Top Questions for CEOs in a Technology Review

In today’s fast-paced digital landscape, CEOs are expected to lead with clarity, confidence, and data-driven strategy. Technology now sits at the center of nearly every business decision, from cybersecurity and cloud performance to budget alignment and digital transformation. That’s why your Quarterly Technology Review (QTR) with your Managed Service Provider (MSP) isn’t just a meeting, it’s a strategic opportunity.

At PCG IT, we help executives translate complex technology insights into actionable business outcomes. A structured, impactful quarterly review empowers CEOs to minimize risk, maximize ROI, and ensure their technology roadmap fully supports organizational goals.

If you’re a CEO preparing for your next review, here are the essential questions you must ask to ensure your business stays secure, competitive, and future-ready.

“Are We More Secure Today Than We Were Last Quarter?”

Cybersecurity evolves at lightning speed, and threats become more sophisticated every quarter. CEOs need a clear snapshot of where their risk stands and where vulnerabilities may be emerging.

Ask your MSP:

• Have any new threats targeted our industry?
• Did we have security incidents, attempted breaches, or anomalous activity?
• Are there patches, updates, or configurations still pending?
• Are employees completing required security awareness training?

A good MSP should not only report on security events but also present clear recommendations to strengthen protection. CEOs must walk away knowing their cyber risk is trending down, not up.

“Is Our Technology Supporting Business Growth?”

Technology should always advance, not limit, your business strategy. Every CEO should understand whether current systems help or hinder operational efficiency.

Important follow-ups:

• Are there recurring bottlenecks or productivity obstacles?
• Are our tools and software platforms scalable for projected growth?
• Are manual processes still consuming staff time?
• Which upgrades or automations could improve output next quarter?

Your MSP should connect the dots between technology performance and business performance, showing how technology can accelerate your goals.

“What Technology Risks Are Emerging?”

CEOs often focus on today’s challenges, but your MSP must help you anticipate tomorrow’s risks. Quarterly reviews are the perfect time to address emerging trends.

These risks may include:

• Expiring software or unsupported operating systems
• Hardware approaching end-of-life
• Capacity issues in cloud or on-prem environments
• Regulatory changes requiring compliance updates
• Industry-specific threat patterns

Proactive CEOs ask questions before issues become disruptions.

“Are We Getting the Best ROI on Our Technology Spend?”

Technology investments should be measurable. A quarterly review is the time to evaluate what’s working and what needs adjustment.

You should be asking:

• Are we overpaying for unused licenses or solutions?
• Can we consolidate tools to reduce redundancy and cost?
• Is our cloud spending optimized?
• What technology delivered the highest value this quarter?

An MSP like PCG IT should provide transparent reporting that ties your technology budget directly to business outcomes.

“How Are Our Backups and Disaster Recovery Performing?”

Downtime is costly, financially and operationally. CEOs need confidence that their MSP has resilient, tested, and reliable continuity systems in place.

Clarify:

• Are backups running successfully and tested within the last 90 days?
• How quickly could we restore critical operations?
• Are there gaps in our data retention or recovery strategy?
• Do we need stronger business continuity planning?

A quarterly review ensures your organization is always disaster-ready.

“What Did We Accomplish This Quarter and What’s Planned Next?”

Your technology plan should be a living roadmap, not a vague long-term wish list. Quarterly reviews allow CEOs to track progress and keep technology aligned with priorities.

Ask your MSP:

• Which projects were completed this quarter?
• Were deadlines met? If not, why?
• What are the top priorities for next quarter?
• Are there strategic initiatives we should begin planning now?

This helps CEOs maintain clear visibility into future needs and timelines.

“How Is Our Remote or Hybrid Workforce Supported?”

In today’s distributed work environment, workforce technology demands are ever-changing. CEOs should confirm their teams have the tools, access, and security needed to perform at their best.

Dig deeper:

• Are remote access tools secure and efficient?
• Are employees reporting recurring issues?
• Do we need improved collaboration platforms or hardware?
• How is endpoint security performing across remote devices?

A strong workforce experience leads to improved productivity and employee satisfaction.

“Are We Positioned for Digital Transformation?”

The most successful organizations continuously evolve. A quarterly review is the perfect time to evaluate your digital maturity and identify opportunities for innovation.

Ask:

• What technologies could give us a competitive edge?
• Are there automation opportunities we are overlooking?
• Should we explore AI, cloud migration, or workflow modernization?
• Are we leveraging data effectively to drive decisions?

Your MSP should act as a strategic partner, not just a break/fix provider, helping shape your long-term vision.

“Is There Anything Keeping You Up at Night About Our Technology?”

This question gives your MSP the chance to speak openly about concerns you may not have thought to ask about.

Their response may reveal:

• Capacity challenges
• Hidden vulnerabilities
• Upcoming cost increases
• Risks requiring immediate attention
• Opportunities for major improvement

A good MSP will always appreciate your openness and willingness to hear the truth.

Final Thoughts: A Quarterly Review Is a CEO’s Strategic Advantage

Quarterly Technology Reviews aren’t about technical jargon or long reports, they’re about strategy, risk reduction, and growth. When CEOs come prepared with the right questions, they gain valuable insights that inform stronger decisions and ensure technology supports their long-term vision.

At PCG IT, we empower leadership teams with transparent reporting, proactive planning, and technology strategies aligned to business goals. Whether it’s cybersecurity, cloud optimization, budget forecasting, or digital transformation, our QTRs are designed to make your job easier and your business stronger.

If you want a more productive quarterly review and a true MSP partnership, PCG IT is here to help you lead with clarity.

PCG IT is a managed service provider who has been proudly serving New Hampshire, Maine, and Massachusetts for decades. We provide complete technology solutions to local small and medium-sized businesses. It’s always been our goal to provide enterprise-level technology solutions to the small business sector at competitive prices. Schedule a complimentary technology assessment today!