Choosing a managed services provider (MSP) is more than a technical decision—it’s a strategic partnership. For C-level executives and IT directors at mid-sized businesses, the right MSP can bolster cybersecurity, streamline IT operations, and guide long-term tech strategy. The wrong choice, on the other hand, might leave you exposed to cyber threats or stuck with subpar service. How do you tell the difference? It starts with asking the right questions. Below, we walk through the top questions to pose when evaluating MSPs, complete with real-world scenarios and insights. These questions will help ensure your potential provider is not just fixing Wi-Fi issues but truly aligning with your business goals in areas like security, cloud, and growth. Let’s dive in.
How Will You Keep Our Business Secure from Cyber Threats?
In today’s environment, cybersecurity is non-negotiable. Threats are escalating – for example, cyberattacks surged 38% year-over-year – and the average data breach now costs nearly $4.9 million globally. So ask your MSP candidate: What are your cybersecurity capabilities? A strong answer will include details about a 24/7 Security Operations Center (SOC), advanced threat detection tools like EDR/XDR (Endpoint/Extended Detection & Response), regular vulnerability assessments, and employee awareness training.
Real-world scenario: Imagine a new strain of ransomware hits businesses in your industry. Does the MSP have eyes on emerging threats and the agility to respond immediately? Do they have a proven incident monitoring and response team watching your network around the clock? The MSP should act less like an “IT handyman” and more like a security strategist, implementing Zero Trust architecture and up-to-date defenses rather than relying on yesterday’s antivirus. If a provider’s big security boast is simply “we install antivirus,” consider that a red flag – you need an MSP that makes cybersecurity the core of everything they do. Look for evidence of security certifications, frameworks (like NIST or ISO 27001) they adhere to, and a track record of keeping clients safe.
Top Questions to Ask:
- What cybersecurity frameworks or certifications do you follow?
- How does your SOC operate, and is it staffed 24/7?
- How do you handle vulnerability management and threat intelligence?
- What tools do you use for EDR/XDR, and how do they integrate with our environment?
- Do you offer employee training or phishing simulations?
Need an IT Partner Who “Gets” Your Business?
What Is Your Plan for Incident Response and Disaster Recovery?
Even with great preventative security, incidents can happen – and natural disasters or outages will occur. So it’s critical to ask: “How will you help us recover when things go wrong?” A quality MSP will have a robust incident response plan and disaster recovery (DR) capabilities tailored to your business. They should assist in crafting (and periodically testing) a business continuity plan, including data backups, failover strategies for critical systems, and clear steps to contain and remediate cyber incidents.
Real-world scenario: Picture a server crash or a ransomware attack encrypting your data on a weekend. The MSP’s response in that first hour can make the difference between a minor hiccup and a major business shutdown. Do they offer guaranteed rapid response 24/7/365? Do they have on-call experts and predefined playbooks for various scenarios (from malware infections to cloud outages)? The best MSPs won’t wait for you to call – they’ll proactively alert you to issues and spring into action immediately to isolate threats or switch over to backups. Also, ask if they will help with cyber insurance requirements – for instance, many insurers now expect documented incident response plans and prompt communication during breaches. An MSP should be ready to support those needs. In short, you want a partner who can confidently say: “If disaster strikes, we’ve got you. Here’s how we’ll keep your business running.”
Top Questions to Ask:
- Do you have a formal incident response plan, and can we see a sample?
- What is your average response time during a critical incident?
- How do you handle disaster recovery testing and failover planning?
- Do you provide backup and recovery services? How often is data backed up?
Can you assist with cyber insurance claims and compliance documentation?
What Does Your Day-to-Day Support Look Like (And Is It Proactive)?
MSPs vary widely in how they deliver managed IT services on a daily basis. This question digs into whether they will truly support your team or just wait for tickets. Ask about their support model: Is help available 24/7? Do you get on-site support if needed, or is it all remote? How quickly do they respond to issues, and what are their service-level agreements (SLAs) for things like critical outages? A good MSP will describe a tiered support structure (e.g. help desk for routine issues, higher-level engineers for complex problems) and might even assign you a dedicated account manager or technical lead who learns your environment.
