I'm playing a thief currently and am trying to perk the Speech tree, but progress is really slow. I believe there's a trick/exploit where you sell tons of stuff to one merchant even though the merchant doesn't have any more money and you level speech quickly that way, but I don't want to do that. I only sell while they still have money which makes for super-slow progress.

My character isn't strong enough to get the Black Market power and she probably won't join the Thieve's Guild (well, not for a long time).

Maybe buy some training, but can't remember who does it for speech and I'm really reluctant to do this on a build's primary skill.

I believe another way to level speech is to incur a bounty and talk the guards out of arresting you. There's some catch where you ultimately get arrested because the first guard can't be convinced twice (or something like that) but it generally gets you pretty far before getting carted off to jail. I plan to try this out soon, my PC is about to embark on an epic burglary spree in all the major cities. Good thing the guards never search your residence for stolen goods; they only search your person!

Anybody have other strategies for leveling speech without using exploits or the command console? I'm on Xbox.

Many thanks!

If you were on a PC, I'd highly suggest getting the "Become a Bard" mod by Pevey. That allows your performances to help level up speech.

Otherwise, there is not much you can do. There are a handful of "speechcraft options" in dialogue boxes that may appear from time to time. Selling is the only "consistent" speechcraft increase activity I have found in vanilla Skyrim. There just is no way to practice it on unknowing NPCs with bribes, flattery, intimidation, or taunting.

Literally sell one item at a time. It's OH so much fun....but it works.
*Go into dialogue
*Sell item
*Exit out of dialogue
*Rinse and repeat

And yes it takes awhile. Not my thing, but have done it for the last .5 point to lvl.

I'm pretty certain that isn't necessary. There is a glitch to where selling all of an item you have many of will only count as selling one of them in leveling your speech, but this can be fixed by selling them one at a time in the same dialogue menu.

As far as non-exploit ways to level the skill, I don't know of much. You might already be aware of this, but I'll throw it out there since the question only mentioned selling. Buying items from merchants also increases speech, which could help move things along a little faster than strictly selling.

Thanks for the input, all. I made some progress overnight, here are my findings based on the guards in Windhelm. I assume the guards across all the holds behave the same.

The interaction with guards will only increase your Speech skill if you bribe them - the, 'I don't really have time for this, do you?' option gets you out of trouble but doesn't increase the Speech skill. With Speech at 41 or 42, I didn't see an Intimidate option.

The bribe option seems to only be available with certain (minor?) violations. For example, a bounty of 25 (which my PC incurred for a failed pickpocket attempt) gets you the option, but assault only gets options for paying the bounty and going to jail etc. There's no Speech increase with these interactions.

If you successfully bribe a guard, the bounty remains but you can't repeat the bribe with other guards. This means you can only use bribing to level Speech once in a given hold. However, I'm guessing the bribe option will re-appear if you leave and come back (just don't know how long that takes).

I think the plan for now is to simply try to pickpocket everyone in each major city until caught, perform the bribe (which costs around 350 gold currently) to improve Speech, and then move onto the next town. Assuming the option re-appears after some interval, you can make a nice circuit of this and build Speech up through a life of petty crime.

How does this differ for you from "training" the skill up? Is it cheaper? Do you RP a pickpocket? Or is it just another way in which to raise the speech skill on its own? Not being snarky, just curious

The other fast path to Speech increases is via Speech Training. For each level of your character, you can pay for training, point by point, up to 5 points per level. HOWEVER, you have to complete the training before leveling up. And if you delay leveling up to where you have accumulated enough experience to advance several levels at once, you lose training opportunities you jumped through while leveling up. (So when you can afford the coin to purchase skill levels, try to get the training out of the way early in the level so when Level Up appears you can advance without losing anything.)

There are several Speech trainers to be found, but the most accessible is Giraud Gemane at the Bards College in Solitude. He is a Master trainer (the best you can get) that can train you up to Speech 90. HOWEVER, unless your game is modded to make training costs more reasonable, training for higher levels of a Skill will get VERY expensive. (Several thousand gold just to gain a one-point increase.)