IT Contract, Service & License Evaluation Checklist
A practical checklist for evaluating IT contracts, SaaS subscriptions, software licenses, MSP agreements, support services, and recurring technology spend before renewal.
About this resource
The #GoodwinGetsIT IT Contract, Service & License Evaluation Checklist is designed to help IT leaders take a structured look at recurring technology spend before simply approving another renewal.
Use it to evaluate SaaS platforms, software licensing, MSP agreements, support contracts, infrastructure services, security tools, cloud services, vendor relationships, and other recurring IT expenses.
The checklist helps you answer questions like:
Are we still using what we’re paying for?
Does this service still solve the problem we originally bought it for?
Are we paying for unused licenses or premium features we don’t need?
Does another platform already provide similar functionality?
Is the vendor meeting expectations?
What does the full cost look like beyond the invoice?
What happens if we decide to leave?
Are there renewal, termination, data export, security, or vendor lock-in concerns?
The resource covers key areas including:
Business fit and continued value
Actual usage and adoption
License utilization and optimization
Total cost and recurring spend
Overlapping tools and consolidation opportunities
Vendor and MSP performance
Security, access, and data considerations
Support and operational fit
Contract renewal and termination terms
Vendor lock-in and transition risk
Final recommendation and decision scoring
The goal is not simply to reduce IT spend.
It is to make sure every contract, license, and service has a clear reason to remain in the environment.
Because “spend less” and “spend smarter” are not the same thing.
Use it to evaluate SaaS platforms, software licensing, MSP agreements, support contracts, infrastructure services, security tools, cloud services, vendor relationships, and other recurring IT expenses.
The checklist helps you answer questions like:
Are we still using what we’re paying for?
Does this service still solve the problem we originally bought it for?
Are we paying for unused licenses or premium features we don’t need?
Does another platform already provide similar functionality?
Is the vendor meeting expectations?
What does the full cost look like beyond the invoice?
What happens if we decide to leave?
Are there renewal, termination, data export, security, or vendor lock-in concerns?
The resource covers key areas including:
Business fit and continued value
Actual usage and adoption
License utilization and optimization
Total cost and recurring spend
Overlapping tools and consolidation opportunities
Vendor and MSP performance
Security, access, and data considerations
Support and operational fit
Contract renewal and termination terms
Vendor lock-in and transition risk
Final recommendation and decision scoring
The goal is not simply to reduce IT spend.
It is to make sure every contract, license, and service has a clear reason to remain in the environment.
Because “spend less” and “spend smarter” are not the same thing.
File Information
- File Type
- Word
- File Size
- 50 KB
- Version
- 1.0
- Last Updated
- October 1, 2026
- Downloads
- 35