Crucially, listen for signs of proactive service. If a provider only highlights “fast ticket resolution,” follow up with: “What happens after you close the ticket?” The best MSPs don’t just put out fires – they investigate root causes and implement preventative fixes so you aren’t calling with the same issue next month. For instance, they might mention using trend analysis on support requests to spot systemic problems or offering regular patch management without being asked. In 2025, simply touting “99.9% uptime and 15-minute response times” is table stakes. Top-tier providers go further, scheduling maintenance windows, health checks, and performance tuning to catch issues before they impact users. When evaluating an MSP’s answer, look for a mindset of continuous improvement and prevention, not just reactive help desk duty.
Real-world scenario: One of your employees has a laptop issue at 4:45 PM on a Friday. Will the MSP still be there to help, or do they vanish at 5? And if your company is working late on a global project over the weekend, can they support that? Your MSP should feel like an extension of your team – available when you need them and taking initiative to keep things running smoothly without being asked.
Top Questions to Ask:
- What does your support coverage include (onsite, remote, after-hours)?
- What are your SLAs for different types of issues?
- How do you handle recurring problems or patterns?
- Will we have a dedicated account manager or point of contact?
- Do you offer proactive services like patching, monitoring, or health checks
Do Your Services Scale with Our Business and Adapt to Change?
Mid-sized businesses aren’t static – you might be opening new offices, undergoing mergers, or suddenly shifting to a remote workforce. Ask how the MSP handles growth and change. A great MSP will have scalable services and flexible contract terms that accommodate adding or removing users, locations, and services without a lot of pain. For example, if you double your headcount, can they seamlessly double your support coverage? If you need to spin up an entire new branch office network next quarter, do they have the resources and processes to make it happen quickly?
Listen for answers that mention flexible staffing or pricing models (e.g. scaling up support for a short-term project, then scaling down), and automation or templates they use to deploy new environments quickly. They should also be able to integrate new technologies as your needs evolve – whether that’s supporting a shift to DevOps workflows, handling IoT devices, or accommodating whatever the “next big thing” in IT is.
Real-world scenario: If your retail company takes on a seasonal surge every holiday, will the MSP be prepared to handle the increased load without charging an arm and a leg for short-term capacity? Conversely, if you divest a business unit, can they adjust your services (and costs) downward accordingly? Beware of providers who make growth feel like a punishment – for instance, rigid contracts that force you to renegotiate (or pay steep overage fees) every time you add a few users. An MSP that truly partners in your success will build in flexibility. As Meriplex puts it, if scaling up feels like a penalty, that provider is holding you back. Look for an MSP who says, “We grow when you grow,” and proves it through adaptable support.
Top Questions to Ask:
- Can you scale services up or down quickly as our needs evolve?
- How do your contracts accommodate changes in team size or location?
- What is your process for onboarding new users or locations?
- Do you support flexible or hybrid cloud environments?
Not Sure If Your IT Strategy Covers All the Bases?
How Much Cloud Expertise Can You Bring to the Table?
Cloud services are a major part of modern IT – and a potential minefield of cost and complexity if mismanaged. Probe your MSP’s cloud savvy. Do they have experience with the cloud platforms you use or plan to use (AWS, Azure, Google, Microsoft 365, etc.)? Can they articulate a balanced cloud strategy rather than pushing “move everything to the cloud” blindly? In recent years, cloud spending has skyrocketed (global cloud spend jumped $60 billion year-over-year, reaching $330B in 2024), and many businesses have felt “sticker shock” after rushed migrations. A good MSP will help you avoid those pitfalls.
Key things to listen for: the MSP should offer to assess your workloads and recommend what makes sense to run in cloud vs. on-premises, with a focus on cost optimization and performance. They might mention cleaning up underused resources, rightsizing virtual machines, or leveraging hybrid cloud to get the best of both worlds. Also, ask if they have certified cloud architects on staff and how they stay current with evolving cloud services.
Real-world scenario: Say you’re considering migrating a critical application to Azure. The wrong MSP might just say “Sure, we’ll move it” and rack up your cloud bill. The right MSP will ask about your requirements, maybe discover that a hybrid solution or a phased migration avoids risk and calculate the projected costs vs. benefits for you. They act as an advisor, not a reseller looking for a commission. In short, the MSP’s cloud expertise should translate into clear guidance: helping you modernize at the right pace, manage cloud costs, and prevent “cloud sprawl” (like dozens of unused SaaS subscriptions eating your budget). If an MSP claims “the cloud will fix everything” without a nuanced discussion, be wary – in 2025, one-size-fits-all cloud solutions rarely work. You want a provider who sees cloud as part of a larger strategy, not a silver bullet.
