What Smart CEOs Ask Their MSP Before It's Too Late

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You’ve handed over your IT to a managed service provider (MSP), and your team says, “We’re covered” when it comes to disaster recovery. But here’s the real question: if disaster struck today, would your MSP be able to recover your systems fast enough to avoid serious damage?

A lot of business leaders assume that outsourcing IT means all the risk is taken care of. Unfortunately, when a cyberattack or system failure happens, they often find gaps in service agreements, unclear responsibilities, and recovery plans that haven’t been tested. The truth is, if things go wrong, it’s your business—not your MSP—that faces the reputational and financial fallout.

With the rapid pace of technology change, many businesses have been focused on digital transformation to stay competitive. But in doing so, they often overlook the importance of ensuring their MSP has robust disaster recovery capabilities. While stronger MSPs may take a proactive approach, it’s far from guaranteed.

These seven key questions will help you figure out if your DR plan really has your back or just gives you a false sense of security.

The Need for Strategic DR Planning with Outsourced IT

Across the UK, many mid-market businesses depend on MSPs for backup and disaster recovery. It sounds simple—expert help, predictable costs, and less pressure on your internal IT team. But issues crop up when businesses focus solely on transformation projects or ticket response times, without giving disaster recovery the same level of scrutiny.

When outages or ransomware hit, three big gaps tend to stand out. First, service level agreements can be unclear about recovery times and responsibilities. Second, there’s often confusion around ownership—who’s actually in charge of getting things back on track? Third, many disaster recovery plans haven’t been tested and only exist on paper.

The effects go beyond technical headaches. Your customers expect your services to run smoothly, no matter who’s managing your IT. When things go wrong, it’s your reputation on the line.

Why DR Accountability Matters More Than Ever

Recovery time isn’t just an IT metric anymore—it’s a critical business KPI that boards take seriously. In 2025, executives will face even more pressure to quickly get operations back on track after disruptions. Cyber insurance providers now want solid proof of disaster recovery (DR) capabilities and provider accountability before they’ll issue policies or process claims.

Regulators and customers are also raising the bar. They expect auditable continuity plans, even if you’ve outsourced services. Simply pointing to an MSP contract isn’t going to cut it anymore.

Ransomware recovery brings its own set of headaches. Modern attacks often target backups, so having quick access to verified, immutable backups is a must—not something every MSP can deliver. Unfortunately, many DR plans are outdated or untested, leaving executives to discover gaps when it’s too late.

Seven Critical Questions for Your MSP

Think of these questions as essential due diligence—the same level of scrutiny you'd give to any critical business partner. They're designed to help you figure out if your MSP can truly deliver when it matters most.

1. What’s our guaranteed Recovery Time Objective (RTO)?

Your MSP should give you clear, contractual commitments on recovery timelines for different systems. Vague promises aren’t enough—you need to know if they can meet your operational needs. Critical systems might need to be back up in hours, while others could handle a bit more downtime.

2. When was our last full DR test, and how did it go?

The only way to know if recovery plans actually work is through testing. Your MSP should run regular, documented tests that mimic real-life failure scenarios. Ask for their most recent test results, including any issues they found and how they fixed them. Theoretical plans often fall apart when put to the test.

3. Are our backups immutable, encrypted, and stored off-site?

Modern problems need modern solutions. Immutable backups can’t be altered or deleted—even by admins—which is critical for protecting against ransomware. Encryption and off-site storage provide extra layers of security that traditional backups often lack.

4. Do we have recovery playbooks for our critical systems?

Your MSP should have detailed, up-to-date recovery plans for each of your critical systems. In a crisis, their team needs step-by-step instructions, not guesswork. These playbooks should outline dependencies and system priorities specific to your business.

5. Who takes charge during cyberattacks or major outages?

It’s crucial to know who’s responsible for what before an incident happens. Your MSP should spell out who’s making decisions, managing communications, and running the recovery process. This includes escalation steps and how they’ll keep your leadership team in the loop.

6. What happens if your team becomes unavailable or compromised?

Your MSP should have strong contingency plans for their own operations. What happens if key staff are unavailable, their systems go down, or their facilities are hit? Understanding how they’ll handle their own challenges shows whether they can still support you when things go south.

7. Can you provide detailed reports for compliance and audits?

If your industry is regulated or you have cyber insurance, you’ll need solid documentation of your MSP’s disaster recovery capabilities and tests. They should provide regular reports that meet compliance standards and create an audit trail for recovery activities. These reports are critical for regulatory checks or insurance claims.

Outsourcing IT Doesn’t Eliminate Risk

Outsourcing IT doesn’t eliminate risk—it shifts who you rely on for business continuity. Smart CEOs treat DR risk as seriously as financial or legal risks: they question assumptions, verify capabilities, and document everything.

These seven questions will help you determine if your MSP is truly ready to protect your business—or if it’s time to rethink your DR strategy. The worst time to find gaps is during a crisis.

Want to get ahead of the risk?

Join our live webinar, How to Make Disaster Recovery a Boardroom Priority, and learn how to mitigate DR risk before it impacts your business.