The 7 IT Questions Every Business Owner Should Ask Their MSP This Fall

It’s fall; a season of planning, budgeting, and setting the tone for next year’s growth. But while you’re mapping out your Q4 goals, your Managed Service Provider (MSP) might be coasting on last year’s playbook.

The truth? Many businesses settle for IT vendors who fix things after they break. That’s not support. That’s damage control. And in today’s world, reactive IT is a liability.

At PCS, your MSP should be your strategic partner, not just your emergency contact.

So if you’re wondering whether your IT support is helping or holding you back, here are seven smart questions every business leader should be asking their MSP this fall.

1. What’s Your Plan to Prevent Downtime—Not Just Respond to It?

If your MSP only shows up when something breaks, you’re not getting proactive support. Ask about their preventive maintenance strategy. Are they monitoring systems 24/7/365? Are patches applied on time? Are vulnerabilities addressed before they become problems?

A true partner doesn’t wait for the fire; they prevent it from sparking.

2. How Are You Aligning IT with Our Business Goals?

Your IT should fuel your growth, not fight against it. A strategic MSP, or better yet, a Virtual CIO, will ask about your long-term goals and design infrastructure that scales with you. If your IT conversations never go beyond “fix this,” it’s time to rethink the relationship.

3. What Risks Are We Not Seeing?

Cybersecurity. Compliance. Shadow IT—aging hardware. Your MSP should be your eyes and ears in the tech world. You deserve more than silence or “you’re fine.” You deserve real risk assessments, complete with recommendations and a plan to close gaps.

4. How Are You Helping Us Stay Ahead of Cyber Threats?

A decent MSP offers antivirus. A great one builds layered cybersecurity with employee training, endpoint detection, real-time monitoring, and a response plan. Cybercrime isn’t slowing down, and if your MSP’s security pitch hasn’t changed in 2 years, that’s a red flag.

5. How Often Do You Think You'll Review Our Systems and Strategy?

Set-it-and-forget-it IT is outdated. Your MSP should hold regular business reviews to go over performance, system health, budget alignment, and emerging needs. If the only time you meet is during a crisis, that’s not strategy. That’s survival.

6. What’s Your Response Time, and Who Picks Up the Phone?

When issues arise, you need a fast response. Ask about average response times, escalation procedures, and if you’re talking to a real technician or just entering a helpdesk queue. At PCS, we call this the LiveLine difference: a real tech answers within 30 seconds.

7. What’s the Plan for 2026 (and Beyond)?

The best MSPs think ahead. Are you planning a cloud migration? Expanding remote work capabilities? Exploring AI? Your IT partner should bring ideas to the table, not wait for you to request them. If they’re not helping you plan for the future, they’re part of the past.

Don’t Wait for Another IT Fire to Ask These Questions

The best time to assess your MSP was before the last downtime. The next best time? Right now.

At PCS, we help business leaders move from reactive to strategic IT—through hands-on support, big-picture planning, and fast answers when it matters most.

Did these questions make you realize your MSP isn’t keeping up? Start with a Free Network Assessment!