It's always easier to deal with your finances in person, but sometimes there are situations that come up that preclude a face-to-face meeting. Many modern accountants have technology in place to make it easier for you to work remotely, but you'll still need to figure out the best way to get your documents and your banking information to them.
1. Always Encrypt Your Emails
Email encryption prevents others from viewing your emails unless they have a certain password. Otherwise, the content of your emails is only as secure as the email address you're sending it to—in other words, if your accountant's email account or your email account is compromised, someone will be able to easily access all of your information. Encryption is provided by many free services.
2. Give Passwords Over the Phone
Sometimes you'll need to give your accountant a password, whether it's the password to download your online banking transactions or to access your mortgage payments. Either way, you should give passwords over the phone rather than through digital media. Digital media can be copied, shared, and viewed without your knowledge, and it may be impossible to know whether your data has been breached.
3. Password Protect Removable Media
Any removable media—from a CD to a thumb drive—should be password protected before you mail it to your accountant. In particular, thumb drives tend to be lost quite often even if the individual who has it is being careful. During tax season especially, accountants will be working with large volumes of information. And, of course, thumb drives are easy to lose in the mail, too.
4. Don't Use the Fax for Sensitive Information
Modern fax machines tend to be linked to a copier, which is often in the center of an office and unprotected. Unless you know for a fact that your accountant's fax machine is secured from prying eyes, you should never use the fax machine to send sensitive information. Even if the machine is protected, you should call your accountant before faxing so that they know to pick up your documents when they come out of the machine. Generally, email and private server uploads are much more secure.
Security and accuracy are the two main concerns when working on your finances remotely. As long as you cover these two issues, you should be just fine. An accounting service, like Hurren Sinclair MacIntyre CPA's LLP, can give you more information on the best strategies to use.