How does one Monk? (Way of the Shadow)

[EphTheorem]

The first time I played d&d I played a ranged Fighter, so I have little experience with melee martial classes. I'm a bit green since I haven't had much actual play time. I'm going to play a Tiefling (Feral) Shadow Monk, and wanted to ask for some pointers about how to play them effectively. I have a lot of questions, so let's get to it. Ability scores are not set in stone yet, but here is where they are right now - STR 12, DEX 16(+2), CON 12, INT 11(+1), WIS 16, CHA 10.

What skills should I take? Since custom backgrounds exist, the way the group does it is any combination of skills that work for the character is allowed, background just determines the feature they give. Stealth is a must, and I think Perception would also be good to have. Is Sleight of Hand good without Expertise from Rogue? (I would like to have them be a full Monk, I'd rather not multicass.) For ASIs or feats, what would you recommend? Is it better to pump up damage output with DEX, take a feat, or get the Stunning Strike DC higher with Wisdom improvements? The plan, with any luck, is for it to be a pretty longform game, so suggestions throughout all the different levels are all welcome.

How can I make the most of the Monk, and by extension, the Shadow Monk, in and out of combat besides just being sneaky in general? What's the best way to utilize Shadow Arts like Darkness [an extra daily use of it with Tiefling =)] and Silence? Should they always be used at the start of combat? Do you want to use Flurry of Blows as often as possible, spend a lot of Ki on Stunning Strike, or something else? (I'm not positive yet, but there is a chance I may end up being the main damage dealer because two other party members are a Bard and Druid, don't know what 4th person will decide on.)

Thanks for the advice. =)

[Chronos]

In combat, you're mostly just a generic monk. What really sets the Shadow Monk apart from the other monk subclasses is out of combat. Pass Without Trace and that free teleport can both solve a lot of problems.

For ASIs, I would recommend Mobile, then maxing Dex. After that, you could work on Wis, or Con, or some other feat-- By that time (if you even get there), you'll probably have a good enough idea of what you need. Remember that Stunning Fist relies on both Dex and Wis to work, because you need to hit.

What you'll want to do in combat (flurry or stunning) will depend on who else you have in your party. Stunning will give everyone in the party advantage on attacks, but it won't add any damage, which you might need. And how often you'll want to use either ability will depend on how many short rests you get.

[Frozenstep]

There are a few things you can do. Main thing you'll always want to do is push for short rests. Being able to use your ki aggressively in every combat will make you much more competitive, and if there's no reason not to take a short breather after a fight, you might as well so you can be better prepared for what's to come. But if you're in a game where the DM tries to prevent short rests or punishes you for taking them you'll be a lot more limited.

The spells you get at level 3 are expensive to begin with, but get cheaper as time goes on, and have very strong utility both in and out of combat. Silence and some form of difficult terrain/movement blocking from an ally can shut down an enemy caster. Darkness can block a lot of spells that require a target to be seen by the caster.

Now, darkness is odd. By rules as written, unless someone has a form of vision that can ignore darkness (tremor sense, devil's sight), both you and the attacker can't see, so the advantage on disadvantage cancel, making it seem useless. Although depending on DM, they may rule that people have to guess what square a person is in to attack them, but I believe the rules specify that your other senses are enough to detect a creature you can't see unless it takes the hide action. However, it does prevent opportunity attacks, which means you monk could potentially cast darkness on themself, next turn run up and hit something, and then move away without the enemy being able to respond. Of course they can just chase you down and hit you after that, but if they're standing next to your melee friend they might take an opportunity attack if they do that (as long as you've moved your darkness away).

Also, darkness can be blocked by opaque object, and lasts 10 minutes. If you feel like combat is going to happen soon, you could cast it on your hair, put on a hat, and just take off the hat when combat starts.

Another cheeky thing, if you pick up the alert feat, "Other creatures don't gain advantage on attack rolls against you as a result of being unseen by you." This basically means in your darkness bubble attacks will have disadvantage on you, while you still attack normally.

One general monk tip: Your health isn't high and your armor class isn't really that great. You aren't meant to stand toe to toe with a line of melee enemies. You can potentially make use of the mobile feat to hit and run an enemy engaged with one of your melee team members, or use your increased speed in general (and eventually your teleports) to reach backline ranged enemies (who you have a better match-up against, because deflect missile).

[sambojin]

If you are allowed to, or are even vaguely considering, multiclassing for a power boost, consider dipping War Cleric.

Gets you Bless, for easier stunning strikes. Gets you Guidance for skills. Gets you Shield of Faith for better AC. Gives you Wis-mod bonus action attacks per day, and martial weapons, and you have fairly high Dex, so you're all-of-a-sudden a pretty good archer for mook killing or need-ranged-now encounters. Gives you Divine Favour, in case Flurry of Blows ever seems like a nova option. Gives you medium and heavy armour, in case there's ever some amazing armour handed out (you do lose martial arts and extra speed, but nothing else. Well, +Wis-mod-AC, but some armour is better than that). A bit of extra healing and stuff as well (you'll have high'ish Wis, so a fair few spells to prepare. But Bless, Divine Shield and Healing Word and you're done. The rest is just situational. Probably Command (there's plenty of good words to use) and Protection from Evil&Good (disadvantage on attacks against you for heaps of enemies) and Divine Favour (meh, domain spell) as a standard set with 16 Wis is normal). Yes, +2AC for you or someone else for 10mins as a bonus action on your concentration is worth it, so is Bless, so is PfE&G, you choose which, twice a day.

