Anyone running a vendor evaluation · 8 min read

Questions to ask a software vendor before signing

A good question comes with a good-answer and a red-flag-answer so you can read the room even outside your specialty. Below are the categories that matter and the questions that move a deal from a pitch to a commitment. Ask them in writing where you can — a written answer is a contractual artifact; a verbal one evaporates.

Scope & requirements

Pin down exactly what is and isn't included before price is discussed.

What specifically is excluded from this fixed price, and what would each exclusion cost?
Which requirements are you assuming we'll handle internally?
What triggers a change order, and is there a cap on change-order spend?

Data migration

The most under-scoped phase in almost every implementation.

Who is responsible for data cleansing — you or us — and is it in this price?
How many records, and what's the rollback plan if migration fails at cutover?
What format is our data returned in on exit, at what cost, on what timeline?

Integration

Each integration point is a project, not a line item.

For each integration, is there a data contract, error handling, and UAT plan?
What are the API rate limits, and what happens when we hit them in production?

Licensing & commercial

Where renewal surprises are born.

How is licensing metered (named vs concurrent), and what triggers a true-up?
What is the contractual cap on renewal price increases?

Resourcing & support

The people who sell are rarely the people who deliver.

Will the named consultants in this proposal be the ones assigned, with a substitution clause?
What does post-go-live hypercare include, for how long, and at what staffing level?

Security & compliance

Map controls to your obligations, not just to certificates.

Where is our data hosted and processed, and is it encrypted at rest and in transit?
Can you map your controls to our specific compliance obligations?

Frequently asked

What questions should I ask a software vendor before buying?

Cover seven areas: scope and exclusions, data migration and exit, integration, licensing and true-ups, resourcing and named staff, post-go-live support, and security and compliance. For each, ask for the answer in writing — a written answer is contractual, a verbal one is not.

What is a red flag in a vendor's answer?

Vagueness about anything that costs money later: "we'll scope that in a change order," "we staff according to project need," or no clear answer on data return at exit. Specific, written, capped commitments are green flags.

Run this on your actual deal

Benchside generates the scope, the interrogation questions, and the lock-in math for your specific vendor — first project free.

Start free