Suppose a bookkeeper in another country has been entering your bills for three months and nobody on your side has opened a single report. That is the usual shape of a failed arrangement: the work leaves the building and nobody watches where it goes. Five mistakes lead there. Each has a plain fix.
Key Takeaways
- No agreed channel or schedule: questions sit unanswered and each side assumes the other is handling them.
- Hiring on a sales call alone: check credentials, references and a sample task first.
- Leaving the work unreviewed: read the reports monthly and check payroll tax payments yourself.
- Two teams with no shared process: write down who owns each task and how work passes between them.
- No plan for the people involved: tell your staff what is moving, why, and what stays with them.
Failing to Establish Clear Communication Channels
Say the bookkeeper asks what a $4,000 deposit was for, you are on a job site, and the entry waits a week. Multiply that by a month of transactions. The books fall behind.
Settle three things on day one. Pick one channel for questions, a reply time both sides can keep and a month-end close date. Add a short call every week or month, and keep a list of what needs your approval, such as new vendors and payments above a set amount. Then pick two or three numbers to check each month, for example the close date, the count of unreconciled items and how long questions take to answer.
Neglecting to Thoroughly Vet Potential Service Providers
A smooth sales call says little about the work. Before you sign, ask for two references from businesses like yours, a paid test task in your own software and the credentials that match the job.
Credentials depend on what you are buying. Anyone paid to prepare a federal return needs an IRS PTIN, and a CPA's license can be checked with your state board of accountancy. A bookkeeper does not usually need a license, so judge by references and the test task.
Ask what happens to your books if the firm closes or changes owner. Bench says it paused operations in December 2024, was acquired by Employer.com and resumed service in January 2025, so keep your own copy of your records whoever holds them. Our guide on how to choose an outsourced accounting firm lists more questions to ask.
Inadequate Oversight and Monitoring of Outsourced Activities
Outsourcing moves the work, and the responsibility stays with you. For payroll, the IRS says the employer is ultimately responsible for the deposit and payment of federal tax liabilities, and it advises employers to register with EFTPS and check payments themselves. It also treats the first missed or late payment by a provider as a red flag.
Oversight is quick if it is regular. Read the profit and loss statement and the bank reconciliation each month, spot-check a few entries and look at who can sign in to your accounts. Our post on data security concerns in outsourced accounting covers access rules in more detail. Keep the bank login and payment approval yourself.
Lack of Integration Between Outsourced and In-house Accounting Functions
Two teams that share no process produce duplicate entries and missing ones. Write down who owns each task, which software holds the record and how work passes from one side to the other. Our post on how to outsource bookkeeping services covers the setup.
Staff who used to do the books may worry about their jobs or their say. Tell them what is moving and why, and give someone on your team the job of working with the outside person.
Working styles differ too, and the difference shows in small things: how fast questions get answered and who flags a problem first. Name those expectations early.
Final Thought
A failed arrangement usually traces back to one of these five gaps. Each is cheap to close at the start and costly to close later. Fix one this week, then book a free consultation call to talk through the tasks and hours you want an assistant to take on.