I was reading through a published adventure a few days ago, and noticed something odd about the way it got started. As written, the player characters are meant to wander into the game world individually, and then meet one another as they travel. The module tells the Dungeon Master to prompt each player to describe and introduce their character to one another, each in turn, as they meet along the road toward the place where the adventure happens. You're meant to do this as part of the game.
I've heard this technique used in some actual play podcasts, and I've played in a one or two convention games that used it. As a Dungeon Master, I don't use this technique, and I find that I don't much care for it as a player either. I have my reasons, not the least of which is that there's a much better way to introduce players and player characters.
A D&D adventure is a story that gets made up as it happens. It's instant storytelling, and nobody knows what's going to happen next. There's a kind of awkward danger to trying to predict even the immediate future. We've all seen it happen: you announce triumphantly the heroic stunt you're about to perform, and then you roll a 1. Your roll negates your pronouncement, and you learn fast not to describe your actions until they've actually happened. D&D, like all the best storytelling, is a game about showing your audience what happens rather than trying to tell them.
Character introductions don't tend to be subject to dice rolls (more on that later, though), but the same storytelling principle still applies. There's no storytelling value in having a player suddenly sum up their entire character backstory in a surprise conversation with a stranger whom they've only just met on the road. It's unnatural, but even worse it has no dramatic impact.
Before the game begins, ask each player to select a single key moment from their backstory that demonstrates who or what their character is all about. If a player hasn't thought about a backstory yet, refer to their Bond, Ideal, or Flaw on their character sheet.
Now construct an introductory "flashback" scene in which the party members are together, in media res, up against impossible odds. Conveniently, each PC is up against something representative of their backstory. It could be literal, or it could only be something that echoes something that happened in their past. The important thing is that each PC gets to overcome a challenge based on their backstory, and you'll close the scene with the party collectively realising the value of one another's unique skills.
For instance, say you start a new game. First, you gift each player with an Inspiration Point. Then you open with the player characters cornered in an alleyway, each of them bloody and weak. Wait, what are they doing here? has the game started? have we missed something? No, this is a flashback, something that's happened in the recent past. Do you know each other, or are you all here together by chance, corralled into the same corner by the city's bounty hunter's guild? Let the players talk figure that out amongst themselves for a few moments, then start the action.
Suppose you have a player who's rolled up a tiefling. Her assailant is demanding a spell scroll back from her. She says "I had no choice but to steal it. I overheard Amnen talking late last night. He's planning to use it for evil, and I've seen too much black magic back in Baldur's Gate to be complicit to it here in Waterdeep."
The thug sneers, "Amnen took you in off the street, love. He trusted you. You're disappointing him. More importantly, is he an enemy you can afford to have right now, what with your 'father' out looking to drag you back to Baator?"
He moves toward her, his weapon raised anew. The player thinks fast.
A hellish rebuke sends the thug flying down the alleyway. It's not over yet, though, because there are three other people who've been backed into this alleyway by the group of hired thugs, and it looks like the tiefling could be of some help.
Each player character gets their turn at a conveniently expository encounter, and gets to roleplay their escape. They each have an Inspiration Point already, so on a bad role they can spend it to role again. As Dungeon Master, you can fudge the scenario to ensure success. This scene isn't actually mechanical, it's exposition, so in the unlikely event that a player rolls poorly even with Inspiration, you just make sure they roll again after taking a hit. The player's attack or stunt eventually lands, and it finishes their encounter.
Once all baddies have been dealt with, the player characters are out of breath, desperate for healing, and alone with each other in the Blackcloak Alley of Waterdeep. They turn to each other in the simultaneous realisation that they actually make a pretty good team.
By opening a game with game play, you get a few things for free:
There are in-game benefits, too.
Or you could just have a bunch of characters meet on the road, each telling their entire life story to the stranger they've just met, while the other players lounge around wondering whether it's rude to get up for a pretzel refill while the first character monologues about their character's past 20 years of "off-screen" life.
Obviously I think my way is better, and you don't lose any roleplay opportunities. Players who want to spend game time chatting with another player about their backstory can still do that. And players who would rather roll a Charisma check to convey that their character emotionaly bonds with the others have the option to do that instead of trying to overcome their social anxiety and conjure up real life conversation. A better story is told, and the game feels like a game of D&D. Everybody wins.