CEOs aren’t losing sleep because they don’t care about cybersecurity — they’re losing sleep because they know they’re accountable for risks they don’t have the time, staffing, or technical depth to see.
Customers are demanding proof that their data—and your business—are secure. Insurance renewals hinge on clear, actionable governance and risk management. And all over the world, no matter where you do business, regulations are changing and tightening.
Yet, most mid-size companies still don’t have a Chief Information Security Officer (CISO) or a formal cyber governance function.
Instead, the responsibility quietly shifts to whoever “knows the most about IT” — often an overextended internal IT manager or a managed service provider (MSP) that’s already juggling 20 other organizations’ priorities.
This doesn’t make your organization unsafe by default, but it does mean you're operating with blind spots.
That’s why the smartest CEOs are starting 2026 with a simple, practical question:
Below are ten questions every CEO should be asking their IT lead, MSP, or technology partner. These questions aren’t about catching anyone off guard; quite the opposite--they’re about getting the visibility you need to lead confidently.
And if you’re exploring outside expertise, we’ve also included a straightforward guide on how vCISO services are typically priced—linked at the bottom of this article.
1. What are our top five cyber risks — and how do we quantify them?
A strong cyber program isn’t about having every tool under the sun. It’s about prioritization.
If your IT leader cannot clearly articulate:
…then your organization is making decisions in the dark.
This is the first signal that you may need structured leadership — whether fractional, vCISO (virtual CISO), or Office of the CISO support.
2. If a ransomware attack hit us tomorrow, what is the business impact and recovery time?
This is a key question and it’s no longer a hypothetical. Mid-size companies are the top target for ransomware because cybercriminals know:
Ask for specifics about:
If the answers sound uncertain, vague, or “it depends,” that’s a real risk — not a theoretical one. A vCISO can help you turn these concerns into clear business continuity and incident response plans.
3. When was our last independent security assessment and what changed because of it?
Many companies do assessments... and very few operationalize them.
If you haven’t had an independent assessment within 12–18 months, or if the last one resulted in a long to-do list and minimal action, it’s time for a reframe.
A CISO--fractional or virtual--turns assessments into:
Simply put, without expert-led translation, assessments become expensive shelfware. Redirecting your dollar to get expertise might well be worth more than another box-checking exercise.
4. Who currently owns cybersecurity decisions — and is it the right person?
This question often reveals the biggest gap:
“Well… cybersecurity is part of our IT manager’s job.”
Your IT lead is likely smart, dedicated, and doing heroic work — but cybersecurity has become a deep (and necessary) specialization!
It requires a different skillset:
If this isn’t someone's primary role, things fall between the cracks.
5. How do we measure our cyber maturity year over year?
Cybersecurity without metrics is just... best intentions. That won’t cut it in 2026.
Ask your team:
If these questions stump your IT leader, remember that a CISO helps translate cybersecurity into a business plan. Current and target states need to be chosen based on informed business plans.
6. What security controls are required by our customers, industry, or cyber insurer?
Warning: this question often sparks uncomfortable discussions.
Today’s mid-market companies face increasing obligations: regulatory frameworks, contractual requirements, and cyber insurance scrutiny. And the bar is rising every year.
Ask your IT lead:
If this creates a long pause, or if it's clear contracts haven't been reviewed, it’s a signal that leadership oversight may be thin.
7. What’s our patching cadence and vulnerability remediation timeline?
Executives rarely ask this question — but your insurers will!
Here’s what you want to hear:
If patching is “whenever our MSP does its monthly cycle,” or "best efforts from our internal IT team," you’re relying on luck.
8. If the Board asked for a cyber readiness update today, what would we say?
Boards are increasingly held accountable for cyber oversight. Which means CEOs are, too.
Ask:
If the answer is “I’m not sure,” then you have a leadership bandwidth problem — not a technical one.
9. Do we have enough internal capacity to manage security alongside day-to-day IT operations?
This is one of the hardest truths for mid-market firms: most IT teams are drowning in work. Their day-to-day operational issues always win:
While security becomes a “when we have time” project — and there is never time.
10. What is our 12-month cybersecurity roadmap — and is it aligned to business goals?A roadmap isn’t a wish list. It’s:
If you don’t have one, you don’t really have a cybersecurity program.
These questions will reveal one of three realities:
What If My IT Team Can’t Answer These Questions Yet?
Well, this is exactly why fractional CISO, Office of the CISO, and vCISO models exist. They provide you with:
…without the $300K+ price tag of a full-time CISO.
After years of delivering cyber leadership programs across multiple industries, we’ve compiled a transparent, anonymized look at:
✓ Three real vCISO engagement scenarios
✓ Their true pricing ranges
✓ The five biggest pricing drivers
If you’re unsure what “right-sized cyber leadership” would cost you, this guide will give you clarity in minutes.
👉 Download the 2026 vCISO Pricing Guide (Three Real-World Scenarios).
You’ll get the insight you need to forecast and make informed decisions — not guesses.