Learn It
Most bookkeeping problems are really communication problems. The client does not know what you need. You do not know what the transaction was for. The fix is not more accounting knowledge — it is better questions.
Ask Specific Questions
A weak question is vague. The client has to guess what you mean. A strong question includes the facts and tells the client exactly what you need.
Weak:
"What is this transaction?"
Stronger:
"There is a $1,850 payment to ABC Equipment on March 12. Was this for equipment, repairs, a deposit, or something else? If you have the invoice or receipt, please send it."
The stronger question includes the date, the amount, the payee, and a specific request. The client can answer it without guessing what you want.
Requesting Documentation
When you need a document, ask for it specifically. Do not say "send me the paperwork." Say "please send the invoice or receipt for the $1,850 payment to ABC Equipment on March 12." The more specific you are, the more likely the client sends the right thing the first time.
Explain Why You Need It
Clients are more likely to respond when they understand why you are asking. Instead of just requesting a receipt, explain: "I need the receipt so I can record this in the right expense account — it affects your profit and your tax return."
Avoid Accounting Jargon
Most clients do not know what "accrual," "reconciliation," or "chart of accounts" means. Use plain English. Instead of "I need to reconcile your A/R aging," say "I need to check which customer invoices are still unpaid so the balances are correct."
Communicate Discrepancies Clearly
When you find a problem, explain it simply. Instead of "your loan balance does not agree with the liability account," say "the loan balance in the books is $31,600, but the bank says you owe $30,900. I need to check the last few payments to find the $700 difference."
Batch Your Questions
Clients are busy. Sending five separate emails over a week is harder to manage than one organized list. Batch your questions, number them, and give the client a single place to respond. This respects their time and increases the chance you get complete answers.
Document Client Answers
When the client answers, write it down. If the owner says "that $2,500 was a transfer to savings," note it in the transaction or in a workpaper. This creates a trail that explains why you recorded something the way you did. See Documentation and Judgment for more on this.
Bookkeeping vs. Tax Questions
Some questions are not bookkeeping questions. Tax advice, legal questions, and entity structure decisions belong to a CPA, tax professional, or attorney. The bookkeeper should recognize when a question is outside their scope and refer the client to the right professional — while still doing their own job correctly.
Set Reasonable Boundaries
It is okay to tell a client you need more time, that you need documents before you can finish, or that a question is outside your scope. Setting boundaries is professional. Promising answers you cannot give is not.
See It
Here are examples of poor and improved bookkeeper communication. Notice how the improved versions are easier for the client to answer.
Unclear bank transaction
Poor:
"What is this?"
Improved:
"There is a $2,500 transfer out of the checking account on March 14. The bank description just says 'TRANSFER.' Can you confirm where this money went — was it a transfer to savings, a loan payment, or something else?"
Missing receipt
Poor:
"I need receipts."
Improved:
"There is an $87.50 charge at Downtown Bistro on March 9 on the business credit card. Was this a business meal? If so, who attended and what was the business purpose? Please send the receipt if you have it."
Old A/R balance
Poor:
"Can you look at the old receivables?"
Improved:
"There is an unpaid invoice to Jensen Corp for $850 that is 150 days old. Should we pursue collection, write it off, or send it to a collection agency? Let me know how you'd like to handle it."
Tax question from the client
Poor:
"Yes, that's deductible." (guessing)
Improved:
"I can record the $1,500 payment to the State Dept of Revenue in the books once we confirm what tax it was for. Whether it is deductible on your tax return is a question for your CPA or tax preparer — I recommend reaching out to them."
Do It
For each unresolved item, type the question you would send to the client. The system evaluates whether your question includes the key facts the client needs to answer clearly.
Do It — Client Questions Workpaper
For each unresolved item, type the question you would send to the client. The system will evaluate whether your question is clear and answerable.
Include the date, the amount, the payee or customer, what information is missing, and a specific request for documentation or clarification. Do not worry about exact wording — the system looks for the key elements.
March 14 · $2,500
A $2,500 transfer out of the checking account. The bank description says only 'TRANSFER.' No receipt or invoice is available.
Prove It
Answer each question, then read the explanation. There's no score — this is just to help the ideas stick.
Question 1
A bookkeeper sees an unclear $1,850 payment to 'ABC Equipment' on March 12. Which question is stronger?
Question 2
A client asks the bookkeeper whether they should classify their business as an LLC or an S corporation. What should the bookkeeper do?
Question 3
Why is it better to batch your client questions instead of sending them one at a time throughout the week?
Key Takeaways
- Ask specific questions with the date, amount, payee, and a clear request — not 'what is this?'
- Explain why you need information so the client understands the importance.
- Avoid accounting jargon — use plain English the client can understand.
- Batch your questions to respect the client's time.
- Document client answers so there is a trail explaining your decisions.
- Refer tax, legal, and entity questions to the appropriate professional.
- Set reasonable boundaries — it is okay to need more time or more information.