First 90 days with an offshore bookkeeper.

Month 1 – onboarding and foundation

Weeks 1–2: setup

The first two weeks are overhead, not output. Plan for this explicitly rather than expecting full productivity from day 1.

• Access provisioning. Accounting platform access (QBO accountant user, NetSuite user provisioning, etc.), Bill.com access, Slack/Teams addition, shared drive access, password manager seat.
• Tooling setup. VPN configured, MFA enforced, workstation verified (camera visible, background clean, disk encryption confirmed).
• Introduction to your stack. Chart of accounts walkthrough, vendor list review, customer list review, recurring transaction patterns.
• Process documentation. Your month-end close checklist (if documented) or initial documentation session (if not).

Weeks 3–4: first production work

First month of actual work starts at reduced scope. Target 60–70% of expected productivity, with higher review intensity.

• First close cycle. If they're joining mid-month, shadow current close. If joining at month start, attempt first close with heavy review.
• Daily or every-other-day sync. Short (10–15 min) calls to catch blocks early.
• Every deliverable reviewed. No sampling yet – review everything to calibrate quality.

What healthy month 1 looks like

• Basic transaction coding matches 85%+ of your prior coding (some differences expected based on judgment calls)
• Questions are specific and show understanding of the business context ("Should I code this uber ride to travel or entertainment given the nature of the meeting?" rather than "What is uber?")
• Bank reconciliation for at least one simple account completed successfully
• Comfortable with your accounting platform (if they weren't already)

Warning signs in month 1

• Unable to name vendors from your transaction history after 2 weeks (signals weak attention)
• Consistently missing deadlines even at reduced scope
• Questions stay generic, don't get more specific as they learn the business
• Deliverables need substantial rework each time (not just minor adjustments)

Month 3 – settling into steady state

Weeks 9–12: independence and reliability

By month 3, the engagement either is working or isn't. Signs of a working engagement:

• Books close reliably without intervention. You sign off on close, not execute it.
• Proactive communication. They flag issues before you notice, propose solutions, not just questions.
• Quality at target level. Rework rate low (under 10% of deliverables need adjustment).
• Process documentation growing. They've added to your SOPs, not just consumed them.
• Relationships with vendors/customers. Vendors recognize them on emails, customers know them by name.

Review cadence at month 3

By month 3, review intensity should be at steady state:

• Monthly close: partner/owner reviews the package and signs off
• Weekly sync: 15–30 minutes covering exceptions and upcoming work
• Spot-check sampling: 10–15% of deliverables get detailed review
• Quarterly deep-dive: more comprehensive review every 3 months

Red flags that mean the engagement isn't working

If you're at month 3 and the following are true, the engagement needs intervention:

• You still review every deliverable because errors are frequent
• Monthly close requires 5+ hours of your time (vs target of 1–2 hours)
• You're doing work "because it's faster than explaining" (suggests skill gap)
• Quality hasn't improved meaningfully between month 1 and month 3
• Communication is still generic/unclear after 12 weeks of working together

What to do if month 3 is bad

Options in order of escalation:

1. Specific coaching. Name specific issues, document expectations, give 30 more days for measurable improvement.
2. Scope adjustment. Maybe they're the right person at wrong scope – reduce complexity, try again.
3. Replacement. Through your provider, request replacement. Good providers have bench depth and handle this without drama.
4. Provider change. If the provider can't deliver an adequate replacement, switch providers. Don't sink further time.