Who this checklist is for
This software vendor checklist is for owners and operations heads who are about to buy a CRM, an ERP, a billing tool, an HR system or any other software the team will live in every day. A demo shows what the product does on a good day. These questions show what it costs, how it fits with the tools you already run, and what happens if you ever want to leave.
Use it on the demo call or send it to the vendor before the contract. The early questions are quick and most vendors answer them on the spot. The later ones take longer to answer, and they are the ones that matter most once the software is running your business.
The 20 questions, and why each one matters
Who owns our data?
The contract should say plainly that your customer, order and finance data belongs to you. Look for the clause in the terms, not just a yes on the call.
Can we export everything?
Some tools export only reports, not the full records, history and attachments. Ask them to show a full export during the demo.
In what file format?
An export you cannot open is no export at all. Ask for CSV or Excel files you can read without the vendor's help.
Price per user or flat?
Per-user pricing grows every time you hire. Work out the cost for your team size today and in two years.
What does year two cost?
Launch prices and first-year discounts often end at renewal. Get the renewal price and any yearly increase in writing.
Which features cost extra?
The feature you liked in the demo may sit on a higher plan or need an add-on. Ask them to mark which plan each feature you need is on.
Is setup included?
Setup, data migration and configuration are sometimes a separate project with a separate fee. Ask what is included and what is billed by the hour.
Who trains our team?
Software nobody is trained on goes unused. Ask how training is delivered, how many sessions are included and what new hires get later.
Does it work on mobile?
If your sales or field team works from a phone, a desktop-only tool will not get used. Ask to see the mobile app or mobile site on a real phone.
Does it connect to Tally?
Swap in your accounting tool. If the new software cannot pass data to it, someone will type the same entries twice. Ask how the link works and who maintains it.
Is there an open API?
An API lets you connect the software to other tools and automate steps later. Ask whether it is included on your plan and whether it has usage limits.
Can it send WhatsApp messages?
If your customers talk to you on WhatsApp, the tool should be able to send updates there or connect to something that can. Ask whether this needs an add-on.
Who answers support, and when?
Ask for support hours, the channels you can use and the usual response time. A ticket answered in three days can stop a working day.
Can we call a customer?
A short call with a current customer of a similar size tells you more than a case study. Ask for one or two you can speak to directly.
What breaks at 50 users?
Some tools slow down or need a plan change as your team or data grows. Ask about limits on users, records, storage and automations.
How often does it change?
Frequent updates are good until a screen your team relies on moves overnight. Ask how changes are announced and whether you can test them first.
Where is our data stored?
Some customers and industries need data kept in a certain country. Ask where the servers are and whether you can choose.
Who can access our data?
Ask which of the vendor's staff can see your records, why they would, and how that access is logged.
What is the notice period?
Annual contracts often renew on their own unless you give notice weeks in advance. Find the date and put it in your calendar.
How do we leave cleanly?
Ask what happens on the day you cancel: how long you keep access, how you get a full export and when your data is deleted. This answer shows how much the vendor expects to hold on to you.
Questions about choosing a software vendor
What questions should I ask a software vendor before buying?
How do I compare two software vendors fairly?
What is the most important question to ask?
Not sure which software your business actually needs?
Tell us what your team runs on today and what you are thinking of buying, and we will map it in a short digital audit, then show what can connect to the tools you already have.
Part of our Business Process Automation hub. Start with our business automation services.