Questions to Ask a New Bookkeeping Client
A bookkeeper or small accounting practice can work through these questions with a new bookkeeping client in two sittings. The first group is for the discovery call, where you size the job and decide whether you want it; the rest are for intake, covering the accounts and who can sign in to them, money coming in, money going out, payroll and tax, and the reports and routine you will keep. Each note covers what the answer shows about the file or the client, and marks the tax questions that belong with the preparer and not with you.
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The questions
Each question, and why to ask it
Discovery call
What happened that made you decide to hand the books to someone else?
Why ask it
A tax bill nobody saw coming puts the back years first, a lender asking for statements puts a deadline first, and a bookkeeper who quit puts the handover first. Make that one thing visibly better inside two months. An owner with no trigger who is comparing prices will probably be comparing them again next year.
What does the business sell, and how do customers pay you?
Why ask it
Have them follow one sale from the order to the bank deposit. Cards at a counter, invoices on terms and payments through an app each park the money somewhere different on the way, and those stops are where unreconciled balances build up. An owner who can trace it cleanly usually has better books than they fear.
What type of legal entity is the business, and how is it taxed?
Why ask it
Owners often give the legal form and the tax treatment as one answer when they are two, so ask to see the last filed return or the registration papers. It decides how owner pay and equity are recorded from the first entry. A shrug here is common and no bad sign, but it makes the tax preparer your first phone call.
Which accounting software are the books in, and who owns the subscription?
Why ask it
If the last bookkeeper's firm pays for the file, getting it moved into the client's name is the first task, and it can drag. Ask who the primary admin is and whether that person still answers email. 'A spreadsheet' or 'a shoebox' is a setup job to quote for, and often an easier start than a file somebody else tangled.
What is the last month you would trust the books for?
Why ask it
Owners date this from the last time they looked, not the last time anything was reconciled. Once you are in, find the last reconciliation report in the file and price the catch-up from that date. 'It should all be in there' usually means transactions were categorized off the bank feed and never checked against a statement.
Who has been keeping the books until now, and may I contact them?
Why ask it
The owner at the kitchen table, a relative, an employee who left and another firm each leave a different kind of file behind. A yes to contacting them saves hours of guessing at old entries. A flat no, or a story in which every past bookkeeper was the problem, is worth weighing before you quote.
Is there anything in the books you already know is wrong, or would rather I heard from you first?
Why ask it
Owners nearly always know where the trouble sits: the loan that was never entered, the year of missing card statements, the account that stopped balancing when a certain employee left. Hearing it now takes five minutes, and finding it alone can take a day. Thank them for whatever comes out, because the next awkward thing will reach you sooner.
Roughly how many transactions go through the bank and card accounts in a month?
Why ask it
Volume drives your hours more than revenue does: a consultant billing six clients and a cafe with the same sales are not the same engagement. If they cannot guess, ask for one month of statements for every account before you price, and count the lines yourself.
What has bookkeeping been costing you so far, in fees or in your own evenings?
Why ask it
Your quote will be measured against this figure whether you hear it or not. An owner who has done the books free on Sunday nights finds any fee steep until those hours have a price on them. If the last firm charged far less than you would, find out what that fee covered before you decide you are too expensive.
Who owns the business, and does anyone else have a say in the money?
Why ask it
Partners, a spouse who signs checks or an investor who receives statements all change who you answer to and who may see what. Take down names and percentages, since they also set up the equity accounts. Two owners who describe the split differently need to settle it between themselves, in writing, before you record anything.
Is there more than one company, location or line of business to keep apart?
Why ask it
A second entity mentioned in week three doubles work you priced for one. Find out whether money moves between them, because transfers among related companies are some of the hardest entries to untangle later. 'It is all sort of one thing' usually means one bank account has been paying for two businesses.
Is there a date behind this: a tax filing, a loan application, a sale of the business?
Why ask it
A real deadline changes the order you work in, since a lender may want two past years clean before you touch the current month. Ask who is waiting for the figures and exactly what they requested. When the date is days away, say plainly what can and cannot be ready before you accept.
What do you want the books to tell you that they do not tell you today?
Why ask it
Some owners want to know whether a job made money, some whether they can afford a hire, and some only want the tax preparer to stop complaining. Those are three levels of service at three prices. Write their words down and hold your first set of reports up against them.
Accounts and access
Which bank accounts does the business have, including ones you rarely use?
