Also keep in mind that if you are running combat with a bunch of the same of certain types of creatures, you can speed things up by skipping the damage dice rolls most of the time. Just use the standard damage printed in the book/module and add or subtract 1. Just roll damage from critical hits or for the boss monster. With players' permission, apply the same rule for their summons. Standard average damage works most of the time.
Just to specify, by rulers I mean that we have a pre-cut “30 ft” spell effect that we use for measuring. What does slow things down with that is when their are characters flying and I have some players that will pull out the pythagorean theorem to measure…some very good ideas though that I will implement. Thanks.
I am just going to leave this shameless plug here:
1: Group your monsters so that they share initiative. Taking a turn where 3 werewolves move forward and then attack, one after the other, is much quicker than taking one such turn, then something else, then back to the second wolf, then 2 more other turns, then the third... in many cases where flanking etc doesn't matter, you can just move all three and then attack with all 3.
2: Use the "On Deck" system, so that the next player knows it's their turn coming up and can plan ahead.
3: Engage other players during each turn. Rather than focussing on the person whose turn it is, describe what you can through the eyes of others. "Bert will attack with his sword, that's a Nat 20 for...18 damage". "Ok; Ernie, you look across and see Bert charging like a streak of striped platemail as he slashes the werewolf across the chest, a perfect strike which should fell the beast. But, Bert, from up close you see the wound is dry, and starts to close even as your swing finishes. What do you do?".
Involving others keeps them engaged when they aren't participating, and helps to keep the dreaded mobile phones at bay.
4: Play fast-and-loose where things aren't so important. For example, if you have the hags summon spiders and then think "oh no, I don't know their stats", don't stop to look them up - throw in some lowball numbers to make them a threat but not overpowered. Really, you need to pick speed, AC, attack modifier, damage, and hitpoints, and that's the main details. If they throw a save at you then you can eyeball that as well, or then say "one moment while I look up their modifier". Keeping the action from stopping for trivial things, like throwaway minions and whether they are +2 or +3 to damage, can make things that bit faster. Many a battle has been fought against monsters who had no statblock at all, and just did what felt right at the time.
5: round some damage, again where it doesn't matter. minions dropping to 1-3hp are dead, especially when it was a good roll to get them there. You can suspend this if it comes in clutch - look at the Battle for Helms Deep in the LOTR movies. Every orc hit by Legolas dies, right up to the point where the orc has a job to do - and then those last hp let it jump on the bombs and breach the wall. Knowing when to be a stickler and when not will help with pacing.
My advice is similar to a few others, but with a focus on streamlining.
DM Turn Efficiency
The DM's turn in a combat with many monsters can be the biggest bottleneck. Here's how I handle it:
Group Enemies & Use D&D Beyond: Organize your enemies into logical groups. For example, "all archers on the left" or "the zombie horde." I roll their attacks and damage in D&D Beyond for each group. When it's their turn, it's a simple, two-button process: click the group attack, click the damage. This method is incredibly fast. I've run battles with thousands of foot soldiers, handled in four blocks of 1,000 each with a few boss mobs. The DM's turn was less than five minutes total after all player saves and damage were resolved.
Simplify Ranged Combat & Movement: Your players pulling out the Pythagorean theorem for movement is a sign that things are getting too bogged down. I find it's insane to be that picky with measuring. For terrain and movement, I use a simple "eyeball" rule. If a character says they're flying, I just ask, "Are you more than 30 feet away from the ground and other monsters?" This avoids the need for complex vertical measurements. If players can fly, then monsters can use ranged attacks or spells. It's a simple, and more importantly, fast adaptation. The game is a fantasy adventure, not a combat simulator.
Player and DM Mindset
The biggest issue seems to be a disconnect between the players' perception of "their turn" and the DM's workload.
Communicate: The best way to address this is to have an open conversation with your group outside of a session. Explain that you want to speed up combat and need their help. You can tell them that you are taking steps to do so on your end and ask them to do the same. This can include them preparing their turns in advance and having their stats ready. I am a huge fan of pre rolling.
Encourage Preparedness: It sounds like your Warlock is a great example of a player who has their turn planned. This is what you want to encourage in your other players. You can even try a "soft" turn timer—something like, "Okay, Bob, you're up John your next, Sally your after that. Remember, you've got about a minute to declare your action so we can keep things moving."
