Before you move your business onto new software
The questions that matter are about leaving, not joining. Export, ownership, lock-in, and what a migration actually costs you in time.
4 min read
Every software evaluation asks the same questions. Does it have the features. What does it cost. How long does setup take.
Those are the easy ones, and they are mostly answered on the vendor's own website. The questions that decide whether you regret the move are different, and almost nobody asks them during a demo because they are about leaving, and you are not thinking about leaving yet.
Here is the list worth asking first.
Can you get your data out, completely, without asking anyone?#
Not "is there an export button". Specifically:
Does the export include everything, or only the obvious tables? Contacts and invoices usually export cleanly. Attachments, email threads, notes, file uploads, activity history and custom fields often do not. Those are frequently the parts that took you years to accumulate.
Can you run it yourself, or do you have to raise a support ticket? An export that requires a request is an export that can be slow at exactly the moment you want it to be fast.
What format? A CSV per table is usable. A proprietary archive that only the same vendor can read is not an export, it is a hostage note with a filename.
Ask to do a full export during your trial, not after you have committed. If it is awkward while they are trying to win you, consider what it will be like when they are not.
Who owns the data, in writing?#
This should be boring and often is not. Read the terms for:
- An explicit statement that your data is yours
- What happens to it when you cancel, and for how long they keep it
- Whether they use it to train anything
- Who they share it with, and in which country it is stored
Storage location matters more than people assume. If your customer records sit in a jurisdiction you did not choose, that is a fact about your business, not just about your vendor.
What happens on the day you stop paying?#
The answers in this market vary more than you would expect.
Some products put the account into read-only, so you can still see and export your records. Some lock the account entirely and you must pay to retrieve anything. Some delete after a stated grace period.
Ask directly: "If I cancel today, what can I still access tomorrow, and for how long?" It is a short question with an uncomfortable answer, which is exactly why it is worth asking before you move in rather than after.
How does it price as you grow?#
The sticker price is the least interesting number on a pricing page. What matters is the multiplier.
Per-user pricing looks cheap for three people and dominates your software budget at fifteen. Per-organisation pricing looks expensive at three and becomes the obvious choice at fifteen. Per-account pricing with unlimited users looks expensive until you count.
Work out what the product costs at your current size, at double, and at the size you are planning for. Then add tax. The ranking frequently changes between those three numbers, and the one you would have picked on sticker price is often not the one you want in eighteen months.
What actually breaks during the move?#
Three things, consistently, and none of them appear in a migration guide.
Historical records lose their edges. The data arrives, but the relationships between records often do not. An invoice that was linked to a project that was linked to a client can arrive as three unconnected rows. Check the links, not just the row counts.
Numbering sequences collide. If you have been issuing invoices as INV-0001 and the new system starts its own series, you now have two documents with the same number in one financial year. Decide before the move whether you continue the old series or start a clean one, and make sure the new system lets you choose.
Your team keeps using the old thing. This is the real cost, and it is measured in weeks. Two systems running in parallel means data in neither of them is complete. Pick a cutover date, make the old system read-only on that date, and accept a rough fortnight.
What does the first week actually look like?#
"Live in a day" and "ready in a day" are different claims, and the gap between them is where frustration lives.
Ask what specifically is working on day one, what needs configuration, and what needs your data to be in place before it means anything. A CRM with no contacts in it is not working, it is installed.
The honest version of a fast setup is: the product runs immediately, your data takes as long as your data takes, and your team takes a fortnight to stop reaching for the old tab.
The shortest version#
Before you ask what a product does, ask three things.
Can I leave with everything? What does it cost at three times my size? What breaks on the day I move?
If a vendor answers all three plainly, that tells you something about the product that no feature list will.
Siddarth Reddy Desai is the founder of TarkHQ LLP, Bengaluru, and builds MantriCEM: connected CRM, ERP and marketing for businesses, freelancers and agencies. These are the questions we expect to be asked, and the ones we ask of anything we adopt ourselves.