Hiring a Managed IT Service Provider? 8 Questions to Ask in 2026
Quick Summary: What to Ask an IT Service Provider in 2026
If you’re comparing IT services providers or evaluating MSPs this year, these are the eight essential questions businesses should ask:
- What’s included in your managed IT service package?
- How do you handle cybersecurity?
- Who will actually support my business?
- What is your onboarding like?
- How do you approach cloud management and modernization?
- What are your response times and SLA guarantees?
- How do you support compliance requirements?
- Can you provide real client references and metrics?
With many businesses already working with managed service providers (MSPs), chances are you’ve had some experience with one – or maybe you’re considering outsourcing IT for the first time.
To those new to managed IT services, we say hello.
To those looking to make a change, we totally get it.
In today’s blog, we’re here to help you cut down your search. By asking these eight questions, you’ll be able to quickly determine whether an IT service provider is the right fit or whether you should keep searching.
Let’s get into it:
Question 1: “What’s Included in Your Managed IT Service Package?”
First things first: you need to know exactly what’s covered and not covered. Some IT providers bundle basic help desk support, but charge extra for:
- On-site labor
- After-hours support
- Cybersecurity tools
- Project work
Clarifying every service offered by your prospective provider now will help you avoid frustration later.
At The 20 MSP, we offer a single flat-rate price that covers unlimited support with no labor charges, ever.
Question 2: “How Do You Handle Cybersecurity?”
Cybersecurity is not optional. Shockingly, only one-third of service providers prioritize cybersecurity as a core offering.
When you ask your IT provider how they handle cybersecurity, pay attention to whether they offer the following services:
-
- Zero trust enforcement: “Never trust, always verify.” The Zero Trust model has already prevented $456 billion in losses worldwide.
- Multi-Factor Authentication (MFA) across all accounts: This simple, easy-to-implement security feature can block 99% of automated hacking attacks all by itself.
- 24/7 threat monitoring and SOC coverage: Cyberthreats don’t wait for business hours. Businesses need to have 24/7 threat monitoring in place.
- Regular security training: With 95% of data breaches linked to human error, having a provider that offers training is critical.
- Routine vulnerability scanning: Hackers are constantly updating their tools, software is always changing, and your business needs to keep its defenses updated.
Question 3: “Who Will Actually Support Our Business?”
You need to know who you will be dealing with on a day-to-day basis. From tickets to projects to on-site assistance, understanding where your support comes from is a key factor in your decision.
Key considerations:
-
- Dedicated teams or pods: Providers like The 20 MSP assign dedicated teams to each client. This team learns the ins and outs of your business while building trust and familiarity.
- Local or outsourced support: An outsourced help desk can lead to ticket confusion, repeated explanations of the same issues, and difficulty building trust. The 20 MSP operates a fully US-based help desk.
- Escalation ownership: A well-built provider has a clear chain of command for escalations. That way, no problems get stuck, left behind, or dropped.
- True 24/7/36 support: Many providers advertise 24/7 coverage, but close on weekends or holidays. A reliable MSP like The 20 MSP offers true 24/7/365, meaning you can call and get service any time, day or night.
Question 4: “What Is Your Onboarding Process Like?”
Transitioning to a new IT service provider takes coordination. Employees need accounts, software needs installation, and monitoring tools need deployment. While some disruption is normal, a clear onboarding plan minimizes downtime.
A strong onboarding process typically spans 60-90 days and includes three phases:
Day 1-30 Initial Discovery
- Introduction and kickoff meeting
- Comprehensive IT assessment to determine what is needed
- Initial tool and system setup (monitoring software, help desk, etc.)
Day 31-60, The Transition
- Migrate existing platforms (email, security tools, etc.)
- Employee training and support familiarization
Day 61-90, Strategic Planning
- Stabilization and proactive monitoring
- Strategic business review meetings
- Planning for future projects and improvements
A clearly defined onboarding process is a hallmark of a mature IT service provider.
Question 5: “How Do You Approach Cloud Management Modernization?”
Cloud technology evolves quickly. Your IT solutions provider should help your business stay current with modern tools and best practices.