By simplifying the logistics and communicating with your players, you can get everyone back to enjoying the game and not just waiting for their turn.
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Also keep in mind that if you are running combat with a bunch of the same of certain types of creatures, you can speed things up by skipping the damage dice rolls most of the time. Just use the standard damage printed in the book/module and add or subtract 1. Just roll damage from critical hits or for the boss monster. With players' permission, apply the same rule for their summons. Standard average damage works most of the time.
I am just going to leave this shameless plug here:
Aerial Combat Distances made Simple
Regarding speeding up combat, I would recommend:
1: Group your monsters so that they share initiative. Taking a turn where 3 werewolves move forward and then attack, one after the other, is much quicker than taking one such turn, then something else, then back to the second wolf, then 2 more other turns, then the third... in many cases where flanking etc doesn't matter, you can just move all three and then attack with all 3.
2: Use the "On Deck" system, so that the next player knows it's their turn coming up and can plan ahead.
3: Engage other players during each turn. Rather than focussing on the person whose turn it is, describe what you can through the eyes of others. "Bert will attack with his sword, that's a Nat 20 for...18 damage". "Ok; Ernie, you look across and see Bert charging like a streak of striped platemail as he slashes the werewolf across the chest, a perfect strike which should fell the beast. But, Bert, from up close you see the wound is dry, and starts to close even as your swing finishes. What do you do?".
Involving others keeps them engaged when they aren't participating, and helps to keep the dreaded mobile phones at bay.
4: Play fast-and-loose where things aren't so important. For example, if you have the hags summon spiders and then think "oh no, I don't know their stats", don't stop to look them up - throw in some lowball numbers to make them a threat but not overpowered. Really, you need to pick speed, AC, attack modifier, damage, and hitpoints, and that's the main details. If they throw a save at you then you can eyeball that as well, or then say "one moment while I look up their modifier". Keeping the action from stopping for trivial things, like throwaway minions and whether they are +2 or +3 to damage, can make things that bit faster. Many a battle has been fought against monsters who had no statblock at all, and just did what felt right at the time.
5: round some damage, again where it doesn't matter. minions dropping to 1-3hp are dead, especially when it was a good roll to get them there. You can suspend this if it comes in clutch - look at the Battle for Helms Deep in the LOTR movies. Every orc hit by Legolas dies, right up to the point where the orc has a job to do - and then those last hp let it jump on the bombs and breach the wall. Knowing when to be a stickler and when not will help with pacing.
Hope this helps!
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My advice is similar to a few others, but with a focus on streamlining.
DM Turn Efficiency
The DM's turn in a combat with many monsters can be the biggest bottleneck. Here's how I handle it:
Group Enemies & Use D&D Beyond: Organize your enemies into logical groups. For example, "all archers on the left" or "the zombie horde." I roll their attacks and damage in D&D Beyond for each group. When it's their turn, it's a simple, two-button process: click the group attack, click the damage. This method is incredibly fast. I've run battles with thousands of foot soldiers, handled in four blocks of 1,000 each with a few boss mobs. The DM's turn was less than five minutes total after all player saves and damage were resolved.
Simplify Ranged Combat & Movement: Your players pulling out the Pythagorean theorem for movement is a sign that things are getting too bogged down. I find it's insane to be that picky with measuring. For terrain and movement, I use a simple "eyeball" rule. If a character says they're flying, I just ask, "Are you more than 30 feet away from the ground and other monsters?" This avoids the need for complex vertical measurements. If players can fly, then monsters can use ranged attacks or spells. It's a simple, and more importantly, fast adaptation. The game is a fantasy adventure, not a combat simulator.
Player and DM Mindset
The biggest issue seems to be a disconnect between the players' perception of "their turn" and the DM's workload.
Communicate: The best way to address this is to have an open conversation with your group outside of a session. Explain that you want to speed up combat and need their help. You can tell them that you are taking steps to do so on your end and ask them to do the same. This can include them preparing their turns in advance and having their stats ready. I am a huge fan of pre rolling.
Encourage Preparedness: It sounds like your Warlock is a great example of a player who has their turn planned. This is what you want to encourage in your other players. You can even try a "soft" turn timer—something like, "Okay, Bob, you're up John your next, Sally your after that. Remember, you've got about a minute to declare your action so we can keep things moving."
By simplifying the logistics and communicating with your players, you can get everyone back to enjoying the game and not just waiting for their turn.