Hell, I’ve been running D&D since before it was published. I’m not “old school,” I’m PRESCHOOL!
Yes, Virginia, there are really very substantial differences between Original Dungeons & Dragons (OD&D) and later editions. There are also differences in the way I run D&D, no matter what the edition.
First – YOU MUST BE SELF MOTIVATING. In October of 1972, Rob Kuntz introduced me to what would become OD&D by saying “Gary’s got this neat new game called Greyhawk. You’re a bunch of guys exploring an old abandoned wizard’s castle full of monsters and treasure and stuff.”
That’s it. No quests to rescue the princess, no magical doohickey to throw into the Zazu Pitts of Fordor, no mysterious strangers meeting you in an inn. We were in a game to explore, and we did. We explored a lot of the dungeon. Then we wondered “What’s over on the other side of those hills,” and we started doing outdoor adventures.
Our characters were entirely self-directing. Yours will need to be as well.
Second – YOU ARE A TEAM. The game is not all about how wonderful your character is. You are part of a team and fulfill your role in that team. These roles, in this world and in these rules, are derived from the traditional composition of medieval armies; heavy troops hold the line, light troops flank, and missile troops fire from a safe vantage because if they get meleed they’re dead. The magic users have heavy firepower and can easily dispose of a threat much faster than the fighters can; but if the fighters don’t protect the magic users, the magic users are going to be useless. Similarly, the magic users represent too valuable a resource to allow to go to waste for the fighters.
It’s not all about you, singular; it’s about you, plural.
Third – GET YOUR SHIT TOGETHER! This game is run in a very simulation-heavy way. For instance, if the players get into an argument and start shouting, it means that the player characters are standing deep in some monster-filled dungeon screaming at the top of their lungs, drawing wandering monsters by the dozen. Have a leader. FOLLOW that leader. If you’re the leader, LEAD. Make decisions. When the players discuss things, do so quietly in short, high content sentences. The game is a game of exploration to find treasure; to explore, you have to MOVE.
We have only a few hours to play; make the most of it.
Fourth – COMBAT IS DANGEROUS. You’ll have to fight, but like any army, make the conditions as favorable as you can. If your attitude to combat is “We’re the player characters! CHARGE!” you’d better bring plenty of paper, because you’ll be rolling up a lot of new characters. In real life, flanking wins battles, it’s not just a “nice little sweetie.” OD&D doesn’t have explicit flanking rules, so I made my own. I’m not going to go into great detail, but I am going to say that, just like real life, flanking wins battles. And flanking does not have to be the modern lame-ass “two figures opposite each other” bullshit. If you hit an enemy in the flank, it’s flanked. And hitting them in the back is far more powerful than flanking.
Of course, the same applies to you. Do be careful, won’t you?
Likewise, close order is your friend. Three humans fill up a ten foot corridor. Fewer than that, and the monsters can get past you to the soft, chewy, unarmored magic users behind you. Also, spears can strike from the second rank. Isn’t that lovely?
Fifth – THIS IS MY WORLD. I am the absolute unquestioned demiurge of this imaginary world. It works exactly and precisely the way I say it does, and nobody else has any say in this at all. This is important because my vision of my world forms the basis for all rulings I make. And there will be far, far more rulings than rules in this game. I can be reasoned with on the basis of logic, historical precedent, or common sense, but “appeal to the rules” will get you nowhere.
Sixth – DESCRIPTION, NOT DICE ROLLS. You don’t roll “observation” to look around, you tell me what you’re doing and how. This subject is covered very well in Matt Finch’s “Quick Primer for Old School Gaming.” You should definitely read this, and you can find it for free at https://froggodgames.com/frogs/product/a-quick-primer-for-old-school-gaming-pdf/
Read it. You’ll be glad you did.
Seventh — REACTION AND MORALE. Not every creature you encounter is necessarily hostile, and not every fight has to be to the death. Negotiation can be a lifesaver, and so can intimidation. Back “in the day” most of us were Neutral and learned the alignment languages of Law and Chaos, just to maximize our chances of getting out of a tight squeeze with minimum bloodshed. Remember, wandering monsters have no treasure and treasure is where the XP is, so don’t fight wandering monsters if you can possibly avoid it!
EIGHTH — WHO FIGHTS AND RUNS AWAY. Don’t be afraid to withdraw from an unfavorable situation. Spiking the door behind you can buy you the time you need to escape. Also, don’t be afraid to say “We’re torn up, let’s go back to town to heal and come back.”