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How Secure Are We? Key Questions for Leadership to Ask the CIO/CISO
Uncovering Cybersecurity Gaps, Coverage, and Readiness to Strengthen Resilience

We are sitting at the intersection of cybersecurity and artificial intelligence in the enterprise, and there is much to know and do. Our goal is not just to keep you updated with the latest AI, cybersecurity, and other crucial tech trends and breakthroughs that may matter to you, but also to feed your curiosity.
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In this edition:
Did You Know - Strengthening Cyber Resilience
Original Article - How Secure Are We? Key Questions for Leadership to Ask the CIO/CISO
Artificial Intelligence News & Bytes
Cybersecurity News & Bytes
AI Power Prompt
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Did You Know - Strengthening Cyber Resilience
Did you know that in 2024, 25% of cybersecurity departments reported layoffs, and 37% faced budget cuts, exacerbating the talent shortage? Source: isc2.org
Did you know that in 2024, U.S. utilities experienced a 70% surge in cyberattacks compared to the same period in 2023? Source: Reuters
Did you know that the education and research sector was the most targeted industry in Q2 2024, with organizations facing an average of 3,341 weekly attacks? Source: Checkpoint
Did you know that in 2024, 67% of organizations reported a shortage of cybersecurity professionals, putting them at significant risk? Source: isc2.org
Did you know that in 2024, organizations experienced an average of 2,200 cyberattacks per day, equating to one attack every 39 seconds? Source: Getastra
Did you know that in 2024, the number of notifications sent to individuals about data breaches in the United States quadrupled, surpassing 1.7 billion? Source: Axios
Did you know that in 2024, the U.S. Cyber Safety Review Board recommended overhauling Microsoft's security culture after a major intrusion by Chinese hackers? Source: Wikipedia
How Secure Are We? Key Questions for Leadership to Ask the CIO/CISO
Reducing Recovery Time from Days to Hours or even Minutes
As leadership, you have limited time to evaluate cybersecurity readiness. These 15 essential questions will help you assess risk exposure, resilience, and strategic alignment with business objectives.
Risk & Threat Landscape
What are our top three cybersecurity risks today, and what are we doing to mitigate them?
How do we stay ahead of emerging cyber threats, and what keeps you up at night?
What is our biggest blind spot in cybersecurity that could lead to a major incident?
Incident Response & Business Resilience
If a ransomware attack hit us right now, how quickly could we detect, contain, and recover?
Have we tested our cyber incident response plan recently, and what weaknesses did we identify?
How confident are you in our ability to restore critical systems and data within our business recovery objectives?
Cybersecurity Strategy & Investment
Is our cybersecurity strategy aligned with our business goals and risk tolerance?
Do we have the right level of funding and resources to defend against today’s cyber threats?
If we could invest in only one cybersecurity initiative this year, what should it be and why?
Technology, Controls & Third-Party Risk
Are we effectively enforcing Zero Trust principles across our network, endpoints, and cloud?
How are we mitigating the risks posed by third-party vendors, partners, and supply chain attacks?
What are the biggest security gaps in our current technology stack, and what’s our plan to fix them?
Workforce, Culture & Metrics
Are our employees our strongest defense or our weakest link, and how do we measure security awareness?
What cybersecurity KPIs should leadership focus on to assess our overall security posture?
What would success look like for our cybersecurity program over the next 12 months?
Artificial Intelligence News & Bytes 🧠
Cybersecurity News & Bytes 🛡️
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AI Power Prompt
This prompt assist in creating a reasonable plan to improve cyber resilience for your organization.
#CONTEXT: Adopt the role of an expert cybersecurity strategist specializing in cyber resilience planning. Your task is to develop a comprehensive, actionable, and reasonable plan to improve cyber resilience for an organization. This plan should account for the latest cybersecurity threats, best practices, and compliance standards while being tailored to the organization's specific industry, size, and risk profile.
#GOAL: You will create a structured cyber resilience plan that enhances the organization’s ability to anticipate, withstand, recover from, and adapt to cyber threats. The plan must be practical, scalable, and aligned with industry frameworks such as NIST, ISO 27001, and CIS Controls.
#RESPONSE GUIDELINES: Follow the step-by-step approach below to construct the cyber resilience plan:
Assess the Organization’s Cybersecurity Posture
Conduct a cyber risk assessment to identify vulnerabilities.
Evaluate existing cybersecurity controls, policies, and response mechanisms.
Identify critical assets and data that require enhanced protection.
Assess compliance with relevant industry regulations and standards.
Develop a Cyber Resilience Framework
Define key resilience objectives based on business needs.
Establish a risk-based security strategy aligned with business continuity.
Implement a layered security approach (defense in depth).
Enhance Threat Detection and Prevention
Deploy advanced threat detection tools (e.g., SIEM, EDR, MDR).
Establish continuous monitoring and anomaly detection capabilities.
Leverage AI-driven security analytics for proactive defense.
Strengthen Incident Response and Recovery
Develop a structured incident response plan (IRP).
Conduct regular tabletop exercises and penetration testing.
Establish clear roles and responsibilities for incident handling.
Implement automated backup and disaster recovery solutions.
Build a Security-Aware Culture
Provide regular security awareness training for employees.
Conduct phishing simulation tests and social engineering assessments.
Establish a clear reporting process for security incidents.
Secure IT Infrastructure and Cloud Environments
Apply zero-trust security principles.
Implement endpoint protection, MFA, and least privilege access controls.
Encrypt sensitive data and enforce strong data governance policies.
Ensure Third-Party and Supply Chain Security
Evaluate vendor security policies and conduct regular audits.
Implement contractual security requirements for third-party access.
Monitor for supply chain vulnerabilities and mitigate risks proactively.
Measure, Monitor, and Improve Resilience Continuously
Establish key performance indicators (KPIs) for cybersecurity resilience.
Conduct periodic security assessments and gap analyses.
Adapt resilience strategies based on evolving threats and business changes.
#INFORMATION ABOUT ME:
Organization name: [YOUR ORGANIZATION NAME]
Industry: [INDUSTRY]
Organization size: [NUMBER OF EMPLOYEES]
Current cybersecurity challenges: [CURRENT CHALLENGES]
Compliance requirements: [COMPLIANCE STANDARDS]
Budget constraints: [BUDGET]
Key assets to protect: [CRITICAL ASSETS]
#OUTPUT: You will deliver a well-structured cyber resilience plan that includes:
An executive summary outlining the importance of cyber resilience.
A detailed risk assessment and security posture analysis.
A step-by-step implementation roadmap.
Practical recommendations for immediate and long-term security improvements.
A cybersecurity training and awareness strategy.
A monitoring and continuous improvement plan.

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