How do I introduce my co-workers to RPGs via a Virtual Table Top (VTT)?


I am fortunate enough to work at a company that twice a year budgets time and expense so we may have a "team-building" activity. I am on a team of ten people total. There is a stipend to pay for expenses. We’ve gone go-karting one afternoon then out for dinner on the company coin, that kind of thing. Another time we have had lunch at the office followed by an afternoon of table top games like Citadels and there was enthusiasm for that. Currently everyone is working from home in the same timezone, meeting over Slack, Zoom, Microsoft Teams, etc.

Since (a) I am a big fan of tabletop RPGs where the players work together as a team to take down BBEG, and (b) there’s enthusiasm for trying new things, and (c) team building always helps morale, I want to float our next "team building" activity as "I run an afternoon RPG adventure on Roll20.net" as a one-off session; something four hours max.

I have played D&D since 1983. I am quite comfortable as Gamemaster/ DM for six players. I believe I can stretch to nine players for an afternoon. One of my co-workers has also been gaming since the Eighties, knows the concepts very well, and has expressed enthusiasm for the idea. I have not sounded out the rest of my team for their enthusiasm and experience with RPGs; I suspect it is all over the map with at least three novices.

I am looking for specific examples from people who have tried this, such as, "I tried Game Foo and it did not work for reason X," or "I introduced my friends to VTT with Game Bar and the following things worked really well:…"

I’ve used Roll20.net four times with my gaming group. I have the hang of it. I’m not wedded to it, but it seems like it would be a solid fit with some preparation on my part which I’m willing to do. Roll20.net has some good introductory videos.

There’s no negative stigma about Role Playing Games at my employer. I am comfortable enough there that I can float the idea and if my co-workers say "Nope, not at this time," that’d be fine.

I’m flexible as to which game we play. My criteria are:

  1. It’s easy for a novice to pick up the basics
  2. My co-workers work together (no stabbing each other in the back)
  3. My co-workers have fun for the afternoon

My favourite game is Pathfinder 1e; I fear that is WAY too deep for novices, unless I strip it down as suggested here. I don’t want to overwhelm/scare off my co-workers with the PFSRD.

I am familiar with DnD 5e. I don’t have a DnDBeyond account. Since I imagine everyone would need a Roll20.net account to start, I’d rather not require everyone to create two accounts.

I have an idea of how I’d make this work in person: I’d provide nine copies of the Universal Table from TSR’s Marvel Super Heroes, I’d draw a large rough map of the downtown core of our city on the whiteboard, and my co-workers would each pick an Avenger from a set I’ve prepared in advance. Those MSH rules are pretty basic (one table! One!) and I’m sure even those co-workers who have never heard of RPGs have heard of the Marvel movies. Each Avenger would have a token the player could stick to the whiteboard. However, I suspect that super heroes don’t scale into Roll20.net; put another way, my first thought was that it’d be easier on the novice players if they were constrained to the walls of a castle and could not fly.

While I would like to offer my team the choice of game genre, I suspect that with nine people I’d get nine different responses.

I have read this question about introducing kids and this question about introducing novices to Pathfinder 1e in a short session. I believe my question is distinct enough from those two and is not a duplicate.