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I end up DMing for a lot of people who have never seen an icosahedron prior to meeting me. I often run short games just to introduce them to the hobby and in these games, it is likely that I am the only one who has opened the Player's Handbook.

One thing I've been struggling with in this process is character creation, and trying to figure out what class this stranger would likely enjoy playing. Sometimes, it's as easy as running them down the table of contents, they see "Barbarian" and the guy says "That. I want to play that." Other times, we go through a back-and-forth discussion that goes something like this:

Bob: I wanna be a shaman who controls winds, shoots lightning, and curses people.
Me: That sounds like either a Sorcerer or a Druid.
Bob: What's the difference?
Me: A Druid's magic revolves around nature, while a Sorcerer's is arcane and comes from a particular origin.
Bob: Let's go with Arcane. Sorcerer!

But, in actual play, he kept trying to calm wolves down with his "magic", and touching trees to "sense its feelings", things a Druid could have done. In hindsight, I could have more accurately told him to play a Druid had I focused more on his emphasis on wanting to play a shaman, instead of going into details. But instead, I gave him a choice that he could not meaningfully make because the only information he had is an apparently unimportant distinction between the two classes.

I'm not trying to look for a fix of what I can do if a player chooses the wrong class (I was more or less able to manage it, at the time), I want to be able to suggest better classes more accurately right off the bat.

I know I can't be 100% accurate because people actually don't really know what they want, and asking someone is a shot in the dark, most of the time, but:

How can I improve my ability to help completely new players pick the right class the first time?

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Despite the good points made by other answers, I (as a DM) find that this problem happens due to lack of knowledge from new players. They don't bother reading the PHB (understandably) and thus cannot make informed decisions. I avoid trying to help them make their calls and instead use popular class flowcharts I've found throughout the years.

I've linked my favorite one below. My new players have a lot of fun reading this and also understand the point of the class they are playing based on the suggestions of the flow chart.

We essentially guide the players towards a class they like; and we guide their expectation towards how we want that class to behave.

Obviously, results are not perfect, but players realize during the game that they have made the wrong choice (as opposed to us misinforming them), and that the next time they play they want to try another character, hoping they can play it the way the really intend to (as opposed to complaining about their choice).

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Reference movies

In my experience, most people who are interested in RPGs at all are into fantasy or scifi. So I reference famous characters and scenes from movies, series, or books.

Unfortunately the two most famous fantasy sources are not much of a help.
In Lord of the Rings almost everyone is a Fighter in DnD terms, Gandalf pulls a sword more often than he casts a spell, and even those pale compared to a simple Fireball.
The same is true for Game of Thrones. Arya might be a Rogue, and Melisandre is also quite far from a stereotipical DnD Wizard (Warlock? Sorcerer?)

Guided questions

Of course I cannot name any famous movie with a Druid in it, so if he wants something like this, I start from generic questions (Weapon or Magic; Heavy armor or Swashbuckling type), narrowing it down step-by-step until we arrive to things only one or two classes can do. Speak with Animals, Animate Dead, Fight with bare hands, etc.
If he wants an undead horde, while in plate, that is a Cleric. (It could be an Oathbreaker Paladin, or Eldritch Knight, but those are complicated, and get Animate Dead to late anyway)

Mini-adventure

After I think we arrived at a conclusion, I tell him a short story, without any dice or numbers. It places the character in a situation typical for that class, to see if our concepts match.
"Your are travelling alone through a dark forest. You hear some growling from behind you, and when you look around, you see four hungry wolves ready to attack you. What do you do?. If he pulls his weapon, a Fighter might fit better, if he wants to incinerate them, pick a Sorcerer or Wizard, if he wants to hide, Rogue might be good.
If the would be Cleric prefers his weapon, I suggest a Paladin instead.

You will still fail sometimes

This is ok, many people do not even know what they want, so you cannot help them reaching it. If he seems unsatisfied after a few sessions, let him create a new character, or completely redesign the existing one.
Just make it clear that this time it is final.

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    \$\begingroup\$ Also multiclassing could be a thing in the case of OP \$\endgroup\$ – Yotus May 13 '17 at 13:57
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    \$\begingroup\$ I do not think it is a good idea. It is even more confusing for a beginner, and if you do not build your character from the beginning with multiclassing in mind, you have a good chance of getting an even more disappointing result. For example, the Sorcerer in the question is unlikely to have a high enough Wisdom for multiclassing, and even if he has, the Charisma is wasted on a Druid. \$\endgroup\$ – András May 14 '17 at 5:41
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Something that helped me and my players (all new to role playing) a lot is the Pathfinder Strategy Guide. Even though this question is about 5e I think it might be similar enough: The Strategy Guide has a very nice questionnaire at the beginning which asks things like

"At the beginning of a fight I...

  • A) draw my weapon and jump right in
  • B) encourage my allies and tell them who to attack
  • C) move from opponent to opponent and deal several blows before hiding again and avoiding their attacks
  • D) cast mighty spells to destroy my opponents
  • E) sigh loudly and wonder how my friends manage to get us into trouble all the time"

There are 13 such questions about how your character stays alive in a fight, wins a fight, what kind of allies they prefer, what kind of magic they prefer (defensive, explosive, supporting, illusionary, etc), how to get into the bad guys castle without a fight, the source of the characters power, the preferred weapon, the way an animal companion supports the character and many more.

The result is a character concepts (not a class) and the whole thing feels like those popular online psychology tests. The character concepts are things like "berserk", "assassin", "thief", "nature's force", "animal lover", "angels child", "healer", "archer" etc.

Each of the concepts has a short description what they do and an example role playing excerpt showing a situation in which the character shines.

The Strategy Guide then explains how to build each of these character concepts with the Pathfinder base classes, but I think it should be easy, based on the answers to the question and the concept description to translate that to 5e classes and recommend a class to players and help them build it to achieve their concept.

As I don't play 5e I don't know whether something like this exists for 5e, if so, please leave a comment.

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Honestly, you sound to be doing really good already. I'd focus on allowing new players to pick a class, but don't hold too tightly to that decision, encourage them to switch after a little bit if it seems like it would suit them better.

Also, what I'm about to say works for some play styles and not others, but I feel like the fixed set of classes is really constricting (which is good when you're doing tactical stuff, but bad when you have cool ideas and they don't work); he has an idea of what sort of character he'd like to play, I would just roll with that even if it means throwing out the spell list and deciding on the fly what's possible and what's not. That's horrible if people get power-game-y but awesome if people mostly want to play and don't get sucked into abusing their abilities.

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Provide guidelines on how D&D is different from video games

Most people new to D&D have played video games and may think choosing a class in D&D is the same as choosing a class in a video game, which is not as helpful when it comes to actual roleplaying and getting into character. I like to focus on these three things:

  1. Explain to the person that roleplaying is not about what the player would do, but what the player's character would do. Explain that they should consider from the character's life experience / backstory what their character would likely do and what information the character has and doesn't have (minor point, the character's backstory shouldn't conflict with their statistics, such as being a "strongman champion" if their strength is 9).

  2. Alignment system - explaining the alignments of good/evil, lawful/chaos, and neutrality can help someone get into the roleplaying mindset, and is generally not gone into depth in video games.

  3. List a few caveats that a new player may not consider:

    • A first time RPer they may want to try something a bit more straightforward, especially if in a game with experienced players whom they could learn from.
    • This is their first character, and part of the enjoyment is your character's limitations.
    • Growing into coolness - many newer players want to be cool immediately and can be impatient with waiting for cool/fun abilities.
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