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I have been reading the Basic Rules a couple times, but could not find any way to gain proficiency in skills past level 1.

For example, if I create a Rogue, I may chose 4 skills among 11:

Acrobatics, Athletics, Deception, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand and Stealth.

Now, a Criminal background grants proficiency in Deception and Stealth already, so I can pick 4 among 9:

Acrobatics, Athletics, Insight, Intimidation, Investigation, Perception, Performance, Persuasion and Sleight of Hand

which still leaves 5 of them on the floor.

I could find two nuggets:

  1. The Human Variant Trait seems to allow to get proficiency in one skill.

  2. The multi-classing rules (Chapter 6) seem to imply that one may get some proficiencies from multi-classing; though they refer to the PHB and do not specifically imply skill proficiencies (could be weapon or armor or tools...)

Are there other sources of skills that would allow one to broaden one's range of skills?

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    \$\begingroup\$ Also remember that this is a party game: one player shouldn't have all of the skills. Rely on your companions (and let them shine). If you are playing a game with only one or two PCs, asking the DM for additional skills might be a reasonable way to help compensate. \$\endgroup\$ – mattdm Aug 19 '14 at 13:05
  • \$\begingroup\$ @mattdm: Yes, of course, however the Rogue (specifically) has been up until now a "skill monkey" here to handle what the others did not. In my current (3.5e) party, I play both the roles of Scout and back-up Party Face for example, which requires mobility, perception and social skills on top of the usual stealth/traps/locks expected. \$\endgroup\$ – Matthieu M. Aug 19 '14 at 13:08
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    \$\begingroup\$ They and bards are still the skill-monkey's, but skill proficiencies alone are not what makes you good at a skill. Rogues and Bards get more skills than any other class, even if not by a large margin. In addition, rogues get the ability to double their proficiency bonus on a couple of skills. They are still elite in the skill arena. \$\endgroup\$ – Aviose Aug 19 '14 at 15:56
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    \$\begingroup\$ Since it has inexplicably not been mentioned yet, I'll comment here to say that the Bard's level 2 feature Jack of All Trades makes being proficient in a skill a little bit less important, since it lets you add half your proficiency bonus to ability check rolls you're not proficient in (including rolls like initiative that have no proficiency you can gain). So dipping at least two levels into Bard might be a good way to improve your skill rolls, beyond the possibility of gaining new skill proficiencies (which you do also get from the class). \$\endgroup\$ – Blckknght Mar 18 '19 at 17:50
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There are a few classes you can multiclass into to gain skills, such as Bard, Ranger or Rogue.

In addition to that, in the player's handbook there is a feat called "Skilled" which allows you to gain proficiency in any combination of 3 skills or tools.

There is also a bard ability in the college of lore that allows you to learn 3 more skills at level 3.

Currently, the downtime rules allow you to gain proficiency in tools but not skills.

In case it isn't clear, you don't have to pick skills from your class skill list when you gain new skills through the "Skilled" feat. You can pick any skill you want.

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  • \$\begingroup\$ Given that downtime is essentially "free", I am not surprised about this restriction. Already, compared to 3.5e, the ability to learn languages "for free" (instead of spending a skill point) is great! \$\endgroup\$ – Matthieu M. Aug 19 '14 at 12:57
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    \$\begingroup\$ Downtime is, thankfully in this case, only as 'free' as the DM makes it. Many campaigns don't have a year or two worth of downtime throughout the entire campaign, and many more don't have more than 2 years. I like the fact that I can control pacing with this, and characters get something tangible out of the downtime, so I can have a campaign that stretches over a long period of time (which is more realistic to me anyway). \$\endgroup\$ – Aviose Aug 19 '14 at 15:59
  • \$\begingroup\$ That depends on how the DM interprets that section. While many people interpret downtime as a reward resource thanks to the Adventurer's League, the wording on downtime could actually allow people to choose how much time they spend on other things and manually play out that time spent outside of adventuring. \$\endgroup\$ – JAMalcolmson Sep 14 '16 at 19:10
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Multi-classing

As others have stated, the only classes that currently get a skill proficiency by multi-classing are a Bard, Ranger, or Rogue. Even if you focus exclusively on one of these classes, it will start with more than most characters.

As noted by T.J.L. in comments here, the Knowledge Domain allows Clerics to get extra skill proficiencies as well.

Feat

A very powerful feat, in my opinion, is Skilled. 3 skills for the cost of 2 ability points is a very fair trade when you consider attribute caps and the bonus you get out of 3 skills.

Race

A couple of races get a free skill in some form, but humans also get a free feat (see above). This means that a variant human gets a total of 4 bonus skills if you take Skilled as your bonus feat.

