# Hiring a Bookkeeping Assistant: When and for What

- Author: AutoBankConvert (https://www.autobankconvert.com)
- Published: 2026-05-14
- Updated: 2026-05-14
- Category: Client work
- Canonical: https://www.autobankconvert.com/blog/hiring-a-bookkeeping-assistant

> Hiring a bookkeeping assistant: the workload signs that say it is time, which client tasks to hand over first, and how to test a candidate on real statements.
Hiring a bookkeeping assistant makes sense once routine tasks crowd out review and client calls for three months running, not after one bad close. Hand the new assistant statement collection, conversion and first-pass categorizing, keep review and client advice yourself, and test every candidate on a real, anonymized statement before you make an offer.

## Which workload signs say a bookkeeping assistant is overdue?

A bookkeeping assistant is overdue when the same pattern repeats for a full quarter: closes finish later each month, review gets skipped, and new client enquiries wait days for a reply. One heavy month after a referral or a tax deadline is noise. Three months in a row is a staffing problem.

Look at your own calendar and your close dates before you look at job boards. The signs that matter are the ones you can count:

- **Close dates drifting.** If clients used to get their reports by the tenth and now get them by the eighteenth, the work has outgrown the hours.
- **Review shrinking.** When you stop opening the uncertain lines and just approve the batch, quality is being traded for time.
- **Admin eating evenings.** Chasing statements, renaming files and filing letters are the tasks that slide into nights and weekends first.
- **Prospects waiting.** A new client who waits a week for a proposal often signs with someone else.
- **No slack for a sick day.** If one missed day pushes every client late, there is no margin left.

The opposite signal matters too. If your hours are long because two difficult clients take a third of your week, an assistant will not fix that. Repricing or releasing those clients might. The guide on [how many clients a bookkeeper can handle](/blog/how-many-clients-can-a-bookkeeper-handle) is useful here, but the decision to hire should rest on your own counted hours, not a benchmark.

## Client tasks to hand a bookkeeping assistant first

The first tasks to hand a bookkeeping assistant are the ones with a clear right answer and a check built in: collecting statements, filing them, converting them and categorizing lines against existing rules. Keep anything that needs judgment about the client's business, such as new account choices, owner questions and month sign-off, for yourself at first.

A useful way to sort your work is by how easy a mistake is to catch. Statement conversion is easy to check, because the opening balance plus the transactions must reach the closing balance. A wrong category on a known vendor shows up in review. A wrong answer to a client about whether an expense is deductible may never be caught.

### A first-month handover list

Here is one example order for handing over work. Adjust it to your clients.

1. **Week one.** Request and chase monthly statements, name and file them, and keep the missing-statement list current.
2. **Week two.** Run conversions and record which statements failed a balance check.
3. **Week three.** Categorize lines that match an existing client rule, and leave everything else for you.
4. **Week four.** Draft the uncertain lines with a suggested account and a short note on why.

The assistant learns the clients through their documents before they learn them through conversations. That order protects the client relationship while the new person is still finding their feet. For the coaching side of this, the guide to [training a new bookkeeper on client files](/blog/train-a-new-bookkeeper) covers how to teach one client's books at a time.

## Testing a bookkeeping assistant candidate on real statements

A bookkeeping assistant candidate is best tested on a short, paid task using one real statement with the client's identity removed. Interviews show how someone talks about the work. A test shows how they do it, including whether they notice when the numbers do not add up.

Pick a statement you have already processed, so you know the right answer. Remove the client's name, the account number and anything else that identifies them. Then plant one or two problems you would expect a good assistant to catch.

### The test task, step by step

1. Give the candidate one month's statement as a PDF, a short chart of accounts and five vendor rules.
2. Ask them to put every line into a spreadsheet with date, description, amount and account.
3. Ask them to check that the opening balance plus the lines equals the closing balance, and to say what they did if it did not.
4. Ask them to list any lines they were unsure about, with a one-sentence question for the client.
5. Give a time limit of about ninety minutes and pay for the time.

### Scoring the test

The table below is an example scoring sheet. The weights are a suggestion, not a standard.

| What you check | Example of a strong answer | Example of a weak answer | Weight |
| --- | --- | --- | --- |
| Balance check | Found the 85.00 gap and traced it to a fee line at the foot of page two | Did not run the check | High |
| Known vendors | All five rule vendors coded to the right accounts | Two rule vendors coded differently from the rule | Medium |
| Unclear lines | Listed three lines with clear client questions | Guessed an account for every line | High |
| Format | Dates and amounts consistent, one row per line | Mixed date formats, merged rows | Low |
| Time | Finished inside the limit with notes | Ran well over without saying why | Low |

A candidate who guesses on every line is a bigger worry than one who asks too many questions. Questions can be trimmed with experience. A habit of guessing tends to show up later as a wrong number in a client's report.

