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.
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