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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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3  
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. –  mattdm Aug 19 at 13:05
    
@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. –  Matthieu M. Aug 19 at 13:08
    
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. –  Aviose Aug 19 at 15:56

2 Answers 2

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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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! –  Matthieu M. Aug 19 at 12:57
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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). –  Aviose Aug 19 at 15:59

Multi-classing

As GMNoob stated, the only classes that currently get a skill proficiency is a Bard, Ranger, or Rogue.

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.

Minor Houseruling

According to the rules (PHB pg. 172), 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. As MattDM stated in his comment 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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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. –  Matthieu M. Aug 19 at 16:20
    
What's the page # for the rules saying you can train in the proficiency of a tool or language? –  briddums Aug 19 at 20:57
    
PHB 172 in downtime.... bottom of page. –  Aviose Aug 20 at 17:42
    
It might be worth noting that it is 14 out of 18 skills you will be proficient in :P –  GMNoob Aug 20 at 19:59
    
lol... true... that's most of the skills in 5e, and is a pretty beastly count, considering. Half proficiency in the other 4... ridiculous. –  Aviose Aug 20 at 20:46

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