40-Point IT Outsourcing Evaluation Checklist
Score 8 critical vendor capabilities with 40 specific questions. Includes weighted scoring to identify providers who won't crash your systems.
Scoring Framework
Rate each answer 1–5 based on specificity and verifiability. Vendors scoring below 3.5 average will likely cause expensive problems. Focus highest weight on technical capabilities and proven performance over price promises.
Evaluation Criteria
Technical Team Capabilities and Certifications
25% weightEvaluate the actual engineers who will manage your environment, not the sales team's promises. Generic computer experience costs you money when VMware updates go wrong.
Sample Questions
- Show LinkedIn profiles of 5 engineers assigned to our account with current VMware VCP-DCV 2022 certifications
- What's the average tenure of engineers on accounts similar to our 25-person company?
- Demonstrate live troubleshooting of a simulated Exchange server failure using our actual environment
- Provide Microsoft MCSA certificates for Windows Server 2022 for engineers who will manage our domain controllers
- What's your engineer-to-client ratio, and how many other accounts will our primary engineer manage?
Proven Performance and Client Retention
20% weightTrack record with companies your size matters more than Fortune 500 references. High churn signals they abandon small accounts after contracts are signed.
Sample Questions
- What's your client retention rate specifically for 25–50 person companies over the past 3 years?
- Provide 5 references from similar-sized companies who renewed contracts at least once
- What was your average P1 resolution time last quarter for environments with 100–500 endpoints?
- Show monthly performance reports you provide to current clients including uptime and resolution metrics
- What percentage of your revenue comes from companies under 100 employees?
Service Level Commitments and Escalation
15% weightSLAs without enforcement mechanisms are marketing promises. You need names, phone numbers, and financial penalties when critical systems fail.
Sample Questions
- Name specific people who get called when our Exchange server crashes at 2 AM Tuesday
- What financial penalties do you accept for missing P1 resolution times three months consecutively?
- Demonstrate your secondary NOC capabilities when primary operations center loses power for 8 hours
- What's your escalation timeline from Level 1 engineer to VP-level intervention for business-critical outages?
- Show your 24/7 staffing schedule with names and direct contact information for our assigned engineers
Pricing Transparency and Hidden Cost Management
15% weightMonthly rate quotes hide 60–80% of real costs in implementation fees, project work, and upgrade charges. Get all-inclusive first-year pricing upfront.
Sample Questions
- What percentage of our tickets will require Level 2 or Level 3 engineers at higher hourly rates?
- List specific tasks excluded from base MSA pricing that will be charged as project work
- What will you charge for inevitable Windows Server 2022 upgrade and Office 365 migration?
- Provide total first-year cost including implementation, setup fees, and typical project work for 25-person company
- What rate increases can we expect in years 2 and 3 of the contract?
Business Continuity and Risk Management
10% weightYour business continuity depends on their operational resilience. Single points of failure in their operations become your emergency situations.
Sample Questions
- What's your E&O insurance coverage for data loss and business interruption caused by your errors?
- How do you handle knowledge transfer when engineers assigned to our account leave your company?
- What backup communication methods exist if your primary NOC and phone systems fail simultaneously?
- Show your disaster recovery procedures when natural disasters affect your primary operations center
- What happens to our SLAs if you lose key personnel or face significant staff turnover?
Contract Terms and Termination Protection
10% weightPunitive termination clauses trap you with declining service quality. Contract flexibility provides negotiating power when performance degrades.
Sample Questions
- What's the exact process and cost for terminating this contract due to repeated SLA failures?
- Do you offer 30-day termination for cause with prorated refunds for unused services?
- What transition assistance do you provide when we move to another vendor?
- Are there any penalties or fees for reducing scope or user count during the contract term?
- How do you handle contract modifications if our business requirements change significantly?
Technology Integration and Documentation Quality
5% weightPoor integration and documentation create ongoing operational friction and knowledge gaps when staff changes occur.
Sample Questions
- Demonstrate live integration between your ticketing system and our existing ServiceNow instance
- Show sample network diagrams and runbooks you've created for similar client environments
- What knowledge management system do you use to maintain institutional memory about our environment?
- How do you document configuration changes and maintain current architecture diagrams?
- Provide examples of monthly capacity planning and security reports you deliver to similar clients
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