As AI investments rise, so do cyber risks, reshaping the evolution of the Chief Information Security Officer (CISO) role from tactical security operations to a strategic, board-facing position.
Today's forward-thinking CISOs will do more than protect your company's data. They will turn security into a competitive advantage, advise on responsible AI adoption, and guide the board on digital risk and governance.
Yet, many CISOs remain defense-oriented, believing that frameworks and compliance are the whole job. With technology and security protocols changing so quickly, how do CIOs, CEOs, and their boards, identify candidates who prioritize growth without compromising defense?
Heller can help. Get beyond the standard interview questions and use these 15 questions, compiled by our CISO talent experts, to hire a CISO who can protect and innovate.
Security strategy: What is your process for establishing an overarching security strategy?
NIST and ISO frameworks are foundational, but where is the strategy? Does the candidate understand how your organization makes money and have a plan for deepening that understanding? Can they quantify exposure, and discuss risk in terms of acceptance, mitigation, or transfer through insurance or other means? How do they frame tradeoffs between investing in controls versus resilience?
Security as market differentiator: For our business, where would you look for opportunities to use cybersecurity as a market differentiator and business driver?
Can the candidate give examples from prior experience, or from observations about your industry? Have they found a way to get ahead of acquisitions so that security happens quickly and seamlessly? Have they worked to make security a positive part of the corporate brand? The mindset matters more than the examples. Do they see that security can be a customer-facing market differentiator?
Security as accelerator: Can you describe a time when you recommended a new security approach or investment to accelerate a strategic initiative?
How does the candidate balance risk exposure and security controls with time-to-market and other business concerns? Is time-to-market treated as a security afterthought---or a strategic priority? Do they see security as an accelerator, not just a gatekeeper?
Approach to AI: If we decide to launch a new business venture with heavy AI components, how would you approach securing that effort?
This question helps further explore the candidate's thinking about uncertainty, opportunity, risk, and cost. Stronger answers may include isolating experimental AI environments from production systems, assessing model integrity and data lineage, or partnering early with legal, privacy, and compliance teams.
Acquisitions: If our company were considering an acquisition, what security factors would you evaluate to ensure the deal supports our strategic goals?
Beyond basic data security and privacy controls, does the candidate examine issues such as differences in the target company's security governance model, the challenges and timing of planned integration, and the priorities dictated by those strategic goals? Do they consider cultural alignment or cyber risks that could delay successful integration or derail the deal's value?
Executive Communication: How do you determine what to report to the executive committee and board? What would you include in a dashboard?
Reporting might initially focus on transparency, to establish that adequate controls and incident response plans are in place for key risks. As a security function matures, reporting can evolve with greater focus on information that is actionable at the board level. That may mean showing trends, business impact, and risk posture---in addition to technical indicators.
Working with budget constraints: How would you continue reducing our risks and driving our growth during times when budget increases are not available?
Can the candidate give examples of partnerships, budget reallocation to higher-risk areas, or continual improvement in cost efficiency of baseline controls? Have they leveraged automation or internal champions to extend security impact without new headcount?
Professional network: What network of communication and support do you bring to the position?
Collaboration is vital, and peer, industry and government groups (such as industry councils and the National Cyber Defense Alliance) are valuable resources. Beyond threat intelligence, participation in non-technical communities and mentorship circles are strong signals of a well-rounded, business-minded leader.
C-suite collaboration: Describe how you have worked with the CFO or General Counsel of an organization on your top two or three shared concerns.
Does the candidate demonstrate a focus on relationships, as well as an ability to listen and make intelligent compromises? Do they describe shared concerns in technical terms or in the language of their fellow executives?
Business alignment: How do you ensure security remains aligned with fast-changing business priorities?
Security strategies are often built annually, but business priorities can shift quarterly---or faster. Does the candidate have a process for staying aligned with sales, product, legal, and operations as those shifts happen? Look for signs they engage proactively and build security into dynamic planning processes, not just static roadmaps.
Security-innovation tradeoffs: Tell us about a time you had to make a difficult tradeoff between security and innovation. How did you handle it?
This question reveals how the candidate operates under pressure when perfect security isn't possible. Do they fall back on rigid controls, or do they find creative ways to manage risk while enabling progress? A strong answer shows business empathy, smart compromise, and collaborative problem-solving.
Future technology preparation: What are you doing today to prepare for the next wave of technology disruption?
This tests whether the candidate is proactive, curious, and thinking ahead---not just reacting to immediate threats. Are they learning about quantum risks? Following developments in AI security? Watching emerging regulations? Strategic CISOs are always looking around the corner.
Team talent development: How do you evaluate and develop the talent on your security team?
A CISO who builds a strong team will be far more effective than one who tries to do it all alone. Look for signs the candidate develops future leaders, supports upskilling, and encourages cross-functional thinking. Bonus points if they're building a security-aware culture across other teams as well.
Security culture building: How do you approach building a security-aware culture across the company?
Strong CISOs collaborate with HR, communications, and other functional team leads to build awareness, engagement, and shared responsibility. Do they approach security as something employees can understand and influence---or as something to fear?
Influence without authority: What's your approach to influencing without authority?
Security leaders often need to guide teams they don't directly manage. Can the candidate build credibility across departments, gain buy-in for tough changes, and foster productive relationships at all levels? Influence, not control, is what makes a strategic CISO effective in the C-suite and beyond.
The leaders who possess the strengths discussed here are rare. At Heller, we cultivate a network of CISOs who can protect, grow, lead, and influence. Let us know if you'd like to talk.
