Anyone running a vendor evaluation · 8 min read
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 artefact; a verbal one evaporates.
Published 14 June 2026
Download the guide(PDF)Pin down exactly what is and isn't included before price is discussed.
The most under-scoped phase in almost every implementation.
Each integration point is a project, not a line item.
Where renewal surprises are born.
The people who sell are rarely the people who deliver.
Map controls to your obligations, not just to certificates.
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.
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.
Related guides
From principle to practice
Benchside generates the scope, the interrogation questions, and the lock-in math for your specific vendor - your first project is free.