Why ask it
The savings account opened for tax money and the old account at a previous bank are the ones that go unmentioned. Request a statement from each, even with no activity, and compare the list with the balance sheet. An account on the books that the owner does not recognize needs an answer before you go further.
Which credit cards carry business spending, and whose name is each one in?
Why ask it
A personal card used for the business has to be handled differently from a company card, so mark which is which. Ask about store cards and fuel cards too, because those seldom come with a feed. Three cardholders and no receipts is a conversation about routine, and it goes better now than in month four.
What does the business owe: loans, credit lines, leases, equipment financing, money from the owner?
Why ask it
For each one you need the lender's statement or the agreement, because the balance in the books is often wrong where whole payments were posted with nothing split out for interest. Money the owner put in belongs on the list, along with whether anyone wrote down that it would be paid back. Forgotten debts tend to surface as automatic payments nobody can explain.
Which payment processors, apps or online stores does money pass through before it reaches the bank?
Why ask it
Every one of them is an account to reconcile, with fees, refunds and holdbacks hidden inside a net deposit. Get a login or a monthly report for each. The usual finding is the bank deposit recorded as the sale, with the fees never entered and revenue understated by that much.
Do personal expenses ever go through the business accounts, or business costs through your own?
Why ask it
Put it as a practical matter, with no judgment in your voice, and you will mostly hear the truth. The odd grocery run can be coded and forgotten. A business account that pays the household bills every month means more sorting at every close, and your fee should say so.
Who has a login to the bank, the software and the payroll system today, including people who have left?
Why ask it
Make the list together while you have them on the call. A former employee or an old bookkeeper who can still sign in is something for the owner to close this week, and offering to walk them through it is an easy early service. Passwords shared by text mean there is no record of who did what.
How will I see the bank activity: my own login, a view-only user, a feed, or statements you send?
Why ask it
What a bank offers an outside bookkeeper differs from one bank to the next, so have the client ask theirs what accountant or view-only access exists. Turn down a copy of the owner's own password even when it is kindly meant, because if money ever goes missing you do not want to be the other person who could have moved it.
Does the business take in or pay out cash, and where is that written down?
Why ask it
Cash that never touches the bank is invisible to you unless a till report, a deposit slip or a log says it existed. Find out who counts it and who carries it to the bank, and whether those are two people. If tips or wages paid in cash come up, stop and have them ask their payroll provider or tax preparer how those must be reported there.
Can you get me statements for every account back to the last month that was reconciled?
Why ask it
This is the first real test of how the client follows through. Someone who sends the lot within a few days will be easy to keep current, and someone who needs four reminders has shown you what month end will be like. Name a date, and do not begin the cleanup on a partial set.
Money in
Who creates invoices, and in what system?
Why ask it
Invoices made in a word processor or a separate job app never reach the ledger unless somebody types them in a second time. Check whether that system can connect to the books or whether you would be importing by hand, since that changes your hours. Then ask who decides a job is ready to bill, which is where work goes uninvoiced.
Do you count a sale when the invoice goes out or when the money comes in, and which way does the tax return do it?
Why ask it
This is the cash-or-accrual question in words an owner can answer. Many small files are a mix, with invoices tracked and bills entered only when they are paid, so look at how the last return was prepared before you tidy anything. Moving from one basis to the other is the preparer's decision, never a cleanup step.
What payment terms do you give customers, and who chases an invoice once it is past due?
Why ask it
'Nobody, really' is the common reply to the chasing part. Decide whether reminders are in your service before the client assumes they are, because collection calls are a different job from recording payments. If you take them on, agree what you may say and at what point the owner steps in.
Do you take deposits, retainers or payment up front before the work is done?
Why ask it
Whether that money is income on the day it lands or something still owed to the customer depends on the basis the books are kept on, and owners seldom know which way it was booked. Ask for a list of what is being held now and for whom. In a business that runs on retainers, that list can move the profit figure more than anything else you find.
If I printed the list of customers who owe you money, would you believe it?
Why ask it
A laugh tells you the list is not maintained. Old receivables are commonly invoices that were paid and never matched, duplicates, or debts nobody expects to collect. Go down the list with the owner early, line by line, because only they know which is which.
Does money come in that is not a sale: grants, rent, refunds, insurance payouts, transfers from the owner?
