OSAP Virtual Seminar: Cybersecurity Questions Every Leader Should Be Asking (But Probably Isn’t)

Cybersecurity is no longer just an IT issue—it is one of the most significant operational, financial, and reputational risks facing organizations today. Yet many executive teams and boards struggle to understand what questions to ask, how to evaluate their risk, and whether their organization is truly protected.

This session cuts through the technical noise and equips leaders with a practical, non-technical framework to assess cybersecurity readiness. Drawing on real-world data, emerging threat trends (including AI-driven attacks), and the industrialization of cybercrime, attendees will gain clarity on why attacks continue to rise and what it means for their organization.

Participants will walk away with a set of critical questions they can immediately use to evaluate their IT team, vendors, and overall security posture—along with actionable steps to strengthen security culture, reduce risk, and improve resilience.

By the end of this session, participants will be able to:

• Understand the modern cyber threat landscape
  Explain the key drivers behind the rapid increase in cyberattacks, including the industrialization of cybercrime and the role of AI in enhancing attack sophistication.
• Recognize the human factor in cybersecurity risk
  Identify why phishing and user behavior remain the leading causes of breaches and how security culture directly impacts organizational risk.
• Evaluate organizational cybersecurity effectiveness
  Apply a set of practical, executive-level questions to assess whether their IT team, MSP, and vendors are implementing appropriate security controls.
• Assess whether their organization is “doing enough”
  Understand how to measure cybersecurity maturity, identify gaps, and determine appropriate next steps based on risk and organizational needs.
• Take actionable leadership steps to reduce risk
  Implement foundational governance practices, including establishing security as a strategic priority, improving training, and initiating assessments and roadmap planning.