Your First 90 Days With a Bookkeeper: What to Expect

You’ve signed the proposal. You’ve leaped. So… now what?

For many business owners, hiring a bookkeeper can feel like handing over the keys to a very messy car — you’re not sure what’s in the backseat, and you’re hoping no one opens the glove box. We get it.

That’s why the first 90 days of working with a bookkeeper matter so much. It’s where clarity begins and confidence gets built.

Here’s what those first three months look like.

Week 1: Kickoff & Intake

We start with a deep-dive onboarding session. This includes:

  • Reviewing your current setup (QuickBooks, spreadsheets, napkins—no judgment).

  • Identifying immediate gaps (missing records, open balances, old liabilities).

  • Clarifying your business structure, goals, and pain points.

This is where we start building your bookkeeping system around how your business runs—not just how software thinks it should.

Weeks 2–4: Cleanups & Catchups

Next comes the cleanup. This is where we:

  • Reconcile past months (or years, we’re not scared).

  • Separate business and personal expenses.

  • Organize your Chart of Accounts in a way that makes sense.

Think of it like bookkeeping triage: we stabilize your financials so you can move forward with confidence.

Weeks 5–8: Routine & Reporting

Once your books are in order, we:

  • Establish a monthly cadence for reconciliations and reviews.

  • Deliver clear, jargon-free reports so you know what’s going on.

  • Flag red flags (like cash flow issues or out-of-whack margins) before they turn into crises.

You’ll start getting that magical feeling of knowing where your money is—and what it’s doing.

Weeks 9–12: Strategic Layer

With your finances in good shape, we go deeper:

  • Start forecasting based on your actual numbers.

  • Discuss tax readiness (yep, even if it’s not April).

  • Identify cost-saving or growth opportunities hiding in plain sight.

You’re not just “keeping books” anymore. You’re building a financial foundation that supports better business decisions.

Bookkeeping That Builds Confidence

Bookkeeping onboarding shouldn’t feel mysterious or intimidating. It should feel like finally being able to breathe—and plan—confidently.

Clarity is closer than you think. Let’s talk.

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Stop Trying to “Catch Up” — Here’s What to Do Instead

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What Happens When You Finally Hand Off Your Books