One way it's easy to tell we're in the presence of a great, rich fascinating story is that there's potentially so much to discuss. In addition to all of the background material I'd like to share with you, we could easily pick any of these topics and spend quite a bit of time hashing them around, picking their fruits.

Characters
Protagonist / Antagonist? - what is the Boss up against in the person of Bartleby? Does Bartleby represent a force beyond himself as an individual?
Major / Minor (Who are the major players in the story? What do we know about them? Are they likable? Sympathetic? Realistic? What's the function of the story's minor characters?)
Dynamic / Static-Who changes? Who stays the same? Is the story about growth or change?
Round / Flat-Who is the round character? Who are the flat characters?

Point of view
Who tells the story? - the first person narrator, who is flawed but human…He's reliable, we trust him. His actions definitely support what he tells us about himself; especially the part about being a man who likes to take the "easy" way. What else is gained by telling this story from the Boss's perspective? Why not Bartleby's perspective? Why not one of the other clerks?

Plot
Exposition-what background information does the narrator relate that gives us a greater understanding of the events unfolding? Why does the information about Bartleby's previous employment come at the end of the story rather than at the beginning?
Complication-how does the Boss react when Bartleby repeatedly refuses to perform his duties? How does his reaction intensify? What is the Boss's dilemma?
Climax-Where do you feel the events reach their pinnacle? Where is the conflict most intense, the clash most "explosive"?
Resolution-What's the outcome of the explosion?
Epiphany-who has gained insight in this story, Bartleby or the Boss, or anybody?

Meaning (Theme)
Does the story leave you thinking anything? Feeling anything? What do you make out of it all?
Passive aggressive people are difficult to accommodate, difficult to ignore.
Passive resistance is a radical form of rebellion.
Offices, where Americans spend the greater part of their lives, are not democracies.
Have a life outside work! Don't expect your occupation to bear the burden of your existence.
What other ideas does the story suggest to you?

Irony
The Boss doesn't recognize that his own passiveness is as persistent and frustrating as Bartleby's. Or that his genteel, self-interested interest in Bartleby is leading to no good.
Can you think of other ironies?

Paradox
Bartleby is stubborn, self-absorbed, rebellious, and insubordinate, yet many readers, and even the narrator, the Boss himself, have a deep sympathy for him. Why?
Others?

Ambiguity
Exactly why does Bartleby always "prefer not to"? Why can't he make friends, or communicate? What's at the heart of his rebellion? Why doesn't he quit and get a different job?
Why does the Boss have sympathy for Bartleby?
What else in the story seems open to individual readers' interpretation?

Symbol
What do the "dead walls" and Bartleby's "dead wall reveries" represent?
What's the significance of the setting? Why is it a story of "Wall Street"?
Why do Turkey and Nipper have nicknames, but the Boss is never named, and we never learn Bartleby's first name? What's in a name?

Your Questions, My Questions….

1. Why don't we know anything about Bartleby other than what we see of him in the story? Is that a weakness of the story?
2. Why doesn't the Boss just fire Bartleby?
3. What does the Boss do for a living? What kind of company is he running?
More questions to follow!