Setting aside the accumulation of knowledge, or research, let's discuss instead how much preparation is necessary for a session, and what sorts of preparation ought we to do? Things we want to think about include the events or conflicts that are likely to arise with the next session; what obstacles, like a dungeon or the aforementioned bandits, are they about to encounter? How "new" is the region that the players are entering? Do we have maps for it? Do we know what's living there, or anything about it's physical dangers? Are we set up to run the combats that might happen, including hit points, number of combatants and an understanding of the spells or advanced powers the enemy has at their disposal?
We need to estimate how much knowledge of the setting, it's encounters and the rules that are going to apply that we need, before actually running the session. We want to avoid giving too much attention to areas that the players might bypass; there's nothing more annoying than spending a week designing a dungeon level the players never enter. On the other hand, if we prepare too little, that's going to mean more reactive running on our part, where the goal here is to be proactive.
Let's be completely honest. We're never going to get this exactly right. Player actions are inherently unpredictable, while successfully judging their interests and habits requires considerable game experience and an upteen number of sessions spent with the same players, to get a real handle on their proclivities. Early attempts at estimation will produce predictable failed results, which we shouldn't take too much to heart. For example, a quick conversation with an NPC that we think is going to run for five minutes ends up running for 30, preventing our getting to the critical part of the dungeon with tonight's session. Or the reverse happens, where a battle we thought would take an hour is wrapped up and done in 15 minutes, through the player's innovations or plain good luck. Suddenly, we have 45 minutes we're not prepared to run, at the end of the session, when we're mentally burned out from running the game.
Another issue is that players will have notions we couldn't possibly have considered — after having carefully arranged a meeting with a merchant, who's going to fill the party in on what they need to know, they unexpectedly attack the merchant instead, seizing his wares and coin. Unfortunately, we have no details about the merchant or his guards, how much coin he has or how to handle the rest of the adventure now that the merchant is dead and the information the party needed with him. Now, we have no idea what the party is going to do, and neither do they... and while we scramble to think about how to transmit this critical information to the party in some other way, they're suddenly realising they forgot just why they'd set up the meeting in the first place. This sounds unlikely, but it's exactly the sort of thing that parties tend to do, much to the frustration of many a dungeon master.
Our best strategy is to have in mind — often no more than a thought with no realised work done — a contingency plan of just what to do if the players do something immortally stupid. Just as a photographer might bring an extra camera to a shoot, when there's no expectation of ever using it, we're always sure to have someone else in mind in the game who ALSO knows what the merchant knows. In the meantime, we might conceive of a "mini-adventure" that can pop up to fill the empty space in a running, that's been created for just such an occasion. An example could be a random ambush by some kind of local wildlife, which may not carry much significance for the players, but it will waste an hour of their time, which is fair considering they've just wasted at least an hour of ours. And while they're fighting this out, or talking about it, we can slip out for a cup of coffee to think of something to do that comes after.
Another example could be to interject some natural event, which the players wouldn't expect: a sudden flooding of a river, explained by suggesting there was a very heavy rainstorm the night before, and now this is happening; or a rockslide randomly occurs, forcing a few characters to make checks to avoid getting pulverised. Even if such things only last five minutes of a running, it can give us time to think... though the downside is that these ideas, while thought out ahead of time, are essentially reactive to the players actions. We didn't plan to do such things and now that we have, our game has been made unbalanced by them.
With time, the stronger answer to these unexpected moments is to, well, expect them. This may seem counterintuitive, but remaining constantly attuned to everything that's happening at the game table, over time, builds a repertoire of patterns that reach beyond our cerebral capacity to recognise them when they're happening. We are, in fact, humans, with human limitations. But, this does not keep us from "noticing" things unconsciously.
For example, we may not see it, but the player on our right always begins playing with his dice just before doing something outlandish. We don't consciously notice this; he most likely doesn't either. Nonetheless, as it happens consistently, the moment he starts playing with his dice, we're subconsciously triggered by it and without realising it, we feel a compulsion to turn on the player and doubly assert the importance of this moment. The player, without anyone noticing, stops playing with his dice... and the game goes on without the disruption that might have occurred... even though no one consciously tried to prevent it.
This sounds crazy; but it is, in fact, something that those in police and fire services are taught to expect, as well as those in the military. There are courses that teach these persons working in these dangerous professions now to develop this heightened sensitivity, called "situational awareness." It's the simple, instinctive feeling that something is "off"... and with additional time spent as a dungeon master, handling random, highly emotionalised game play, we too can take advantage of it.
But it takes time... and until some years pass, we have to do our best to shape the game's details, within reason, trusting that we will get better at it. Much of the resistance to this kind of preparation comes, first, from the fact that it isn't as interesting as actually running the game. Planning excitement can be, for some, very frustrating and even boring. But the more difficult hurdle to overcome is the feeling that it's just not worth doing... especially if it's boring. For a long time, it doesn't seem to do any good, and it's easy for us to be convinced that we're just wasting our time.
Many DMs embrace this belief and never adjust themselves to anything except running on the fly. They then pollute dialogues and discussions about being a dungeon master with arguments from their untrained and uncommitted point of view, urging others to be just as lazy and just as ignorant as they are, as though this is the best strategy. Once again, we've discussed at various points that yes, the game can be played with this mindset; D&D allows that. But this "advice" isn't; it's simply excuse making, along the lines of saying, "I didn't work at it, and if you do, it makes me look bad." Well, that can't be helped. It's easy to make some DMs look bad when they are bad.
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