## Employee or contractor status for a bookkeeping assistant

A bookkeeping assistant can be engaged as an employee or as an independent contractor, and the choice is not just a preference. In the United States, the business has to decide the worker's status from the real relationship, and the IRS looks at who controls how the work is done.

The [IRS page on independent contractors and employees](https://www.irs.gov/businesses/small-businesses-self-employed/independent-contractor-self-employed-or-employee) groups the evidence into three kinds: behavioral control over how the work is done, financial control over the business side of the job, and the type of relationship, such as contracts, benefits and how permanent the arrangement is. If you set the assistant's hours, train them in your methods and supply the software, those facts point one way. If they serve several firms, set their own methods and invoice you, they point the other way. The IRS page also notes that either side can ask the IRS to decide when the status is unclear.

This post cannot tell you which status fits your arrangement. Talk to your own accountant or an employment adviser before you sign anything, and write down the reasons for the decision you make.

Status also shapes the practical setup. A remote contractor working from their own machine raises different questions about where client files live than an employee using your equipment. The guide to [working with a remote bookkeeping team](/blog/working-with-a-remote-bookkeeping-team) covers shared access and handoffs, and the comparison of [desktop accounting software and cloud tools](/blog/download-accounting-software-or-cloud) matters if your clients' books still sit on one office computer.

## How many hours should a first bookkeeping assistant work?

A first bookkeeping assistant usually needs fewer hours than the owner expects, because the handed-over tasks are the fast ones. Start from the hours you spend on those tasks today, add time for learning and questions, and offer that as a part-time role you can grow.

Work it out from a real month. Suppose, as an example, you track your time for four weeks and find:

| Task | Your hours per month (example) |
| --- | --- |
| Requesting and chasing statements | 9 |
| Naming and filing documents | 5 |
| Converting statements and fixing failed checks | 12 |
| Categorizing rule-matched lines | 10 |
| **Total that can move** | **36** |

An assistant will take longer than you on those 36 hours for the first few months. Allow perhaps half again, which puts the role near 54 hours a month, or roughly 12 to 14 hours a week. That is a part-time role, and it frees your 36 hours for review, calls and new clients.

Be careful about tasks that shrink with tools. If statement conversion and categorizing take you 22 hours because you type lines by hand, automating that step may remove more hours than a hire would. AutoBankConvert, for instance, converts a month of client statements in one batch, checks each statement's balance and sends uncertain lines to a review queue, which changes what the assistant spends their week on. Price the tool against the hours before you write the job advert.

## Hiring a bookkeeping assistant before the work is written down

The most common reason a first bookkeeping assistant fails is that the work only exists in the owner's head. The new person asks the same questions every week, the owner answers them in a hurry, and both decide the hire was a mistake. Writing down the routine first fixes most of it.

You do not need a manual. You need one page per recurring task and one page per client:

- **Per task.** Where the inputs come from, the steps, and what "done" looks like. For conversion, done might mean every statement passed its balance check or is on the exceptions list.
- **Per client.** Which accounts exist, how statements arrive, which vendors are tricky, and who at the client answers questions.

The client pages are the same facts you gather at onboarding, and the [bookkeeping client onboarding checklist](/blog/bookkeeping-client-onboarding-checklist) is a good template for them. If a client was onboarded before you had a checklist, filling in their page is a good first task for the assistant, with you checking it.

There is a related mistake on the other side. Some owners write so much that the assistant spends the first month reading. Keep each page short enough to use while doing the task, and let the assistant fix pages as they find gaps.

## The bookkeeping assistant's first ninety days with clients

A bookkeeping assistant's first ninety days should move them from watching to doing to owning, one client at a time. By the end, they should run the routine tasks for most clients with you reviewing, and know when to stop and ask.

### Days 1 to 30

The assistant shadows a full close, then does the collection and filing tasks for every client. You check their work daily at first, then every few days. Keep a running list of their questions. The questions show where your written pages are thin.

### Days 31 to 60

The assistant runs conversion and rule-based categorizing for your simpler clients. Pick clients with one or two accounts and few unusual lines. You review every client before sign-off, and you note each correction so the same one does not repeat.

### Days 61 to 90

The assistant takes on the more involved clients and starts drafting the uncertain lines with a suggested account. Introduce them to clients by email as the person who will send statement reminders, so the first contact is a small, useful one.

At the ninety-day mark, sit down and compare your hours with the month before the hire. If your review and client time went up and close dates came back in, the hire is working. If you are still doing the same tasks and also checking theirs, look at which tasks never moved and why. When you are ready to see what an automated statement run would take off both your desks, [request a spot on AutoBankConvert](/get-started).