Published 2026-01-29 by TechNet New England
With 72% of SMBs planning to outsource IT operations, many businesses are evaluating managed service providers for the first time. The questions you ask during evaluation determine whether you end up with a strategic partner or a source of frustration.
Service Scope and Expectations
What is included in your standard service?
Get specific documentation of what is covered. Common inclusions and exclusions:
- Help desk support - during what hours?
- Remote monitoring and maintenance - what systems?
- On-site support - how much is included?
- Security services - what specific protections?
- Backup and recovery - what is protected?
What costs extra?
Understand what triggers additional charges:
- After-hours support
- On-site visits beyond included amount
- Hardware procurement
- New employee setup
- Projects vs. break-fix work
- Special software licensing
What are your service level agreements?
Understand response time commitments:
- How quickly will you respond to different severity levels?
- What happens if SLAs are not met?
- How are severity levels defined?
Security and Compliance
How do you handle our data?
- What access does your team have to our systems?
- How are credentials managed and rotated?
- What happens to our data if we end the relationship?
What security certifications do you hold?
Look for relevant certifications like SOC 2, ISO 27001, or industry-specific compliance capabilities (HIPAA, PCI-DSS).
What security tools do you use and provide?
- Endpoint protection
- Email security
- Backup solutions
- Security monitoring
Experience and Fit
Do you have experience with our industry?
Industry-specific requirements matter. A provider experienced with your industry understands compliance needs, common software, and typical challenges.
What size clients do you typically serve?
Providers optimized for 500-employee companies may not give adequate attention to 20-employee companies, and vice versa. Look for fit with your size.
Can we speak with current clients?
References from similar businesses provide insight into actual service delivery.
Operational Questions
How do we reach you when we need help?
- Phone, email, portal?
- How are tickets tracked and escalated?
- Can we see ticket status?
Who will actually work on our account?
- Will we have dedicated contacts?
- What are their qualifications?
- What happens when they are unavailable?
How do you communicate proactively?
- How will we learn about issues affecting our systems?
- What regular reporting will we receive?
- How often will we meet to discuss our technology strategy?
Contract Terms
What is the contract length?
Multi-year contracts may offer discounts but reduce flexibility. Understand termination provisions.
What happens if we want to leave?
- How much notice is required?
- What are the termination fees?
- How will our data and access be transferred?
- What documentation will be provided?
How are price increases handled?
Understand if and how pricing can change during the contract term.
Red Flags
Watch for:
- Unwillingness to provide detailed service documentation
- No references or references that do not match your profile
- Vague answers about security practices
- Pressure to sign quickly without due diligence
- Extremely low pricing that seems unsustainable
- No formal contract or SLA documentation
TechNet New England welcomes these questions and provides clear documentation of our services, security practices, and terms.
Sources: MSP Industry Best Practices, TSIA Building a Managed Services Provider Business Guide