The MSP Interview: 5 Hard Questions to Ask Before You Sign

Outsourcing your information technology is a decision that impacts every facet of your organization. When you hire a Managed Services Provider (MSP), you’re not simply buying a software subscription or hiring a repair service. You’re bringing on a partner who’ll have intimate access to your proprietary data, your financial records, and your daily operations.

Despite the gravity of this decision, many business leaders approach the hiring process based solely on price or a generic sales presentation. The reality is that the IT industry varies wildly in terms of competency and maturity. Some providers are highly sophisticated operations with rigorous security standards, while others are reactive and underprepped.

To distinguish between a high-quality partner and a liability, you need to conduct a rigorous interview. Before you commit to a contract, you must look past the marketing language and ask the difficult questions that reveal how the provider operates when the pressure is on.

1. “Can you show me your written Service Level Agreement (SLA)?”

Every IT provider will tell you they have “fast response times.” But “fast” is a subjective term. To a technician juggling ten tickets, four hours might seem fast. To a business owner whose server is offline and losing revenue by the minute, four hours is an eternity.

You need to move from subjective promises to objective guarantees. Ask to see their Service Level Agreement. This document should clearly define:

• Response Times: How quickly they guarantee to acknowledge a problem.
• Resolution Targets: The estimated time frames to fix issues based on severity.
• Prioritization: How they distinguish between a single user unable to print (low priority) and a company-wide email outage (critical priority).

If a provider cannot show you a written SLA, they’re asking you to trust their best effort. In a business environment, the “best effort” is rarely good enough.

2. “What is specifically excluded from your monthly fee?”

The appeal of the managed services model is budget predictability. You pay a flat monthly rate, and your IT is taken care of. However, “all-inclusive” rarely means truly unlimited. There are always boundaries, and you need to know where they are before you receive a surprise invoice.

Ask for a detailed list of out-of-scope items. Common exclusions often include:

• Onsite Labor: Is a trip to your office covered, or is it billed hourly?
• Projects: Are server migrations, office moves, or new software implementations included?
• Hardware Replacement: Who pays for the labor if a PC needs a new hard drive?
• After-Hours Support: What is the billing rate for a call at 2:00 AM on a Saturday?

A transparent MSP will walk you through these costs upfront so you can budget accurate for the year.

3. “Describe your internal security stack and compliance experience.”

It’s no longer enough for an IT provider to simply keep the lights on; they must also keep the criminals out. You need to verify that the MSP practices what they preach. If their own internal security is lax, they become a gateway for hackers to enter your network.

Ask them about the tools they use to protect their own systems. Do they require Multi-Factor Authentication (MFA) for their technicians? How do they store the passwords for your network?

Ask about their approach to your security. If their standard package only includes basic antivirus and a firewall, they’re behind the curve. You want to hear about:

• Endpoint Detection and Response (EDR): Advanced tools that hunt for malicious behavior.
• Patch Management: Automated updates for security flaws.
• Email Filtering: Protection against phishing and spam.

If you’re in a regulated industry like healthcare or finance, ask specifically about their experience with HIPAA or CMMC compliance.

4. “How often will we meet for strategic planning?”

There is a major difference between an IT mechanic and a technology partner. A mechanic fixes things when they break. A partner helps you plan so things do not break in the first place.

Ask the provider about their account management process. Do they offer Quarterly Business Reviews (QBRs) or strategic planning sessions? During these meetings, a vCIO (Virtual Chief Information Officer) should review your ticket history, identify aging hardware that needs replacement, and suggest new technologies to improve efficiency.

If an MSP has no process for strategic planning, they remain in a reactive “break/fix” cycle. This stagnates your business growth and leads to unpredictable emergency spending.

5. “What is the offboarding process?”

This is the question most business owners forget to ask, but it’s perhaps the most important.

Some unethical providers attempt to lock clients in by holding administrative passwords or documentation hostage. You need assurance that you own your data. Ask them to confirm, in writing, that if you cancel the contract:

• You retain ownership of all data and credentials.
• They’ll cooperate with your new provider to transfer knowledge.
• They’ll remove their monitoring agents from your systems promptly.

A professional MSP knows that they must earn your business every month and will not rely on fear or hostage tactics to keep you as a client.

FAQs

What is the difference between Managed Services and Break/Fix?

In a break/fix model, you pay an hourly rate whenever something breaks. The IT provider profits when you have problems. In a Managed Services model, you pay a flat fee for proactive maintenance. The provider profits when your systems run smoothly, aligning their incentives with your business goals.

How long are standard MSP contracts?

Contract lengths vary, but most providers ask for a 12-to-36-month commitment. This allows them to invest the upfront time and resources required to document and secure your network properly. However, always review the termination clauses to understand your options if service levels are not met.

Will I work with a dedicated technician?

While you will likely have access to a full help desk team for quick fixes, high quality MSPs usually assign a lead engineer or account manager to your business. This person learns the nuances of your specific workflow and infrastructure, preventing you from having to explain your setup every time you call.

Does an MSP replace my internal IT person?

Not necessarily. This is called “Co-Managed IT.” An MSP can handle the heavy lifting of backend security, backups, and patching, freeing up your internal IT staff to focus on immediate user support and strategic company projects.

A Partnership Built on Transparency

The goal of these questions is not to trap, but to establish a foundation of transparency. A reputable Managed Services Provider will welcome this level of scrutiny because it shows you are serious about your technology.

Your IT infrastructure is the backbone of your operations. Do not leave it in the hands of the lowest bidder or a provider who operates in the shadows. By demanding clear answers on security, strategy, and service levels, you’re signing a contract with a partner who can truly rescue you from technical chaos.

At tekRESCUE, we believe in open communication and documented results. If you’re ready to ask the hard questions, we’re ready to provide the answers your business deserves.