Advice From Facilitating 100+ Successful Online Workshops

When COVID hit in 2020 and my work transitioned from in-person to online, I focused on learning how to run great online workshops. I read many articles, watched many videos and even took part in an online workshop (highly recommended). During this time, I presented and attended many online events, talks, panels and workshops, observing what worked well and what didn’t. 

Since the start of COVID, I’ve run at least 100 online workshops (some very structured like Shortcut to Tech Leadership, others more ad hoc or once offs) and want to share some lessons learned. Shout out to Anna Shipman (Technical Director at the FT), who gave me a nudge to write this as we swapped experiences.

How online workshops differ

Over my career as a consultant, retrospective facilitator and trainer, I have run many in-person workshops and meetings, but I believe there are some unique challenges with online workshops. Here are some differences and what you can do about them.

Participants might be unfamiliar with your workshop tools

I run most of my workshops on Zoom. Despite being a popular VC tool, not everyone has used it with many alternatives like BlueJeans, Microsoft Teams, and Google Meet. (I’m sorry if you have to use anything like WebEx or GoTo Meeting 😅). Although each tool offers similar fundamentals, not all tools have the feature set, or the same feature might behave differently. Unfamiliarity with tools makes it more difficult for participants to focus on the content and discussion. Ever been in a meeting with a person trying to update JIRA or a project planning tool and struggling with it? Yeah, it’s painfully similar.

To deal with this:

  • Avoid using features you slightly suspect may be unfamiliar to your audience. For example, you can use Miro in many ways, but I typically ask people to only add (or copy/paste) sticky notes to keep it to the basics. 
  • Plan for extra time at the start to introduce the tools and how you will use them.
  • (Sometimes) Give a pre-workshop exercise to give people time to interact with the tools at their own pace. Anticipate that not everyone will complete the pre-workshop activity.
  • Use a less significant and short activity (e.g. ice breaker) that gives people a chance to practice using the tools.

Digital tools continually evolve

Today’s tools continually evolve. New software releases add new capabilities and sometimes mean existing features behave differently. One example was when Miro changed how one moves the canvas in the browser with the mouse. They shifted from a switch to “move-mode” and drag to a right-click and drag approach. I still struggle with my previous habit of the keyboard/mouse combination.

To deal with this:

  • Keep your client-installed software up to date
  • Encourage participants to do the same
  • Read the release notes and changelogs to explore new or changed features
  • Practice using new features before you choose to use them in a workshop

Digital tools are not perfect

I often keep to simple tools like flip charts, pen and paper, and sticky notes in the real world. There’s not a lot that can go wrong with these tools. Unfortunately, many things can (and do) go wrong with digital tools. Some of these that I have experienced include:

  • Slow or flaky internet connections
  • A computer or application crashing
  • Issues that only a few participants are having

To deal with this:

  • Add a co-facilitator – If you’re the only workshop facilitator and have issues, it’s hard to keep things running. Bring in a co-facilitator whose role is to provide real-time tooling support.
  • Prepare backups and redundancy as the facilitator – For network connections, you can use a phone as a secondary network backup. I usually have a second laptop on standby if I have issues with my computer.
  • Ask people to try the tools in advance – With Shortcut to Tech Leadership, I send workshop information in advance and give people three simple tasks so they can interact with the tools in advance.
  • Understand the quorum for your workshop – For most workshops, one or two people with technical issues in a group of 10+ might be okay. But if those one or two people are key decision-makers or the sponsor, you might consider pausing and rescheduling the workshop. Determine your quorum for your workshop in advance and decide what you will do if it is not met.

Online is more distracting and exhausting

Ever taken part in an online event (conference, webinar, etc.) and found yourself responding to an email, slack message or switching to a different application like Twitter? Yes, me too. The digital world is simply more distracting. With in-person workshops where everyone is in the same room, it’s easy to spot someone having a different conversation, such as noticing whispering, someone picking up their phone or leaving the room. One approach to minimise this in an in-person meeting is to ask people to keep laptops closed for the workshop. Unfortunately, this approach doesn’t work when everyone uses their laptops to join!
Combine the many distractions of a digital world with the distractions from a working-from-home environment, and it’s even harder to keep focus and attention. Parents of young children will know how difficult it can be to separate home from work matters (like this famous BBC interview).

To deal with this:

  • Ask participants to turn on their “do not disturb” mode and close all other applications.
  • Schedule regular breaks (10 mins in every hour is good).
  • Plan a variety of activities that don’t require full-time synchronous attention. For example, avoid running a workshop where the only planned activity is people talking one-by-one. Instead, consider activities where everyone can simultaneously participate, such as a poll, sticky note brainstorm, or breakout room discussions.
  • Leave a generous time for lunch or longer breaks to check email/ messaging apps.
  • If you’re dealing with senior leaders (e.g. Directors, VPs, CxOs), plan additional breaks to allow them to deal with any emergencies.

