This is Part 1 of our 3-part series on selecting and managing fractional CISOs. Our previous post explored the strategic rationale for deploying a fractional CISO before hiring your first permanent Chief Information Security Officer. Part 2 covers evaluating experience, program-building skills, cultural change capabilities, and threat response experience.This series provides a comprehensive guide to finding the right change agent for your organization’s security transformation.

Following the first industry-wide layoffs in more than a decade, there’s now a glut of information security talent in the market. Many have hung out shingles as “virtual” or fractional CISOs (F-CISO), but the role demands far more than technical expertise: there are huge differences between building, and “having worked in” an information security program.

The challenge to chief executives, then, is to separate candidates capable of implementing revolutionary organizational change from those simply seeking their next consulting gig.

“Information Security pain stems from failing to integrate information security into culture and business structures. Your F-CISO must have proven ability to broker the critical organizational agreements and stakeholder alignment that make security programs successful.”

This F-CISO strategy transforms organizational security capabilities by handling the heavy lifting of developing a program based on clear business outcomes while providing a foundation for a permanent hire who can focus on optimization and growth rather than foundational building.

It takes preparation and patience to identify candidates capable of “Stage One: Define and Build” work. That is where your F-CISO is supposed to introduce the revolutionary change that transforms organizational security capabilities through cultural integration and foundational program construction.

One caveat: as we will discuss in Part III, regardless of who sits in the F-CISO chair, they will need the unwavering and vocal support of the CEO, COO, and CFO. Without this visible support, your F-CISO will be perceived as an outsider making suggestions and not a senior executive implementing CEO strategic priorities. Simply put, without that CEO-level support, the initiative is very likely to fail.

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

Experience and Sector Expertise

Depth and breadth of experience are crucial during Stage One program building. Your F-CISO must be able to be dropped cold into a new environment, navigate obstacles, and both understand and be able to explain what success looks like.

They also must know which security tools can actually work in your environment, understand your sector’s specific compliance requirements, and align threat modeling with the attack vectors that actually target your industry.

Question: Have you been a full-time CISO before? If so, how many times?

What You Need to Know: Multiple CISO roles can demonstrate the ability to replicate results across different organizational challenges, political landscapes, and resource constraints. Someone who’s only held the title once might have gotten lucky with timing, inherited a strong program, or worked in an unusually supportive environment. Ask how these roles ended, and be sure to follow up in reference interviews, with a focus not on how they left the role, but on the outcomes they achieved.

Question: What sectors have you worked in, and how does that translate to building a security infrastructure for our organization?

What You Need to Know: Industry experience is important to a CISO’s ability to construct the right security stack, compliance framework, and threat posture for your business.

Private sector experience means understanding shareholder pressures, quarterly earnings impacts, and board dynamics driven by business performance. These CISOs know how to frame security investments in ROI terms, navigate resource constraints tied to revenue cycles, and work within fast-moving business environments where “security can’t slow us down” is a constant refrain.

Public company experience adds layers of complexity: SEC reporting requirements, insider threat programs, material disclosure obligations, and the unique challenges of securing organizations under constant regulatory and investor scrutiny. These professionals understand how security incidents impact stock prices and how to communicate with boards focused on fiduciary responsibility.

Government sector experience builds entirely different skills: working within rigid procurement processes, managing classified information systems, navigating bureaucratic decision-making structures, and understanding the unique threat landscape facing critical infrastructure. These professionals understand FISMA compliance, FedRAMP authorizations, and the specialized requirements of securing high-value targets.

Vertical industry expertise is equally crucial. An F-CISO with financial services expertise understands NIST, CIS, ISO 27001, PCI-DSS, FINRA and State departments of financial services, and other related financial services requirements, plus fraud detection systems, regulatory reporting frameworks, and the unique challenges of securing high-frequency trading systems.

Healthcare experience means familiarity with HIPAA compliance, medical device security, patient data protection, and the life-or-death implications of system availability.

Manufacturing expertise indicates experience with OSHA’s safety technologies mandates, PSM standard for facilities handling hazardous chemicals and related monitoring and control systems, etc.; this candidate understands operational technology security, supply chain risk management, industrial control system protection, and understanding how cyber attacks can cause physical harm.

Program Building and Organizational Navigation

Building a successful security program requires someone who can quickly replicate past foundational processes and has navigated organizations and the cultural and political obstacles that come with them.

Questions: Give us some examples of building or improving security teams while managing organizational resistance. What was the organization’s security posture when you arrived? What did you build first, and why? How did you structure teams and prioritize roles? How did you handle budget constraints? Most importantly, how did you navigate the political dynamics of introducing security requirements into existing business processes?

What You Need to Know: Security pain stems from failing to integrate information security into culture and business structures. Your F-CISO must have proven ability to broker the critical organizational agreements and stakeholder alignment that make security programs successful. They need to demonstrate experience turning resistance into partnership. Look for systematic approaches that address people, process, and technology in a logical sequence.

Question: How did you measure success in past engagements? For this F-CISO role, what does success look like at the 6-month mark?

What You Need to Know: The right candidate will be able to articulate measurable outcomes, realistic timelines and what improvement or change can be realistically expected at this point.

Questions: What’s your approach to transitioning your work to a permanent CISO? How do you ensure knowledge transfer?

What You Need to Know: It’s crucial this answer reassures you the candidate has a clear handoff strategy, along with the abilities to develop the program that will position the full-time CISO for success.

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.