A Comprehensive Checklist for Selecting an MSP - Insights from Managed IT Services Provider in Chicago

Chicago, United States - February 4, 2025 / The Isidore Group - Chicago Managed IT Services Company /

Chicago Managed IT Services Provider Shares a Checklist for Choosing an MSP

Choosing the right managed IT services provider is one of the most important decisions for a business, especially since many organizations struggle with poor IT performance due to misaligned partnerships.

According to CloudSecureTech, there are over 40,000 MSPs in the US alone, which is still growing. This statistic emphasizes how essential it is to have the right provider.

As Sebastian Abbinanti, President of The Isidore Group, notes, “It’s vital for businesses to evaluate potential managed IT providers thoroughly to avoid service gaps and ensure long-term success.”

In this blog, a leading managed IT services provider in Chicago will walk you through an MSP checklist designed to help you make the best choice for your business.

Step 1 – Assess Your IT Needs Using a Managed IT Services Questionnaire

Before evaluating providers, you must first assess your own IT needs. Create a managed IT services questionnaire to identify the gaps in your current infrastructure. This will allow you to align your specific needs with what potential providers offer.

Some key questions to include in your managed IT services questionnaire:

What areas of IT management need improvement? (e.g., 24/7 support, cybersecurity, cloud services)

How important is scalability to your business? Can the provider grow alongside you?

Does your business require compliance with specific regulations such as HIPAA or GDPR?

By answering these questions, you’ll have a clearer idea of the type of services you need. This self-assessment will set the foundation for selecting the right provider.

Step 2 – Evaluate Providers with Managed Services Qualifying Questions

Once you’ve established your business needs, it’s time to evaluate potential providers. Managed services qualifying questions will help you narrow your search by ensuring the provider has the necessary expertise and resources.

Here are some important managed services questions to ask:

What certifications does the provider hold? Look for industry-specific certifications.

Can they provide case studies or client references that demonstrate their ability to work with businesses like yours?

What is their experience in your industry? For example, businesses in healthcare or finance may require specialized knowledge of compliance.

These questions are essential because they allow you to gauge whether the provider can meet your business’s unique demands.

Step 3 – Key Managed Services Questions to Ask About Security and Compliance

Cybersecurity is one of the most critical factors to consider when choosing a managed IT provider. Ensuring that the provider has robust security protocols in place should be a top priority on your managed IT services checklist.

Key managed services questions to ask about security and compliance include:

What cybersecurity protocols do they have in place to monitor threats and mitigate attacks?

Do they offer 24/7 system monitoring to ensure that potential breaches are identified and dealt with immediately?

How does the provider handle compliance? Do they have experience with regulatory requirements such as HIPAA, GDPR, or PCI-DSS?

Security and Compliance Checklist

Service	Importance	Managed Service Question
24/7 System Monitoring	High	Do you offer around-the-clock monitoring?
Regulatory Compliance	Essential for healthcare, finance	Do you comply with HIPAA, GDPR, or PCI-DSS?
Incident Response Time	Crucial for data protection	How fast can you respond to a security incident?

Understanding the provider’s approach to security and compliance will help ensure your business is protected from cyber threats while staying compliant with industry regulations.

Step 4 – Analyze Their Service Levels and Response Times

When IT problems arise, you need a provider that can respond quickly. The managed IT services checklist should include a thorough review of the provider’s Service Level Agreements (SLAs).

These agreements outline the provider’s response and resolution times, which directly affect your business’s operations.

Questions to ask about response times and SLAs:

What is their average response time for critical IT issues? Look for a provider that guarantees a 15-30 minute response for critical issues.

How are issues escalated? Understand the provider’s escalation process to ensure that your most critical problems are handled promptly.

Are there penalties or guarantees in the SLA? Ensure that the SLA outlines what happens if the provider fails to meet their commitments.

Having clear and enforceable SLAs will give you confidence that your IT needs will be addressed swiftly.

Step 5 – Ensure Scalability and Flexibility in Services

A managed IT services provider should not only meet your current needs but also grow with your business. It’s essential to evaluate the provider’s ability to offer scalable solutions.

Here’s what to look for in terms of scalability and flexibility:

Can they scale their services to support your growing IT infrastructure as your business expands?

Do they offer flexible contracts that allow you to add or remove services based on your evolving needs?

By choosing a provider that offers scalable and flexible options, you can ensure that your business’s IT operations won’t be hindered by growth.

Step 6 – Transparency in Pricing and Contracts

Another important part of the managed IT services checklist is transparency in pricing. Hidden fees or unclear terms in contracts can result in unexpected expenses that disrupt your IT budget.

According to a survey by Mastercard, 47% of small businesses highlighted cost as the main barrier to securing IT systems.

Key managed services qualifying questions related to pricing:

Are there any hidden fees, or is pricing fully transparent from the start?

Do they offer flat-rate pricing or charge by the service?

How flexible are the terms of the contract? Are there options to scale up or down without penalties?

By ensuring the provider is upfront about pricing, you’ll avoid surprises down the line.

Step 7 – Verify Client Satisfaction and Testimonials

Finally, take the time to review the provider’s reputation by looking at client testimonials and customer satisfaction ratings. These provide valuable insights into their reliability and performance.

Some metrics to check:

What is their average customer satisfaction score?

Do they have a track record of high retention rates and low technician-to-client ratios?

Asking for references from current clients can also give you firsthand knowledge of their experiences, helping you make an informed decision.

Take the Next Step in Your IT Strategy with a Trusted Managed Services Provider in Chicago

By following this managed IT services checklist, you’ll be well-prepared to evaluate potential providers. Start by assessing your IT needs, then ask the right managed services questions to ensure a good fit.

Verify the provider’s experience in security and compliance, and don’t forget to analyze response times, scalability, and pricing transparency.

The Isidore Group offers tailored solutions, industry expertise, and proven results. Contact a premier Chicago IT managed services provider today to schedule a consultation and discover how we can help your business thrive.