Why ask it
Deposits like these get coded as sales by whoever was in a hurry, which inflates revenue and sometimes the sales tax figure along with it. Have the owner flag every large deposit that did not come from a customer in the months you are catching up. Their memory will beat any memo line on the statement.
Money out
How do bills reach you: paper mail, email, a supplier portal, automatic charges to a card?
Why ask it
You are counting the places you would have to look to know what is owed. One inbox that everything gets forwarded to is the simplest fix and worth proposing on the spot. Where a bill exists only as a charge on the card statement, the books can show what was paid and never what is owed, and the owner should know that is the trade.
Who decides that a bill gets paid, and who actually sends the money?
Why ask it
In a small business both are often the owner, and that is fine. The setup to worry about is an office manager who adds suppliers, approves bills and releases payments alone. Record the answer in your file even where changing it is not your job.
Do you want me to pay bills for you, or to record what you have already paid?
Why ask it
Plenty of clients assume a bookkeeper pays the bills, and plenty of bookkeepers assume the reverse. If you do take it on, an arrangement where you prepare the payments and the owner releases them protects you both. Put the choice in the engagement letter in a sentence the client could repeat.
How does a receipt get from the person who spent the money to the books?
Why ask it
Glove compartments and camera rolls are the usual honest answers. Pick one route, such as a capture app or a dedicated email address, and say what happens to a charge that still has no receipt at close. How much paper must sit behind an expense depends on where they file, so check the local rule before you promise them a cutoff.
Do you or your staff pay for business costs out of pocket, and how does that get repaid?
Why ask it
Out-of-pocket spending leaves no trace in the business bank account, so those costs go missing unless there is an expense report or a mileage log. An owner who has never claimed any of it may be owed money by their own company. Agree how often it gets settled.
Which suppliers do you owe right now, and is anything overdue or in dispute?
Why ask it
Compare what they tell you with the unpaid bills report, if anyone has been using one. Old open bills in the file are frequently ones paid by card and never marked off. A real overdue balance with a supplier the business depends on is news the owner needs to hear said aloud.
Do you carry stock or materials, and when did someone last count them?
Why ask it
Skip it for a business that sells only its time. Where there is stock, find out where the count is kept and whether the figure in the books has ever been adjusted to match it. A balance that has sat unchanged for two years means every margin on the reports since then is a guess.
What large purchases fall in the months I am catching up: vehicles, equipment, a build-out?
Why ask it
Big items tend to be sitting in an expense line or in an account called 'ask my accountant'. Collect the invoice and any financing papers for each and send the list to the tax preparer, who decides what is treated as an asset and over how long. The bank description is not enough to make that call.
How do the owners get paid: a salary through payroll, transfers, checks to themselves?
Why ask it
The right way to record it depends on the entity and on local tax rules, so this goes to the preparer together with the entity answer. What you need from the owner is the pattern: how much, how often, from which account. A transfer labeled 'loan' with no paperwork behind it is worth a question.
Payroll and tax
Do you have employees, and who runs payroll?
Why ask it
A payroll provider, the software's own module and an owner doing it by hand are three very different starting points. Get the pay schedule and a recent payroll report, and see whether the wages in the ledger agree with it. Before you agree to run payroll yourself, check that you are permitted and insured to do it where you work.
As far as you know, are all payroll tax filings and payments up to date?
Why ask it
'As far as you know' leaves them room to admit they are not sure. Ask to see the confirmations from the provider or the tax agency's online account. A missed payment is far better found now than by a notice next year, and the fix belongs with the preparer or the payroll provider, not in a journal entry of yours.
Do you pay contractors or freelancers, and what paperwork do you collect before the first payment?
Why ask it
What has to be collected and reported for a contractor depends on the country, so find out the local list and build it into the routine before the next payment goes out. Owners commonly have nothing on file and find at year end that the contractor has stopped answering. If someone on the list works set hours under the owner's direction, flag it for the preparer and leave the judgment to them.
Do you charge sales tax or VAT, and where are you registered to collect it?
Why ask it
Take down every registration, its filing frequency and the login. Whether they ought to be registered somewhere else, because of online sales or work across a border, is a determination for a tax professional. Your part is to notice sales going to places that are not on the list and to say so.
Who files the sales tax returns today, and when is the next one due?
Why ask it
Software can calculate the tax and still leave the return unfiled, and owners often assume otherwise. Each return needs a named person, and if that will be you, the due dates go in your calendar before the call ends. Find out as well whether the tax collected is set aside or spent as it comes in.
