What to Ask When Taking Over a Security Program: Essential Questions for New Cybersecurity Leaders

When stepping into leadership of a cybersecurity program, the documentation may look perfect, the previous owner might claim everything's "under control," and executive management likely expects a rapid assessment. However, effective security leadership begins with asking the right questions, not making immediate changes, according to cybersecurity expert Marc Menninger.

Understanding your security landscape

New cybersecurity leaders should resist the urge to implement immediate changes before thoroughly understanding their inherited program. Menninger outlines five critical questions that reveal a program's true strength and potential vulnerabilities.

"Your first job isn't to make changes, it's to understand what you're working with," writes Menninger in his November 2025 analysis. "The best way to do that is by asking the right questions."

Identifying critical assets

The fundamental question "What are we actually protecting?" often catches organizations off-guard. Many security teams operate without a clear, updated inventory of critical assets and data.

This visibility gap represents a significant vulnerability, as Menninger points out: "You can't protect what you don't know exists." When requesting a list of critical assets, vague or outdated responses serve as an immediate red flag for new security leaders.

Security professionals should ensure their asset inventory remains current and comprehensive. Regular asset discovery and classification processes help maintain visibility across increasingly complex technology environments.

Developing a thorough cyber security risk assessment methodology can help organizations identify and prioritize their most valuable information assets.

Understanding critical vulnerabilities

Asking "What could take us down tomorrow?" provides insight into an organization's risk awareness. Consistency in answers across engineering, IT staff, and business leaders indicates alignment on priority risks.

"If everyone says something different, your risk management process probably isn't working," Menninger notes.

This question helps identify not just technical vulnerabilities but also potential business continuity gaps and single points of failure that may require immediate attention. Security leaders can use these insights to prioritize remediation efforts and resource allocation.

Assessing incident response readiness

Testing incident response capabilities reveals more about organizational readiness than any policy documentation. Menninger suggests that answers like "never" or "I think last year" to the question "When was the last time we tested incident response?" immediately highlight a critical area for improvement.

"A simple tabletop exercise will reveal more about your team's readiness than any policy document," he advises. "You'll quickly see who knows their role, who hesitates, and where confusion slows things down."

Regular incident response testing builds muscle memory for security teams and helps identify process gaps before a real crisis occurs. These exercises should involve cross-functional stakeholders to ensure coordinated response capabilities.

Organizations looking to strengthen their security posture should consider implementing comprehensive cybersecurity steps that align with industry frameworks for a more structured approach.

Evaluating security fundamentals

Beyond strategic questions, new security leaders must assess tactical controls and organizational culture to build an effective program.

Verifying access control effectiveness

Access management fundamentals remain critical to security effectiveness. Menninger recommends asking about admin access distribution, multi-factor authentication implementation, and access review frequency.

"Strong access controls aren't glamorous, but they're one of the easiest ways to prevent a breach," he states.

If obtaining clear answers about access controls takes days or generates uncertainty, it signals potential gaps in one of security's most fundamental protections. Security leaders should prioritize access governance as a foundational control.

Organizations can implement regular access certification processes, strengthen privileged access management, and ensure proper offboarding procedures to enhance this critical security domain.

Gauging security culture

Perhaps the most crucial question addresses organizational culture: "What's the culture around security here?" The perception of security as either a partner or blocker significantly impacts program effectiveness.

"Culture determines whether your program succeeds or fails," Menninger emphasizes. "A team that sees security as everyone's job will follow policies, report issues, and support your goals. A team that sees it as an obstacle will work around it."

Building a positive security culture requires consistent communication, executive support, and demonstrating how security enables rather than impedes business objectives. New security leaders should focus on relationship-building across the organization.

Developing a well-defined cybersecurity strategy that aligns with business objectives can help foster this positive security culture by demonstrating value to stakeholders.

Leading with insight

Menninger advises new security leaders to focus on listening before acting. "Your first few weeks running a cybersecurity program shouldn't be about proving how much you know. It should be about understanding the reality of where things stand."

The answers to these five questions provide a foundation for identifying weaknesses, prioritizing improvements, and building credibility from day one. This approach helps security leaders develop targeted strategies rather than implementing generic solutions that may not address organizational needs.

Security leaders can use these insights to:

1. Develop a prioritized roadmap based on actual risk rather than theoretical frameworks
2. Allocate resources to the most critical security gaps
3. Build executive support by demonstrating understanding of business priorities

By starting with thorough assessment rather than immediate action, new security leaders can establish more effective, sustainable programs that address their organization's specific security challenges.

Additional considerations for new security leaders include documenting the current state of security controls, identifying quick wins to demonstrate value, and establishing metrics to measure progress. The NIST Cybersecurity Framework provides an excellent structure for evaluating existing capabilities and planning improvements across the identify, protect, detect, respond, and recover functions.