--- title: "Questions to Ask a vCISO - Christian Espinosa" description: "Hiring a vCISO? Learn the essential questions to ask about industry experience, audit capabilities, strategic planning, and dual-role expertise to secure…" lang: en json-ld: | [ { "@context": "https://schema.org", "@type": "Person", "@id": "https://christianespinosa.com/#person", "name": "Christian Espinosa", "url": "https://christianespinosa.com/", "image": "https://christianespinosa.com/__l5e/assets-v1/de07e44b-a8e0-4bcc-bcb0-13aec15421f1/headshot-front.jpg", "sameAs": [ "https://www.facebook.com/christian.espinosa.official", "https://x.com/Ironracer", "https://www.instagram.com/christian.espinosa.official/", "https://www.youtube.com/@ChristianEspinosaOfficial", "https://www.linkedin.com/in/christianespinosa/" ], "jobTitle": "Bestselling Author, Keynote Speaker, Entrepreneur", "worksFor": { "@type": "Organization", "name": "Blue Goat Cyber", "url": "https://bluegoatcyber.com/" } }, { "@context": "https://schema.org", "@type": "WebSite", "@id": "https://christianespinosa.com/#website", "name": "Christian Espinosa", "url": "https://christianespinosa.com/", "publisher": { "@id": "https://christianespinosa.com/#organization" }, "inLanguage": "en-US" }, { "@context": "https://schema.org", "@type": "Organization", "@id": "https://christianespinosa.com/#organization", "name": "Christian Espinosa", "url": "https://christianespinosa.com/", "logo": { "@type": "ImageObject", "url": "https://christianespinosa.com/logo.svg" }, "founder": { "@id": "https://christianespinosa.com/#person" }, "sameAs": [ "https://www.facebook.com/christian.espinosa.official", "https://x.com/Ironracer", "https://www.instagram.com/christian.espinosa.official/", "https://www.youtube.com/@ChristianEspinosaOfficial", "https://www.linkedin.com/in/christianespinosa/" ] }, { "@context": "https://schema.org", "@type": "Article", "headline": "Questions to Ask a vCISO - Christian Espinosa", "description": "Hiring a vCISO? Learn the essential questions to ask about industry experience, audit capabilities, strategic planning, and dual-role expertise to secure…", "image": "https://christianespinosa.com/__l5e/assets-v1/e67a8eb5-02a2-4149-b18b-056916387a6b/questions-to-ask-a-vciso-card.png", "datePublished": "2021-09-04T04:29:10+00:00", "dateModified": "2026-06-26T05:36:36.034Z", "mainEntityOfPage": { "@type": "WebPage", "@id": "https://christianespinosa.com/blog/questions-to-ask-a-vciso" }, "author": { "@type": "Person", "name": "Christian Espinosa", "url": "https://christianespinosa.com/about" }, "publisher": { "@type": "Organization", "name": "Christian Espinosa", "logo": { "@type": "ImageObject", "url": "https://christianespinosa.com/logo.svg" } } }, { "@context": "https://schema.org", "@type": "FAQPage", "mainEntity": [ { "@type": "Question", "name": "What is the core idea behind \"Questions to Ask a vCISO - Christian Espinosa\"?", "acceptedAnswer": { "@type": "Answer", "text": "Many companies rush into finding fractional vCISO services and end up with a relationship they did not expect. Ask the right questions first." } }, { "@type": "Question", "name": "Who is this post for?", "acceptedAnswer": { "@type": "Answer", "text": "Honestly, security leaders, medical device teams, and technical operators who want the honest version, not the vendor version. If you want a listicle, this is not that. If you want the honest version of what I have actually lived and worked through, keep reading." } }, { "@type": "Question", "name": "How do I actually apply this, not just nod along?", "acceptedAnswer": { "@type": "Answer", "text": "Pick the single line in the post that made you flinch or look away, and change one thing in your week because of it. One choice this week beats a whole framework you never touch." } } ] } ] --- [Skip to content](#main) [](/) [About](/about)[Speaking](/speaking)[Cybersecurity](/cybersecurity)[Programs](/programs)[Books](/books)[Media](/media) Writing Search Ctrl K[Connect](/connect) [Cybersecurity](/blog/category/cybersecurity) # Questions to Ask a vCISO September 4, 2021 4 min read 969 words I've seen it too many times: a company rushes into a vCISO relationship and ends up with something they didn't expect. I know, because sometimes I'm the one they call to fix it. If you're thinking about a CISO-as-a-Service, you need to compare providers. I'm going to tell you the questions I ask when I'm evaluating a potential partner. ![](/__l5e/assets-v1/41b2490e-f77a-482c-ab49-1051ee5c215f/questions-to-ask-a-vciso-hero.webp) The takeaways 1. 01 Companies choose a CISO-as-a-Service for a lot of reasons. What to do next Add ciso-as-a-service to the next leadership review as a standing item, not a one-time slide. 2. 02 It gives any company, big or small, a strong cybersecurity strategy. What to do next Open your current strategy plan today and identify the one gap you would not want an auditor to find. 3. 