How CEOs Should Vet a CISO
A Clear Path to Protecting Your Company’s Future
How CEOs Should Vet a CISO
A Clear Path to Protecting Your Company’s Future
Imagine this.
It’s 2:47 a.m. You’re woken by a call no CEO wants to receive: your systems have been breached, sensitive customer data may be compromised, and legal is already on the line. Your mind races—where’s the CISO? What’s the plan? Is this contained or catastrophic?
Now rewind six months.
You’re interviewing candidates for your first (or next) Chief Information Security Officer. You’re asking the usual questions, checking resumes, scanning for credentials. But here’s the truth: hiring the wrong CISO can cost you everything—your reputation, revenue, customer trust, and peace of mind.
The challenge is, as a CEO, you’re not a cybersecurity expert. You’re not supposed to be. But your job is to ask the right questions and hire the right leader to keep the business secure while enabling innovation and growth.
This guide is here to help you do just that.
The Stakes Are Higher Than Ever
Let’s set the context.
Cyberattacks aren’t just happening to Fortune 100 companies. They’re hitting mid-market companies, family-owned firms, nonprofits, universities, luxury brands, and startups alike. The attackers aren’t just after data—they’re after leverage. And when they find it, they monetize it.
Meanwhile, regulators are cracking down. Investors are paying attention. Boards are asking tougher questions. And customers are expecting more from the companies they trust.
So let’s be clear: your next CISO is not just a technologist.
They are a business-critical executive who must:
Help the company stay resilient during digital disruption
Support safe innovation, not stall it
Communicate complex risks in plain language
Inspire trust from the boardroom to the back office
The right CISO will be a growth enabler. The wrong one will be a bottleneck—or worse, a liability.
You’re the Hero—Here’s the Map
In Building a StoryBrand 2.0, the core idea is this: your customer (you, the CEO) is the hero of the story. And every hero needs a guide who gives them a plan, helps them avoid failure, and drives them to a successful future.
Here’s your plan.
Step 1: Know What You Actually Need
Don’t start by looking for credentials. Start by asking what your business truly needs.
Here are three questions to ask yourself and your executive team:
What stage of cybersecurity maturity are we in?
Are you starting from scratch, building on existing efforts, or optimizing a mature program?
What are our most valuable digital assets?
Is it customer data? Intellectual property? Uptime? Trust?
What type of leader fits our culture?
Do you need a builder? A translator? A risk strategist? A trusted board presence?
Most CEOs start the search looking for a “security expert.” What they actually need is a CISO who aligns with the business strategy and culture.
If your company is scaling fast, your CISO needs to move quickly but responsibly.
If you’re highly regulated, they need to navigate complex compliance environments.
If you’re digitally transforming, they need to support safe innovation—not stall it.
Step 2: Look Beyond Certifications
Certifications are useful signals, but they don’t tell the full story. A CISO with every credential in the book could still lack the mindset to thrive in your business.
What matters most is how they think, how they lead, and how they communicate.
Qualities to look for:
Strategic thinking - They should tie cybersecurity investments to business outcomes.
Plain-Spoken Communication - Can they brief the board without drowning in jargon?
Crisis Leadership - Do they have actual experience leading through incidents instead of just theories?
Business Acumen - Do they understand how your company makes money, serves customers, and grows?
Change Management - Can they influence other leaders, not just enforce policies?
In interviews, test for how they translate complexity into clarity. Give them a business scenario and ask what they’d prioritize and why. Look for nuance, judgment, and influence—not just technical knowledge.
Step 3: Ask the Right Questions
Your job isn’t to “speak cyber.” It’s to ask questions that reveal leadership, alignment, and adaptability
Here are powerful questions you can ask—even without being a cybersecurity expert:
How do you align cybersecurity with business growth?
Look for an answer that includes enabling speed, agility, and trust—not just locking things down.
Tell me about a time you had to influence another executive to change behavior.
Cybersecurity isn’t enforced. It’s embedded. This question reveals their influence skills.
When was the last time you said no to a cybersecurity investment?
You want a CISO who thinks critically—not one who treats every risk as high-priority.
How do you prepare the board for cybersecurity oversight?
They should have a plan for making the board feel informed, not overwhelmed.
What would you do in your first 90 days here?
Great CISOs listen first, prioritize fast, and make quick wins visible.
Step 4: Test for Business Alignment, Not Just Technical Chops
You don’t need a CISO who can configure firewalls. You need one who can:
Build a business case for cybersecurity investments
Partner with legal, finance, marketing, and operations
Turn risk into resilience
Make the board feel confident—not confused
Ask them how they’ve worked with go-to-market teams. How they supported a product launch. How they’ve improved customer trust. How they enabled, not just restricted.
The best CISOs see themselves as business executives first, cybersecurity experts second.
Step 5: Watch for Red Flags
When vetting a CISO, don’t just listen to what they say—watch how they show up.
🚩 Do they speak in absolutes? “We must block this or else…”
🚩 Do they default to fear instead of clarity?
🚩 Do they struggle to explain tradeoffs in plain language?
🚩 Do they throw previous companies or teams under the bus?
🚩 Do they treat cybersecurity as a silo, not a team sport?
The wrong CISO will create friction, confusion, and resistance. The right one will create alignment, empowerment, and forward motion.
Step 6: Get Input From People Who Will Work Closely With Them
Once you’ve narrowed the field, get your COO, CTO, CFO, legal counsel, and key team leads involved. Why?
Because cybersecurity touches every part of the business.
Let those future partners assess cultural fit, collaboration style, and operational awareness. If your CISO can’t work across silos, your security program will stall before it starts.
Step 7: Paint the Picture of Success
Before you hire, clarify what success looks like in this role. Not just in technical terms—but in business outcomes.
Examples of a clear success roadmap:
In 90 days: risk assessment completed, key business risks identified, clear communication plan with the board delivered
In 6 months: cybersecurity program roadmap aligned with business objectives, compliance gaps addressed
In 12 months: measurable improvements in risk posture, security culture, and operational resilience
This gives your new CISO clarity. It also gives you and your board a benchmark for accountability
When You Get This Right
When you vet and hire the right CISO, here’s what happens:
✅ Cyber becomes a growth enabler—not a blocker
✅ Your board feels informed—not exposed
✅ Your teams feel supported—not restricted
✅ Your customers feel safe—not skeptical
✅ Your future feels secure—not vulnerable
You’ll gain a strategic partner who helps you move faster, protect better, and lead with confidence—especially when it matters most.
Next Steps for the CEO
As the CEO, your mission is clear: protect your company while empowering it to grow.
You don’t need to become a cybersecurity expert. But you do need to ask better questions, look for the right mindset, and make decisions that reinforce your company’s vision for long-term, trusted growth.
So here’s what to do next:
Audit your current cybersecurity leadership. Do they think like this?
Align your CISO hiring profile to your business needs—not just a resume.
Get guidance from executive search partners or advisors who understand both business and cybersecurity.
Make CISO interviews a test of clarity, collaboration, and commercial savvy—not just technical expertise.
Final Word
The right CISO won’t just protect you from cyber threats. They’ll help you lead better.
As the hero of your business story, you deserve a guide who understands both the battlefield and the boardroom. Someone who brings not just protection—but perspective. Someone who can help you build trust, accelerate safely, and keep your name out of the headlines.
Vetting a CISO isn’t about checking boxes. It’s about building your legacy—and protecting it.
Choose wisely.