D&D 5e: Experience and Character Advancement

I touched on this briefly before, in my first entry on how the rules affect the players in fifth edition, but I think this topic bears a brief follow up. This is especially true as more and more DMs consider how best to hand out experience or advance their players' characters in level.

Skyflourish recently considered a very interesting method for Adventure League or casual play where some players may not be able to make each session. This proposal (adjusted or partial milestoning) smooths out some of the bumps in public play and allows perfect attendance to still be suitably rewarding without unduly punishing players who can't always make it.

Even so, this proposal seems to indicate that in the end a DM needs to ultimately fall on one side or the other: either give out experience points for each monster kill or quest completed, or else dole out experience when PCs hit milestones. Conventional wisdom seems to suggest that if you do any actual combination of both that PCs will be hard for the DM to manage and may result in rewards being, frankly, less individually rewarding.

I'd like to offer an alternative. While I'm still running my friends through our first campaign in the 5e ruleset, I'm confident this solution will be useful to the DM and encourage the players to see individual rewards as beneficial, useful, and special.

Let's say, hypothetically, that players are fourth level. Their current quest involves investigating the disappearance of a missing elven noble from her woodland court, and the next milestone will occur when they discover (through whatever means) that she was abducted by her illegitimate half-brother, the half-elf who has hitherto been patron to the PCs. The standard path to discover the secret will result in an award of enough experience to take the PCs to fifth level. Alternatively, a DM could award the fifth level as a milestone.

• If the PCs follow the path of least resistance, they might discover the half-brother's involvement in three or fewer encounters (i.e. a hunch from a character, a few great skill checks, and an investigation of the half-brother's mansion). In this scenario, ordinarily milestone experience is a boon to the players because they'd advance in level without a lot of traditional experience gain.
• If they follow the most likely path prepared by the DM, it might take six or even ten encounters (the half-brother could realize he's in danger and send them on a wild goose chase to a neighboring town, kingdom, or dungeon. Random encounters in the forest combined with an assassination attempt would spur the PCs to see that someone they know is in on the plot). In this case, either milestone or traditional experience gain would see PCs suitably rewarded for their efforts.
• If the PCs "go off the rails" entirely and ignore the missing elf noble in favor of whatever errand the half-brother has sent them on, they might explore an entire dungeon complex and recover a magic item for their patron--one that has nothing to do with the milestone originally set out that would advance the campaign. In this method, players would be desperate to have their characters hit the milestone (and a good DM would likely award the magic item's recovery as a milestone in this instance) but the dungeon exploration might include upwards of fifteen encounters before all is said and done--a real windfall for traditional experience groups, but not necessarily for the milestone camp.
• If the PCs just have a rough session--terrible dice rolls, some bad leads/hunches, or just a combat that goes poorly and sets them back--the players may similarly end up slogging through several more encounters than they might otherwise have normally encountered before realizing that it's there is a connection between the elf's kidnapping and her half-brother's patronage of the party. In this scenario, it could go either way (a few rough encounters might take all night, but the characters may still discover what they needed to; alternatively, a night of fighting their way out of an awful situation might have included a dozen encounters).

So how do we allow the party to advance in all four possible ways at a pace that seems appropriate?

Here's how I'd run each option:

• In the first case, the PCs have--through pluck, luck, skill, or all of the above--done an amazing feat. As they adventured, they were awarded encounter experience, but upon hitting the milestone, I'd award the difference to fifth level.
• In the second case, the PCs have followed a relatively predictable track. If they hit fifth level before hitting the milestone, so much the better; they keep whatever "overage" they've collected, and the milestone is acknowledged, but ignored for reward purposes. The PCs start toward the sixth-level milestone with some experience toward sixth level.
• In the third case, the trials and tribulations of the PCs hopefully result in reaching fifth level--and possibly a significant amount toward sixth. No mention is made of the milestone because it wasn't achieved. As the PCs wend their way back toward their supposed mission, they will eventually hit the milestone (where it will be acknowledged, but ignored for reward purposes). Alternatively, the milestone may pass the PCs by--maybe the noble was murdered while the PCs went spelunking in the dungeon, and the half-brother has committed to a coup to overthrow his elven family's court and take his "rightful place." Now the milestone involves discovering a way to stop the madness of their former patron; this new milestone represents a significant change in the campaign's direction based on the PCs actions. It's up to the DM to determine whether this new milestone should be the fifth or sixth level milestone.
• The final case could also go any way. Either it will end up like the first case (milestone awarded) or like the second-or-third case (so much combat/exploration/interaction experience awarded that the milestone is surpassed), or like the alternative third case (the campaign moves in a new direction; milestones are reassessed).

The bottom line is this:
If the PCs will level first from accruing traditional experience, they level up. If they would level up first from hitting a milestone, they level up. Generally, if the PCs level up from the traditional  experience, finishing the encounters that were "balanced" or "prepared" for their previous level will be a tad easier, but not a pushover. Similarly, if the PCs are awarded a milestone sooner than they otherwise would have, they're in appropriate shape for the harder encounters planned in the next stage of the adventure.

For those of you running Hoard of the Dragon Queen with a party that just finished The Lost Mine of Phandelver, you may see this method as particularly helpful. The players enter Hoard a lot more powerful than first level characters, but their experience gains from the encounters are not so vast that the level gap remains; by the time the characters hit the fifth or sixth episode, they're likely to be only fifth level--but they did make it all the way to fifth on the traditional experience gains (since the milestones only activated if they were levels one-through-three).

This also solves the problem of lower-level party members. If a level 3 character is adventuring with level 6 characters, when the level 6 characters hit a milestone that was budgeted as a level 4 milestone, the level three character levels up. The others don't.

I don't necessarily think this "catch-all" will work for everyone, but I think it's a useful model, and more importantly I think it enhances the fun involved for everyone.

Happy leveling!