40-Point IT Outsourcing Evaluation Checklist
Score IT outsourcing providers on bench depth, SLA enforceability, cost transparency, and disaster recovery. Surface project-work upcharges and certified-engineer bait-and-switch before you sign.
Scoring Framework
Rate each answer 1 to 5 based on specificity and verifiability. Vendors that consistently score below the midpoint typically run into expensive trouble in months four through nine, when the gaps in technical depth, SLA enforcement, and cost transparency tend to surface together.
Evaluation Criteria
Technical team capabilities and certifications
25% weightEvaluates the actual engineers who'd manage your environment, not the sales team's claims. Generalist experience is where routine VMware or Windows Server work tips into avoidable outage cost.
Sample Questions
- Can they share LinkedIn profiles of five engineers assigned to your account with current VMware VCP-DCV credentials?
- What's the average tenure of engineers on accounts comparable to yours?
- Can they demo live troubleshooting of a simulated Exchange failure against your actual environment?
- Can they share current Microsoft credentials for Windows Server for the engineers managing your domain controllers?
- What's the engineer-to-client ratio, and how many other accounts will the primary engineer carry?
Proven performance and client retention
20% weightTrack record at companies in your size band matters more than enterprise references. High small-and-mid-market churn is one of the strongest predictors of post-year-one service drift.
Sample Questions
- What's their client retention rate specifically for companies in your size band over the past three years?
- Can they provide several references from comparable companies who renewed contracts at least once?
- What was their average P1 resolution time last quarter for environments with 100 to 500 endpoints?
- Can they share monthly performance reports they provide to current clients including uptime and resolution metrics?
- What share of their revenue comes from companies under 100 employees?
Service level commitments and escalation
15% weightAn SLA without an enforcement mechanism is a marketing claim. Named individuals, target times, and financial penalties are what move it from theoretical to operational.
Sample Questions
- Can they name specific people who get called when your Exchange server crashes at 2 AM Tuesday?
- What financial penalties will they accept for missing P1 resolution times three months consecutively?
- Can they demonstrate secondary NOC capabilities when their primary operations center loses power?
- What's the escalation timeline from Level 1 engineer to VP-level intervention for business-critical outages?
- Can they share a 24/7 staffing schedule with names and direct contact details for assigned engineers?
Pricing transparency and hidden cost management
15% weightMonthly rate quotes routinely hide a meaningful share of real first-year cost in implementation, project work, and known upgrade fees. All-inclusive first-year pricing is the comparable unit.
Sample Questions
- What share of tickets historically requires Level 2 or Level 3 engineers at higher rates?
- Which routine tasks are excluded from base MSA pricing and billed as project work?
- What rates will they commit to for the Windows Server and Microsoft 365 work coming in the next 18 months?
- Can they share an all-in first-year cost including implementation, setup fees, and a typical project-work allowance?
- What rate increases should you expect in years two and three of the contract?
Business continuity and risk management
10% weightYour continuity rides on their operational resilience. Single points of failure in their operations become your emergencies on the days they actually fail.
Sample Questions
- What's their E&O insurance coverage for data loss and business interruption caused by their errors?
- How do they handle knowledge transfer when engineers assigned to your account leave?
- What backup communication methods exist if their primary NOC and phone systems fail simultaneously?
- Can they walk through disaster recovery procedures when natural disasters affect their primary operations center?
- What happens to your SLAs if they lose key personnel or face significant turnover?
Contract terms and termination protection
10% weightPunitive termination clauses keep clients in declining engagements. The negotiated terms before signature are what give you actual leverage in years two and three.
Sample Questions
- What's the exact process and total cost for terminating the contract due to repeated SLA failures?
- Do they offer 30-day termination for cause with prorated refunds for unused services?
- What transition assistance do they provide when you move to another vendor?
- Are there penalties or fees for reducing scope or user count during the contract term?
- How do they handle contract modifications if your business requirements change significantly?
Technology integration and documentation quality
5% weightWeak integration and documentation create ongoing operational friction and predictable knowledge gaps when staffing changes.
Sample Questions
- Can they demo live integration between their ticketing system and your existing ServiceNow instance?
- Can they share sample network diagrams and runbooks created for similar client environments?
- What knowledge management system do they use to maintain institutional memory about your environment?
- How do they document configuration changes and maintain current architecture diagrams?
- Can they share examples of monthly capacity planning and security reports delivered to similar clients?
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