy to put all of the focus on the facilitator, the host, the speaker, the teacher and organize the purpose around that person.

But, when we do that, we lose out on the collaborative experience of it. So the more you can think about why we’re gathered together and what we’re accomplishing together, the better your experience will be and the better the structure for your experience will be.

Choose the format of your online event

Online events typically fall into two big, broad categories: conversation and content. 

But let’s not think of online events as two separate categories. Let’s think of them on a spectrum––because the most effective online events are actually a combination of both conversation and content. 

Unfortunately, our default choice is either one or the other. 

When events skew hard into content, engagement goes down. People don’t hang around as long. They can’t take it all in at once.

And when events skew hard into conversation, people are often unmoored or unguided because online conversation can be challenging—for introverts, ambiverts, and extroverts alike. 

Type of online event formats

Online events should be dynamic and engaging for all attendees by blending both conversation and content together. It doesn’t always have to be a perfect balance but your format should work for the type of event you want to host. 

Here’s a deeper look at the types of events my company has hosted in the past and how we structure them.

Virtual Conferences

We host a quarterly virtual conference at the What Works Network and, to date, we’ve hosted a total of 11 of them. 

It’s a day-long event—about 6 hours—that’s broken down into multiple interview-style sessions: 

  • Welcome Session
  • Speaker Session
  • Speaker Session
  • Integration Session
  • Speaker Session
  • Speaker Session
  • Closing Session

Our virtual conferences are broadcasted on CrowdCast and skew to the content side of things. 

To balance the content aspect of the virtual conferences, we encourage our attendees to actively participate by asking questions, hanging out in the chat, and responding to questions posed by speakers. 

Mastermind Sessions

Small group masterminds are a key part of our business and service model at What Works: about 60% of our revenue comes from these small mastermind groups. We host these groups over the course of a year. 

During online sessions, we blend a combination of content and conversation with hot seats. One person in the group shares a challenge or question they have and the rest of the group talks with them about it. 

Content is also a part of the mastermind sessions—but the content isn’t from me as the leader. 

It’s sourced from the group where they share what’s working for them—whether they’re discussing a system they use or a marketing campaign that worked really well or how they hired their last team member—and, thus, everyone learns from it.

Virtual Retreats

Virtual retreats skew heavy towards conversation but they are fairly structured and not so open-ended. In general, when we host virtual retreats, we facilitate group conversation as much as possible. 

Part of that is creating structure around breakout sessions which we do through Zoom.

Flash Masterminds

Flash Masterminds are a community-wide event where we invite the whole community to come together in Zoom. We randomly place 3-4 people in a Zoom breakout room and we guide them through hot seats just within that little group. 

This type of event is a great way for members to not only get real-time feedback but also meet new people. Plus, it’s a fun format and allows for us to facilitate more small group interaction without having to handhold people as a facilitator. 

Coworking Sessions

Coworking sessions allow people to see what others are working on in real-time. Members meet together on Zoom, share their screen, and ask for real-time feedback on something they’re working on: it might be a sales page, a website revamp, or a brand guide. Whatever it is, everyone gets a chance to show what they’re working on. 

Clarify your role as the host

Your role as host of an online event will vary depending on the type of format you choose and the culture of the group you’re gathering.

But I believe that every online event host should keep this idea in mind…

A facilitator is someone trained in the skill of shaping group dynamics and collective conversations. My job is to put the right people in a room and help them to collectively think, dream, argue, heal, envision, trust, and connect for a specific larger purpose.

— Priya Parker, The Art of Gathering

There are a couple of things going on in this definition that will help you create more dynamic online events. 

The first is this idea of shaping group dynamics. 

Again, it’s tempting to think that your job as someone who’s hosting an online event is to show up with an hour’s worth of content and tell people as much as you can possibly tell them. 

Sharing content may be a very real part of what you want to do with your online event—but it doesn’t mean it’s the only thing you’re doing. 

A big part of creating an engaging online event is helping people connect to each other–just as they would in person.

Maybe you start your online event a few minutes early and facilitate some virtual “mingling” in the chat room. Maybe you set up some polls ahead of time so you can call out the different experiences or goals of people in the group. Maybe you ask for questions and, after providing your own answer, crowdsource other answers from attendees.

