Roadmap & strategic alignment RFP Questions

Questions on the vendor's roadmap, R&D investment, strategic priorities and end-of-life policy, and whether the product's direction fits your needs over the contract term.

91 questions to put to a software vendor, each with the reason to ask it, what a good answer looks like, the red flags and the follow-ups. Delivered as an Excel workbook that scores the answers for you.

Inside the Workbook

• 22 RFI questions for the long list
• 27 RFP questions for the shortlist
• 42 deep-dive questions for the finalists
• An evaluator guide on every question: why it matters, good-answer signals, red flags and follow-ups
• A weighted scorecard that totals each depth and each section from your 0–5 scores
• An RFP cover template in Word, to send with the questions

Sections

• Published roadmap & commitment levels (23)
• R&D investment & engineering depth (20)
• Stated strategic priorities & focus (27)
• Feature & product end-of-life policy (21)

How the Questions Were Checked

A language model drafted the questions and a second model critiqued them. They were then audited in three passes for wrong citations, outdated standards, invented thresholds and unsupported claims. The audit made 141 changes, and the workbook lists every one with the old and new text.

Built For

IT, security and procurement teams running a software selection, and consultancies running one for a client. The Consultancy License covers use with any number of clients.