How to Run a Boss Fight

Yeah! I like to throw boss or mid-boss encounters at my players when appropriate, and I've had both good and bad experiences. It seems hard to know why something goes good or bad, though. I'd like to see a video about you preparing to run a couple of different types of boss battles.

"What's more important, my corpse or innocent lives? Leave now, and you may be able to catch up with my lieutenant before the screaming starts."

Heroes always want to save the village, but if your a few sessions deep in a dungeon I find they're more worried about saving their own bacon and stolen loot and wondering when the next long rest is going to be. A ticking clock helps; perhaps with each round you spend in combat, the villains construct that his crown controls get's closer to village, and you know this because there are a pair of mirrors that reflect what the golem is seeing.

There should also be choices in the combat that the bad guy can make that the players can't. Maybe you're focusing firepower on the boss when he suddenly clenches his fist and one of his minions that was harrowing you screams and dies, his essence transferred to the big bad as a chunk of extra hit points; do you continue to attack him, or try to eliminate his resources?

Finally, the bad guy wants to live. It's fun to imagine the big bad sits lounging in his chair while sending minion after minion to dispatch you. Fun, but that never made since to me. He could continue ignore the players, all while muttering about how they don't make skeletons like they used to, or part way through he could send his skeleton lieutenant (or 'Skele-tenant" if you will) to the nearest town to burn it to the ground. Extra bonus points if said lieutenant is NOT going to turn to smoke if his boss dies, which may convince the party to split up at the last section making both encounters more difficult.