I have run a lot of sessions for (half) a table full of newbies, so people who had never played D&D or any RPG. I used to agonize over it. I was and remain invested in making sure they would have a great time and not do something that might turn them off RPG / make it a one time thing. Things below is what I found out/do which really helps me and them out.
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Keep It Simple. Almost all the other good practices can be boiled down to this. OSR excels at offering simpler, less rule dense systems. If it helps to get them interested, just call it an easier to learn, faster, more exciting and less constraining version of D&D called “XYZ”. Emphasize that anyone can learn this game within a short period of time. Especially if there are also more experienced people playing, explain that in your game (not) knowing the rules makes little difference since you are playing collaboratively and that will let them know how to play as you go.
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When creating characters, don’t overwhelm them with options, if your system has quite a few options, don’t use every option on the character record sheet/use a simplified character record sheet for the first game, you can always add more options, stats and rules at the beginning of the the second session. Doing it this way avoids confusion and worry on the newbies part (“am I building my PC right?” “Not sure what that will mean in practice,…”) and it also ensures you will spend 30 to 60 mins on character creation tops! Elsewise it is a bit of a waste of a 3 or 4 hour session. Creating characters can be fun, but playing the actual game is also important. I make sure to emphasize that if they feel at the end of the session they really mucked up some stat or score for their PC build because they didn’t understand the rules or implications, I will usually let them change or switch things around a bit at the start of the next session.
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Use few rules on the first sesh. While actually playing, having to refer to the rulebook a lot or even a bit, to explain minor details is not great nor is using a lot of jargon, or spending a long time explaining rules or terms that will rarely be needed by the players and are not strictly necessary this first session.
Really focus over rulings over rules if that is faster and more fun in the moment and use the D20 (or whatever base mechanic your game runs on) a lot, introduce a few rules that give them options, are important and used every session, and keep the rest for the next session. Spend another 5 mins after filling in the sheet explaining the most used rules and concepts, the different type of dice if people are not familiar with them yet and just go! I am fortunate that there are short, clear Youtube videos that explain the rules I do(n’t) use rather well, so for “extra credit” type players I send those before the session, timestamped so they skip the pre-amble.
- Before the session, draw them into your world but don’t give them the impression that being in a D&D group involves a toooon of (hard) reading and homework.
In our DnD Telegram group I post a flavour and set-up text of 10 to 20 lines maximum in which I explain where they are, how/if the know each other, the vibe of the city or world, their characters situation (very low on money, how little they know that area or the people and possibilities in it) and sprinkle in some nice lore that makes them interested to learn more during the game.
I also ask them to post a 20 lines maximum character background/archetype, explaining that evil stuff or things that give them a great advantage ("my PC is the favourite son of the local richest noble or “my PC a a princess that can command a 100 men”, or “my PC knows every street and alley of this city backwards”) are not really the idea. Humble beginnings full of possibility and archetypes is what I ask them to focus on.
- Try to give them a rich but varied experience. I have found having some collaborative world-building/exploring, getting to know one or two key NPCs that are likely to recur, doing a little bit (very limited since they should be poor) of shopping, 1 instance of combat (I like to have it be a single, stronger enemy so that it is simple and that they have to cooperate in order to succeed) and one very small “dungeon”. In my last game the Dungeon was a small, long abandoned mine, it was literally one cavern/mining area, a shaft down to a forgotten a small room/shrine to Oghma and a tunnel leading out of that shrine (alternative exit). Keeping the first dungeon extremely small in size means you might get through the whole thing, even if players are being careful or conversing a lot about what to do.
Throw a 8+ chambers dungeon with 5 locked doors, varied dangers and traps or puzzles that take a long time to navigate at them and you might have to forget about any other typical activities during a session since your players will be “down there” most of the sesh.
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Keep an eye on the players, if one (newbie) player is deciding and speaking way more and another is quiet and seems shy, it is ok to gently redirect, asking the quiet player what he or she thinks they should do. You will find out fast whether it is preference for them to not contribute as much or they just felt a little overwhelmed and needed encouragement.
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A picture does tell a 1000 words. I print out 10 A4s for my first session. 2 Striking NPCs, the entrance to the first dungeon, the 2 chambers of dungeon itself, 2 atmospheric print outs showing of their starting location/city, a map of the city, a picture of a curious item they might find and a few other things. Whether you use a screen to show them things, you are good at drawing or have some nice terrain, it really fires people’s imagination to not only describe with words but to show them, rather than only!, tell them. Saves time and avoids confusion too.
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Ideally don’t kill your your PCs. This one might be controversial for OSR purists. But killing one or several PCs with no backup character the players build/chose ready to go might halts the game for up to an hour and bring down the mood. Of course if a newbie is about to do something very reckless or even stupid, you ought to ask them if they are reeeeally sure and emphasize what the possible or likely consequences are,. i.e., death, if they still persist, kill away!
Don’t be afraid to make it very challenging, if a few of them or all of the, almost! die, that is often a good thing. I make sure that I explain at the end of the session that one or more of them will almost surely die the next few sessions and that, that is part of the game, luck of the dice roll and how we play. Then I spend the first 15 mins of the second session making a quick, back up character with them. If they die, they will of course lose out on a lot and have to start from scratch with the new character.
- Have and offer fun. Set some expectations. Don’t take it all too serious, humor puts people at ease and is a bonding experience, share snacks and drinks, if people need a break, also to get to know one another OC, just take a small break and chat about non RPG stuff for a bit if that is the mood. After the session it is good to always thank the players, assuming you had a good time, tell them that! And offer encouragement. This all sets a good precedent and makes players more secure that they “were doing it right”.
If you have a problem player, make sure you kindly but very clearly adjust right now by sending a private message, nip it in the bud. Or, if you really think it is just truly not going to work/a fundamental difference, this is the time to tell them that. If you are sure, prolonging the situation only makes it harder.
What do you other things do you do to make sure the first sessions goes as smooth as it can and to hook new players into the hobby?