You probably know all of these, but each one leads to the majority of breaches when not well attended or ignored too long. Guess which are the most powerful.                   

Managing information security is complex and challenging due to several factors, but some of the most difficult parts include:

1. Keeping Up with Evolving Threats: Cyber threats evolve rapidly, with new vulnerabilities, exploits, and attack methodologies emerging continuously. Staying ahead of these threats requires constant vigilance, research, and updates to security protocols. How does the CISO do that and when can they get that learning in.
2. Human Factor: One of the biggest vulnerabilities in information security is human error. This can include anything from employees falling for phishing attacks to improper handling of data. Training and maintaining a security-conscious culture are crucial but challenging. Who is doing this and how is it working?
3. Resource Allocation: Allocating sufficient resources—both financial and human—to effectively manage information security is a constant challenge for many organizations. Budget constraints can limit the ability to implement the best security tools or hire the most qualified personnel. Do you have either? If you did, what would you do?
4. Integration of Security Practices: Integrating security practices into the daily business processes without hindering operational efficiency can be difficult. Security measures often require additional steps or checks, which can be seen as obstacles by other departments. I would bet no one bothers without an incident.
5. Regulatory Compliance: Ensuring compliance with a growing list of regulations and standards (like GDPR, HIPAA, or PCI-DSS) is not only challenging but also resource-intensive. Non-compliance can result in severe penalties. Whom on your team has responsibility for compliance and is s/he keeping you out of trouble?
6. Incident Response and Recovery: Developing and maintaining an effective incident response plan that can minimize damage and recover normal operations after a breach is complex. It requires detailed planning, regular testing, and continual improvement. Do you have one and is it tested in a simulated attack setting?
7. Technological Complexity: The diversity of technologies used in organizations (cloud services, IoT devices, mobile applications, etc.) adds layers of complexity to security management. Each technology can introduce new vulnerabilities and requires specific security considerations. Is your network guy capable of explaining your topology to an audience?
8. Securing Remote Work: With the increase in remote working, securing remote access to company resources while maintaining the user experience is challenging. It involves ensuring the security of data across potentially insecure networks and devices. What specifically have you done? And what do you plan on doing? It’s been 3 years.

Ranking these aspects of managing information security from hardest to easiest involves considering the complexity, resources required, and the impact of failure for each. Here’s how they might typically be ranked:

1. Keeping Up with Evolving Threats: This is often the hardest due to the relentless and rapid evolution of cyber threats.
2. Human Factor: Addressing human error and maintaining security awareness across an entire organization is challenging because it involves changing behaviors and maintaining vigilance.
3. Technological Complexity: The wide array of technologies used and their specific vulnerabilities make this a complex challenge.
4. Incident Response and Recovery: This requires extensive planning and testing, making it hard to manage effectively, especially under the pressure of an actual incident.
5. Regulatory Compliance: Staying compliant with multiple and sometimes overlapping regulations is highly challenging and requires continuous attention.
6. Resource Allocation: While crucial, the challenge often lies in justifying the need for resources before a breach happens, which can be less complex than the technical aspects but still difficult.
7. Securing Remote Work: This has become more manageable with advances in technology and widespread adaptation, but it still requires significant effort to secure effectively.
8. Integration of Security Practices: Although it’s complex, integrating security into business processes is a solvable challenge if the organization prioritizes security.

This ranking is somewhat subjective, though I agree with these, because they are mine. Threats, Human Risk Management and Complexity are the real killers.

But, no matter which challenge you take on, today is a far better day than tomorrow, when time waits for no one.