If there is something of Heidegger's with which I totally agree, it's that you never really notice something until it's absent (or broken). An anecdote: I was having lunch the other day with a few new acquaintances. One of my lunch-mates, a Delaware native, was regaling us with a story that, as far as I could tell, was intended to be funny or interesting or both. And, bless his heart, he was bombing. I mean, seriously, it was long and incoherent and pointless and overly-detailed and BO-RING. I tried, I really tried, to pay attention and to look engaged, but I just slowly drifted away. And then I thought to myself: You know, this could be a great story. What is he doing wrong?
So, here are some tips for telling a good story (or telling a bad story good):
1. Pick your battles. Not every story is worthy of recounting. And if it isn't, you have to let it go. Maybe you can pick it up again later, but if it ain't ready, it ain't ready. Think of it like a small fish or an unripe vegetable... put it back into the world and let it grow a bit. Maybe it will die on the vine, but maybe it will present itself again as something that could actually consitute a meal.
2. Don't let the facts get in the way. Most of the time, no-one is checking your sources or verifying your details. Embellish a little. Hell, lie a little. Or a lot. It's in the service of a greater cause, and your interlocutors will thank you for it.
3. Find the universal in the particular. Read Aristotle's Poetics. Then, read it again. Then, imagine how you might apply the same insights to comedy (instead of tragedy). Or, in other words, try to formulate Aristotle's lost theory of comedy.
4. Know the punchline. You should know, before you begin, what the ending of your story is. And then you should direct all preceding material toward that end. It's like bulding a house of cards... it's okay if there are points in the story in which your listeners may think to themselves "where is this going?", so long as when you put that last delicate card on top, you inspire something like an "ooooh....aaaahhh....i can't believe it stands up!" response.
5. Don't go down with the ship. If you're losing your audience, ABORT! Don't be a hero.
6. Make it personal. First-person accounts are the best. Even if it didn't actually happen to you, you can tell it like it did (see #2). If it is a tragic story, a first-person account makes it all the more tragic. And as tragedy goes, so goes comedy.
7. Diamonds are a storyteller's best friend. The four "C's" used to calculate the value of diamonds are: Cut, Clarity, Color, and Carat. Translate those into criteria for judging your story. Then add more color.
There you go. You're welcome.