I think a lot of people don't attempt to go paperless because they can't imagine how they'd operate without any paper. Here's the dirty little secret of most paperless setups – they still have paper.
Trying to achieve paperless might be a little too ambitious for most people. Why don't you just try for less paper instead? That's much easier.
Here are some simple steps for using less paper:
Put a scanner on your desk.
If you have more than one person in your office, put a scanner on their desk too. If you make someone get up and walk to the scanner, they won't do it.
Get a Fujitsu Scansnap iX500. These get universally good reviews and people have been swearing by them for years. They're not the cheapest you can find, but they're worth it.
Start scanning everything.
Scan everything that comes across your desk. Get a pre-inked stamp that says “SCANNED” so you can stamp each document on the back. That way you'll know what's been scanned and what hasn't.
Come up with a file-naming convention.
This is a fancy way of saying that you should make sure everyone is naming the scanned documents the same way. Quick tip – if you include a date in your file names, use YYYY-MM-DD and include the leading zeros. That way you can sort it by date correctly.
Recycle the stuff you don't necessarily need a hard copy of.
If it's something that you think you'll need to access regularly (or if you know you'll have to reproduce a paper copy,) keep the paper copy. If not, recycle it. When it's time to close out a file, you can verify that everything is scanned by looking for any documents that don't have the SCANNED stamp on the back.
Back up your scanned files.
Make sure you have a good backup strategy that includes your scanned files. See my post on backup strategy tips.
Tell your clients that all of your files are electronic.
If you are in a business where a client has a file (like a lawyer,) let them know that if they want a copy of their file, you will only provide an electronic copy.