The sixty-second answer
Run both systems in parallel and pay for both for a month. Migrate in the order contacts, history, automations. Cut over on your quietest day, keep the old system readable for a full cycle, and cancel only after you have found real data in the new system that you last saw in the old one.
Migrations fail at the cutover, not the export
Ask people about a software change that went badly and they will describe the same week every time. The export worked. The import worked. Then somebody needed an invoice from fourteen months ago, or a note attached to a customer file, and it was not there — and the old subscription had lapsed nine days earlier.
That is the actual risk. Not data loss during transfer, which is rare, but data that never came across and was not missed until access to the source was gone. Every practice below exists to make that specific failure impossible.
It is a small-business problem in particular because there is nobody whose job this is. As of December 2024, 1.08 million of Canada's 1.10 million employer businesses were small [3]. Migrations at this scale happen in evenings, around real work, with the owner doing the checking.
Before you move anything
Get a real export from the old system and open it. Not a screenshot of an export button — the file itself, opened, with the row count checked against what the system says it holds. Do this before you sign anything with the new vendor, because if the export is bad, the whole plan changes.
Write down what "working" means. A short list: invoices go out, bookings appear in the right calendar, the customer list is complete, last year's history is searchable. This is what you will test against at cutover, and writing it beforehand stops the goalposts moving under enthusiasm.
Confirm what the change actually costs. Ask specifically about setup, migration assistance, and minimum terms. Canadian marketing law is unusually direct here: under subsection 74.01(1.3) of the Competition Act, a price that is not attainable because fixed obligatory charges or fees have been excluded is a false or misleading representation, with an exception only for charges imposed under an Act of Parliament or a provincial legislature [4]. A compulsory onboarding fee that appears at signature is exactly that pattern, and you are entitled to see it up front.
Ask how you would leave the new system. The best time to ask about the exit is before the entrance. There is no general legal right to portability for business software, which is why the domain-name comparison is instructive: under ICANN's Transfer Policy, registered name holders must be able to transfer registrations between registrars, transfer processes must be clear and concise, denial is permitted only on enumerated grounds — evidence of fraud, a reasonable dispute over identity, non-payment for a previous period, or a request within sixty days of creation or of a prior transfer — and a transfer lock must be removed, or an accessible removal method provided, within five calendar days [1]. Nothing obliges a software vendor to behave that well. Ask whether they do.
The order: contacts, history, automations
Contacts first. Everything else points at them. Move the customer list, deduplicate it properly while it is small enough to look at, and confirm the count in both systems. Resist the urge to "clean up later" — later is after the old system is gone.
History second. Invoices, jobs, notes, past bookings. This is the part people skip because it feels like archaeology, and it is the part they miss six weeks later. If the new system cannot take the history, decide consciously how you will keep it: a read-only archive, an exported file stored somewhere durable, or a period of overlap long enough to stop needing it.
Automations last. Scheduled reminders, mailing sequences, integrations, anything that sends. Migrate these with the sending switched off, verify them against a test record, and only then enable. A migration that fires a two-year-old reminder sequence at your whole customer list is a bad day made permanent — and Canada's Anti-Spam Legislation makes it more than embarrassing, since a commercial electronic message requires consent and must carry prescribed identifying and contact information regardless of which system sent it [5].
Parallel running is not optional
Keep the old system alive and readable for one complete cycle of whatever it does. For invoicing, that means through a month-end. For a booking system, through a full seasonal pattern if you have one. For a sales tool, one average deal length.
During that period, the new system is the source of truth and the old one is a reference. Do not enter data in both — that is how the two diverge and how you lose confidence in either. Read from the old, write to the new.
Cut over on your quietest day, not on the first of the month, and not the day before your busiest week. Give yourself a rollback point: a documented, specific answer to "if this is wrong at noon, what do we do". Most of the time you will not need it. The value is in having decided in advance.
Communications systems deserve extra margin because third parties are involved and their timelines are not yours. The Telecommunications Act opens by affirming that telecommunications performs an essential role in the maintenance of Canada's identity and sovereignty, and sets out policy objectives including the orderly development of a telecommunications system throughout Canada [6]. That is a statement about national infrastructure, not about your migration timeline — which is precisely the point. Number and mail routing changes move at the pace of the carriers, so schedule them with slack.
Closing the old system properly
When the parallel period ends and everything checks out, do three things in order. Take a final full export and store it somewhere you will still be able to open in three years. Confirm in writing what the vendor will do with your data after cancellation. Then cancel.
That last step is a legal obligation, not just tidiness. PIPEDA requires that personal information no longer required be destroyed, erased or made anonymous, and that the organisation develop guidelines and implement procedures to govern the destruction [2]. A dormant account still holding a live copy of your customer list is data you are responsible for and no longer watching. It also complicates the access right at Principle 9, which entitles an individual on request to be informed of the existence, use and disclosure of their information and to challenge its accuracy [2] — a right that is far harder to honour across systems you have stopped logging in to.
Migrate one thing at a time
The single best predictor of a calm migration is scope. Replacing one system while the others stay put means one export, one test list, one rollback decision. Replacing four at once means every problem is entangled with every other, and there is no clean way back.
If you are consolidating several tools into one place, do it as a sequence of single moves over months. It is slower, it is less satisfying, and it is dramatically more likely to finish. Our subscription audit walkthrough is a good way to decide the order, and whether you need a CRM is worth reading before you move a customer list anywhere.
Where we sit
MapleWorkSuite is modular specifically so that a switch does not have to be an all-or-nothing event. Each app is enabled and billed separately, so you can move booking across this month, invoicing next quarter, and leave anything that is working alone indefinitely. If an app does not fit, you switch it off and the rest keeps running.
We will export your data on request, in a format you can open without us, and we would rather tell you that plainly than let it be a discovery. A vendor that makes leaving hard is telling you something about their confidence in staying.
Whatever you are moving to, the rule holds: overlap the systems, move contacts before history before automations, and never cancel the old subscription until you have gone looking for something old and found it in the new place.