Who prepares the business tax return, and may I speak to them directly?
Why ask it
A direct line to the preparer saves the client money, because the two of you can agree on the chart of accounts, the year-end adjustments and who does what. Their office may want the client's written permission first. No preparer at all with a return coming due is something to raise the same day.
What was the last year filed, and can I see that return and the year-end entries that went with it?
Why ask it
The books should open the next year in agreement with what was filed, and in a neglected file they seldom do. Where the preparer made adjustments on their own worksheets that never came back to the ledger, ask for those entries before you reconcile forward. Note the year-end date while you are there, and hear how many years are unfiled before you quote.
Are there open letters, balances or payment plans with a tax agency?
Why ask it
Read the letters themselves, since owners summarize them hopefully. A payment plan is a fixed monthly outflow to record and a liability to find in the books. Answering an agency is generally work for the preparer or another licensed representative, so know where your own limit sits and say it.
Are there other filings or renewals somebody has to remember: business licenses, annual reports, insurance audits?
Why ask it
None of these is bookkeeping, and all of them land in the bookkeeper's inbox once they are missed. Either track them or say who does. An insurer's yearly audit, where the client has one, will want payroll and contractor totals from you, so find out when it falls.
Reports and routine
Which reports do you want each month, and what will you do with them?
Why ask it
The use they name tells you what to build. An owner who mentions a decision, such as setting prices or timing a hire, should get a report shaped to it. One who says 'whatever is normal' will probably not open the attachment, so start that client on one page with a three-line summary.
By what day do you need last month's numbers?
Why ask it
Work backward from their date to yours: figures by the tenth mean statements and answers in your hands by about the fifth. Say that aloud so the dependency is theirs too. A client who wants numbers on the second and sends documents on the twentieth should hear now that both cannot be true.
Does anyone outside the business get the financials: a lender, an investor, a landlord, a grant maker?
Why ask it
Outside readers often want a set format or basis, and a loan agreement may contain reporting dates and ratios the owner has forgotten. Go by the agreement, not the owner's memory of it. With no outside reader, you are free to shape the reports around how the owner thinks.
Who inside the business may see the reports, and is there anything some of them should not see?
Why ask it
Wages and what the owners take out are the usual answers. That decides who gets a login to the software and at what permission level, and whether the monthly email goes to the owner alone or to a manager too. Settle it before the first report leaves, since one forwarded to the wrong inbox cannot be recalled.
Do you need results broken out by job, location, product line or anything else?
Why ask it
Tracking like this is cheap to set up at the start and painful to add backward across a year of entries. Ask what question the breakdown would answer and build only that. An owner who wants seven breakdowns and marks nothing on the receipts will get an empty report, so settle who tags each transaction.
When I have a question about a transaction, who do I ask, and how soon will I hear back?
Why ask it
You want one named person and one place to ask, not whoever picks up. The owner is frequently the only one who knows what a charge was and also the slowest to reply, so propose a single list of questions each week in place of a stream of messages. Explain what you do with items still unanswered at close, so that the holding account does not become permanent.
When you say bookkeeping, which jobs are you picturing me doing?
Why ask it
Let them say it first, then correct the picture. Clients fold tax advice, payroll, bill paying and collections into the one word, and the engagement letter should name what is in and what is out. Whether you may prepare a return or give tax advice at all depends on your credentials and where you practice.
Would you like the catch-up work quoted as its own job, apart from the monthly fee?
Why ask it
Keeping the two apart stops a messy past from distorting the price of an ordinary month. Quote the cleanup after you have seen the file, as a range tied to the number of months and accounts, and say what would move it. A client who presses for one flat figure before granting access is asking you to carry the risk of whatever is in there.
What would next tax season have to look like for you to call this money well spent?
Why ask it
Ask it last, once they have heard what you would do. Owners tend to name small, checkable things: no hunt for papers, no surprise bill, the return in without an extension. Repeat theirs in your follow-up email, and hold it up against how that season really goes.
How to run a bookkeeping client intake
Practical guidance for the conversation itself
On the discovery call
Keep the call to the first group
The Discovery call group is sized for a first conversation of about half an hour, and on a short call the first six will do. They tell you what kind of business it is, what state the file is in, why the owner is calling and whether you want the work. Everything from Accounts and access onward belongs in an intake form or a second meeting, when the client has documents within reach and you have decided to go ahead.
