10 Cybersecurity Questions Every CEO Should Ask
You don’t need to manage firewalls or review log files. But as CEO, you do need to know whether your organization is actually protected. These ten questions will tell you.
1. What Risk Management Framework Are We Using – and Is It the Right One?
A framework gives you a structured way to assess your security posture and track improvements. The main options:
- NIST Cybersecurity Framework (CSF 2.0) – the most widely adopted; works for organizations of any size
- CIS Controls – prioritized, practical actions; good for small and mid-size businesses
- ISO 27001 – international standard; useful if you work with global partners
- COBIT – IT governance focused; common in larger enterprises
- CMMC – required for Department of Defense contractors (enforcement ramped up in 2025)
If you don’t have a framework in place, NIST CSF 2.0 is the best starting point for most businesses.
2. What Are We Doing Right Now to Prevent Attacks?
Ask your team to map out every protective measure currently in place: firewalls, endpoint protection, email filtering, access controls, backup systems, monitoring tools. This gives you a baseline.
Look for a defense-in-depth approach where multiple layers of protection overlap. No single tool stops everything, so you need:
- [ ] Network-level defenses (firewall, intrusion prevention)
- [ ] Endpoint protection (EDR/XDR on every device)
- [ ] Email security (anti-phishing, attachment scanning)
- [ ] Identity protection (MFA everywhere, SSO where possible)
- [ ] Data protection (encryption at rest and in transit)
- [ ] Monitoring and alerting (SIEM or managed detection)
3. How Is Leadership Involved in Cybersecurity?
Annual reports aren’t enough anymore. Leadership needs ongoing visibility into:
- Current threat landscape relevant to your industry
- Status of security initiatives and any gaps
- Incident response readiness
- Budget adequacy vs. actual risk
SEC cybersecurity disclosure rules (effective 2024) now require public companies to report material incidents within four business days and describe board oversight of cybersecurity risk annually.
4. Is Cybersecurity Part of Our Enterprise Risk Management?
Cyber risk isn’t just an IT problem. The financial penalties for data breaches keep climbing:
- Meta: $1.3 billion (EU, 2023)
- Amazon: $886 million (Luxembourg, 2021)
- T-Mobile: $500 million settlement (2023)
- Equifax: $700 million (FTC, 2019)
- Capital One: $290 million (OCC, 2021)
Your enterprise risk management process should treat cyber risk alongside financial, operational, and legal risks. That means regular assessments, defined risk appetite, and funded mitigation plans.
5. How Do We Handle Third-Party Risk?
Two questions to ask about every vendor relationship:
- What confidential data are we sharing with them?
- What access do they have to our systems?
Only work with vendors who can demonstrate security maturity through certifications like SOC 2 Type II or ISO 27001. Include specific security requirements in contracts and verify compliance regularly.
Your supply chain is only as strong as its weakest link. The 2020 SolarWinds attack and the 2023 MOVEit breach both spread through trusted vendor relationships.
6. Are Our Employees Trained on Cybersecurity?
People cause the majority of breaches, usually through honest mistakes rather than malice. Your training program should cover:
- [ ] How to spot phishing emails and social engineering
- [ ] Password hygiene and MFA usage
- [ ] Safe handling of sensitive data
- [ ] Reporting procedures for suspicious activity
- [ ] BYOD security requirements
Training needs to happen regularly (quarterly at minimum, not just during onboarding) and should include simulated phishing exercises.
7. How Often Do We Test Our Incident Response Plan?
Your plan should cover:
- [ ] Classification of incident types and severity levels
- [ ] Clear roles and responsibilities
- [ ] Communication protocols (internal, customers, regulators, media, law enforcement)
- [ ] Containment and eradication procedures
- [ ] Recovery and post-incident review steps
- [ ] Legal notification requirements and timelines
Test it with tabletop exercises at least twice a year. Update it after every real incident and whenever your infrastructure changes significantly.
8. How Protected Are We Against Emerging Threats?
Ask your security team how they stay current. They should be:
- Monitoring threat intelligence feeds relevant to your industry
- Tracking new vulnerabilities through CISA advisories and CVE databases
- Assessing exposure to zero-day vulnerabilities
- Evaluating AI-powered attack techniques (deepfake voice/video, automated phishing)
- Reviewing ransomware trends and defense readiness
9. What’s Our Actual Risk Exposure?
This means understanding:
- What data and systems are most valuable to an attacker
- Where your biggest gaps are
- How much risk you’re willing to accept vs. what you’re actually carrying
- Whether third-party providers are adding unacceptable risk
Penetration testing and red team exercises give you real answers here, not just theoretical assessments.
10. How Do We Compare to Our Industry Peers?
If your competitors have stronger defenses, attackers will focus on easier targets – like you. Benchmark your security program against industry standards and peer organizations.
Consider whether you’ve had:
- [ ] An external security audit in the past 12 months
- [ ] A penetration test in the past 12 months
- [ ] A third-party risk assessment
- [ ] Cyber insurance with adequate coverage
- [ ] A documented and tested business continuity plan
Don’t wait for a breach to find out where you stand. These ten questions give you the starting point for an honest conversation with your security team.