Class questions

There are some good built-in questions that you can ask in D&D to flesh out your character and your story based on the class you've chosen, but the game doesn't actually ask these questions, so they can be easy to ignore. Here are some good questions for any D&D character, starting with "What are you hiding?" Each class will also have two more specific questions as well.

Barbarian

• What are you hiding?
• What do you rage against?
• What confuses you about these people and their customs?

Bard

• What are you hiding?
• What do you play?
• Why do you play it?
  

Cleric

• What are you hiding?
• Why were you chosen?
• What do you miss about the church?
  

Druid

• What are you hiding?
• How did you first wild shape?
• What do you hate or fear most about civilization?
  

Fighter

• What are you hiding?
• Where did you fight before?
• Who do you admire?
  

Monk

• What are you hiding?
• How were you trained?
• Why did you leave the monastery?
  

Paladin

• What are you hiding?
• What do you stand against?
• How do you pray?
  

Ranger

• What are you hiding?
• Who is your favorite animal?
• Why do you hunt for yourself?
  

Rogue

• What are you hiding?
• What was your greatest heist?
• How have you lost it?
  

Sorcerer

• What are you hiding?
• How has your bloodline affected your family?
• How did your bloodline awaken?
  

Warlock

• What are you hiding?
• Why did you take the deal?
• How do you feel about your patron?

Wizard

• What are you hiding?
• Who taught you magic?
• What do your spells look like?
  

Artificer 

• What are you hiding?
• What was the first magic item you saw?
• How do you get materials?
  

Notes

The incredible Cavegirl over on Cavegirl's Game Stuff is working on an incredible game called Dungeon Bitches. That's where I got this idea from, and I highly recommend checking out her blog (if you somehow follow this one but not that one). This was fun to make because it's kind of easy to come up with questions but each one creates so much empty space that people could fill out with their characters. I have a lot of trouble writing characters, so I really like seeing stuff like this (again, thanks Cavegirl) because it helps guide things a lot more. No art this time, but I hope you enjoy the stuff that I've made anyways.

Guilds for adventurers

Cartographers guild

Principally concerned with mapping and exploration of distant lands for colony and plunder, their presence in more well-known areas turn attention more towards the discovery of lost and hidden places, the types adventurers tend to find. With time their pursuits have branched into knowledge and information of other kinds, and a good cartographers guild library can look like a jungle of strange papers and inscrutable writings. Technically the leader of the guild is the ever-absent Choriam Bangra, currently believed to be searching an underground jungle for an entrance to the Eternal Path. The true power is held by a supposedly temporary council, the eight Chief Scribes.

Olaf the Meat Tenderiser by Ricardo Robles

Butchers guild

One of the most powerful food guilds in the land. Any butcher worth their salt will have guild certification, and for many taverns the certification is a mark of prestige. In the adventuring world however, the butchers guild is mainly known for their meat markets, willing to buy all manner of huge dead beasts (as long as they can be proven edible), and even employing a good number of alchemists. The guild is headed by the Kythel twins, who are known for taking joy in cutting apart large monsters.

Salvagers guild

Once a lower-grade offshoot of the builders guild, this group has found renewed purpose in stripping the oldest, abandoned places of anything potentially valuable. The leader is elected semi-democratically, with votes given to guild members based on their performance. Currently the guild is headed by Saliiz Mernir, known for keeping such a myriad of personal items that their office is almost akin to a junk heap. Their diligent style of precise leadership sharply contrasts with that of the previous head, Erham Loen, who was more of a hands-off, minimalist type.

Early Mourning by Patryk Olas

Burial guild

There are countless places deep in the earth where the dead are left in old stone halls and caves, lost to their gods. This small but spirited group has dedicated themselves to gathering the abandoned dead and giving them their proper rites. They are generally hostile toward practitioners of necromancy, with certain exceptions. There are necromancers in the guild, known as the Stewards, who use their art exclusively to gently guide the dead toward a proper resting place. Many of the guild's funerary rites include sanctification of various kinds to prevent future necromancy, and they usually give rites based on the culture of the one who died, if they can find it out. Word of the burial guild's Grave Tower has spread far and wide, a rising catacomb where the honored dead are interred and the occasional meetings of the guild leadership are held.

Sitting hijabit fashionista by Rabia El Mouden

Mercers guild

Once focused on solely women's fashion, their stakes have broadened to include not just fashion but all manner of far off cultures. It is said by some that a spider controls the guild, though they vehemently deny such claims and believe the rumor was started by their rivals in the weavers guild. Officially they have no overarching leader, only localized chapter heads in different areas. 

Mages guild

Less a meeting of the minds and more a club of magically well-wishers, mostly low-ranking nobles and bored merchants seeking to fill empty days with some mild intrigue. They might have a bit of money for purchasing a fanciful trinket, but their prices can most likely be matched or bettered by a wealthier patron or more practical-minded organization. Their etiquette rules are extensive and stringent.

The Storyteller by Lucas Sorrenti

Storytellers guild

Collectors of tales and folklore, finding their nearest outpost can often reveal the legends of almost every village for miles around.

Blank space and mechanical fluff

Perhaps my favorite part of any character sheet is the 'appearance' section, especially if it has an area for drawing a character portrait.

People should be allowed and encouraged to engage in creative pursuits, irrespective of technical skill, and it helps them to explore the character. Likewise, when I'm having trouble fleshing out a character, it can really help to have some guidance or framework to start with. To this end, part of the character creation process in my game generates connections to the larger setting, along with open-ended questions inviting further worldbuilding on the player's end.

one million by Lois van Baarle

It's important to have this kind of blank space, and sometimes it's necessary to point players toward it. Some games try to make every part of character development mechanical, and I generally find that to be a very clumsy, unhelpful approach (generally mind you, there are exceptions) much like trying to mechanically simulate every physical element of a fight or adventure. Oftentimes it's best to just leave the relatively unimportant details up to the players, they can reason a situation intuitively or come up with interesting details for themselves.

Part of this is how magic users in Skies Below must keep an arcane focus to use their magic in combat. This can be any item they possess, such as a wand, tome, or lute, or even such items as a hat, flaming sword, or key. The arcane focus doesn't do much mechanically, besides adding some tension if it gets lost or stolen, its main purpose is to make the player think about their magic, what it looks like and what it says about their character. A character who casts magic through a musical instrument might think of their character as sort of a bard, or one with a blanket may think of that as a shelter the character has held onto their whole life.

Tavern Hijinks by Lap Pun Cheung

Now I'm extending this philosophy to some of the martial classes. In order to enter rage, a berserker must perform a brief, ritualistic action such as eating a certain food or calling out a warcry. Similarly, to use their cooperative abilities, the infantry must use a team name that the party has agreed on. These mostly won't impact actual gameplay, but will push players to add a bit of character building to their PCs, and the infantry's team name encourages them to talk to the other characters and really work together creatively.

Berserker rage ritual

1. Shout out "For mount and stone!"
2. Call out "Blood of the bloodmaker!"
3. Declare "By the skulls power!"
4. A quick, violent dance.
5. Don a fierce mask.
6. Remove a placid mask.
7. Swallow a flame.
8. Bite into shield.
9. Devour raw meat.
10. Drink personalized draught.
11. Anoint in sacred perfume.
12. Anoint in ash.
13. Anoint in honey.
14. Cut a rune into chest.
15. Shatter a clay disc.
16. Rip a sacred cloth.
17. Crush a soul cricket.
18. Crack knuckles.
19. Tear off shirt.
20. Clasp hands in a moment of meditation.

Holographic battle by Diana Tsareva