posttitle = How I run Online Workshops titleClass =short len =26

How I run Online Workshops

(An alternative to “online courses”.)

Context: with a small team, I’ve been running online workshops a couple times a year (30 sessions total) since 2017, called the Goal-Crafting Intensive. It’s been a huge success, with many returning participants and lots of rave reviews and referrals. The GCI is about life-effectiveness (goal-setting, planning, execution, reflection) but the event format could be used for many other topics! I’m sharing this guide because I’d like to see other people make events like this for what they have to teach (and I’d like to attend sessions like this).

Summary/Table of Contents

📅 Long One-off Event

Why? Self-paced courses end up never-paced courses, and cohort courses are easy to fall behind in or feel burdened by. Instead, get some huge progress made in a single 5h session! Participants only have to make it to one date.

When? Pick a weekend and host 2 events at 2 different times if you want to suit a global audience. We usually do North American Saturday night (suits East Asia & Oceania) & Sunday morning (suits Europe & Africa). You can do a few weekends in a row, if enough demand (we usually do multiple weekends around New Years since that’s prime-time for goal-setting, and then we’ve been exploring doing a single weekend at other times of year).

How? For a 5h session, it’s good to encourage folks to take breaks. We do set-up & wrap-up in the first & last half-hour, and the remaining 4h is divided into 8 half-hour blocks which we do as 25min pomodoros with 5min breaks.

During the breaks, I encourage people to stretch their legs & look away from their screens.

We also note that while usually you wouldn’t chat during a pomodoro, the coaching channels are totally great for that purpose.

⚔️ Choose-your-own-Adventure Workbook

Why? Your learners are all starting at different places and may have different goals and different struggles. This is very obvious in the context of a goal-setting workshop like GCI, but it applies to some degree with any course.

How? If you’re thinking of making an online course, presumably you’ve got something to teach. You may even already have your own teachable, YouTube series, or other writing people could apply to their lives. Host that somewhere.

Where? We’ve got a simple password-protected wordpress site. Easy for multiple editors to access & update. The videos are hosted on gdrive & embedded. Could also use a teachable.

What? Have a few default recommended content+exercise combos. Some people like video but others don’t, so offer both where possible. Aim for exercises that can be usefully completed in a halfhour, but with more value if someone spends longer. Have a solid high-level framework & Table of Contents that shows how it all fits together and guides people on how to go about choosing what to look at. (More on how to steer, below)

Key: Choose-your-own-Adventure is different from self-paced in that there’s no single linear path. Some people might spend the whole session on exercise 1, start partway through, or even spend most of the time talking with coaches about a unique situation.

💬 Chat-based Coaching

Why? People get stuck. They may have Qs that need answers; they may just need encouragement. Chat scales & parallelizes unlike video/audio.

For goals workshop, coaching is often psychological, but for eg photoshop workshop, it might be more technical. If you have people who’ve gone through your course in a self-paced way already, they could make great coaches, or maybe call them “mentors”. Even people who are only one step ahead of the other participants can have useful stuff to say.

How? Set up a new slack workspace for each 5h session. Add some of your favorite custom emoji or ones that are relevant to your workshop or your brand. Public channels:

  • #_general
  • #_intros
  • #_links
  • #_techsupport

As each participant joins, make new locked channel:🔒name_coaching & add {them + all coaches}

Why coaching, not open discussion? Partially it’s privacy, particularly in the context of people talking about their lifegoals. But there’s another reason why even if your workshop is on something like programming why you may want to keep most of the discussion to private channels… many people are helpful to a fault 😅

Given this choice:
 • face my own challenges
 • help fellow participants
…guess what they’ll focus on?

Tell those folks “you can coach next session!” Indeed, some of our coaches are past participants (in addition to friends etc). Our coaches are all volunteers, since it’s fun & low-stakes—just show up & say stuff & ask Qs. They also may get blog post ideas, & find ongoing clients (if they’re looking). We have a mix of people who do coaching professionally and folks who are just experienced with

We aim for 1 coach for every 4-7 participants, but it’s pretty flexible. Fewer coaches just requires more focus on workbook. Above ~50 participants it’s hard to coordinate coaches between all 50 channels though! We do have a private 🔒_coaches channel.

Other tips for coaches to coordinate 50 parallel channels:
 ⭐️ star channels you’re active in
 🔕 turn off notifications except @-mentions & get participants to @-mention A LOT
 🎽 tag other coaches in
 🔰 practice: start with ~20 people then scale

(aside: I think with software that was actually optimized for this precise purpose, we could reach like 100 participants without losing track of people, but tbh I’m still not sure that’d actually be better than just having 2 sessions—would love to have that software tho!)

📺 Video Call for Co-Presence

Why? Just having a chat system, especially without open discussions, people wouldn’t get the chance to see each other, and it would be harder to keep people in sync.

How? Zoom or similar. Lately we’ve explored having a few breakout rooms, whether for coaches to do short out-loud coaching sessions in, or for me to run a 7min workout during the long break. Turn on “let participants choose room”.

