I was on the Critical Success podcast (episode forthcoming) with two infinitely better players and game masters (GMs,) Kat Murphy and James D'Amato and the topic was building better boss encounters. The conversation was good, I hopefully interjected well enough to keep the ball moving and just passed it off to Kat whenever I could.
But the conversation jogged my mind afterwards and there are two ideas that are crawling up the walls of my skull. The main big idea is this: A session is an experience you create for your players. In other words, it's a gift.
There are better and worse gifts, of course. Some show signs of deep care and others are gift cards or "I didn't know what to get you." Craft an session with your players specifically in mind. (And for the record, not everything a GM does is a gift. That way lies self-aggrandizement.)
Discussed, often, is "you want to create challenge for the players" and that is often interpreted as "crank up the Challenge Rating." And to be fair, there's something to that, for the people that sincerely enjoy the math components of tabletop. I do not. I find the game less interesting now that I see the math behind it.
Skill obstacles, again, are another non-combat challenge. Also good, and it rewards people that put points into things or role-players. Role-playing eludes me.
Challenge, applied best in my opinion, is not when it's a direct numbers game, but instead when a GM successfully gets inside the heads of the players and crafts something that pulls them in strange ways. Give them a goal and then multiple avenues to achieve it, or do not cut off an avenue to the goal that you haven't thought of. This is where One Shot (a podcast where improv comedians play tabletop, of which Critical Success is a spinoff) is most instructive: sessions are often rules-lite improvisation. Give the players what they need and riff off them.
This leads to the second idea: Borrow from videogames. If the above paragraph sounds a whole lot like a Deus Ex or a Dishonored level, well, good, that's the idea. Those spaces are poured over to facilitate vastly differently forms of play. The obvious example: Heist. Any GM worth their salt will have a series of dexterity and thievery checks as one avenue. Full frontal assault is also popular. But what about diplomacy and streetwise? Can the party (or one duly appointed member) talk their way into the room and get someone else to turn off the security system? But also: Dwarfs, not normally considered a sneaky race, can be useful here. Why? Dungeoneering.
(And etc etc. Be limited only by your player's imagination and even then, limit very loosely.)
For boss encounters, specifically borrow from Call Of Duty multiplayer. Multiplayer maps and boss encounters, fundamentally are both combat arenas. Treat your boss encounters that way.
This leans on the boss encounter portion of the podcast, but multiplayer shooter levels are designs with a couple things in mind, but three of the main things are verticality, locations that grant advantages and lanes that players are shepherded through. The terrain in a multiplayer shooter level is not neutral. Your boss area shouldn't be, either.
The Call of Duty specific portion here is the shield class. I hate Call Of Duty, because everyone there is better than me and most of them are bigoted or children. But! With the shield class, I can take more hits than an average player, be super annoying and still charge in with my players and contribute to the team's success. Apply that to boss encounters. Even if the player character (PC) can't be as useful to the party as whomever dishes out a lot of damage, create opportunities for the not-so-useful character to contribute.
If you set a fight in a quarry, then take away a barbarian's huge axe, maybe talk the PC into using her athletics skill to climb up to a bunch of rocks and kick a whole bunch down to wipe out a couple minions. Caster stymied by an anti-magic field? Perhaps reinforcements ought to arrive in a form that makes it easy for the caster to hit them. Don't nerf the player without giving them something awesome/dramatic to do instead.
The rest follows, I think.
Mostly for the drum tattoo that opens this song, but also because Save Ends is a band that has a lot of D&D nods, but isn't a D&D band. Plus, they come through town next week. I'll say hello.