Handing your IT environment to a Managed Services Provider (MSP) is more than outsourcing help desk tickets. You are choosing a partner that will influence uptime, security, compliance, and how well technology supports your growth.
On paper, many MSPs look similar. The real differences show up in their processes, communication, and what is or is not included in the monthly fee. The best way to see those differences clearly is to ask specific, practical questions before you sign.
Below are core areas to cover with any provider you are considering, along with example questions to guide the conversation.
Start With Scope: What Are You Actually Managing for Us
You should know exactly what systems and responsibilities fall under the agreement.
Questions to ask:
Which devices are covered?
- Servers, workstations, laptops, network gear, mobile devices
Do you manage cloud platforms such as Microsoft 365 or Google Workspace?
Will you support our line of business applications, or only the underlying infrastructure?
Is on site work included, or is everything done remotely?
What tasks are considered projects and billed separately?
- Office moves, major upgrades, migrations
Ask for a service description or statement of work that spells out inclusions and exclusions. If something is important to you, it should be written down, not implied.
Clarify Support Process: How Do We Get Help And What Do We Wait For
How an MSP handles day-to-day issues will shape your staff’s experience.
Key questions:
How can users contact support?
- Phone, email, ticket portal
What are your standard support hours?
Do you offer after hours or weekend coverage, and how is that billed?
What are your target response times for different priority levels?
How do you communicate status during an ongoing incident?
What is your escalation process if a problem is not resolved quickly?
You should come away with a clear picture of what happens when someone’s email stops working at 10 a.m. on a weekday, or when a server has trouble at 9 p.m. on a Sunday.
Dig Into Security and Compliance: How Will You Protect Our Environment
Any provider you hire will have extensive access to your systems. Their approach to security matters as much as their ability to fix a printer.
Questions to cover:
What tools and controls are standard in your security stack?
- Endpoint protection, email filtering, web filtering, patch management, monitoring
How do you handle security updates for servers and workstations?
Do you enforce or recommend multi-factor authentication for remote and cloud access?
What is your strategy for backup and disaster recovery?
What is backed up, how often, and where is it stored?
How often do you test restores?
Can you help us meet specific compliance or cyber insurance requirements?
Also ask how they protect their own systems:
- How do technicians securely access our network?
- How are administrative passwords stored and managed?
Look for consistent standards rather than one off tools added only when something goes wrong.
Understand Pricing and Agreements: What Will This Really Cost Over Time
Managed services are meant to bring predictability to IT spending, but only if you know what is included.
Questions to ask:
Is pricing based on users, devices, or a flat rate?
What is included in the monthly fee?
- Help desk, monitoring, security tools, onsite visits, strategy meetings
What is considered out of scope and billed separately?
What is the initial contract term and renewal process?
How are fee increases handled?
What happens if we need to add or remove users or locations?
Ask the provider to walk you through a sample invoice for a client similar to you. This often exposes add-ons and assumptions that may not be obvious in a proposal.
Ask About Onboarding and Documentation: How Will You Learn Our Environment
The first few months with a new MSP often determine whether the relationship feels organized or chaotic.
Questions to explore:
What are the steps in your onboarding process?
- Discovery, tool deployment, cleanup, documentation, training
How long does onboarding usually take for a company our size?
What kind of documentation will you create?
- Network diagrams, asset lists, application lists, password vault entries
Who owns that documentation and how is it shared securely with us?
Do you perform any initial remediation as part of onboarding?
- Removing unsupported software, standardizing configurations
The provider should be able to describe this process in a structured way instead of saying they will figure it out as they go.
Evaluate Experience and Fit: Are We the Type of Client You Serve Best
Technical skills are important, but familiarity with your size and industry often matters just as much.
Questions to ask:
What types and sizes of organizations do you primarily support?
Do you have experience in industries with similar regulatory or security needs?
Are you familiar with our critical applications?
Can you provide references from current clients who are similar to us?
How long have most of your clients stayed with you?
Pay attention to how specifically they talk about real clients and outcomes. General claims without examples are less helpful.
Clarify Strategy And Communication: How Will You Help Us Plan, Not Just React
A strong MSP relationship should include more than ticket resolution. It should help you plan.
Questions worth asking:
Will we have a dedicated account manager or vCIO function?
How often will we meet to review performance, risks, and plans?
Do you help with IT budgeting and lifecycle planning?
What kind of regular reports will we receive?
- Ticket metrics, system health, security status, backup verification
You want to see that the provider has a process for ongoing communication, not just ad hoc calls when something breaks.
FAQs
What is a managed services provider and how is it different from traditional IT support
A managed services provider offers ongoing monitoring, maintenance, and support under a recurring agreement. The goal is to prevent problems and keep systems stable. Traditional break fix support usually responds only when something goes wrong and bills by the hour. Managed services shift IT from reactive to proactive.
How long should we commit to an MSP contract?
Contract lengths vary. Many MSPs prefer one to three year terms. For a first engagement, some organizations look for a one-year contract or a shorter initial term to evaluate fit. The right answer depends on your risk tolerance and how much up-front work the provider will perform. Whatever the term, make sure exit clauses and offboarding support are clear.
Is it better to switch everything to an MSP at once or phase it in
For most small and midsized organizations, moving fully to an MSP model at the beginning of the relationship works best, because the provider can standardize tools and processes. That said, there may be systems that stay in house or with specialized vendors. The important point is to define who owns which responsibilities, so there are no gaps.
Can we keep an internal IT person and still use a managed services provider?
Yes. Many businesses use a hybrid approach. Internal IT may handle on site support, user training, and application administration, while the MSP manages infrastructure, security, monitoring, and strategy. Clear division of responsibilities and regular communication are critical in this model.
What are warning signs that an MSP may not be a good fit?
Red flags include vague service descriptions, no written service level commitments, limited transparency about security practices, reluctance to discuss pricing details, and little interest in understanding your specific environment. If a provider focuses only on tools and not on process, communication, and planning, that is also a concern.
Using The Right Questions to Choose the Right Partner
Selecting a Managed Services Provider is not something to rush. The provider you choose will touch nearly every aspect of your technology and data. Taking time to ask detailed questions about scope, support, security, pricing, onboarding, and experience helps you see past marketing language and understand how they will actually operate day to day.
Sundance Networks welcome these questions and answer them clearly. The result should be a relationship where expectations are understood on both sides, and where IT becomes a stable foundation for your business rather than a recurring problem.
If you are evaluating providers now, using these questions as a checklist can help structure your conversations and clarify which partner is best positioned to support your goals.
