Before hiring a Managed Service Provider (MSP), ask questions about response times, cybersecurity, pricing, experience, onboarding, backups, strategic planning, and guarantees. For a business with 5-50 employees, managed IT may represent an investment of roughly $150-$250 per user per month, so choosing the right provider deserves careful consideration.

More importantly, you're not simply buying technical support. You're trusting another company with access to your systems, data, cybersecurity, and day-to-day operations.

For more than 25 years, NextX has helped businesses throughout Billings, Montana, and Yellowstone County manage technology more effectively. Based on that experience, we've created this 15-question MSP evaluation framework to help business owners compare providers and make a more informed decision.

Why Asking the Right MSP Questions Matters

At first glance, many IT companies appear similar.

Their websites may mention:

  • Managed IT services
  • Help desk support
  • Cybersecurity
  • Cloud services
  • Microsoft 365
  • Backup
  • Monitoring

However, the way those services are delivered can vary significantly.

For example, one provider may include cybersecurity in its standard managed services package, while another charges extra. Likewise, one company may provide strategic technology planning, while another focuses primarily on fixing problems.

Therefore, don't compare providers based solely on a list of services.

Instead, use the following 15 questions to understand how each MSP actually operates.

The 15-Question MSP Evaluation Framework

1. How Long Have You Been in Business?

Experience isn't everything. However, it can reveal whether a provider has successfully adapted to decades of technology changes.

An established MSP has likely worked through:

  • Major operating system changes
  • Cloud migrations
  • Cybersecurity threats
  • Hardware failures
  • Internet outages
  • Business continuity events
  • Changing compliance requirements

Ask not only how long the company has existed, but also how much experience its team has supporting businesses similar to yours.

NextX has served businesses for more than 25 years, giving our team extensive experience helping organizations navigate changing technology.

2. What Size Businesses Do You Typically Support?

An MSP serving companies with thousands of employees may not be structured for a 15-person business. Conversely, a one-person IT consultant may struggle to support a growing 50-person organization.

Therefore, ask about the provider's ideal client.

If your business has 5-50 employees, look for an MSP that understands the technology, budgeting, support, and cybersecurity challenges businesses of your size face.

The right fit matters.

3. What Is Included in the Monthly Fee?

This is one of the most important questions you can ask.

Don't simply ask:

"How much does managed IT cost?"

Instead, ask:

"Exactly what does our monthly fee include?"

Depending on the provider, managed IT may include:

  • Help desk support
  • 24/7 monitoring
  • Microsoft 365 administration
  • Cybersecurity
  • Patch management
  • Backup monitoring
  • Vendor management
  • Strategic planning

Additionally, ask what is not included.

For businesses with 5-50 employees, comprehensive managed IT services may typically fall in the $150-$250 per user per month range. However, the value of that investment depends heavily on what the agreement actually covers.

4. What Will Cost Extra?

A low monthly price can become expensive when common services are billed separately.

Therefore, specifically ask about additional charges for:

  • Onsite visits
  • After-hours support
  • Projects
  • Employee onboarding
  • Employee offboarding
  • Hardware installation
  • Office moves
  • Vendor coordination
  • Emergency service

Most importantly, request examples.

A transparent MSP should be able to explain which situations create additional charges before you sign an agreement.

5. How Quickly Will You Respond When We Need Help?

When an employee can't work, response time matters.

Ask:

  • What is your average response time?
  • What response times do you commit to?
  • How are critical emergencies prioritized?
  • How do employees request support?
  • What happens after normal business hours?

Furthermore, distinguish between response time and resolution time.

A provider may respond to a ticket quickly but take much longer to actually solve the problem.

Understanding both gives you a better picture of the support experience.

6. Who Will Answer When My Employees Need Support?

Technology problems are frustrating enough without employees struggling to reach the right person.

Ask whether your employees will contact:

  • A local help desk
  • A centralized support center
  • A dedicated technician
  • An outsourced third party
  • An automated system

Also, ask how technical information is communicated.

Your employees shouldn't need an IT degree to understand what's happening.

At NextX, we call this No Geek-Speak. Technology should be explained clearly so people can make informed decisions without unnecessary technical jargon.

7. What Cybersecurity Protections Are Included?

Cybersecurity shouldn't be an afterthought.

Ask whether the managed services agreement includes protections such as:

  • Multi-Factor Authentication (MFA)
  • Endpoint Detection & Response (EDR)
  • Email security
  • DNS filtering
  • Patch management
  • Security awareness training
  • Continuous monitoring
  • Backup monitoring

Next, ask how these tools are managed.

Simply installing security software isn't enough. Someone needs to monitor alerts, maintain configurations, respond to threats, and continually improve protection.

8. How Do You Protect and Test Our Backups?

Almost every IT provider will tell you they provide backups.

Therefore, ask the more important question:

"How do you know our backups will actually restore?"

A strong backup process should include:

  1. Automated backups
  2. Daily monitoring
  3. Off-site or otherwise appropriately separated copies
  4. Regular restore testing
  5. Documented recovery procedures

Additionally, discuss your recovery objectives.

How quickly does your business need critical systems restored?

How much data could you afford to lose?

Those answers should influence the backup and disaster recovery strategy.

9. What Happens During the First 90 Days?

Switching IT companies shouldn't feel chaotic.

A professional MSP should have a documented onboarding process covering approximately the first 30-90 days, depending on the complexity of your environment.

The process may include:

  • Technology inventory
  • Network documentation
  • Cybersecurity assessment
  • Backup verification
  • Microsoft 365 review
  • Monitoring deployment
  • Account and permission review
  • Risk remediation
  • Technology roadmap development

Before signing, ask to see the onboarding process.