How to run successful online workshops

We’ve looked at concrete challenges with online workshops and some mitigating actions. Here are some additional tips for effective online workshops.

If one is remote, everyone should be remote

This is a fundamental principle of all good remote working practices. Suppose you’ve ever been the only person dialled into a meeting where everyone else was in person. You know how easy it is to feel left out or more challenging to interrupt as co-located people converse with each other.

If you are facilitating, find out who is going to be remote. If there are some remote participants, ask everyone to dial in to establish equality. If you have some people in the same physical room, explicitly redirect the conversation to remote people. Redirecting the conversation to remote participants encourages those co-located to involve those online.

Allocate even more preparation time

Great facilitators know that the key to any successful meeting is preparation. Don’t YOLO your workshop. It doesn’t work well in real-life, and the stakes are even higher in an online environment. I run through the 5Ps (Purpose, Preparation, Process, Participation and Progress) of any effective meeting as part of my preparation.

I plan additional preparation time for online workshops because there is simply more that can go wrong. My approach to preparing looks like this:

  1. Define the goal – I want a single overall goal for the workshop. I would consider using separate workshops if there are many goals.
  2. Create a schedule – I create a timetable of the workshop in Google Docs to understand the flow, timing and add facilitation notes. I have a section for the intro, breaks and conclusion. I also consider an appropriate activity for each part.
  3. Check the flow against the Diamond of Participatory Decision-Making – This step is more relevant for workshops where you make decisions or gather agreement. Different activities support different phases. For example, brainstorming sticky notes is excellent for the divergent zone, where dot-voting might be more appropriate for the convergent zone.
  4. Prepare the tools – I would prepare flipcharts and print handouts in real-life workshops. In an online workshop, you want to have everything laid out in advance and configured so people can participate immediately.
  5. Do a practice run – For high-stakes workshops, think about doing a trial run with people to make sure things flow.

Plan for more discussion time

If you’ve ever been part of any virtual meeting with multiple people, you would have experienced the challenge of agreeing on the active speaker. Either there is a long silence waiting for someone to jump in, or suddenly two or three people start talking over each other. Even with the best internet connection, this process takes more time than in real-life. Add in a heated topic or an interesting discussion and you’ll need to plan extra time.

To help the conversation flow more smoothly online, consider using a verbal “baton”, an approach I’ve used a lot when moderating online panels. Explicitly pass the “baton” on to the next person by calling them out by name. Remind people to continue the conversation by explicitly passing the “baton” to the next person who might be back to you as the facilitator or another person. Ad hoc “Baton” passing can work well if everyone is comfortable speaking. If you suspect some people are uncomfortable contributing, ask them to indicate their willingness to receive the “baton” visually. A visual indicator might be as simple as a raised hand (or virtual hand). In larger groups, consider asking those speaking, or who want to, to turn on their video. The active speaker can see those who would like to speak and be ready to pass the “baton” to the next person before turning off their video.

Keep the number of tools to a minimum

Each digital tool adds cognitive complexity to an online workshop and presents another point of failure, so keep the number of tools to a minimum. Although it may be tempting to use a different online tool because of its unique feature set, balance this with potential problems for each participant. Don’t assume that participants have large screen real estate (e.g. a laptop screen and external monitor). Each new tool might mean a new window, and it’s easy for participants to “lose” a window. Fewer tools reduce the opportunity for someone to get “lost” during a particular workshop.

As an example, for one of my online workshops, I use Mentimeter for specific interactive polls, Miro for some activities, Zoom for the workshop and break out rooms. I sent information via email and a Notion page as a permanent resource. At some point, I realised I didn’t need to point people to a specific Notion page as I could add the information directly to the Miro board and point people to that specific part. I continuously monitor the feature sets to see if I can reduce them further, but the tools aren’t quite there.

Provide as much contextual help as possible

Workshop activities are where many things might go wrong, particularly in an online environment. Finding people struggling in an in-person workshop is a lot easier as you can often physically see if someone looks puzzled or raises their hand. Providing support online to a single participant without distracting all participants is more challenging. You don’t have the option of a quick 1-1 conversation in a large online meeting.

Anticipate ways people might be confused and prepare for this in advance. When offering instructions, I try to:

  • Give visual cues before the workshop – This means I provide the instructions on a slide, and I talk through each point bit by bit.
  • Leave instructions available – Give people an opportunity to refer to instructions during the activity if they have any problems.
  • Show a concrete example – People respond to visual cues, so I leave an example of the output near the activity.

This screenshot shows an activity I use with instructions and an example of the expected output next to the activity.

Example of an activity that includes instructions and an example expected output

Even with the best contextual help, some people might still struggle. Be explicit about how they should reach out for help. Here are some examples of how I’ve done that in the past:

  • “If you fall out of your Zoom breakout room or have trouble connecting, please reach out to Jesse, my co-Facilitator today,  via DM via Zoom or email, who can help you reconnect.” 
  • “If you are struggling with this activity, please send me a DM via Zoom or leave a large sticky note on the board in a bright colour.”
  • “If you are unsure about your activity in your breakout rooms, please speak up and ask someone in your group. If your group cannot resolve this, please use the Ask for Help function, and I will join your breakout room.”

