What does a new bookkeeper actually need from me?

At minimum, every invoice with its direction and status, expenses categorized with receipts attached, and contracts and tax documents filed by fiscal year — all in one place they can open and export.

I'm moving from a shoebox of receipts — where do I start?

Start by recording each expense with its category, vendor, date, and amount, and attach the receipt to it. Work month by month using a simple onboarding checklist until each period is complete.

Can I just hand over one bundle?

Yes. Once your records are organized, you can prepare an accountant-ready export of invoices, categorized expenses, and attached documents to hand over as a single package.

Cash Workspace

Use the Freelancer template

Bookkeeper handoff · Records setup

Get your records ready for a new bookkeeper

Hiring a bookkeeper only saves you time if they don't have to spend the first month chasing your shoebox. A new bookkeeper needs every invoice with its direction and status, expenses categorized with receipts attached, and your contracts and tax documents filed by fiscal year. Cash Workspace gives you a place to assemble all of it into one organized, exportable bundle so your bookkeeper can start on day one instead of week four.

Start a free workspace See the accountant document checklist

The problem

Why bookkeeper handoffs start badly

Most solo operators bring a bookkeeper a folder of mixed PDFs, a few spreadsheets, and a phone full of receipt photos. The bookkeeper then bills hours just to figure out what's there.

Invoices live in three places, so the bookkeeper can't tell what was paid versus still owed.
Receipts are photos with no category, vendor, or amount recorded alongside them.
Contracts and tax documents are scattered across email, with no fiscal-year structure.
Money you sent out and money clients paid in are jumbled, so direction is unclear.
There's no single export to hand over, so the first meeting becomes a scavenger hunt.

The workflow

A guided setup to assemble a bookkeeper-ready bundle

Work through these steps once and you'll have everything a new bookkeeper needs, organized in one place.

1
List every invoice
Record each invoice with its direction (money in or out), amount, dates, and a status of draft, sent, partially paid, paid, or overdue.
2
Categorize expenses and attach receipts
Record each expense by category, date, vendor, and amount, then attach its receipt so figure and proof stay together.
3
File contracts and tax docs by year
Put signed contracts, prior returns, and tax documents into fiscal-year folders so the bookkeeper sees one period at a time.
4
Confirm the period is complete
Run down a simple onboarding checklist to make sure each month has its invoices, receipts, and statements accounted for.
5
Prepare the export package
Produce an accountant-ready export of invoices, categorized expenses, and attached documents to hand over in one bundle.

Record structure

What every record needs before handoff

Consistent fields turn a shoebox into a bundle a bookkeeper can actually open and use.

Direction: Whether the invoice is money you billed or a bill you owe, so the bookkeeper isn't guessing.
Status: Draft, sent, partially paid, paid, or overdue for each invoice.
Fiscal year: The period the record belongs to, so each year stays self-contained.
Expense category: A product-defined category for each cost so similar expenses group together.
Vendor and amount: Who you paid and how much, recorded next to the receipt.
Date: When the invoice was issued or the expense incurred.
Attachment: The receipt, contract, or tax document attached to its record.
Client / counterparty: The client or vendor the record relates to, kept consistent across the bundle.

Example setup

An example bookkeeper-ready bundle

One way to lay out the workspace so a new bookkeeper finds everything fast.

Invoices by fiscal year

Every invoice for the period, marked with direction and status, in date order.

Expenses with receipts

Each expense recorded by category, vendor, date, and amount, with the receipt attached.

Contracts and tax docs

Signed contracts, prior returns, and tax documents filed in fiscal-year folders.

Handoff export package

The prepared accountant-ready export ready to share with the new bookkeeper.

Common mistakes

Handoff mistakes to avoid

Handing over loose receipt photos with no category, vendor, or amount recorded.
Leaving invoice status blank, so the bookkeeper can't tell paid from outstanding.
Mixing two fiscal years in one folder, forcing the bookkeeper to untangle periods.
Keeping contracts only in email, so they're missing from the bundle entirely.
Skipping a completeness check, so a whole month of records is discovered missing later.

How it helps

How Cash Workspace helps

One organized record set

Record invoices, expenses, and documents in one place so the whole bundle lives together, not across apps.

Receipts attached to expenses

Attach each receipt to its categorized expense so the figure and its proof never get separated.

Fiscal-year folders

Keep each year's contracts and tax documents together so a bookkeeper can work one period at a time.

Accountant-ready export

Produce a single export of invoices, categorized expenses, and attachments to hand over on day one.

Accountant document checklist

Know which documents to gather before handing off.

Send documents to accountant

Package and share your records in one bundle.

Monthly bookkeeping checklist

Keep each month's records complete and current.

Freelancer handoff checklist

A step-by-step handoff for solo freelancers.

Self-bookkeeping workspace

Organize your own books before bringing in help.

All finance workflows

Browse the full Cash Workspace workflow library.

FAQ

Bookkeeper handoff FAQ

What does a new bookkeeper actually need from me?: At minimum, every invoice with its direction and status, expenses categorized with receipts attached, and contracts and tax documents filed by fiscal year — all in one place they can open and export.
I'm moving from a shoebox of receipts — where do I start?: Start by recording each expense with its category, vendor, date, and amount, and attach the receipt to it. Work month by month using a simple onboarding checklist until each period is complete.
Can I just hand over one bundle?: Yes. Once your records are organized, you can prepare an accountant-ready export of invoices, categorized expenses, and attached documents to hand over as a single package.

Organizing help — not tax, accounting, or legal guidance

Cash Workspace is a free workspace for organizing invoices, expenses, receipts, clients, and documents. This page is organizing guidance only — not tax, accounting, legal, or bookkeeping guidance. Cash Workspace does not connect to your bank, does not scan or read your receipts for you, and does not move or collect payments. Whether an expense is deductible depends on your situation, so confirm it with a qualified accountant or tax professional.

Hand your bookkeeper a clean bundle on day one

Start a free workspace and assemble every invoice, categorized expense, receipt, and contract into one organized, exportable bundle so your new bookkeeper can start immediately.