Choosing a Managed service provider (MSP) can feel like checking a box, but few Chicago companies realize it is really a strategic decision that can define your business's success.
The wrong choice can lead to costly downtime, security vulnerabilities, and a lack of IT support when you need it most. But the right MSP? They’ll become a trusted partner, ensuring your business is secure, efficient, and ready to grow.
At Intelligent Technical Solutions (ITS), we’ve helped hundreds of businesses in Chicago just like yours navigate the complexities of managed IT services. With years of experience supporting diverse industries and solving real-world IT challenges, we know what separates a good MSP from a great one—and we’re here to share that knowledge with you.
In this checklist, you’ll find 20 essential questions to ask before choosing an MSP in Chicago. These questions will help you uncover a provider’s capabilities, assess their reliability, and evaluate their fit with your business. By the end, you’ll know exactly what to ask to ensure your MSP aligns with your goals and delivers the support your business needs to thrive.
Understanding Their Capabilities and Offerings
1. What experience do you have supporting businesses in our industry?
Seek industry-specific expertise to ensure they understand your unique challenges.
2. What specific services are included in your standard managed IT and cybersecurity packages?
Clarify what's included upfront to avoid surprises later.
3. Do you offer 24/7/365 support? How is your support team structured?
Ensure round-the-clock availability and efficient escalation processes.
4. What is your approach to cybersecurity, and how do you protect against emerging threats like ransomware and business email compromise (BEC)?
Look for proactive measures like endpoint detection, vulnerability management, and regular training.
5. How do you help us vet and manage third-party vendors, such as software providers, on our behalf?
Effective vendor management can save you time and reduce complexity.
Reliability, Transparency, and Accountability
6. Can you share references or case studies of businesses similar to ours?
Verify their track record and client satisfaction through real-world examples.
7. How do you handle service level agreements (SLAs), and what guarantees do you offer for uptime and response times?
Look for specific, measurable commitments.
8. What is your process for monitoring and reporting on the health of IT systems?
Regular and transparent reporting builds trust and ensures accountability.
9. How do you communicate with clients during major incidents or outages?
Ensure clear, timely, and consistent communication protocols.
10. What tools and platforms do you use to manage and secure IT environments, and why?
Look for modern, best-in-class solutions tailored to your needs.
Growth, Flexibility, and Long-Term Fit
11. How do you support scaling businesses, including onboarding new locations, staff, or systems?
Choose a Chicago MSP that can grow with your business seamlessly.
12. What happens if we need to terminate our agreement? What is your offboarding process?
A professional MSP ensures a smooth exit process with no disruptions.
13. Do you provide IT strategic planning and budgeting guidance, such as vCIO services?
Proactive planning is crucial for long-term success.
14. Can you integrate and support hybrid environments, such as on-premises and cloud-based systems?
Flexibility is essential for modern IT infrastructure.
15. What measures do you take to ensure compliance with regulations relevant to our business (e.g., HIPAA or the Health Insurance Portability and Accountability Act, GDPR or the General Data Protection Regulation, CMMC or Cybersecurity Maturity Model Certification)?
Regulatory expertise is critical in compliance-heavy industries.
Security, Data Protection, and Continuity
16. What is your process for creating, testing, and maintaining a disaster recovery and business continuity plan?
Robust backup and restoration processes are non-negotiable.
17. How do you approach employee security awareness training, and how often is it conducted?
Training is essential to minimize human error, a leading cause of security incidents.
18. What’s your protocol for responding to a cybersecurity incident, and do you provide incident response services?
Effective incident response ensures faster recovery and mitigates damage.
19. Do you have cyber liability insurance, and do you assist clients in meeting requirements for cyber insurance coverage?
An MSP should help mitigate risks and navigate insurance requirements.
20. What makes your services stand out from other Chicago MSPs in terms of value, expertise, and client outcomes?
Understand their differentiators to evaluate their value proposition.
Ready to Make the Right Choice for Your Chicago Business?
As you evaluate potential MSPs in Chicago, pay attention to their responsiveness and communication during the vetting process—these initial interactions often reflect the level of service you can expect. In addition, ensure their pricing structure is transparent, with no hidden fees, so you can budget confidently. Finally, consider their cultural fit with your organization; the best MSPs act as a seamless extension of your team, aligning with your values and goals to support your long-term success.
By asking the 20 questions in this checklist and paying close attention to how each provider aligns with your needs, you can identify a partner who offers more than just IT support. Look for transparency, accountability, and a cultural fit that makes the MSP an extension of your team.
Now it’s time to take the next step—try asking these questions to us in a meeting and see how we measure up as your trusted MSP partner.
You may also check out the following free resources from our Learning Center:
- Best Managed IT Service Providers in Chicago
- The Cost of Managed IT in Chicago (+ Price Factors Explained)