In The Elder Scrolls V: Skyrim for the PC, PS3, and Xbox 360, speech is one of those skills that can raise very slowly. There are some techniques you can use however that will speed up the process and make it little less painful.
The natural route to leveling speech is through buying and selling, which you will be doing a lot of in the game. While this method is slow, there is a method to speed it up quite a bit.
It seems that the rate at which you level up in speech through bartering is based on the value of the item you’re buying and selling. Use my tips to level enchanting quickly, and you can increase the value of your sold items immensely, making your speech rise higher and allowing you to make a lot of gold in the process.
Bribing and persuading is another way to level up your speech, and can be much faster than bartering if you can find enough opportunities to do them.
Once you become a member of The Thieves Guild, you’ll get more options when you get caught stealing and breaking into houses. You’ll be able to bribe guards to get the bounty off of your head. Each of these attempts increases your speech skill, so you can kind of blatantly go around trying to pickpocket and get caught on purpose to make these opportunities come up. You may want to leave any followers at your house however, because they will automatically fight if you get caught.
If you want an easier method and you’re not against exploits, then visit Ungrien in the Black-Briar Meadery in Riften. It’s on the west side of town, directly below The Pawned Prawn. If you have a speech level of at least 25 you can persuade Ungrien to tell you the truth about Maven Black-Briar over and over as many times as you wish.
If you’re ok using a rather “cheap” method to level Speech extremely fast, then check out the first tip in my skill trainer pickpocketing guide where you simply find a Speech skill trainer, buy a skill point, then pickpocket the money back. Ogmund in Markarth is a high level Speech skill trainer, and so is Geraud Gemane at the Bards College in Solitude.
This trick is only effective up to 51 skill points unless you have a pickpocketing skill of 100, since after 51 skill points the cost is increased by 1000 gold, making pickpocketing much more difficult.