A structured transition is one of the strongest indicators that the MSP operates proactively rather than reactively.

10. Will You Help Us Plan Our Technology Budget?

Great IT providers don't just tell you what's broken today. They help you anticipate what you'll need tomorrow.

Ask whether the MSP will help develop a 1-3 year technology roadmap covering:

  • Computer replacements
  • Server or cloud strategy
  • Network upgrades
  • Cybersecurity investments
  • Microsoft 365
  • Software changes
  • Business continuity
  • AI adoption

This planning helps transform technology from an unpredictable expense into a manageable business investment.

11. How Often Will We Review Our Technology Strategy?

Strategic planning shouldn't happen only when something fails.

Ask how often you'll meet to review:

  • Business goals
  • Cybersecurity risks
  • Technology performance
  • Upcoming replacements
  • Projects
  • Budget
  • New opportunities

For many small businesses, quarterly technology reviews provide a useful rhythm.

Most importantly, these meetings should connect technology decisions to business goals.

12. How Do You Handle Employee Onboarding and Offboarding?

Employees joining and leaving a business creates both productivity and cybersecurity challenges.

Ask whether the provider has a standardized process for:

  • Creating accounts
  • Preparing computers
  • Assigning licenses
  • Configuring permissions
  • Enabling MFA
  • Disabling former employee accounts
  • Protecting company data

For example, when an employee leaves, access should be removed promptly.

Without a consistent process, forgotten accounts can become unnecessary security risks.

14. What Happens If We're Not Satisfied?

This question reveals a lot about the provider's confidence and business philosophy.

Ask:

  • Is there a satisfaction guarantee?
  • How are service concerns escalated?
  • What happens if expectations aren't met?

A technology partnership should be built on performance and trust rather than complicated fine print.

NextX backs its services with a 100% No-Small-Print Satisfaction Guarantee because we believe long-term relationships should be earned.

15. Why Should We Choose You Instead of Another MSP?

Finally, ask the simplest question.

"What makes you different?"

Listen carefully to the answer.

If every provider offers monitoring, help desk support, Microsoft 365, and cybersecurity, what actually distinguishes one company from another?

Look for meaningful differences such as:

  • Proven experience
  • Local support
  • Communication style
  • Guarantees
  • Industry expertise
  • Strategic planning
  • Customized solutions

For NextX, those differences include more than 25 years of experience, Customized IT Solutions, No Geek-Speak, our 100% No-Small-Print Satisfaction Guarantee, and a focus on giving clients Peace of Mind.

MSP Comparison Scorecard

Once you've interviewed several providers, score each one instead of relying solely on impressions.

Use a simple 0-2 point system for each of the 15 questions:

  • 0 points: Weak or unclear answer
  • 1 point: Acceptable answer
  • 2 points: Strong, specific answer

With 15 questions, the maximum score is 30 points.

As a practical framework:

  • 25-30: Strong candidate
  • 19-24: Investigate gaps carefully
  • 0-18: Significant questions remain

Of course, a scorecard shouldn't replace judgment. Nevertheless, it makes provider comparisons more objective and helps your leadership team identify important differences.

Red Flags to Watch For

As you interview MSPs, watch for providers that:

  • Won't clearly explain what's included
  • Avoid discussing additional charges
  • Can't describe their onboarding process
  • Rely only on basic antivirus for cybersecurity
  • Don't regularly test backups
  • Don't offer strategic technology planning
  • Use confusing technical jargon instead of answering questions
  • Can't explain how service concerns are handled

One red flag doesn't automatically make a provider unsuitable. However, several unclear answers should encourage additional due diligence.

Frequently Asked Questions About Choosing an MSP

How much should managed IT cost for a small business?

For businesses with 5-50 employees, comprehensive managed IT may typically cost approximately $150-$250 per user per month. However, pricing varies based on cybersecurity, infrastructure, cloud services, compliance requirements, and what's included in the agreement.

Therefore, compare scope and value rather than price alone.


Should I choose a local IT company?

A local provider can offer advantages such as onsite support, community knowledge, local references, and greater accountability. However, local presence should be considered alongside technical expertise, cybersecurity capabilities, responsiveness, and service quality.


How many MSPs should I interview?

For many businesses, comparing 2-3 qualified providers is enough to identify meaningful differences without making the process unnecessarily complicated.

Use the same 15 questions with each company so you can compare answers consistently.


How long does switching MSPs take?

For many businesses with 5-50 employees, onboarding can take approximately 30-90 days, depending on the complexity and condition of the technology environment.

A good provider should explain the transition plan before the relationship begins.


What's the most important question to ask an MSP?

There isn't one question that determines everything. Instead, focus on how the provider answers the complete framework.

You want evidence that the MSP can support your employees, protect your business, communicate clearly, plan strategically, and deliver predictable value.

Choose an IT Partner, Not Just an IT Vendor

Choosing a Managed Service Provider is ultimately about trust.

After all, this company may have administrative access to your network, Microsoft 365 environment, computers, backups, and other critical systems. Therefore, the decision deserves more consideration than simply comparing monthly prices.

Use these 15 questions to evaluate each provider consistently. Ask for specific answers, examples, processes, and references. Moreover, don't be afraid to ask follow-up questions when an answer is unclear.

For more than 25 years, NextX has helped businesses throughout Billings, Montana, and Yellowstone County simplify technology, strengthen cybersecurity, and plan for the future.

We believe businesses deserve Customized IT Solutions, straightforward No Geek-Speak communication, a 100% No-Small-Print Satisfaction Guarantee, and the Peace of Mind that comes from knowing their technology is being managed proactively.

If you're evaluating IT providers, contact NextX for a no-obligation conversation. Bring these 15 questions with you.

We'll answer every one.