Ask about:
-
- Migrating legacy systems: Moving older systems onto cloud-native solutions.
- Cloud cost optimization: The average company wastes ~ $135,000 on unused, underused, or duplicate SaaS tools annually.
- Regular updates: Cloud environments are constantly being updated. Your IT provider must manage those updates.
- Cloud-specific security: Many cloud environments come with built-in security features, but only work if properly configured and monitored.
Question 6: “What Are Your Response Times and Service Level Agreement (SLA) Guarantees?”
Knowing how long you can expect to wait for support is critical to a functioning help desk.
Ask about:
-
- Average response times: Understand the expected response for critical and non-critical issues. For example, The 20 MSP has a one-hour SLA for initial ticket responses.
- Guaranteed resolution times: Check the SLA to see how long it should take to resolve issues.
- Escalation procedures: Ask how tickets are handled if they are not resolved within the SLA timeframe.
- Hours of coverage: Does “24/7” actually mean 24/7?
Question 7: “How Do You Support Compliance Requirements?”
From HIPAA, GDPR, or PCI, your IT service provider should help you stay compliant. Falling out of compliance can result in legal, financial, and reputational consequences.
A strong IT service provider should support:
-
- Regular audit and reporting: Systems and processes meet compliance requirements.
- Data protection and access control policies: Protect sensitive information and limit access to authorized personnel.
- Employee training: Training your team in compliance best practices doesn’t just reduce risk; it’s required.
- Documentation for regulators: Provides evidence that your business meets necessary compliance standards.
- Certifications: Some IT service providers have certifications that demonstrate their ability to maintain compliance, such as The 20 MSP’s SOC 2 Type II certification.
Your IT service provider should help your business stay audit-ready at all times.
Question 8: “Can You Provide Real Client References and Metrics?”
References, testimonials, and metrics show that the IT solutions provider isn’t just talk.
Ask for:
-
- Case studies or success stories: Real-world examples of how your IT partner made a difference.
- Testimonials or satisfaction ratings: Feedback from current or past clients says a lot about an IT service provider. You can check out The 20 MSP’s testimonial archive here.
- Performance metrics: Request data on uptime, response times, ticket resolutions, and other measurable results.
These insights reveal whether the managed IT service provider consistently delivers results.
Quick Comparison Checklist
Before deciding, evaluate each IT service provider on:
-
- Service coverage (Help desk, monitoring, cybersecurity, on-site labor)
- Cybersecurity measures (Zero trust, MFA, 24/7 monitoring, employee training, vulnerability scanning)
- Support model (Dedicated team, US-based help desk, escalation process)
- Onboarding clarity and 60-90 day plan
- Cloud management capabilities
- SLA guarantees & Response times (Average response times, guaranteed resolution times, escalation process, coverage hours)
- Compliance readiness
- Reference & proven metrics
Red Flags to Watch Out For
If you see any of the following when looking for an IT service provider, proceed with caution:
- Vague or incomplete service descriptions
- Outsourced support with no dedicated point of contact
- Weak or outdated cybersecurity practices
- No structured onboarding process or unrealistic timelines
- Poor or missing SLAs for response and resolution times
- No compliance support for your industry
- Lack of client references for performance data
Finding the Right IT Service Provider
Choosing the right IT partner can be overwhelming, but these eight questions provide a solid framework to evaluate potential providers.
If you want to skip the search, reach out to The 20 MSP. We can answer every single one of these questions. We know what it takes to stand out in the crowded market of IT service providers. Let’s talk.
Want more tips like this?
Subscribe using the form on the right and get our latest insights delivered straight to your inbox.
About The 20 MSP
As a leading provider of managed IT services, The 20 MSP serves thousands of businesses nationwide, including single and multi-location organizations, delivering white-glove service, secure and streamlined IT infrastructure, and 24/7/365 support. We believe in building lasting relationships with clients founded on trust, communication, and the delivery of high-value services for a fair and predictable price. Our clients’ success is our success, and we are committed to helping each and every organization we serve leverage technology to secure a competitive advantage and achieve new growth.
