http://www.gamesas.com/index.php?/topic/1226487-the-smart-thief/--- this goes the same for the Assassin.
A lot of posts and topics have been asking the same kinds of questions. How do you kill a dragon with the thief skills? How can a thief survive without any combat or magic skills? Well I’m going to attempt to show how using preparation and intelligence, the thief can be equally if not more dangerous than the mage or the warrior. (While I know that there are no classes in Skyrim, the discussion comes from the fact that Guardian Stones make skills in each archetype level up faster so a thief would be at a disadvantage if he had to use skills from other archetypes.)
What makes playing a thief for most characters hard is that it isn’t as straight forward. You can’t just go into combat situations slinging spells or swinging axes. You can’t even just sneak into combat and kill everybody because chances are after you make the first attack, if they’re not dead, everybody will swarm you.
This is how it works. Thieves use lock picking, sneak, pickpocketing, and speechcraft to make money fast and pilfer the best equipment available. They should always have significantly better equipment than the mage or warrior and always more gold to play with. Next, they explore the world picking alchemical ingredients and testing combinations to make the best potions and poisons. This means a thief has to spend a lot of time in preparation, making potions and stealing gold. But, when the battle comes they can use a combination of potions to fortify the skills that they need to fight, and along with having better equipment this should help to balance out the fight. What makes it even more lethal is when poisons become involved. If anybody ever explored alchemy in Oblivion, they would know that the simplest of damage health potions could be devastating and were easily mass produced. Then, if they start getting low on health, stamina, or magicka, they will have the most and the best restorative potions available for a quick replenish. Combine all these with the ability to get a stealthy and powerful first strike, and you have yourself a fearsome combatant.
The thief is defined in the preparation. That is where all of their skills will be used and where they will level up. Yes shouts, magic, and ranged attacks will probably have to be used to take down dragons, but it is the poison on the arrows that makes it just as if not more effective than an arrow shot by an archer, and the restorative and fortifying potions that make the magic more effective.
You're forgetting one more important catalyst in a thief: terrain. The ability to utilize your surrounding terrain (whether it be dungeon, city, or open ground) to your advantage is also paramount in the succession of a thief... Especially when dealing with Dragons. Stick to covered ground; wooded areas, as much as possible when travelling. If you must cross open ground, make it swift and if there's a dragon in tow, make if even faster. Find cover and use "hit-and-run" tactics. Invisibility/Chameleon are also handy. Like the OP said: Poison and potions. Poison and potions will be your best friends. Let's just hope the "paralyze" effect can be used on dragons as well. Thieves aren't known as noble and honorable fighters, so fight dirty.
Also, another tactic is as some have mentioned: "Hirelings"
In part of 'preparation,' hiring a companion to aid you in your efforts to take down a dragon.
I know this says "thief" but these tips also abide to the Assassin as well.