Freely adapted from role-playing games where players create their own skills - like Fate - the idea is to allow players to tap into a side of the character that's part reputation, part character cliché, and essentially just "being good at being that character". Think of Wolverine's "I'm the best at what I do, bub!", but of course, it has to be something that's not already on the character sheet. What Wolverine does is chop people into bits, which is already covered by his Fighting stat. Or is it?
Let's use another example. Say you have a character who was raised in a bunker, away from society, and therefore awkward in social situations. The player mentions it often, and uses it to explain why he's good at certain things when the dice roll in his favor, or even to ask for bonuses ("Can I get a bonus on my Fear test in this claustrophobic situation because my character was raised underground?"). This has been going on for dozens of sessions and you feel it is a core element to the character. Bunker Life could be a nice skill to give this character, allowing the player to use it to do things he might have done around the bunker, or substitute (usually with a lower difficulty number) for Survival or Fear tests in the appropriate situations.
Or maybe we have a were-bat in the group and the game doesn't really give the character any kind of echolocation powers for such a being. You've simply been giving them "infravision" bonuses in darkness as it's functionally the same. A good custom skill might then be Bat Senses, allowing them to judge distances, call dogs with ultrasound, whatever stunt they can think of.
Now let's come back to Wolvie. What he does best IS covered by the extant skills, but perhaps not HOW he does it. When other characters use claws, the results are a bunch of scratches. When HE does, he's in a berserker state. So what if he decided to roll on "Being the Best at What I Do" instead of Attack/Claws? Might cut down (ha!) on combat time if it means he decimates the opposing group while he's "out of his mind". One roll and he takes out a large number of goons. Ask the player what he wants to happen and set a difficulty, with misses meaning he's killed someone he shouldn't have, or taken more damage than expected. It's probably not the game's rules according to Hoyle, but it's the right FLAVOR for this character.
A satisfying custom skill stems from one of several places, but are always grounded in character. They can be:
1. Based on a character's background (the PC was raised by Elves or seeks revenge for the destruction of their village)
2. A manifestation of who they are, biologically or culturally (a Frankenstein's monster or a logical Vulcan)
3. Grounded in one of their shticks (the PC is always playing a Romance card or prefers improvised weapons to actual ones)
It's also important for that skill NOT to already be available. Some games have very granular skill rules, so that it's hard to find something not already in the list. Others have a small selection that denies specialties in favor of widely-useful macro-skills (for example, Science covering every type of science, and Air Vehicles covering everything that flies). Either way, the problem for the GM is the same, and so are the solutions:
1. Make the custom skill cover many different skills, but only in certain situations. Say your Monster Hunter has a Monster Hunting skill. It might cover Tracking (but only monsters), Science (but only monster biology), and for something a bit more unique, "Know Monster Weakness".
2. Difficulty is lower when using the Custom Skill. Using the same example, our Monster Hunter may already have Tracking, but if he's tracking a werewolf and it's got a difficulty number of 10 (a number that would make sense in our imaginary game here), tracking it with Monster Hunting gives it a difficulty number of 8. No such help if he's tracking a normal human.
While I've already mentioned WHEN such skills should be handed out - generally once the characters or player styles are well established, not that you couldn't do it a character generation, for flavor - there's still the question of HOW. It can, of course, be negotiated with the specific player. They might have some good ideas and a direction they'd like to take. On the other hand, if this is a "gift", the GM might decide what the skill is. The GM is, after all, a more impartial observer than the invested player, and will certainly be better able to balance its effect on his game than a player would. In an online game where the character sheet is accessible and modifiable to the GM, like mine, you can stealthily add it to the sheet and wait for the players to notice, or call for a "Raised by Elves" roll, let the chuckles die down, and say "No, really, roll on Raised by Elves" and watch their eyes open wider.
Rewarding your players can be a reward unto itself. Now roll on your "Nice GM" skill. No, really, roll.
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