How to Choose a Managed IT Service Provider: 15 Questions to Ask

Choosing a managed IT service provider (MSP) is one of the most important technology decisions your business will make. The right partner becomes an extension of your team. The wrong one becomes another headache.

After 30 years in this industry, we've seen what separates excellent MSPs from those who overpromise and underdeliver. Here are the questions that matter.

Questions About Service Delivery

1. What's included in your standard agreement—and what costs extra?

Why it matters: Some MSPs advertise low monthly rates, then nickel-and-dime you with "out of scope" charges. Get a detailed list of what's included before signing.

Red flags:

• Vague descriptions of services
• Long lists of exclusions
• "That would be a project" as a frequent answer

2. What's your average response time for support requests?

Why it matters: "24/7 support" means nothing if it takes 4 hours to get a response. Ask for actual metrics, not marketing claims.

What to look for:

• Emergency response: Under 15 minutes
• Standard requests: Under 1-2 hours
• Documented SLAs with consequences

3. Who will actually be supporting our systems?

Why it matters: Some MSPs use offshore help desks or rotate technicians constantly. You want people who know your business.

What to look for:

• Named account manager or team
• Local technicians for on-site needs
• Low staff turnover

4. How do you handle after-hours emergencies?

Why it matters: Server crashes don't wait for business hours. Understand exactly what happens at 2 AM on a Saturday.

What to look for:

• 24/7 monitoring with automated alerts
• On-call technicians (not voicemail)
• Clear escalation procedures

Questions About Security

5. What security tools and practices are included?

Why it matters: Basic managed services aren't enough anymore. Security must be built into everything.

Minimum expectations:

• Endpoint detection and response (EDR)
• Email security and filtering
• Firewall management
• Patch management
• Security awareness training

6. How do you handle backup and disaster recovery?

Why it matters: Ransomware attacks are targeting backups. You need air-gapped or immutable copies that attackers can't encrypt.

What to look for:

• Multiple backup copies (local and offsite)
• Air-gapped or immutable backups
• Documented and tested recovery procedures
• Clear RTO/RPO commitments

7. What compliance frameworks do you support?

Why it matters: If you're in healthcare, finance, or handle payment data, compliance isn't optional.

What to look for:

• Specific experience with your requirements (HIPAA, PCI-DSS, etc.)
• Documentation and audit support
• Not just "we can help with that" but demonstrated expertise

Questions About Experience

8. How long have you been in business?

Why it matters: IT is littered with companies that appeared, grew fast, and disappeared—taking their clients' institutional knowledge with them. Stability matters.

What to look for:

• 10+ years in business (ideally longer)
• Consistent ownership and leadership
• References from long-term clients

9. Do you have experience in our industry?

Why it matters: A restaurant's IT needs are different from a law firm's. Industry experience means faster problem-solving and better recommendations.

What to look for:

• Current clients in your industry
• Understanding of industry-specific applications
• Knowledge of relevant compliance requirements

10. Can you provide references from similar businesses?

Why it matters: Anyone can claim expertise. References prove it.

What to ask references:

• How responsive are they really?
• Have they had any major issues? How were they handled?
• Would you choose them again?

Questions About Business Terms

11. What's your contract length and termination policy?

Why it matters: Avoid getting locked into multi-year contracts with providers who underperform. Reasonable contracts protect both parties.

What to look for:

• Month-to-month or annual agreements (not 3+ years)
• Clear termination process
• Data handoff procedures if you leave

12. How is pricing structured?

Why it matters: Understand exactly what you're paying for and how costs might change.

Common models:

• Per-user: Scales with your team size
• Per-device: Scales with your equipment
• Flat fee: Predictable but may not scale well
• Tiered: Different service levels at different prices

13. What happens if we grow (or shrink)?

Why it matters: Your IT needs will change. Your provider should adapt.

What to look for:

• Flexible scaling up or down
• No penalties for reducing scope
• Clear process for adding locations or users

Questions About Partnership

14. How do you approach technology planning and recommendations?

Why it matters: A true partner helps you plan for the future, not just fix today's problems.

What to look for:

• Regular business reviews (quarterly)
• Technology roadmap discussions
• Proactive recommendations for improvement
• Budget planning assistance

15. What makes you different from other MSPs?

Why it matters: This open-ended question reveals priorities and culture. Listen for substance vs. marketing speak.

Good answers focus on:

• Specific capabilities or expertise
• Client outcomes and retention
• Cultural values that align with yours

Beware of:

• "We're the best" without specifics
• Price-only differentiation
• Overselling capabilities

The Most Important Question

After asking all 15 questions, ask yourself:

"Do I trust these people with my business?"

Because that's what you're doing. Your MSP will have access to your systems, your data, and your operations. Technical competence matters—but so does integrity, communication, and genuine partnership.

Finding the Right Fit

The best MSP relationship feels like having an internal IT department—without the overhead of hiring, managing, and retaining technical staff.

At Layth Solutions, we've been that IT department for NYC businesses since 1995. We're not the right fit for everyone, but for businesses that value experience, responsiveness, and genuine partnership, we'd welcome the conversation.

Schedule a no-pressure consultation to see if we're the right fit for your business.