Ask for the document behind the answer
Owners answer from memory, and memory is kind. For the entity, ask for the last filed return. For debts, the lender's statement. For payroll, a recent report from whoever runs it. You are not doubting the client. Opening balances built on recollection get corrected later, one awkward email at a time.
Look at the file before you name a price
The owner's description of the books and the books themselves are often far apart, in both directions. If you can, get view access or a backup and spend half an hour in it before you quote: the date of the last reconciliation, the size of any uncategorized or suspense account, and the age of the oldest unpaid invoice tell you most of what you need. If the client will not allow a look, quote the cleanup as a range and say what would move it.
Drop what does not apply
A solo consultant has no inventory, no cash drawer and perhaps no payroll, and asking about all three makes the call feel like a form. Use the answer to what the business sells to decide which later questions to skip. Add your own for the trade in front of you: job costing for a builder, tips for a restaurant, trust or client funds for a professional firm, where the rules on handling them should be checked with the client's regulator or tax preparer.
At intake
Build one list of accounts and who can get in
As the client answers the Accounts and access questions, fill in a single sheet: each bank account, card, loan, payment processor and system, who owns it, who can sign in today and how you will see it. That sheet becomes your reconciliation checklist every month, and it is the first thing a successor would need if you ever handed the client on.
Get your own access, never a borrowed password
Most accounting packages and many banks and payroll services have some way to invite an outside bookkeeper under a separate login, sometimes with view-only rights. What exists differs by provider, so have the client ask each one. A login of your own leaves a record of what you did, and it can be switched off without the owner changing every password they have.
Give the paperwork a deadline
Send one request listing every statement, return, agreement and report you need, with a date. Hold the start of the cleanup until the set is complete. Work begun on nine of eleven accounts has to be reopened when the other two arrive, and the client learns that sending things late costs them nothing.
Call the tax preparer in the first two weeks
Several intake answers end at the same door: the entity, how the owners are paid, what counts as an asset, how deposits and contractors are treated. Collect those into one short list and ask the preparer in a single conversation, along with how they like to receive the year-end file. A preparer who knows you exist before the deadline is far easier to work with at it.
Write the scope back in plain words
After intake, send the client a short summary of what you will do each month, what you will not do, what you need from them and by which day, and how the cleanup is priced. Use the answers they gave under Reports and routine. If something in it surprises them, you would much sooner find out before the first invoice.
Reading the answers
Signs of a client who will be easy to keep current
They know roughly when the books were last right. They send what you ask for within a few days. They can name their tax preparer and are happy for you to talk. They ask what you need from them. None of this requires tidy books: an owner with a two-year backlog and quick replies is a better client than one with a clean file who goes quiet for a month.
Answers worth slowing down for
Every earlier bookkeeper was at fault. Access will come 'once we get started'. Nobody is sure whether payroll or sales tax filings were made. The owner wants the result changed, not the records fixed. A single one calls for a follow-up question. Several together call for a higher quote, a narrower scope in writing, or a polite no.
Questions you collect but do not decide
Whether a worker is an employee or a contractor, where the business must register for sales tax, how the owner should be paid and what can be deducted all turn on tax law that changes with the country or state, and on the credentials of whoever answers. Record what you see, pass it to the preparer or another licensed adviser, and book it the way they tell you. Saying 'that one is for your tax preparer' is part of the service.
Mistakes to avoid
Pricing the monthly work from a messy file
A backlog makes every month look heavier than it will be. Quote the catch-up as its own job, and base the monthly fee on what an ordinary month will take once the accounts are reconciled: the number of accounts, the transaction volume, payroll, sales tax and the reports they asked for.
Starting without an opening point you trust
If you begin entering the current month on top of balances nobody has checked, each reconciliation inherits the old errors. Find the last date at which the bank, card and loan balances in the books agree with the statements, or with the filed return, and work forward from there even if that date is further back than the client hoped.
Letting the word 'bookkeeping' stand in for a scope
To one client it means categorizing the bank feed. To another it means paying bills, chasing customers, running payroll and answering the tax agency. Name each task as in or out, in writing, and say what a request outside the list will cost.
Accepting every key you are handed
Grateful new clients offer the bank password, signing authority and the company card in the first week. The more of the money you can move alone, the less either of you is protected if something goes wrong. Take the least access that lets you do the work, and leave approving and releasing payments with the owner wherever that is practical.