03 You can bring in a CISO-as-a-Service for both strategic and tactical help. What to do next Add ciso-as-a-service to the next leadership review as a standing item, not a one-time slide. 4. 04 Time to Ask the Right Questions There are many options for CISO-as-a-Service for businesses. What to do next Open your current ciso-as-a-service plan today and identify the one gap you would not want an auditor to find. I've seen it too many times: a company rushes into a vCISO relationship and ends up with something they didn't expect. I know, because sometimes I'm the one they call to fix it. If you're thinking about a CISO-as-a-Service, you need to compare providers. I'm going to tell you the questions I ask when I'm evaluating a potential partner. ## Why Should You Consider Hiring a CISO-as-a-Service? Companies choose a CISO-as-a-Service for a lot of reasons. It gives any company, big or small, a strong cybersecurity strategy. It's a cheaper way to manage cyber, and it helps organizations mature their security. Most startups or smaller businesses can't afford a full-time CISO's salary. You can bring in a CISO-as-a-Service for both strategic and tactical help. There's no training period like with a new hire, so there's no delay in getting started. ## Time to Ask the Right Questions There are many options for CISO-as-a-Service for businesses. However, they aren’t necessarily equal in their capabilities, experience, or breadth of services. Some providers also treat the service as one-size-fits-all, and that’s not in anyone’s best interest. Every company is unique and has its own sets of risks and challenges. To best compare the offerings, ask the right questions. ### 1\. Do they have experience in your industry and the compliance regulations specific to it? Highly regulated industries, such as healthcare and finance, have specific needs when it comes to CISOs and cybersecurity. There are laws and regulations to which you must adhere. If that applies to your business, it’s imperative to ask about their past experience with these compliance measures. Without specific experience, you may find the provider hitting a learning curve, which could cause delays and exposure to risk. ### 2\. Do they have audit experience? On day one, the CISO-as-a-Service should perform audits to understand where your cybersecurity is and where it needs to go. These are fundamental activities, but this doesn’t mean every provider offers them or has experience with them. The most important audits are a data Breach Prevention Audit (BPA) and a CMMC (Cybersecurity Maturity Model Certification) audit. Ask the provider about how they conduct the audits and what the deliverables will look like. Request samples of these audits if available. ### 3\. Have they developed and implemented strategic security plans? The main objective of hiring a CISO-as-a-Service is for the firm to develop a strategic security plan and then implement it. When assessing vendors, dig deep into their experience with these two things. It’s one thing for a provider to say they’ve created plans in an abstract way. It’s another when they have specific examples of doing so for other customers and what they have helped them achieve. For a CISO-as-a-Service to be legitimate and reputable, they don’t need a long list of well-known brands as customers. What they do need is case studies and data that show they were able to execute on developed plans. Viewing a high-level cybersecurity roadmap example can instill great confidence that the company has the experience to lead your security efforts. ### 4\. Do they have expertise in strategic and tactical roles? As noted, a CISO-as-a-Service can serve both a strategic and tactical role. In most cases, businesses want to use both. They must have expertise in both areas. Here are the differences: - Strategic CISO-as-a-Service roles assist leadership teams with cybersecurity strategies that align with business objectives. This strategy includes one-, two-, and three-year roadmaps. You’ll receive guidance and recommendations on cybersecurity best practices to prevent incidents and breaches. - Tactical CISO-as-a-Service roles actually execute the tasks within the strategy. The CISO-as-a-Service acts as a project manager to offer oversight on these activities. ### 5\. Is there one point of contact? Typically, CISO-as-a-Service isn’t one individual. Rather, it’s a team of experts that have knowledge in multiple areas. That’s certainly the model you want to find because it means you have access to a group of experts. But what helps is having one point of contact to discuss tasks and deliverables. A dedicated project manager helps keep things organized and streamlined so you’re always up to date. ### 6\. What kind of reporting do they