A second-place option is the Half-Elf. They get two skill proficiencies. Not as much as a Human with the Skilled feat, but more than a human without it.

Minor Houseruling

According to the rules (PHB pg. 187), you can train in the proficiency of a tool or a language by spending 1 gold per day of downtime for 250 days of downtime to train that proficiency.

Technically, skills aren't allowed on that list, but talking to your DM might not hurt. Although there is nothing specifically referencing skills in this regard, it wouldn't seem out of place or inappropriate to use this system for skills as well. Many, if not most, games will not allow enough downtime for frequent proficiency training (likely only 1 proficiency in most cases). Even if a DM allowed this as a minor houseruling, it is unlikely to come up often.

Synopsis

Your best bet to start a true skill-monkey that can tackle multiple roles in the way you stated from level one is to make them a variant human, and make "Skilled" the extra feat. This is a completely legitimate build, and most DM's will likely allow variant humans since they are directly in the PHB and Basic Rules.

This would give you 10 skills (4 class, 4 race, 2 background) to work with, making you very feasible as a jack of all trades spy-like character, a paragon of skills and expertise. The 4 feats from race/racial feat can be from any source as well, giving you a lot of versatility to work with.

If you want to focus after level 1, then picking up the Skilled feat is a great path to look at.

Also, you can look in to multi-classing as a bard. It does give a skill, and skill expertise, and a bard/rogue fits the Face/Infiltrator Spy trope of characters like James Bond. Although Ranger can give you another one, a 17 Rogue (Assassin)/3 Bard (Lore) is very solid and the one skill point is not worth losing a major ability as a Rogue. This character, when they hit Rogue 1/Bard 3, would have 14 (4 starting class, 4 race, 2 background, 1 Bard, 3 Bard(Lore) bonus) skill proficiencies, not even considering tool proficiencies.

Should you do it?

Depends on the group. Generally speaking, a single player shouldn't have all the skills, and the ability to have all the Player Characters rely on each other makes for a better game. Unless your group, for some reason, is very low on diverse skill selection, you may want to run this type of character concept by both your DM and the other players before creating this character.

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  • \$\begingroup\$ Oh, I definitely advise party synergy for skills do not worry. In a hypothetical Cleric/Fighter/Rogue party for example, you might need to spread yourself out rather than focus on some core skills to avoid situations where the party really is at a disadvantage. That being said, it is true that the proficiency bonus (from +2 to +6) is much less significant than the ranks you could get in 3.5e (from +1 for trained-only to +23 for maxed out skills) so it might matter much less. \$\endgroup\$ – Matthieu M. Aug 19 '14 at 16:20
  • \$\begingroup\$ Error in my 'build' comment of Bard/Rogue... as restated in my main answer, it is Bard(Lore)/Rogue(Assassin) (for disguise kits, mostly, although Rogue(Thief) still works very well). Bard(Wit) changed to Bard(Lore) after the final beta, and I keep forgetting that. \$\endgroup\$ – Aviose Aug 20 '14 at 20:48
  • \$\begingroup\$ You're missing out on a few here - Half-Elves get to choose two skills (which is better than Human because you can take the feat later), as does Knowledge Cleric. \$\endgroup\$ – T.J.L. Aug 16 '17 at 12:20
  • \$\begingroup\$ @T.J.L. The reason I didn't mention Half-Elves is because of the level 1 feat for humans giving them an edge on skills. With the skilled feat at first level, they end up with 4 trained skills at level 1 and don't lose a later proficiency because of it. I could add a note about half-elves. \$\endgroup\$ – Aviose Aug 16 '17 at 15:50
  • \$\begingroup\$ The question actually says after L1 and makes no indication that another Feat or ASI has more value to the querent than additional skills. \$\endgroup\$ – T.J.L. Aug 16 '17 at 15:53
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It's actually possible, if you want, to gain proficiency in all 18 skills.

  • Human (variant): 1 skill
  • Feat: Skilled: 3 skills
  • Background: 2 skills
  • Initial class: Rogue lvl 6: 4 skills (4 expertises)
  • Bard lvl 10: 1 skill (4 expertises)
  • Lore bard: 3 skills
  • Cleric lvl 1 Knowledge domain: 2 skills (with doubled proficiency bonus, essentially expertise).
  • Warlock lvl 2 Eldritch invocations: Beguiling influence: 2 skills

While this is quite extreme, it is possible at later levels to gain proficiency with any skill you want using feats and multiclassing.

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It is worth noting that if your campaign gets to the point where you start getting Epic Boons (5e's attempt to have post-level-20 progression), there is a Boon of Skill Proficiency that gives you proficiency in every single skill.

Epic Boons are described on DMG p. 231, with a list of official boons (including the Boon of Skill Proficiency) on the following page.

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