If it all goes survival'y, you've got Create Water and Purify Food and Drink. If it goes magic-hunty or find-the-meddler, you've got Detect Magic or Detect Evil&Good. For NPC guard duty, you have Sanctuary. There's plenty of change-ups you can do, day to day with your prepared spell-list, depending on what bit of an adventure you're in, which is nice for a 1lvl dip. But mostly you'll just buff AC, or to-hit/saves for you and two others, or give certain big-bads disadvantage on attacks against you. But it's nice to have those little extras when you need them.

If you take 2lvls of War Cleric, you get +10 to-hit on your stunning strike 1/sr. Which is amazing. They still get the Con save, but the near-auto-hit is there, to make sure they *have* to take it. It really doesn't matter if it's against super-heavy armour, if you've got disadvantage for some reason, or whatever. A flat +10 to-hit, no action used, 1/sr. Have an extra spell slot too, just so you've got +2AC for an extra encounter a day (and another spell to prepare for no reason).

After about lvl5-7 of Shadow Monk, seriously consider a level of War Cleric. Maybe two. It's very handy to have. Monks don't scale that well after lvl8, so it's asking for a fighter or cleric dip eventually.

[sambojin]

Skill-wise: go for Stealth and Insight. See the lies, be the shadow.
Background: Sailor (or Pirate). Athletics (anti-grapple, a bit of mobility) and Perception (necessary). And you can steer/steal/buy passage on ships (meh). *Or*, randomly punch people for fun and profit (Pirates are awesome. You are in a travelling group of murder-hobos that break stuff, steal stuff, and generally commit minor crimes by just existing. Be one. You do you, without minor problems like law and order. Think of it as being an aesthetic half-feral-demony thing. You really don't value other people's idea of value or possessions, nor their personal space. You're above that. I mean, you only punched him, right?).

Everything else gets done with high Dex and Wis, reasonable other stats, and judicious use of Guidance from your War Cleric dip.

ASI-wise, it's pretty much +2Dex at 4th, Alert at 8-10th (depending on if you do multiclass), choose whatever at 12-14th. That's how I'd do it, anyway. Alert is amazing for the +5 initiative, and you're expected to initiate most encounters with a stun eventually, so do that.

[J-H]

I had previously ignored Way of Shadow, but it does look kind of fun. I'd angle for a way to get more ki points (not sure how).
You have multiple ways to gain advantage over time (teleport, invisibility), so I would consider Elven Accuracy (double advantage when you have advantage). I like crits!

[Throne12]

I love shadow monk I've played 3 different ones. They way I play my shadow monk is get to the caster or who ever is running away and stun lock them Silence and pass with out trace are going to be your bread and butter out of they spells they get.

You have fantastic movement use it. My first monk I would grapple enemy's and unarmed strike as headbutts and stunning strike allowing my team mates beat the turtles out of the enemy I had.

[sambojin]

I had previously ignored Way of Shadow, but it does look kind of fun. I'd angle for a way to get more ki points (not sure how).
You have multiple ways to gain advantage over time (teleport, invisibility), so I would consider Elven Accuracy (double advantage when you have advantage). I like crits!

Kind of why a lvl1 dip in a caster class is so useful. It's essentially +4ki (+6 for "bad" ki classes like 4elements) a day. To do stuff you normally can't, or to do stuff you always do, better. Open Wis-based spell lists are nice (cleric/druid), but honestly, any full caster dip makes monks a lot better.

It doesn't sound like much, since you refresh ki on short rests, and two spells a day is pretty "meh", but they can be very useful.

Even something like Warlock for Expeditious Retreat (10min Step of the Wind, plenty of ki saved) and Hex (yay damage boosting) is worth it. Casting stats are kind-of irrelevant if you do it right. Hexblade fits the bill perfectly, but it does for every melee class.

[Yunru]

One does not play a Shadow Monk.
One plays Batman :P

[Crgaston]

Kind of why a lvl1 dip in a caster class is so useful. It's essentially +4ki (+6 for "bad" ki classes like 4elements) a day. To do stuff you normally can't, or to do stuff you always do, better. Open Wis-based spell lists are nice (cleric/druid), but honestly, any full caster dip makes monks a lot better.

It doesn't sound like much, since you refresh ki on short rests, and two spells a day is pretty "meh", but they can be very useful.

Even something like Warlock for Expeditious Retreat (10min Step of the Wind, plenty of ki saved) and Hex (yay damage boosting) is worth it. Casting stats are kind-of irrelevant if you do it right. Hexblade fits the bill perfectly, but it does for every melee class.

Warlock makes sense for the short rest recharge synergy. A Great Old One patron for the telepathy, and 2 levels for Devil's Sight and Disguise Self or Beguiling Whispers or Misty Visions seems on point.

It'd have to be on a character with decent rolled stats, though. Not so much for the OP's build.

[BloodSnake'sCha]

Your bonus action shadow jump is good for stealth.

It is also good for combat as it gives you advantage and high mobility.
Use it to safely lock a high profile enemy.
For example: you run to the Drow cleric, attack twice and try to stun her.
You bonus action jump away in order to avoid her minions attacks from movement.

I recommend giving all the party darkvision with your ki and taking a short rest to recover it at the start if every day.

You are highly mobile and have the ability to lock down enemies and disable casters(stun make you lose concentration).