Check-in more frequently during activities

As you add more interaction to an online workshop, you’ll uncover secondary issues such as people/groups finishing at different times and/or noticing if people are struggling with an activity. In an in-person workshop, I would wander the room, look at the generated outputs, listen to discussions (or lack of), and observe body language if people look engaged or bored. 

In an online environment, I can watch the output generated even easier than in-person, but listening to group discussion or body language is harder without feeling like an intruder. Sometimes it’s helpful to “drop into” a breakout room but let people know you’ll do so in advance to avoid surprises and remain on mute. If I’m dealing with a long activity (e.g. 15+ minutes), I would also try to plan for breaks where everyone can review overall progress to give you more of a chance to synchronise progress across all people/groups. 

For example, in one workshop, each group had 30-mins to prepare a 5-minute presentation based on their discussions and learnings from the day. For this activity, I asked groups to spend the first 15-minutes defining their overall approach, and each group should produce a skeleton outline for their presentation. For the last 15-minutes, each group could refine, add some nice visuals and rehearse. After 15-minutes, groups were expected to share a link that I could review and provide any feedback. If I noticed a group didn’t have anything to share, it provided an excellent point to join and see if they were struggling.

Accommodate different timezones

For online workshops, don’t assume that everyone will be joining based on your timezone. Don’t provide workshop information or emails without a timezone. If you know many people are joining from specific parts of the world, help them out and provide the date/times in their timezones. For example, when I send information for a workshop focused on the East Coast US and Europe, I include dates and times in both timezones. I also provide a link that allows anyone to confirm the meeting time in their local timezone, as people might travel and be in a different timezone. I like the Event Announcer from

Different timezones also imply different daylight savings times. Unfortunately, shifts to and from daylight savings are rarely synchronised, so I never assume the hour differences between timezones are the same. I always use an online tool to confirm the times in different locations on the same date using websites like, and

Use a visual timer

Many workshop facilitators know the challenge of gathering participants after a break or during an activity. You can’t physically chase people in a digital environment, and people may not have an external clock nearby, so use a visual timer for activities and breaks. For activities where I’m using Miro, I use their in-built timer, and for workshop breaks, I switch over to a presentation with a countdown timer to allow people to self-monitor. Here’s an example below.

Screenshot of a countdown timer I used for breaks

Consider using background music

For some breaks and individual activities, consider elevator-style background music. This is useful for cutting through the “dead” silence when everyone is deep in thought or on mute. Let people know it’s okay to mute the music as not everyone appreciates the noise. Choose the music carefully to avoid licence violations (are you allowed to play this to a group and for your activity?) and choose music that won’t distract people. I don’t play any background music during any group discussions as this will add additional noise and make it harder on participants.

I won’t link to any specific sites, but you’ll find plenty of options if you search for “royalty-free music”, or “no copyright music.”

Take advantage of online tools

Online tools offer some advantages that are more difficult or more expensive in the real world, such as: 

  • Automated transcription– Many VC tools now include automatic transcription. While not perfect, an automated subtitle service helps many people (e.g. those without English as a native language and those who are harder of hearing).
  • Emoji responses – Online tools remotes emotions, so find ways to add emotions back. One approach I like is encouraging people to share reactions through emojis or thumbs up.
  • Working alone, but together – A well structured self-driven activity on a shared document/whiteboard gives people a chance to focus on their work and see the output from others simultaneously. Separate generation from discussion or plan discussion after generation to gather more insights.
  • Mute all – At the start of workshops, I ask people to keep themselves on mute to minimise background noise for others. I also warn people that I will mute people if I notice people unmuted and contributing background noise. I emphasise I am not trying to be rude but to ensure everyone can easily keep focus. With large groups, the “mute all” button can be great.
  • Anonymous polls – Asking individuals to contribute is sometimes tricky, even with in-person meetings. Increasing anonymity helps some people to contribute more. Many online tools like or Mentimeter offer activities like asking questions or placing polls anonymously to encourage more participation. Of course, you’ll need to balance this with a moderation process if you anticipate potentially controversial or inappropriate contributions.

Online workshops are not better or worse, but different

I often get asked if I prefer running workshops in-person or online, but I think each has its different advantages and disadvantages. Although in-person workshops feel “warmer” and “more personal” to me, I recognise that online workshops can be even more inclusive (e.g. automated transcription, remote-friendly) in ways that in-person workshops are not by default.

Online workshops can be engaging, powerful and highly successful, but like any successful meeting, they require preparation. A different medium brings different challenges, so prepare for this in a different way. I hope you’ll benefit from my experiences, and be sure to share any tips you have below as a comment.

Want to experience a great online workshop? Join the online workshop, “Shortcut to Tech Leadership“, and level up your technical leadership skills in the process.

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