However you choose to engage your audience, you’re setting the tone for how they engage with each other and shape the dynamics of the group.

The other thing that’s key here is putting the right people in the room.

As an online event host, you have varying degrees of control over who ends up in the “room” with you.

One of the easiest ways to influence who is in the room with you is through clarity. Get clear on what you’re doing, why you’re doing it, and who you’re doing it for. When you communicate your purpose, your audience, and the structure of the event clearly, that impacts who shows up.

Provide a clear structure for your virtual event

Structure, structure, structure. 

This is the framework of how your event is put together.

It’s the bits and pieces; the nuts and bolts. It might be a schedule, an outline, the different learning objectives, or the purpose that you have for the day. It’s also the social expectations and cultural cues that you want to communicate so that your attendees feel comfortable participating.

At an in-person event, you hand out agendas at the beginning of the meeting or when you register for the conference. That’s what gives an event its most basic structure.

Online events are also structured by their schedule & agenda.

Where online and in-person events differ in regards to structure, though, is the lack of all other cues and expectations. An in-person event is literally structured by the space that it’s in, the way the tables and chairs are set up, the food that’s served, and the dress of the guests.

Online events are missing this key component of structure––and it can mean that your attendees end up feeling uncomfortable, unless you take on the job of creating additional structure.

Think of structure as keeping your online event grounded and your attendees’ needs met. 

Your attendees have emotional and social needs. They need to know how to talk with each other, how to talk with you, and how to behave in between. They need to feel at ease and prepared for what’s coming.

Your attendees have physical needs. They need time to stretch, use the bathroom, re-up their coffee or water. After a full morning of sessions, attendees might need a solid afternoon break for lunch and time to integrate everything they’ve learned. 

Creating space in your agenda helps everyone feel more at ease and more comfortable. It helps people participate. It helps people know when they can skip out or when they need to stick around. 

Ways you can create a clearer structure for your online event:

  • Create an agenda as a PDF, Evernote note, Notion page, or with another online tool and share it early and refer to it often 
  • Use a slide deck to keep attendees grounded and clear about where you are and what’s coming next
  • Welcome people to the event and remind them what they’re there for
  • Share housekeeping tips on how to have the best online experience, depending on the tool(s) you’re using; when and where to ask questions
  • Provide ample time for breaks and integration
  • Reference the purpose of the event often both visually and verbally

Build out the content for your online event

In the past, most online events skew towards content.

Now, more people are planning conversation-style events to make up for the time we’re not spending together at the office, the pub, or the coworking space.

But it’s likely that even spontaneous, flexible online events between friends and family (or coworkers) could benefit from some “content.” After all, that’s what’s fueling the rise of virtual viewing parties and game nights!

If your event is fun & friendly, a basic agenda with some icebreaker questions, a pre-selected movie, or a game is enough to provide a shared experience and grease the wheels for great conversation.

If your event is educational, focus on a clear learning objective. You should be able to finish this sentence: “By the end of this session, you will be able to…” and you should use this learning objective as you communicate the structure & purpose of the event. 

When I taught on CreativeLive (12 classes, over 150 hours of video content!), I cycled through a different learning objective every 10-20 minutes. Each of those learning objectives was nestled into larger learning objectives. Educational online events thrive on learning objectives!

Beyond clear learning objectives, you also want to aim for interactive content. Ask questions, share responses, and solicit examples from attendees. The more questions you can ask your audience, the better. 

And, if you can, involve participants in creating the content by building their questions or comments into what you’re sharing live. This can be as simple as letting them ask questions. If you have a guest, ask them to suggest topics. That probably seems obvious but it goes a long way in creating a more engaging, useful, and valuable event.

When people are engaged in creating and self-organizing that learning experience the more engaged they’re going to be. 

Schedule your online event

Knowing where your audience is physically located is an important part of scheduling your online event. Once you know where your community is dispersed, you start to find times that are convenient to them. 

For instance, at What Works, we work largely with a global audience which makes scheduling challenging. After hosting hundreds of online events, we’ve found that 2pm or 3pm Eastern/11am or 12pm Pacific has the most potential overlap for our own membership.

