The Oblique Dungeon Master

Because I couldn’t go five minutes without a dose of irony I couldn’t think of another word for “lateral” so I ended up just opening a thesaurus and grabbing the one I wanted. In an article ostensibly about the value of lateral thinking that is probably as good a start as any. If you want to know what was going through my head while writing this just click here.

Why lateral thinking? I was reading a thread on Reddit the other day where a player was experiencing some friction with their DM over their use of Shield Master and a relatively high AC in the early game. I know the challenge as I currently have a Shield Master War Cleric in my game and sometimes the high AC can be a bit of an annoyance when they’re not usually fighting things worse than orcs, goblins or other fodder. The discussion surrounding it contained the usual helpful refrain of “Quit” or “Your DM is bad” and variations thereof. The extreme suggestions aside they’re all pretty fair assessments of what is going on but it prompted me to think about the importance of creative solutions to combat especially from the side of the DM.

The instinct on how to rectify a problem like this almost always tends to be linear in so much as if you’re trying to break down a brick wall then simply hit it harder, right? Sure and much like the brick wall in the metaphor you’ll succeed in completely destroying it, much like the player who is presenting you with a challenge. They can be eaten by a dragon, have their brain melon-balled by a Mind Flayer or dissolved by a Gelatinous Cube but then what are you left with? A mess, both literally and figuratively.

In these situations its sometimes hard to remember that the players are working with a limited toolbox, especially in the early levels, so sometimes solutions that seem eerily similar to button mashing will present themselves. A DMs job is to, much like a river, find ways to flow around these simple tactics and find new ways to challenge them if for no other reason than to keep the game interesting for themselves. Its also helpful to remember that combat encounters are not the only encounters available in D&D and a character who excels in them may do so because they struggle elsewhere, for example in social encounters. Players and their characters will tend to not shine in every situation so stifling them in their moment can discourage them from playing or actively participating at all.

Another common move for some more inexperienced DMs maybe to try and excise the rule, skill or interaction that allows the situation to occur at all, like being able to use your bonus action to shove a creature prone before attacking so you can do it with advantage. In spite of RAW/RAI the DM may decide that their interpretation is that you can only shove after the attack which if done in the moment can lead to the ruling feeling petty or punitive. House-rules are nothing new to D&D but they shouldn’t just crop up whenever you run into something you aren’t willing to deal with properly. Contrary to what some may believe the DMs discretionary power is not without reasonable boundaries, at least it isn’t if you want the game to continue.

The only real solution lies in finding new and creative ways around these hurdles instead of just through, fortunately for us we have the whole of D&Ds collective history to draw from for inspiration.

Lets see if we can come up with a few good options –

The first way I can see to mix up the combat is to start introducing either new enemies or to adjust the ones you are currently throwing at them. Since they are level 3 and running Lost Mine of the Phandelver their enemies should look something like –


Red Brands (Bandits)



For simplicity sake we’re just going to throw out the wolves because short of straight stat buffs or upgrading them, a few at least, to dire wolves the fixes are fairly linear. The solution may be as simple as beefing up their stats to make them more of a challenge but you should always consider re-evaluating your tactics as a DM. We can sometimes get a bit bland in our usage of enemies by just having them move in and swing, bite or claw. It’s important to make sure the flaw isn’t in your tactics before deciding how to proceed. Assuming the wolves are just being outclassed lets look at the others in your stable.

Goblins are nimble and fairly versatile creatures in addition to being quite at home in something resembling a horde. Your party may carve through them face to face but there is no reason for that when they have ranged options. Even at a base Wis of 8 there is no rule that says they have to charge in so they can be conveniently ground into the dirt. Many creatures have traits that go completely unused during combat, for a variety of reasons, but a bit of forethought and prep can make them quite the adversary in spite of their obvious weaknesses.

Nimble Escape: The goblin can take the Disengage or Hide action as a Bonus Action on each of its turns.

A +6 to their stealth and a shortbow at their disposal with a +4 to hit can be a dangerous or even lethal combination with the advantage they gain from hiding successfully. Even if the heavily armored and hard to hit front-line fighters don’t lose their view of their ranged attackers, others might. Enough hits on other party members might encourage those front-line tank types to make desperate or ill-advised moves  making them vulnerable to flanking or traps in an effort end the threat.

Goblin Bosses while much more robust than the smaller rank and file they still come equipped with Nimble Escape, a much improved AC at 17 and, a shield they can use to further increase their survivability.

Redirect Attack: When a creature the goblin can see targets it with an attack, the goblin chooses another goblin within 5ft of it. The two goblins swap places, and the chosen goblin becomes the target of the attack.

This additional feature gives you even more reason to surround them with plenty of fodder that can be used to make the Goblin Boss elusive and tough to kill, giving your archers more time to wear down the tank.

