Guide
Choosing New Software: Questions to Ask Before You Sign
The right questions before you sign save money and trouble later. Check the fit, the security and the exit.
Why it matters
Switching systems is expensive, and contracts are easy to sign and hard to leave. A few written questions up front tell you whether a vendor will protect your data, let you take it with you and still make sense in three years.
Step by step
- Write down what you actually need, and what you use today, before any demo.
- Ask the vendor security questions in writing.
- Check that it supports MFA, exports your data and removes users easily.
- Compare the full cost over three years, not only year one.
- Get an independent second opinion before a big contract.
Common mistakes
- Choosing from a demo before writing down what you need
- Not asking whether your data trains their AI
- No way to export your data if you leave
- Comparing year one price instead of three year cost
Free tools for this
Vendor Security Questions
Twelve questions to ask before any software vendor holds your data.
A real case
Fixed the same day, client ever since
- Situation
- After an early job for the agency, a firewall I had installed and configured developed an issue that their IT provider at the time could not resolve.
- What was done
- They called me back. I came out and fixed it the same day.
- Result
- They brought me on as their consulting Head of IT, and I have supported them ever since.
Questions people ask
Do you sell hardware, software or licenses?
No. I have no product to sell. When a project needs equipment, I give you the full list and you buy it directly, with no markup. My recommendations are based only on what fits your organization, your staff and your budget.
We already have an IT person or provider. Can you still help?
Yes. I do not replace your team. I offer another perspective, a second opinion on big decisions, and what has worked for other organizations like yours.
Not sure where to start?
One conversation and a straight answer about where your organization stands. No cost, no commitment, no pitch.