It’s pretty straightforward. We like to have the coaches introduce themselves on zoom at the start & give a 1-2 sentence intro to their interests/specialties. (We also have coach bios listed on the website and in the #​_intros channel.)

🤔 Optional Advance Content

Why? Since we start selling tickets a month before the sessions, it’s good to give people something right away. Plus some of our exercises benefit from not just being done in one block:

  • Dream List benefits from background rumination & reverie.
  • Time Audit benefits from logging over the course of a week.

How? One way we encourage people to work on the advance content proactively is saying that they can get access to the rest of the course content before the event only if they email us saying they’ve finished the advance content!

Important to have this be optional—can get tons from event regardless. We say:

“It’s not arbitrary homework designed to waste your time. If you feel like this is going to be a waste of time, then change the instructions until it feels worthwhile.”

🎡 Intake Form for Steering

At the same time as the advance content, we also encourage folks to fill out our intake form. It takes <5 minutes and gives us extremely useful context on what to encourage our participants to focus on during the session.

The two key Qs, which you can copy:

• If there is only a single thing you get from this, what do you want that one thing to be?
• If you imagine that you’re at the end of the event and you’re feeling disappointed… what would the reason(s) be?

Then, the magic happens at the start of the event, when we have coaches go through the form responses and paste in participant answers to these questions, so we’re starting the conversation with the person’s priorities top of mind.

Sometimes this we direct them at a particular video or exercise based on their main challenge. Another common “why I’d be disappointed” is “already knew all this”, in which case we encourage these veterans to bring it on & talk directly with us.

The intake form also has a 1-10 scale for each of our 12 submodules, to gauge which ones people already grok. For example, two people might say “I have trouble setting goals”, but one might be blocked on G1 and the other on G2, which is a totally different situation!

  • G1) I have a hard time knowing what I want or envisioning goals for the future that motivate me
  • G2) There are so many things I want that it’s hard to know what to focus on.

So this helps us spot bottlenecks. Also, sometimes someone thinks their block is execution and they just need more techniques to stay on task, but when we go look at their intake form responses, they’ve actually got a lot of conflict or ambiguity about what they’re even trying to achieve and why, which almost always makes it hard to feel motivated. So we encourage them to get clarity there first.

💸 Pay-What-You-Want

Why? Lots of reasons:

  • Interested people can attend even if they’re short on spare cash.
  • It lets people pay what they feel the event was worth to them, meaning no buyer’s remorse (I’ve been there).
  • It incentivizes us to make the event be really impactful, and gives us really tangible feedback on that front.
  • It makes it easier for people to refer their friends since the up-front cost is lower.

How? At a high level, we have two payment options:

  • $275 up front (partially to anchor a market price and partially because some people don’t like the psychology of PWYW and would rather just pay up-front)
  • PWYW with $25 up front (most people pick this one)

The $25 deposit ensures that we don’t get never-willing-to-pay-for-anything people signing up, and also that folks are serious about coming. We get some no-shows but that’s life. We frame the $25 as a deposit but in practice it’s kind of a minimum ticket price. If someone said they really got nothing from the event though, we’d gladly refund it.

Importantly, despite what some people think (I got a question about this recently) it’s not a donation. It’s flexible pricing. At the end of the workshop I speak out loud for a few minutes about why we do PWYW, and encourage people to contribute whatever feels right based on:

  • the value they got from the event
  • their budget
  • their desire to support our work & other people with less money being able to attend

Also: I thank people by name as they contribute. We only recently added that part, and it increased contributions significantly! Social proof & appreciation matter to people.


So! That’s most of it. I still didn’t cover quite everything. There’s also:

  • ticket sales & PWYW payment pages, which for us are custom code on the Complice site
  • ongoing community of practice in a separate slack, for all cohorts together (could also use a Circle or some other community platform for this)
  • onboarding-related stuff about how to get people familiar oriented to slack and the course content
  • feedback & testimonial forms at the end
  • after the end of the event, we socialize for a little bit: unmute our mics on zoom and just kinda chat
  • how we do marketing (mostly blog posts / newsletters, twitter, the Complice app itself, and mailmerge to email past participants)

But this is basically a sufficient playbook for someone to run this kind of workshop based on their own material.

I’d love to see more events like this happen, so if you’re interested in running such a workshop, I’m available for consulting (so is @SarahAMcManus, or maybe other GCI teammates) to help you get things off the ground. If you’re interested in building a software platform for this sort of thing, definitely get in touch too!

And if you want to come to the events we’re running next weekend, there are still some spots! Click here to learn more & sign up. (It would probably be a good first step if considering hosting your own similar event, to get a feel for it. Could even talk with us in your coaching channel about your idea, at the workshop!)

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About Malcolm

Constantly consciously expanding the boundaries of thoughtspace and actionspace. Creator of Complice, a system for improvisationally & creatively staying in touch with what's most important to you, and taking action towards it.



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