You can also further mix-up your goblins by adding in a Worg for one of them to ride. The Worg’s bite attack comes with the added tangle of knocking the target prone if it doesn’t succeed on a DC13 strength check to stay upright. If one of your players is constantly knocking your creatures prone then don’t be afraid to return the favor. The Worgs are not all upside for the Goblins either as they are not entirely domesticated mounts and they will turn on their riders if they feel they are being mistreated. The players may not have to kill the best to remove it from the fight. In addition to the mount if you like to keep your world consistent and need to justify the Goblins using more intelligent tactics look up your basic Hobgoblin, no better way to whip that disorganized tribe into a pack of organized warriors.

Bugbears are somewhat simpler as these generally fall into the berserker/barbarian categories with what they lack in finesse they make up for in sheer brutality, with one notable twist.

Surprise Attack: If the bugbear surprises a creature and hits it with an attack during the first round of combat, the target takes an extra 7 (2d6) damage from the attack.

Clearly this necessitates a particular sort of encounter setup where the bugbears have the chance to surprise the party or at the very least close the distance as quickly as possible. Even better if they’re working in pairs for the potential to flank to earn advantage on that opening round.

Brute: A melee weapon deals one extra die of its damage when the bugbear hits with it (included in the attack).

In addition to making their normal hits even more deadly this also has the potential to really ratchet up the damage potential of the opening round making your encounter design essential. Since the bugbears are so straight forward in their use and tactics there isn’t a lot you can do outside of buffing their stats to make them heartier but it emphasizes how important the setup for an encounter can be. If you don’t give them the opportunity to ambush your party or at least get in close early then you may as well have swapped them out for any creature of equivalent stats as they will be about as effective. Playing into the advantages of their racial traits will make them stand out in your players minds, the next time they see evidence of bugbears they’ll know to watch for ambushes or choke points. Your players will effectively learn along with their characters about how your world and its denizens operate, a win for immersion if ever I heard one.

Alright, lastly lets take a look at the Red Brands or otherwise known as your fairly generic human bandits. I’m going to go a little differently here and forgo talking about the specific bandit stat blocks or how they are geared and instead talk about customization. A lot of the various races in D&D make it difficult to give them additional abilities without breaking a bit of the immersion or at least without a lot of explanation to not make the whole table start questioning things. Its not that they don’t trust in you as the DM to have some sort of explanation but generally when moving along a narrative you want to minimize the things that make your audience stop and go, “Wait, what?”. Humans are unique generally because you reskin them to be basically anything you want or need them to be. If your bandits aren’t giving your players much trouble then perhaps they managed to recruit a wizard or sorcerer into their service, perhaps a rogue or ranger of some kind. Little if any explanation will be needed to justify a human that wears any of these professions whereas its a little harder to convince people that the goblin really is a druid, like, for real. It can take a bit of finagling to get the difficulty just right but you can start on p342 of the Monster Manual under the Non-player Character stat-blocks to get a rough starting point. Its a lot easier to tweak existing stat blocks like those into something resembling the challenge you want them to be rather than building one from the ground up.

While they can certainly be seen as the most generic of generic bad guys in games like these which give you creatures such as Beholders and Gibbering Mouthers to play with their blandness also allows them ultimate flexibility. That flexibility provides you with an incredibly versatile enemy type which can be adjusted to serve literally any purpose you can imagine with almost no need for detailed explanations as to why. Whats more is anything your PCs can do so can a human NPC in theory, of course you want to be careful designing them to be too close to the players but within reason is fine.

I know it’s easy to read a post like the one at the beginning of this article and dismiss that DM as little more than a lost cause because he can’t adapt but even with two years experience under your belt there are still things to learn. If you’ve been around the hobby for any length of time you’ve probably heard ten or twenty year veterans who will tell you they’ve never stopped learning. Its important for DMs to know themselves and their tendencies before taking the reigns of a campaign but you’ll also learn as you go which makes flexibility key.

Your ability to think laterally, creatively about how to answer the challenges presented by your players will dictate by and large the enjoyment of everyone so give it the consideration it deserves.

Happy Dungeon Mastering!

  • Non-Washable



6 thoughts on “The Oblique Dungeon Master

  1. This was such a great read with some very useful reminders–I’m about to run a goblin’s lair adventure and this post was timely. Thanks for sharing your insight!

    1. Its my pleasure and I’m ecstatic you got something out of it, thank you for reading! Good luck and I’d love to read about the goblin lair session once you’ve run it!

  2. This is something I definitely try to keep in mind as a novice DM, trying to think abstractly in encounters so it isn’t just a straight forward hack and slash. Unless the encounter itself calls for it of course, zombies aren’t known for their battle strategy.

    1. Yes! Saves are something I forget about too often. You fall into the habit of trying to beat a PC at their own game. They have weaknesses, use them. Make them find creative solutions to you. Road runs both ways!

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