How to Know If Your Books Are “Too Messy” for Your CPA

Many business owners assume their CPA will “fix” their books at tax time. That’s not how it works—and it’s why so many owners end up stressed, confused, or hit with unexpected fees in February and March.

CPAs prepare tax returns.
They rely on clean, accurate books to do that job efficiently.

So how do you know if your books are too messy to hand over without problems? Here are the most common warning signs.

1. Your CPA Asks More Questions Than Expected

A few clarification questions are normal.
A long list of follow-ups is not.

Red flags include:

• repeated requests for the same information

• questions about basic totals

• confusion about income or expenses

• requests for missing statements

This usually means the books aren’t reliable yet.

2. Your Accounts Aren’t Reconciled

If bank and credit card accounts haven’t been reconciled, your numbers are guesses—not facts.

Common symptoms:

• balances don’t match the bank

• old transactions are still “uncleared”

• you’re not sure which months are accurate

Unreconciled books almost always require cleanup before tax prep can begin.

3. Your Profit & Loss Doesn’t Make Sense

If you look at your P&L and think:

• “That seems way too high”

• “There’s no way I spent that much”

• “Why is income negative this month?”

• “I don’t recognize half these categories”

That’s a strong signal your books need attention before they go to a CPA.

4. Personal and Business Transactions Are Mixed

This is one of the biggest causes of tax-season delays.

If:

• personal expenses run through the business account

• business income hits a personal account

• owner transfers aren’t clearly labeled

Your CPA will either:

• send the books back for cleanup, or

• charge extra to untangle the mess

Neither option is ideal.

5. You’re Missing Receipts or Documentation

Large purchases without backup documentation create problems fast.

Watch for:

• missing receipts for equipment or travel

• unclear vendor payments

• lump-sum expenses with no detail

Even if the numbers are right, missing documentation can slow everything down.

6. You Haven’t Issued (or Prepared for) 1099s

If you paid contractors and haven’t:

• tracked totals

• collected W-9s

• reviewed who needs a 1099

Your books aren’t tax-ready yet.

This alone can delay filing.

7. You Feel Uneasy Sending the Reports

This is the simplest test.

If you hesitate before sending your reports to your CPA—or you feel the need to explain or apologize—that’s your answer.

Clean books create confidence.
Messy books create stress.

What to Do If This Sounds Familiar

The fix is not “wait and hope.”

The fix is:

• clean up transactions

• reconcile accounts

• organize documentation

• clarify owner activity

• deliver clean, reliable reports

That’s bookkeeping cleanup—and it’s best done before tax prep starts.

Final Thoughts

Your CPA isn’t judging you—but they do need clean inputs to do their job well. Addressing bookkeeping issues early saves time, money, and frustration for everyone involved.

This information is for educational purposes only and not tax, legal, or financial advice.

If you’re unsure whether your books are ready for your CPA, a cleanup review can give you clarity fast. Schedule a Bookkeeping Review and find out what needs fixing before tax season ramps up.