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5 Questions Every Business Leader Should Ask About Cybersecurity

Sep 4, 2025

Countdown to Cybersecurity Awareness: 5 Questions Every Business Leader Must Ask

As businesses gear up for 2026, cybersecurity remains a top priority for CEOs, CIOs, CTOs, IT managers, and decision-makers navigating an increasingly digital world. With new challenges on the horizon—from AI-driven attacks to a rapidly expanding Internet of Things (IoT) ecosystem—it’s more critical than ever to ask the right questions about your organization’s security posture.

This guide answers the five most-asked questions about cybersecurity, providing clear, business-focused insights that help leaders strengthen defenses today and prepare for tomorrow’s threats. As we count down to Cybersecurity Awareness Month, let’s explore the essential questions that will empower your company to stay one step ahead.

1. What Are We Really Protecting?

Cybersecurity starts with clarity. Leaders need to identify their most valuable assets—customer data, intellectual property, financial systems, and critical infrastructure. Without this inventory, it’s impossible to know where to focus protection.

  • Do we know where our sensitive data resides?

  • Have we mapped data flows across departments and vendors?

  • Is access aligned with business roles—or are there unnecessary privileges that increase risk?

👉 Why it matters: Understanding your “mission-critical assets” enables smarter investments and ensures resources are focused where they matter most.

For more guidance, see NIST’s Cybersecurity Framework.

2. Are We Prepared for the Most Common Threats?

Not all breaches are Hollywood-style hacks. Most succeed because of simple oversights—weak passwords, unpatched systems, or phishing emails.

Ask your teams:

  • Do we enforce multi-factor authentication (MFA) across all systems?

  • Are we patching and updating software on a business-critical schedule?

  • How effective are our employee awareness and training programs?

👉 Why it matters: By addressing common, preventable threats, organizations reduce the bulk of their cyber risk and free up resources to address more sophisticated attacks.

Check out CISA’s Phishing Guidance for practical steps.

3. How Ready Are We for an Incident?

Even the strongest defenses can be breached. The real test of leadership is resilience—how quickly can your business detect, contain, and recover from an attack?

Key leadership questions:

  • Do we have a documented, tested incident response plan?

  • How quickly can we isolate and recover systems?

  • Have executives participated in tabletop exercises to rehearse response scenarios?

👉 Why it matters: A practiced plan transforms a crisis from a long-term disaster into a manageable disruption.

For best practices, review SANS Institute’s Incident Response Planning Guide.

4. Are We Compliant With Evolving Regulations?

From GDPR to HIPAA to PCI-DSS, regulations continue to evolve. Noncompliance isn’t just a technical gap—it’s a business risk with financial, legal, and reputational consequences.

  • Do we monitor upcoming regulatory changes that affect our industry?

  • Can we demonstrate compliance in the event of an audit?

  • Do third-party vendors meet our security standards?

👉 Why it matters: Compliance is more than a checkbox—it’s a risk management strategy that preserves trust with regulators, partners, and customers.

Visit BakerHostetler’s Privacy Blog for detailed updates on data privacy regulations.

5. How Do We Measure Cybersecurity Success?

Executives don’t accept “trust us” as an answer in finance or sales, and they shouldn’t in cybersecurity either. Clear metrics are essential.

Key KPIs for leaders include:

  • Average time to detect and respond to threats

  • Results of penetration tests and red team exercises

  • Percentage of employees completing training and passing phishing simulations

  • Number of attempted vs. blocked attacks

👉 Why it matters: Metrics turn cybersecurity from a cost center into a measurable business function that supports decision-making and ROI.

For benchmarking, refer to the IBM Cost of a Data Breach Report.

Addressing 2025 Cybersecurity Challenges

The 2025 landscape is already testing businesses:

Cybersecurity Awareness Month is the perfect time for leaders to reassess their security posture and prepare for these challenges before they escalate.

Looking Ahead: Preparing for 2026 Threats

Forward-thinking leaders must also anticipate future risks:

By investing now in R&D, external partnerships, and workforce upskilling, organizations can build resilience against tomorrow’s cyber threats.

📌 See how our Managed Cybersecurity Services keep businesses future-ready.

Building a Resilient Cybersecurity Strategy

Leaders can strengthen defenses by:

  • Conducting regular risk assessments to identify top priorities

  • Implementing a multi-layered defense strategy that combines people, process, and technology

  • Practicing incident response through simulations and executive drills

  • Leveraging external experts, MSPs, MSSPs, and industry information-sharing groups

  • Promoting a culture of security awareness across all employees

Cybersecurity isn’t just an IT challenge—it’s a business imperative.

Final Word for Decision-Makers

The countdown to Cybersecurity Awareness Month is more than a reminder—it’s a call to action. By asking these five essential questions and preparing for both today’s and tomorrow’s threats, business leaders can protect their organizations, safeguard customer trust, and create a resilient foundation for growth.

The future belongs to businesses that treat cybersecurity not as a technical issue, but as a strategic business advantage.

📌 Ready to take the next step? Explore our Cybersecurity Solutions or Contact Us to start building a more resilient future.