As a DM, what changes do I need to make to my preparation when transitioning to online play?

Question

I, like many others, have been forced by the current situation to re-evaluate how my games are played. I current run/play in pathfinder 1e and D&D 5e campaigns that have been played entirely in person with pen/paper character sheets and hand-drawn battlemats.

We are investigating the move to online play instead. Likely using a combination of Roll20 and Discord but this question is intended to be digital platform agnostic unless it has significant bearing on the answer.

Specifically I am looking for advice on what parts of my DM preparations need to be modified, extended, added or removed in comparison to in-person play.

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Typical preparations for me look like:

• World Building / Adventure Planning: Large scale worldbuilding in Onenote. Places, people, adventure hooks and lore. Often I am months or even years ahead of my campaign in this area.
• Session Planning: On a session level I usually go on fairly light on detailed planning. Some stats or details for NPCs and creatures they might encounter in this region. Occasional write-ups of set pieces for specific situations.
• Encounter Building: I typically build my encounters on the fly. Free handing my battlemat based on the current environment and then choosing appropriate stats for the monsters and NPC.

I have found this style of lots of world prep, little specific session prep, allows me to run a very sandboxed world where I can be ready for pretty much anything my party can throw at me with minimal fuss. However I'm not sure how well it will adapt to online play.

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Some things that I am concerned about:

• Creating encounters on the fly may be more difficult with digital tools. Do I need to pre-make more encounters and maps to keep the game flowing?
• Decreased immersion due to lack of visuals. Should I prepare visuals for NPCs or environments to help maintain immersion?
• Other limitations I haven't even thought of that may arise during the session and be difficult to adapt to without disrupting gameplay.

Answer 1

this question is intended to be digital platform agnostic unless it has significant bearing on the answer.

Unfortunately, It does. In almost every way. Because each tool you choose will be chosen to replace one or more of the functions you otherwise have in real life. And we all role-play just a little differently than each other.

Theatre of the Mind

How 'Theatre of the Mind' are your games? Do you play with no miniatures or maps at all? Do you pull out the minis just when things get thick? Do you map and mini even the tavern scenes no matter how non-combat role-play heavy they may be?

If you don't need minis on maps... you honestly don't need a VTT (Virtual Table Top). You'd be fine with Discord, you can send "hand-outs" to the group, including maps. You will almost definitely want to use a voice chat channel (but not necessarily, you could type everything).

If your players are experienced, you can even describe the combat and handle the minis yourself, and only once-in-awhile fire a picture of the battle situation to them.

In those above cases... your prep time almost doesn't change. As with all options... YOU need to explore the tools and understand them, but once you're comfortable it should feel basically the same come game time. As the game will play out virtually the same, your prep time will also be virtually the same. Perhaps a few minutes for you to 'digitize' your otherwise physical materials.

Minis and Grids

If you use minis and grids... you're going to want a VTT. You can do it other ways, but you will be fighting an uphill battle.

As far as how this effects your prep-time for games; Once you're familiar with whatever tool you're using, it goes rather quickly. If you want a number... maybe 10% more time importing assets and setting permissions for what player's get to see, what they get to see later on, and what they'll never get to see. These tools have been designed by gamers and they know what we need and don't need in our way.

Your instincts are correct, though. It's your preference for winging-it on the encounters that could be an issue. Your players will either need something to do while you set up something from scratch, or YOU need to pre-spend that time by having a few environments and maybe a few stacks of baddies ready to go. If you do that, you'll be putting in literally minutes extra on prep... but you will save each and every one of your players the same number of minutes waiting.

But, these VTTs usually do several things your in-person table doesn't do. Like handling line-of-sight, vision angles and distance accounting for lighting, walls and elevation. These additional perks are NOT mandatory. If you don't use them, you don't add any time to your prep. If you want to use them (and they're pretty cool) it will cost you prep-time. Again, it's hard to say how much because you need to play with them and decide how much you want of each of those things. But I'll say, some basic perks can cost you an hour before a game. In depth fog-of-war, actual walls baked into your maps, invisible traps waiting to be flagged as visible (and painful)... you could spend several hours building a dungeon for your players.

The fact is, though, some time is going to be 'lost' while you familiarize yourself with the platform. That's unavoidable. And some time will be spent telling your players how to use their ends of the tools. And your patience will likely be tested when you have to tell them for the 18th time what they need to do to roll a Dex Save with Advantage. But these things will pass, and it will become comfortable for everyone, and it will just be the new table you play your RPGs around.

