Free Resource
Technology Modernization Readiness Assessment
Most technology modernization programs that fail do so for predictable reasons — unclear outcomes, underestimated integrations, capacity that was never actually allocated, or change management that started too late.
This self-scoring diagnostic covers 38 questions across five readiness dimensions. Score each item 0–2, tally your results, and get an honest picture of where your program will run into trouble before it starts.
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Five readiness dimensions
- 1
Strategic clarity
7 questions on outcomes, alignment, and sponsorship
- 2
Technical landscape
8 questions on systems, integrations, and data quality
- 3
Organizational capacity
8 questions on resource allocation and decision authority
- 4
Vendor & partner readiness
7 questions on selection process, TCO, and governance
- 5
Change readiness
8 questions on adoption, training, and stabilization
Includes score interpretation: ready to proceed, proceed with a plan, or not ready — with guidance on addressing gaps.
What this assessment is for
Technology leaders typically run this assessment in one of three situations: before issuing an RFP (to understand what needs to be resolved first), when a program is stalling (to diagnose what is actually wrong), or when preparing a business case (to anticipate board or executive questions about readiness).
The scoring thresholds are based on patterns observed across retail, manufacturing, and enterprise technology programs — not theoretical benchmarks. Sections where you score below 60% represent the highest-probability failure points for your program.
About the author
Morris Stern is a technology modernization consultant and former VP of Retail Systems. He has led ERP migrations, unified commerce programs, and store system transformations — and has seen every failure mode this assessment is designed to surface.
Learn more about Morris →Also available
ERP Selection Checklist for Retail
60+ questions covering business readiness, integration, vendor evaluation, and governance.
Also available
Retail Technology Pilot Playbook
How to structure pilots that produce decisions — not just delay.
Want help interpreting your results?
If your assessment surfaces significant gaps, Morris offers a structured advisory engagement to help technology leaders build program readiness before committing to a vendor.
Schedule a strategy call