offer? Reporting is key to cybersecurity. From regular reporting, you learn about vulnerabilities, threats, user behaviors, and more. At a minimum, you should receive monthly reports on these concerns and what the CISO-as-a-Service has deployed. ### 7\. Do you have Incident Response Plan experience? If you don’t currently have an Incident Response Plan (IRP) or haven’t revisited it in a while, this need will shift to your CISO-as-a-Service. Make sure this deliverable is part of their services. They can quickly develop an interim one, then work to craft a formal IRP and ensure all parties are aware of it and know their roles. ### 8\. How do they stay up to date with cybersecurity trends? Cybersecurity threats are always evolving. Threat actors use sophisticated phishing techniques, and hackers deploy many attempts to penetrate networks. You need a team that has a pulse on what’s going on right now in the security world. Ask potential partners how they stay up to date and learn about new challenges, solutions, and tools. ## Ready to Hire a CISO-as-a-Service? If you’re planning to hire a CISO-as-a-Service, be sure to ask these questions as you evaluate vendors. Our solution is comprehensive, cost-effective, and delivers value for your business. You can get started by booking a [discovery session](https://christianespinosa.com/cerberus-sentinel/) with me today! Frequently asked ### What is the core idea behind "Questions to Ask a vCISO - Christian Espinosa"? ### Who is this post for? ### How do I actually apply this, not just nod along? ### Work with me I help founders and cybersecurity leaders build teams that ship, not teams that stall. If that's the problem you're trying to solve, let's talk. [Start a conversation](/contact) Share this essay [X ](https://twitter.com/intent/tweet?url=https%3A%2F%2Fchristianespinosa.com%2Fblog%2Fquestions-to-ask-a-vciso&text=Questions%20to%20Ask%20a%20vCISO) [LinkedIn](https://www.linkedin.com/sharing/share-offsite/?url=https%3A%2F%2Fchristianespinosa.com%2Fblog%2Fquestions-to-ask-a-vciso) [Facebook](https://www.facebook.com/sharer/sharer.php?u=https%3A%2F%2Fchristianespinosa.com%2Fblog%2Fquestions-to-ask-a-vciso) [Email](mailto:?subject=Questions%20to%20Ask%20a%20vCISO&body=https%3A%2F%2Fchristianespinosa.com%2Fblog%2Fquestions-to-ask-a-vciso)Copy link ![Christian Espinosa, headshot](/__l5e/assets-v1/de07e44b-a8e0-4bcc-bcb0-13aec15421f1/headshot-front.jpg) About the author [Christian Espinosa](/about) · Founder & CEO, Blue Goat Cyber Christian is the founder and CEO of Blue Goat Cyber, a medical device cybersecurity firm. He's an Air Force Academy graduate, 24x Ironman, climber of two of the Seven Summits, and the author of The Smartest Person in the Room and The In-Between: Life in the Micro. Keep reading - [ ### Remote Work Is Here to Stay: The Impact on Cybersecurity - Christian Espinosa Same thread: cybersecurity. Read essay → ](/blog/remote-work-is-here-to-stay-the-impact-on-cybersecurity) - [ ### The Power of Questions - Christian Espinosa Related take on christian, questions. Read essay → ](/blog/the-power-of-questions) - [ ### Top 10 Organized Cybercrime Syndicates - Christian Espinosa Same thread: cybersecurity. Read essay → ](/blog/top-10-organized-cybercrime-syndicates) [← Previous essay Top 10 Largest Healthcare Data Breaches by Number of Records Stolen - Christian Espinosa ](/blog/top-10-largest-healthcare-data-breaches-by-number-of-records-stolen)[Next essay → Cybersecurity Risk Needs to be Simplified - Christian Espinosa ](/blog/cybersecurity-risk-needs-to-be-simplified) Related, Leadership ### Bring this conversation to your team Christian keynotes on cybersecurity leadership, ego in tech, and building human-first technical teams. Available for corporate events, conferences, and executive offsites. [Book Christian to speak](/speaking) Christian Espinosa Bestselling author, keynote speaker, and Founding CEO of [Blue Goat Cyber](https://bluegoatcyber.com/). Helping technical leaders develop the soft skills that turn brilliance into impact. [](https://www.linkedin.com/in/christianespinosa/)[](https://x.com/Ironracer)[](https://www.instagram.com/christian.espinosa.official/)[](https://www.youtube.com/@ChristianEspinosaOfficial)[](https://www.facebook.com/christian.espinosa.official) Explore - [About](/about) - [Timeline](/timeline) - [Speaking](/speaking) - [Cybersecurity](/cybersecurity) - [Programs](/programs) Read - [Books](/books) - [Guides](/guides) - [Blog](/blog) - [Media](/media) - [Podcast Interviews](/podcasts) - [Success Stories](/success-stories) Connect - [Contact Christian](/connect) - [LinkedIn ↗](https://www.linkedin.com/in/christianespinosa/) - [Blue Goat Cyber ↗](https://bluegoatcyber.com/) - [Resources](/resources) © 2026 Christian Espinosa. All rights reserved. [Privacy](/privacy-policy)[Terms](/terms-of-use)