In nearly every campaign there comes a time when the characters have done enough, seen enough, and nearly died enough to earn the XP required to level up. Many games have a leveling system, others let you spend XP on improvements. Either way, there needs to be a decision made on when a player can level up their character. This article is not about the in game justifications. Deciding on how a character represents growth in game and where those extra spells really came from is a whole other can of worms. Rather, I am going to discuss the player end of it and real-world timing. Today books are much easier to come by than when I grew up playing it. Amazon and other sites provide discounted options compared to in store purchases. PDFs are readily available for much cheaper as well. Throw in things like hero builder and your players don't even need the books available to them to make characters and level. All this adds up to the problems of having any control over character generation.
For some DMs this may not be a problem. In fact, certain games or campaigns may benefit from having players come in with ready made characters that the DM knows little about. Be careful though. Letting players make characters on their own and without discussion requires a trust among the group and maybe some rules (like no evil characters). You have to be ready to both trust the players to know how their mechanics work and be able to adjudicate mechanics you may not know are coming into play. Ways around these problems include having players send you copies of their character ahead of time, sitting down with the player to make the character, or making them all together as a group.
Each game, campaign, and group benefit from these different methods and I have personally used all of them, but be careful making this decision because it will inform the players how they are to be allowed to level up. When the time comes the initial assumption will be that leveling up will follow the method of character creation. As a DM it is important to decide (or guide the group decision on) what will work best for the party, and there are a few things to consider.
The first is to consider, of course, how the characters were made. If players came in with characters they made on their own, why were they allowed to? Consider the reasons you allowed it. Was it time friendly or did you want them to be true strangers in the beginning? Perhaps you wanted a one-on-one chat as each made their character. Are those reasons applicable to the characters now that they know each other and have experienced the way they work?
Allowing players to level between sessions in their free time is a great solution to many problems, and with resources so readily available, they will probably look into that new level and have everything decided regardless. There can be some problems with this though. New spells can be found by the dozens in books, supplements, articles, blogs, and more. Perhaps you don't want to allow some or they don't make sense for the setting. Making sure you and your players talk is very important. Nothing would be more disappointing to a character than not being allowed to utilize his improved build. And if allowed it can be quite a pain on the DM to justify and squeeze in such things.
Another concern is whether or not the players will get to leveling up. Are they lazy? Busy? If they don't come prepared, do you make everyone else wait so they can catch up or do you give him his extra HP and make him suffer for his own inability? There is no right or wrong answer, and it all depends on the situation. Someone who squeezes in D&D between two jobs and a family probably doesn't have time to level and it would be a nice gesture to help them at the table. Someone who spends half the day looking up possibilities for the next level, however, probably has no excuse to being unprepared.
The most obvious solution to all of these problems is to have leveling sessions where all or part of the game is devoted to leveling up and discussing possibilities. This imposes some spending of precious time away from the game itself, but comes with a lot of benefits. Aside from the benefit of avoiding self-leveling problems, you can also get the players helping each other and suggesting things. Their characters develop synergy, why not have the players work that out mechanically too? "Oh if you take that and I take this then we could do this!" is something you may not get sending them off on their own. Additionally, as the DM you are right there answering questions, making suggestions, encouraging or discouraging options, and making sure things are done completely and properly. And you know what hoops they may try to make you jump through!
If your time at the table is exceptionally precious, then perhaps meeting in the middle is the best idea. Let the players level up on their own, but spend a little time having them share decisions with you and each other. Anyone who had trouble or responsibility now has a chance to get some of the leveling done, and prepared players can be a helpful asset to making that happen. This also gives a specific time to address any questions they may have had and for you to ask questions about their choices. Being informed about how things will work, intent of players, and ruling of the DM is important and will save time when these things rear their heads in game.
Aside from all the time and personality and DM style that these type of problems and concerns come from, you should also make sure to consider the mechanics of the game. Are all the players set enough with the math to do it on their own? Are things simple choices or complex mechanic affecting ones? How often does leveling come into play and are there certain levels that benefit from time spent talking things over than others? Also consider whether a house rule may change someone's choice and try to warn players and spearhead any problems caused from lack of information.
In the end it comes down to three things: time, trust, and group personality. Not necessarily in that order. First is group personality, some people like keeping new things surprises and others want to work together leveling up. The next is time. When it comes right down to it, what benefits the group and the game most with this costly resource? Finally is trust. Hopefully everyone trusts their group, but trust comes in many forms. You may have a chronic misinterpreter of the rules who really needs to discuss the mechanics of his choices. Just remember that for each level you use a method it will become more and more difficult to change. Habits will become formed, so try to fix problems before they become habitual. And communicate, communicate, communicate; it solves so many problems.
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