Most of the pain in a bookkeeping engagement is created in the first two weeks, usually by things nobody asked for at the start.
Here is the checklist that removes it. Work through it once per client, in this order, and the rest of the year is quieter.
Not optional, even for a friend, and especially for a friend. It needs: scope, what is explicitly out of scope, fee and how it changes, payment terms, what you need from them and by when, and how either side ends it.
The most valuable line in a bookkeeping engagement letter is the one about what happens when records arrive late. Write it before it happens, not after.
Collect access as its own step rather than piecemeal over a month:
Note the date each was granted. CRA authorisations in particular are the ones that quietly expire or get revoked when someone else is added.
Agree, in writing, the date you are taking over from and what the balances are on that date. Cash, receivables, payables, HST owing, loans. If the previous records are a mess, say what you are relying on: "opening balances taken from the T2 filed for the year ended 31 December" is a sentence that protects you later.
| What | When | Whose job |
|---|---|---|
| Receipts and bills in | By the 5th | Client |
| Bank statements available | By the 5th | Client (or feed) |
| Bookkeeping done | By the 15th | You |
| Questions answered | Within 3 days | Client |
| Reports out | By the 20th | You |
Send that table with the engagement letter. Half of all chasing disappears when the client knows the 5th matters and why.
They are much harder to raise in month six: personal expenses run through the business, cash sales, a vehicle used for both, family on payroll, and whether there are other entities. None of this is accusation — it is scope. What you are really asking is "what will I find, and is it in my fee?"
Set up one route for documents and refuse the others politely. Email attachments scatter, texts vanish, and a shared folder nobody opens is worse than nothing. Whatever the route, it should work from a phone, because that is where receipts live. More on that in how to stop chasing clients for documents.
Book it at the start, in the calendar, before anyone needs it. Fifteen minutes at day 30 to ask what is working, what is confusing, and what they expected that has not happened. Almost every engagement that ends badly showed the signs in month one, and nobody scheduled the conversation where they would have surfaced.
General guidance for Canadian bookkeeping practices. Professional obligations differ by designation and province — check your own body's requirements for engagement documentation.