Getting the level of challenge right is a bit of an art. It is,
however, important in order to engage players. I hope to give my
advice on how challenge should be considered in tabletop role-playing
games.
Remember That There is No Reload
When playing tabletop role-playing games, there is typically no
reload (you could, in theory, allow for a Prince of Persia style time
rewinding mechanic). Even if present, players probably often don't
want one. They want to get on with the story, see new things and
role-play new situations. However, this means that players can't
retry a combat encounter and use the very best tactics. There will be
some experimentation needed. Also, since dice are a core part of the
game, bad luck is possible. This means that the level of difficulty
will need to allow for some less-than-optimal gameplay.
Different Groups Need Different Challenges
The experience of the group as well as their knowledge outside the
game plays a massive part. Some players are very good at combat
systems in general and can make what the rules call a difficult
encounter look easy through great tactical use. Others may have
issues with a normal encounter, especially if the terrain is used
against them. It's not only limited to combat though. A too rough
riddle or puzzle can cause a massive problem for a party, especially
if answering the riddle or puzzle is the only way to progress. The
preference of the group to the kind of challenge (thinking through
puzzles or through combat) also effects the enjoyment of the players.
Different Kinds of Challenges
A mix of different kinds of challenges is also generally helpful.
Some people could play combat encounters in D&D until the
universe ends. My players prefer that the challenges they face are
varied. I'd say this is more typical than not but still, knowing your
players is important. The most obvious ones are combat encounters and
puzzles. However, convincing someone can also be a challenge (this
relies heavily on role-play). Battles tend to be similar to combat
encounters but have different rules. They also tend to have more
pieces on the board in my experience and different tactics. In other
cases, the challenge can come from solving a mystery. This is kind of
like solving a puzzle, but it's a bit different than solving the
puzzle lock on a door in a dungeon. Instead, the challenge comes from
finding or noticing clues, creating plausible conclusions and then
trying to cleverly confirm or reject them. There is also a different
way to look at puzzle besides just difficulty. Convincing a king may
be difficult because of the work, time, and effort they need to use
to do it. The favours required would be long and dangerous. In this
case, the challenge isn't necessarily one event (role-play and/or
dice roll) but the long journey to accomplish the goal (with many
smaller challenges were failure may lurk).
Challenges Should Reflect the Story
The challenges presented to the players should be coherent. In my
case, my players typically pay special attention to this kind of
thing. The villain, if established as extremely powerful, should be
so when they face them in combat. There is some allowance (maybe when
they were lower level the villains henchmen were harder than the
villain after they prepared for the final battle) but the relative
difficulty of tasks should be considered to prevent breaking
immersion. Storming a castle should be harder for a single person
than storming a small house in the middle of the forest.
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