Top Questions to Ask:
- What cloud platforms do you support, and how deep is your experience?
- Can you help us determine what should and shouldn’t move to the cloud?
- How do you manage cloud costs and avoid waste?
- What certifications do your cloud engineers hold?
Will You Align IT with Our Business Strategy (and Not Just Fix Computers)?
This question gets to the heart of whether an MSP will be a strategic partner. You’re looking for someone who will understand your industry, your business objectives, and help plan technology initiatives to meet those goals. Ask if the MSP provides virtual CIO (vCIO) or strategic consulting services as part of their offering. Do they conduct regular quarterly business reviews or planning meetings with your leadership? The ideal MSP will say “yes” – they’ll help you develop an IT roadmap, budget for future needs, and make decisions like prioritizing projects or evaluating new tech (from AI to automation) in a business context .
Real-world scenario: Suppose your company is expanding into a new region or launching an e-commerce platform next year. A strategic MSP will proactively bring ideas to the table: maybe suggesting the right infrastructure to support expansion, identifying security compliance requirements in new markets, or advising on tools to improve customer experience. They should be comfortable talking to your C-suite about ROI, risk management, and opportunities – not just geek out on tech for tech’s sake. If an MSP avoids these big-picture conversations or only shows up when it’s time to upsell you on hardware, that’s a red flag. Instead, look for answers that include examples of strategic guidance they’ve provided other clients (e.g. “We helped a client in your field transition to a hybrid cloud to reduce costs by 20% while meeting compliance”). You want a collaborator who is transparent and consultative, not sales-driven. The right MSP will proudly describe how they’ve acted as a trusted advisor – effectively part of the client’s internal strategy team.
Top Questions to Ask:
- Do you offer vCIO services or strategic planning?
- Will we get quarterly reviews or roadmap planning sessions?
- How do you help clients plan for future tech and budget needs?
- Can you help us evaluate and adopt new technologies?
Looking for a Strategic MSP Partner?
How Do You Communicate and Provide Transparency in Our Partnership?
Last but not least, don’t overlook communication and transparency. Ask the MSP: “How will we stay in the loop on what you’re doing, and how do we measure success?” A reputable provider will have a clear answer: they might promise monthly or quarterly reports showing key metrics, regular check-in calls or meetings, and a single point of contact for your questions and feedback. Look for mentions of outcome-based metrics – not just “uptime” but things like reduction in security vulnerabilities, faster resolution times, user satisfaction scores, and business impact (e.g. how much downtime was prevented, or how a new system improved productivity). Providers that focus on these outcomes demonstrate a commitment to transparency and continuous improvement.
Also, consider their communication style. Do they explain technology in plain language to your executives? Being human-first and transparent means the MSP isn’t hiding behind jargon or a ticket portal. They should be candid about issues and proactive about recommending improvements. For instance, if they find that a particular software is causing frequent problems, you should hear it from them along with options to address it. You’re looking for an MSP who will own up to challenges, celebrate wins with you, and educate your team along the way. Clear, frequent communication builds trust – and trust is paramount in an outsourcing relationship. Before signing, make sure you’re comfortable with how the MSP will keep you informed and accountable. If they can’t easily explain their reporting process or communication cadence, think twice.
Top Questions to Ask:
- How will we receive updates, reports, and insights?
- Who is our main point of contact, and how often will we meet?
- What metrics do you report on, and how do they tie to business outcomes?
- How do you ensure accountability and continuous improvement?
Conclusion
Hiring an MSP is about futures-thinking as much as it is about solving today’s IT issues. By asking the questions above, you’ll get past the sales fluff and uncover how each provider truly operates. Pay attention to their depth in cybersecurity, their commitment to keeping you running no matter what, their knowledge of cloud and modern tech, and whether they genuinely treat your business priorities as their own. An MSP should be transparent in communication, flexible in service, and proactive in strategy – essentially, an extension of your team that’s invested in your success.
In summary, the right MSP will check all these boxes: they keep your defenses sharp, your systems humming, your costs optimized, and your leadership informed. They’ll give you peace of mind that as technology and threats evolve, you have a partner who’s got your back and is thinking two steps ahead. As you evaluate providers, don’t settle for less. Your business deserves an MSP that will be a growth partner – one that elevates your IT from a cost center to a strategic asset. With the proper due diligence and these key questions in hand, you’ll be well on your way to finding an IT ally that empowers your organization for the long haul.
