Data security is one of the most critical challenges for any organization, regardless of size or industry. As a CEO, you must ensure that your company’s assets are protected against threats that could damage its reputation or lead to severe financial losses. Understanding and monitoring your IT department’s efforts in securing sensitive information is a fundamental part of risk management. While cybersecurity is a vast topic, the following 10 questions will help you assess whether your company is taking the right steps to safeguard its data.
Effective information security management requires knowledge and expertise across multiple domains. Many organizations leverage external resources to support the development and implementation of security strategies. This allows them to benefit from specialized skills and tools that enhance their ability to defend against evolving threats.
It’s time to evaluate your company’s cybersecurity posture and ensure that your business is well-protected. Start by asking these key questions to your IT team—how they respond will provide valuable insights into your organization’s data security readiness.
Question 1 – What are the most critical data assets in our organization, and where are they stored?
Why this question matters:
Your company relies on data—whether it’s customer records, financial information, intellectual property, source code, or trade secrets. Protecting this data appropriately is essential. This question helps determine whether your IT team understands which data assets are mission-critical, where they reside, and how they are classified. Proper classification ensures that security investments are proportionate to the risk, preventing both overprotection of low-risk data and underprotection of crucial assets.
A common challenge is the disconnect between IT security and business objectives. If IT lacks awareness of what needs the highest level of protection, it poses a serious risk. Effective security strategies align with business priorities, ensuring that critical data is safeguarded without unnecessary expenditures on non-essential assets.
Question 2 – What systems and data can “John Doe” access?
Why this question matters:
This question allows CEOs to assess whether the company is managing user access permissions in an organized and controlled manner. It verifies whether the principle of least privilege (PoLP) is applied—ensuring that employees have access only to the data and systems required for their job roles. It also helps identify risks related to excessive or outdated privileges, which can be exploited in security breaches.
Additionally, this question can highlight gaps in offboarding processes. Does your organization immediately revoke access once an employee leaves? Failure to do so increases the risk of unauthorized access. Effective access control policies, continuous monitoring, and clear accountability measures form the foundation of a robust cybersecurity strategy.
Question 3 – Are all critical systems and applications fully patched with the latest security updates?
Why this question matters:
Most cyberattacks exploit known vulnerabilities in outdated systems. This question evaluates whether your organization has an effective patch management strategy in place—monitoring, testing, and applying security patches to eliminate potential attack vectors.
Efficient vulnerability management significantly reduces exposure to cyber threats such as ransomware, data breaches, and advanced persistent threats (APTs). A failure to apply patches in a timely manner increases the likelihood of successful cyberattacks, leading to financial and reputational damage. Consistent patching is one of the most cost-effective measures in cybersecurity.
Question 4 – If we were under a cyberattack right now, how would we detect it, and what actions would we take in the first 60 minutes?
Why this question matters:
This question assesses how well-prepared your organization is for incident detection and response. Rapid identification and mitigation of a security breach are essential to minimizing damage.
A strong security posture includes real-time threat intelligence, continuous security monitoring, and automated alerting systems. Additionally, your IT and security teams should have a well-defined incident response plan (IRP) that outlines immediate actions, including isolating affected systems, notifying stakeholders, and initiating containment strategies.
Since most cyber incidents escalate within the first hour, a slow or uncoordinated response can significantly amplify financial and operational damage.
Question 5 – How do we secure access to corporate data in a remote work environment?
Why this question matters:
Remote work introduces new cybersecurity risks, including unsecured networks, phishing attacks, and unauthorized device access. This question determines whether your company has implemented the necessary controls, such as Multi-Factor Authentication (MFA), endpoint security, encrypted VPNs, and Zero Trust Architecture to mitigate these risks.
A comprehensive remote work security strategy ensures that employees can securely access company resources while preventing potential breaches caused by compromised credentials or unsafe connections.
Question 6 – What is our data backup and disaster recovery (DR) plan?
Why this question matters:
This question evaluates your business continuity and disaster recovery (BC/DR) strategy. Critical elements include:
Backup frequency – How often are backups performed?
Recovery testing – When was the last full system recovery tested?
Recovery Time Objective (RTO) & Recovery Point Objective (RPO) – How long does data restoration take, and how much data could be lost?
A well-structured backup and disaster recovery plan ensures that data loss, ransomware attacks, or system failures do not disrupt operations or result in irreversible damage.
Question 7 – What measures are in place to prevent ransomware and phishing attacks?
Why this question matters:
Ransomware and phishing are among the most common attack vectors targeting businesses today. CEOs must ensure that their company has robust defense mechanisms in place, such as:
Email security filters to block phishing attempts
Advanced Endpoint Protection (EPP) and Extended Detection and Response (XDR) solutions
User training and awareness programs to help employees recognize suspicious activities
Network segmentation and threat hunting to limit attack impact
Being proactive in cybersecurity significantly reduces the likelihood of falling victim to malicious campaigns that can disrupt business operations and compromise sensitive data.
Question 8 – How are employees, vendors, and partners informed about our security policies?
Why this question matters:
Cybersecurity is not just about technology—it’s also about people and processes. Organizations must ensure that employees, contractors, and third-party partners are fully aware of security policies, acceptable use guidelines, and compliance requirements.
This question helps identify gaps in security awareness and whether the company provides ongoing training and resources to educate its workforce on best practices for data protection.
Question 9 – How do we train our workforce on cybersecurity best practices?
Why this question matters:
Many security breaches result from human error. Regular security awareness training ensures that employees recognize phishing attempts, social engineering tactics, and the importance of strong passwords and MFA.
A strong cybersecurity culture starts with education. Investing in training significantly reduces the risk of data breaches, credential theft, and insider threats.
Question 10 – Are we fully compliant with all relevant cybersecurity regulations?
Why this question matters:
Non-compliance with industry regulations—such as PCI DSS, GDPR, DORA, and NIS2—can lead to legal penalties, operational restrictions, and reputational damage. This question helps determine whether your organization regularly undergoes security audits, risk assessments, and policy updates to stay compliant with evolving security requirements.
Compliance is not just about avoiding penalties—it also enhances your company’s credibility and ensures that security measures align with international standards.
Conclusion
Cybersecurity is not just an IT issue—it’s a business priority that requires the involvement of leadership. CEOs must take an active role in evaluating their company’s security posture and ensuring that risk mitigation strategies are aligned with business objectives.
By asking these 10 essential questions, you gain insight into your organization’s preparedness, risk exposure, and ability to prevent cyber threats. However, security is an ongoing process—keeping your company protected requires continuous monitoring, investment in expertise, and a proactive approach to cybersecurity governance.
If you need guidance in improving your company’s security posture, Patronusec is here to help. Our experts specialize in cyber risk management, compliance, and security strategy development to ensure your business remains protected in an evolving threat landscape.
Let’s talk about securing your business today!
