Dungeon no Naka no Hito

Both are slice-of-life anime that make places that are widely to humans considered inexplicable and fatal into "companies" or otherwise workplaces. 

Both are "cute girls doing cute things" shows that seem simple on the surface, but have a surprising amount of writing in them. 

Both anime have a comedic and humorous tone, featuring absurd situations and eccentric characters. The protagonists of both anime are unique and have interesting personalities. In "Maoujou de Oyasumi," Princess Syalis is a heroine who prefers to sleep and relax, while in "Dungeon no Naka no Hito," the main character is a girl who lives in a dungeon and has a peculiar outlook on life. Both anime are set in fantastical worlds with fantasy and RPG elements such as monsters, magic, and mythical creatures, we see more interactions between the monster characters than with human characters. Both anime use comedy, satire, and parody to break away from the conventional anime genre. read more 

Cute girls with dark humor, saying the most insane unhinged stuff with a cute smile 

The two may not belong to the same genre, but they share a similar essence. Behind both of them, it feels as if workers are operating behind the scenes of an overall bigger complex operation. 

Both anime are about working in an underground dungeon and contain beast characters 

Two adventure comedies set in a fantasy world where humans cohabit with monsters, tho in DnNnH the monsters don't live on the surface like the ones in KHM does. Their art styles are quite similar and have a bit of action in both but the directions in genre face differently despite having the same genres. KHM is very much more gag comedy and DnNnH's comedy isn't as crazy but there are still funny moments. DnNnH has more plot compared to which some may deem more heavy plus the use of blood too, although not entirely melodramatic serious. 

Both feature dungeon construction/operation, though Dungeon People puts more focus on it. 

The relative depth, eccentricity and freedom of thought allowed to both the main character Clay in Dungeon no Naka no Hito and Kino in Kino no Tabi is great. they both share a dead-pan expression that sometimes give way to a warm smile, a smirk or a sad look. Their priorities in life, of being sole survivors, independent and somehow(mostly in secret) compassionate makes both dynamic as leads. They challenge the worlds around them: similar fictional sociopolitical landscapes are mostly ruled by bragadocious men who I and a lot of other non-men will never really be able to connect to. I really like how both main characters move through their worlds, only using actual violence out of absolute neccessity except when there's some moral imperitive to challenge authority. read more 

If you've ever wondered what it's like managing a dungeon behind the scenes, then you'll enjoy both these series.