BONUS

I know, you didn't ask, but someone will. What tools should I use? There's arguments for all of them... I'm not gonna get into that.

Start with Discord for your voice and text chat.

If you need a VTT: (can also replace Discord for chats, if you'd like)

• Roll20 is the gorilla (requires subscriptions if you really get into it at all)
• FoundryVTT is the best (does everything, friendly single-person indie developer)

If you need character and material management:

• DnDBeyond (official source of digital material, excellent character management)
• Beyond20 (chromium/firefox extension bridges DnDBeyond characters into VTT, amazing)

If you're using Discord, you'll likely want a dice roller:

• Using the Beyond20 plugin above... already can send rolls from DnDBeyond to Discord.
• Sidekick Is the dice roller you'll want to add to Discord, otherwise.

Answer 2

I've run a lot of D&D online with various tools and various editions of the game. Much of the game is similar to offline, but the lack of physicality may require certain adaptions. You may face the following challenges:

1. Adapting to digital tools. It's going to take a certain amount of time before you can master the digital tools. Roll20 in particular is popular and works reliably, but has a certain learning curve on the DM's side as you need to learn the editing system. I suggest starting as soon as possible to learn the system. Encourage players to get up to speed with the tools as soon as possible.
2. Preparing "miniatures" for your digital gametable. Roll20 and various other tools provide a good miniature simulation, which you can use as a good digital replacement for real maps and miniatures. However, regardless of your map software, you need to find or create your "minis" in advance. This isn't too difficult, but you don't really want to pause a game session to open Photoshop and create a new mini. Digital minis are also referred to as "tokens" or "pogs", and you can find some at short notice at IMarvinTPA's monster database. In my opinion you ideally want the circular sort, rather than any kind of top-down view representation of a physical mini, as these are hard to identify and you may waste time adjusting facing which is normally irrelevant in D&D 5e and Pathfinder 1e. You might also use a program called TokenTool to create minis. Be sure to keep your minis well-organized so that you can find them when you need one.
3. Draw digital maps in advance. In my experience, drawing with a physical pen or pencil can be fast and straightforward, whereas digital tables require you to use the various drawing tools (line, rectangle, etc), and this may be cumbersome in a hurry if you aren't very familiar with them. Where possible, you should create the maps in advance. With many tools you can uncover the parts as the players explore. Again, this is a function of the tool you will need to adapt to. Depending on the tool and how easy you find it to use, you may be able to draw maps on the fly as normal.
4. Recruit more players when starting new online campaigns. In my experience, in-person D&D games have a stronger sense of responsibility to attend than online ones. My online players often dropped out, skipped sessions, or played video games in between their combat turns. As such, when starting a new game with online people, I usually recruit more players (say, 6) on the assumption that at least one will quit early in the campaign. If you're just converting an existing regular in-person game to online play, your existing complement of players may be fine.
5. Have a policy for missing players. Players may be missing from a session due to technical issues or (depending on how dedicated your players are) a reduced sense of commitment. You should have a rule for what happens in this situation. Does someone play their character? Do they "fade out" and come back when the player returns? Do they get XP for missed encounters or sessions?
6. Have a solution for character sheets, etc. In-person, you can pass a character sheet to the DM to check, pass a book to another player, and so on. You will need some alternative, such as digital character sheets (or just have the player photograph their sheet), and making sure players have ready access to sites with the game rules such as the D&D 5e basic rules, Pathfinder SRD or the official PDF sales sites.
7. Set up a Discord. Discord servers are free to set up, and you can use these for voice calls, which work well and work across desktop and mobile platforms. It's also convenient for private messaging between the DM and players, although this is more useful for something like Paranoia RPG than D&D.
8. Consider the impact of non-miniature play. The D&D 5e and Pathfinder 1e rules make miniatures optional, and I've played many campaigns this way. The primary reason you might have to do this is if not all players own a PC or something that can run the minis system. However, if your tool works for everyone (Roll20 has an advantage here because it's web-based), your players may like to keep using miniatures and maps if that's worked for them so far.

A lot of what you do in-person will still be relevant. You can still invent monster stats on the fly, adjudicate combat encounters as normal, draw maps on the fly (many use fancy graphical map sheets but this isn't necessary), and describe things as you would normally.