This is Part 2 of our 3-part series on selecting fractional CISOs. In Part 1, we covered evaluating experience and program-building skills. Today, we focus on the harder-to-assess but equally critical capabilities: driving cultural transformation and managing real-world security threats.

The most overlooked aspects of F-CISO selection are cultural change management and hands-on threat response experience. Technical expertise alone won’t transform your organization’s security posture; you need someone who can navigate resistance, build consensus, and apply hard-earned lessons from actual security incidents.

As in Part 1, what follows are questions we recommend including in the vetting process of an F-CISO and what you should be looking for in their answers.

“Answers to interview questions should demonstrate not just technical knowledge, but practical implementation experience and clear understanding and ability to explain in plain, business terms how these threats impact your specific business operations.”

Cultural Change and Communication

Cultural transformation is the heart of successful security program building. Fixing security during planning is always cheaper and easier than afterward, yet most executives and managers struggle to apply this logic to information security. When understanding a candidate’s abilities here, the themes are navigating obstacles and clear communication.

Question: Give me examples of how you’ve communicated security risks to a CEO or board. How have you articulated your CEO’s vision for the business goals of information security?

What You Need to Know: Their answer should demonstrate an ability to translate technical issues into language that helps senior leadership understand business outcomes and risks. This skill is critical to getting the C-Suite support needed for success.

Questions: How do you plan to integrate security into your existing business processes? How have you moved people from thinking “We can fix security later” to “We need to build in security earlier”? How have you handled pushback from other departments when implementing security controls that impact business operations?

What You Need to Know: Security can’t be an afterthought or external overlay;it must become embedded in how your organization turns ideas into money. Answers should include specific examples of process changes, training programs, and incentive structures that support security-conscious behavior. Above all, you need someone who can navigate cultural integration challenges and build consensus, not just issue mandates.

Questions: Have you faced auditors and regulators intent on dissecting your programs? How did those engagements turn out? Do you have specific audit results, and if so, what were the findings and how were they addressed?

What You Need to Know: This speaks directly to whether the candidate can build not just programs that look good on paper, but the infrastructure, procedures, and foundations that survive adversarial scrutiny. The best candidates will have audit documentation showing program maturity improvements over time through multiple audit cycles, and be able to tell you easily the most important metrics with which you may track improvement progress and how they are derived.

Threat Actor Expertise and Incident Experience

Perhaps the most overlooked aspect of F-CISO selection is their experience with the threat actors and incident types most relevant to your organization. This isn’t theoretical knowledge; it’s hard-earned experience defending against real attacks and learning from actual breaches.

Threat Landscape Alignment

Different industries face fundamentally different threat actors with varying motivations, capabilities, and attack methods. As just a few examples:

• Financial services organizations face a unique combination of financially motivated cybercriminals, nation-state actors seeking economic intelligence, and insider threats with access to high-value data.
• Healthcare organizations deal with ransomware groups specifically targeting patient care systems, medical device vulnerabilities, and the challenge of balancing security with life-critical system availability.
• Critical infrastructure faces nation-state actors seeking to establish persistent access for potential disruption during geopolitical conflicts.

Your F-CISO should have direct experience with the threat actors most likely to target your industry.

Questions: What advanced persistent threat groups have you tracked? How did you track them? How have you responded to ransomware incidents? What insider threat cases have you managed? Describe your experience with [specific threat relevant to your industry]. How do you prepare for these attacks?

What You Need to Know: Answers should demonstrate not just technical knowledge, but practical implementation experience and clear understanding and ability to explain in plain, business terms how these threats impact your specific business operations.

Incident Response Leadership

How the F-CISO candidate has handled incidents reveals their true capabilities under pressure. The best F-CISO candidates have battle scars. They’ve stayed up for 72 hours straight coordinating breach response. They’ve sat in boardrooms explaining to angry directors how attackers accessed customer data. They’ve worked with FBI agents and federal prosecutors. They’ve managed the aftermath, rebuilding systems, implementing new controls, and regaining stakeholder trust. And most important, they’ve learned the lessons of those experiences and bring with them a mature approach to improving your incident handling capacity to reduce the frequency and impact of cyber incidents.

Questions: What is the most sophisticated attack you’ve defended against? Walk us through how you detected it, responded, and what the business impact was. What was your worst day? What went wrong? How did you manage stakeholder communication? What did you learn?

What You Need to Know: This experience is invaluable during Stage One program building because it provides a real-world perspective on what matters. Someone who’s lived through a ransomware attack understands which backup strategies work under pressure. Someone who’s managed a data breach knows which detection capabilities provide meaningful early warning versus expensive noise.

Questions: What’s your philosophy on threat intelligence? How do you translate threat data into actionable security improvements?

What You Need to Know: Whether they can clearly and readily articulate their approach and actions reveals if they can build programs that proactively address real threats rather than just checkbox compliance. Did you understand their priorities and explanations, or did their answers leave you seeking clarity?

Question: Do you have experience with forensic investigations and collaboration with external forensic firms? Do you understand evidence preservation requirements? Have you coordinated with law enforcement? What were the outcomes?

What You Need to Know: The F-CISO who has managed multiple forensic investigations will build monitoring systems that determine what happened, who did it, and what data was accessed. They’ll implement logging standards that support legal requirements and create incident response procedures that preserve evidence while enabling business recovery.

This post is one of four on selecting and deploying F-CISOs.

In the precursor to three installments on Selecting a F-CISO, Strategic Deployment of a Fractional CISO, we discuss how best to deploy a Fractional CISO.

In the first installment on Selecting a F-CISO, we cover evaluating experience and program-building skills.

In the second installment on Selecting a F-CISO, we explore how to evaluate a candidate’s ability to drive cultural transformation and their real-world experience managing security incidents and threats that are most relevant to your organization.

In the third installment on Selecting a F-CISO, we cover the red flags to avoid, how to structure the engagement, and key strategies for setting your F-CISO up for success once you’ve made your selection.