What to Ask Before Signing with a Managed Services Provider

Outsourcing your IT is one of the most strategic operational decisions a business owner can make. Finding the right partner means gaining efficiency, security, and peace of mind. However, choosing the wrong partner can lead to frustration, hidden costs, and prolonged downtime.

The market is flooded with IT companies. Some are highly sophisticated operations with deep benches of talent, while others are essentially one person with a laptop and a cell phone. On the surface, their websites and proposals might look identical. They all promise “proactive support” and “24/7 monitoring.” So, how do you distinguish these companies and their guarantees?

You have to ask the hard questions.

Interviewing a Managed Services Provider (MSP) should be just like interviewing a candidate for a C-level executive position. You’re handing them the keys to your data, your network, and your employee productivity. Before you sign the dotted line, ask these questions to verify they can deliver on their promises.

1. What Is Your Guaranteed Response Time?

“Fast” is subjective. To a business owner with a server down, five minutes feels like an hour. To an IT technician working on three other tickets, an hour might feel like five minutes. You need to remove the ambiguity.

Ask the MSP to define their Service Level Agreement (SLA). A provider will have written guarantees regarding how quickly they’ll acknowledge a ticket and how quickly they’ll begin working on it.

Ask how they prioritize issues. A printer jam for one user should not be treated with the same urgency as a company-wide email outage. Understanding their triage process will help you manage expectations within your own team. If they cannot provide specific numbers or a written SLA, that is a major red flag.

2. What Is Included in Your “All-Inclusive” Price (and What Isn’t)?

The Managed Services model is built on the concept of a flat monthly fee for unlimited support. This provides budget predictability for the client and incentivizes the MSP to keep things running smoothly. However, “unlimited” rarely means “everything.”

You need to know exactly where the line is drawn to avoid surprise invoices later. Specific things to clarify include:

• Onsite Visits: Is travel time and labor included if a problem cannot be fixed remotely, or is that billed hourly?
• Projects: Are major upgrades, like installing a new server or migrating to Microsoft 365, included in the monthly fee, or are they billed as separate projects?
• After-Hours Support: What is the cost if you call the help desk at 8:00 PM on a Saturday?
• Hardware: Does the fee cover the replacement of broken parts?

A reputable MSP will be completely transparent about their billing structure. If the provider is vague about these details, proceed with caution.

3. How Do You Handle Cybersecurity and Compliance?

Ten years ago, an MSP’s primary job was to keep the internet running and the printers printing. Today, their primary job is keeping your business safe from cybercriminals.

• Do not settle for a simple “yes, we do security.” You need to dig deeper. Ask them about their security stack.
• Do they use Endpoint Detection and Response (EDR) or just standard antivirus?
• How do they handle patch management for your software?
• Do they offer security awareness training for your staff?

If you’re in a regulated industry like healthcare (HIPAA) or finance (FINRA), ask specifically about their experience with compliance. They should be able to explain how their tools and policies help you meet your regulatory requirements. If they seem dismissive of compliance or unsure of the regulations that affect your industry, they’re not the right partner for you.

4. What Is Your Strategy for Disaster Recovery?

Data loss is a business killer. Whether it’s due to a ransomware attack, a natural disaster, or a disgruntled employee deleting files, you need to know that your MSP can get you back up and running.

Ask them to explain their backup strategy. Do they use local backups, cloud backups, or a hybrid of both? Most importantly, ask them how often they test those backups. Seeing a “backup successful” notification is not enough; the backup needs to be verified to ensure the data is actually recoverable.

Ask the tough question: “If our data got compromised or our IT setup crashes, how long would it take for us to be operational again?” Their answer will tell you a lot about their disaster recovery capabilities.

5. How Will You Help My Business Grow and Be More Efficient?

A “break/fix” guy fixes things when they break. A true Managed Services Provider acts as a Virtual Chief Information Officer (vCIO). They should be a strategic partner, not just a repair service.

Ask the provider how often they meet with clients for strategic planning. Do they conduct Quarterly Business Reviews (QBRs)? In these meetings, they should be analyzing your ticket history to identify trends, discussing the lifecycle of your hardware so you can budget for replacements, and recommending new technologies that could improve your efficiency.

If an IT provider is only talking to you when something is broken, they’re reacting to your business, not helping to lead it.

FAQs

What is the difference between an MSP and a break/fix shop?

A break/fix provider charges you an hourly rate to fix a specific problem. Their incentive is for you to have problems so they can bill hours. An MSP charges a flat monthly fee to keep your systems running. Their incentive is to prevent problems from happening in the first place because that makes them more profitable and keeps your business running smoothly.

How long are typical MSP contracts?

Contract lengths vary, but 12 month to 36 month terms are common in the industry. These terms allow the MSP to invest in the upfront costs of onboarding your business and installing their management tools. However, some providers offer month to month options. Always review the cancellation policy and exit terms before signing.

Will I get a dedicated technician or a call center?

This depends on the size of the MSP. Larger MSPs often have a help desk team (Tier 1) that handles routine issues and a dedicated escalation team (Tier 2 and 3) for complex problems. The best MSPs assign a primary account manager or lead technician who learns the nuances of your specific network, so you are not explaining your setup from scratch every time you call.

Is it difficult to switch IT providers?

It can feel daunting, but a professional MSP makes the transition seamless. The new provider should handle the heavy lifting, including contacting the old provider to transfer passwords, documentation, and domain administration. You should not have to be the technical middleman. If you are unhappy with your current support, the fear of switching should not hold you back.

The Value of the Right Partnership

Signing an agreement with a Managed Services Provider is the beginning of a long-term relationship. You’re trusting them to protect your livelihood and empower your team. By asking these questions upfront, you move past the sales pitch and get to the operational reality of how they do business.

At Pacific Cloud Cyber, we welcome these questions. We believe that an informed client is our best client. If you’re evaluating your IT options and want straight answers about response times, security, and strategic value, we’re ready to have that conversation.