The Distance Dilemma: Best Practices for Working with a Remote Bookkeeper (From Someone Who Is One)

So, you've hired a remote bookkeeper. Maybe you met them through a referral. Maybe they slid into your inbox with a perfectly timed LinkedIn message. Maybe you were just tired of spreadsheets screaming at you in the middle of the night. Regardless of how you got here, congrats—you’re not flying solo through your financial fog anymore. 

But now the question is: How do you make the most of this digital relationship without it turning into a game of “Where’s that receipt again?” That’s where I come in—not just as a bookkeeper, but as your partner in financial sanity. 

Let’s unpack the best practices. No jargon. No judgment. Just real talk from someone who lives in the cloud. 

1. Communication: Not Just for Emergencies 

Look, your bookkeeper isn’t a fire extinguisher. Don’t just pull the alarm when tax season explodes. You want a regular rhythm—think monthly check-ins, quick weekly recaps, even a shared Slack channel if that’s your style. 

And please—if something in your business changes (new income stream, shifted payment platform, hired your cousin to run ads), say something. Surprises are for birthday parties, not balance sheets. 

2. Cloud-First, Paper-Never 

Let me be blunt: if you’re emailing photos of crumpled gas station receipts, you’re doing it wrong. 

Use apps. Use portals. Use literally anything that doesn’t involve printing. 

We live in the golden age of document capture: Dext, Hubdoc, Google Drive, Dropbox, even QuickBooks and Xero let you snap and attach. Set up a system once and make it muscle memory. That way, when we ask, “Where’s the receipt?” you’re not diving into a digital haystack looking for a pixelated needle. 

3. Shared Access—With Boundaries 

Let’s talk logins. 

We need access, yes. But securely. Use password managers (1Password, LastPass), set up user roles in your accounting software, and please—please—don’t just email us your bank credentials with the subject line “hope this works.” 

Also: two-factor authentication isn’t annoying. It’s necessary. 

4. Real-Time, Not Rearview 

If your books are updated only when your taxes are due, you’re operating in the dark. 

We want to keep your books current—not perfect, but present. The goal is that you can pull a P&L on a Tuesday afternoon and actually understand it. 

That means timely uploads from you, regular categorization from us, and mutual commitment to staying current. Think of it as a financial Fitbit—little steps, tracked daily, that keep you healthy in the long run. 

5. Clarity Over Complexity 

If we ever send you a report that makes your eyes glaze over, tell us. 

Our job isn’t to bury you in numbers. It’s to translate them. Your financial statements should speak your language. They should tell a story: what’s working, what’s not, where the money leaks, and when to plug the holes. 

So if you don’t get it, raise your hand. Because the best bookkeeping relationship isn’t just accurate—it’s collaborative. 

Here’s the truth: working with a remote bookkeeper can be just as smooth as working with someone down the hall—if you set it up right. 

Communicate early, not late. 

Share clearly, not chaotically. 

Stay involved, not invisible. 

And remember, your bookkeeper isn’t a robot clicking boxes. We’re part of your team. We care about your business, your bottom line, and—when things get wild—your peace of mind. 

So let’s keep it simple, human, and maybe even a little fun. After all, who says bookkeeping can’t be a bit of both? 

This information should never be taken as advice. Please talk to your bookkeeping and tax business professionals to discuss your individual situation. By the way, we’d love to partner with you on that! Give us a call or schedule your no-obligation consultation today, click here to book a call.