Your audience might be relatively local to you. That’s great! Start with a time frame that works best for you now—and you can adjust and tweak it as you continue to offer online events. 

Communicate about your event

Contrary to popular belief, there’s no such thing as overcommunication—especially when it comes to hosting online events. 

Pre-event communication 

Sharing your event and reminding people of its value is critical.

Remember to contextualize everything through the problem that you’re solving, the need that you’re meeting, or the desire that you’re fulfilling for the people you’re gathering. 

  • We have found that there’s a 2-4 week communication build-up for larger events. 
  • If it’s an all-day event or a multi-day event, we send out a save the date even further out than that—up to two months in advance. We want to make sure people can block that time out on their calendar if they want to. 
  • The most essential time frame for communication is 48 hours in advance. Most people are actually more flexible closer to the event and you will get better attendance and better engagement. This works especially well for 60-minute or 90-minute sessions. 

Follow-up communication

Provide some sort of follow up, whether it’s in the form of notes, documents, resources or as an invitation to keep the conversation going.  

If you have an online community, direct attendees back to that platform to extend the life of the event.


  • Where can folks keep the conversation going after the fact? In a private Facebook group? A Mighty Network? 
  • Share a follow-up recap document. If you’re hosting a webinar, share your notes. If you’re doing an online classroom teaching, how can you follow up with students afterward?

Recommended Tools For Hosting Online Events

Let’s focus now on how to actually pull this off and the tools we use. 

We use Crowdcast (affiliate link) for large events (25+ people) and use the chat & question features to get audience members talking to each other. Crowdcast is a great tool for a multi-session event and it’s super easy for people to watch the recordings later.

We use Zoom for smaller events (25 or fewer people) and often use breakout rooms to encourage participation. Breakout rooms have been huge for us. It gives everyone the chance to talk and it gives people who may be intimidated by technology a little bit more space to think through and share with a smaller group of people.

We have a community on a Mighty Network (affiliate link) that gives us a chance to communicate between live sessions. It’s a platform for building a community around a specific topic or goal. Mighty Networks also make a great home base for people to carry on conversations after online events are over.

We often put together an agenda in a Notes app or Notion and screen share that agenda so that people can see where we’re at. For larger, more planned events, we use a slide deck to reinforce structure and instructions

We use Voxer to create more intimate asynchronous communication during virtual retreats. It gives us a nice way of communicating with the benefits similar to a phone call but also with the benefit of being asynchronous. 

I love the book The Art of Gathering (affiliate link)— and, even though it’s geared to in-person events, it would be an incredible resource for thinking through truly incredible virtual events.

Gather virtually

Sure, no online event will even be quite the same as gathering with your colleagues or friends around a table, at the bar, or in a conference room.

But online events can be dynamic and engaging in their own right. They can provide access to information and relationship-building to people who don’t normally get to travel to in-person experiences. And they can help fill a need for connection and human communication that we desperately need to be filled.

So gather virtually–and do it with purpose, structure, and clear communication.

Cover of What Works book by Tara McMullin

Read More

How To Create A Plan To Grow Your Small Business in 2022

How To Create A Plan To Grow Your Small Business in 2022

So you want to grow your small business in 2022? Awesome! But... how exactly do you do that? In the past, I would have tackled this from a purely marketing standpoint. I would have written about developing new relationships, growing your audience, and creating more...

Sometimes You Have To Break What’s Not Broken

Sometimes You Have To Break What’s Not Broken

“If it ain’t broke, don’t fix it.” I’ll be the first to admit that I sometimes “break” things just to have something to do. Everything is going along nicely but, instead of accepting the good for what it is, I pick a fight or cause a problem or just generally create...

Why Clarifying The Vision For Your Business Matters Today

Why Clarifying The Vision For Your Business Matters Today

I'm a Trekkie. I grew up immersed in Star Trek: The Next Generation. I devoured Deep Space Nine and Voyager. And while I'm not as up-to-date with the more recent incarnations, Star Trek is still an important part of my identity. Quick aside: I suspected Sean--my...

What Works offers in-depth, well-researched content that strips away the hype of the 21st-century economy. Whether you love the podcast, the articles, or the Instagram content, we’d love your support