Overcoming vCISO Imposter Syndrome: A Path to Confident Business Leadership

As demand for vCISOs grows, the role has become a strategic asset among SMBs. Yet, many vCISOs—especially those transitioning from technical roles or newer to leadership positions—experience imposter syndrome. It’s that nagging feeling of self-doubt that we don’t belong in the C-suite and we may be exposed as somehow “not enough” to be guiding security and compliance at the executive level.

But guess what? You’re not alone, and you don’t have to feel that way. In this post, we’ll look at why imposter syndrome is particularly prevalent in vCISOs, how it impacts performance, and some proven methods to build confidence and establish yourself as a capable, effective security leader.

Imposter Syndrome for vCISOs – More Common Than You Think

Imposter syndrome is a widespread phenomenon across the security and IT industries and among MSPs and MSSPs. Specific statistics are limited, but the abundance of articles, podcasts and forum discussions shows that that nagging feeling of inadequacy and doubt are commonly shared across the industry. In other words, no, it’s not just you curling into a ball under the covers.

For example, this Reddit thread about feeling like an imposter when starting a job at an MSP generated dozens of compassionate replies and this podcast episode references multiple conversations with MSP owners about dealing with imposter syndrome. Not to mention dozens of articles and posts that come up when googling “Imposter Syndrome” + MSP, MSSP, IT, tech, or security. 

Why Do vCISOs Experience Imposter Syndrome?

There is no shortage of reasons vCISOs are experiencing imposter syndrome. Do any of these ring a bell?

1. Multiple Hats, Multiple Expectations – As a vCISO, you hold responsibility for multiple roles. You are expected to be a security strategist, a policy expert, a technological expert, a compliance expert, an advisor to internal teams AND a business leader. Balancing these roles while maintaining professionalism, a client-facing approach and adapting quickly to diverse organizational needs can easily lead to questioning one’s own adequacy.
2. Constantly Shifting Priorities – Serving as an external provider brings great flexibility. However, the downside is that each new client requires adapting to – their security needs, their business style and their organizational culture. This fluidity can make even seasoned professionals feel like they lack competence and knowledge.
3. Isolation from Internal Teams – There’s a good chance you’re working remotely or part-time with your clients, which creates a disconnect from team dynamics. The distance can amplify feelings of being “out of the loop,” which, in turn, feeds imposter syndrome.
4. Perception of “Real” CISO – Your peer group is other vCISOs, but also professionals in permanent CISO positions. The perception of being “temporary” or “external” can feed self-doubt, despite having the same responsibilities and decision-making power as a traditional CISO.
5. Security Background – If you’re an MSP-turned vCISO, your previous focus was probably in IT management and support for the organization. And while you excel in infrastructure management, software maintenance, cloud services, user support, etc., making the leap to security and compliance expertise may raise feelings of doubt in your knowledge and ability to deliver on it.
6. Lack of Experience in Strategy – Some MSPs and MSSPs focus on hands-on work before entering the vCISO domain. MSPs concentrate on the day-to-day management of IT infrastructure and end-user support and MSSPs on security monitoring and response services, with limited long-term planning and advisory. Being a vCISO requires being hands-on, but the main focus is guiding the security strategy, building a plan and implementing it. This shift requires a change of mindset, rethinking internal processes and different communication with clients. This adaptation can leave service providers feeling insecure. 
7. The Common Security Imposter Syndrome – It’s not just vCISOs. Security imposter syndrome is a common feeling in the cyber security world. This is due to rapid changes in the landscape, the need to constantly learn about new threats and risks, the high stakes risks in a security failure, and even FUD encouraged by security vendors attempting to market and sell their products.
8. Compliance Importance and Knowledge – Security alone just won’t do. Now, organizations need to meet compliance regulations as well. Those are complicated, written in legal lingo, are becoming extremely prevalent and the consequences of noncompliance are severe. According to a recent Cynomi survey, 89% of MSP leaders feel overwhelmed by regulatory compliance frameworks. How can a vCISO keep up?

The Impact of Imposter Syndrome on vCISOs

Imposter syndrome is more than just a personal hurdle—it impacts performance and relationships. A vCISO grappling with self-doubt might underplay their expertise or hesitate to push back on poor decisions. This can have consequences on the organizations’ security posture, since the right professional decisions are not being made. In other cases, insecure vCISOs might overcompensate with perfectionism. Getting bogged down in minutiae affects productivity.

Finally, imposter syndrome often silences achievements, meaning critical wins may not reach the ears of stakeholders, resulting in underappreciation of the vCISO’s true impact. This can have real business consequences for MSPs and MSSPs.

What You Can Do: 4 Strategies to Overcome Imposter Syndrome as a vCISO

Many of the well-intended recommendations for overcoming imposter syndrome encourage vCISOs to “get over it”. While this is not stated verbatim, service providers are encouraged to believe in themselves and pull through, based on the premise that if they were doing a poor job, their clients would let them know and let them go.

Unfortunately, this technique is ineffective on its own, since the underlying reasons of imposter syndrome are grounded deep in the individual’s psyche, and it takes a stronger force to change this state of mind.

Below are some methods grounded in external validation, which can help establish a change in your inner thinking:

1. Document Your Experience and Accomplishments

Reporting is key in any vCISO activity, and this includes reporting to yourself. Whenever self-doubt surfaces, an inventory of accomplishments serves as a reminder of the expertise you already hold. In addition, the ongoing process of listing and detailing your achievements nurtures self-confidence from within.

Do to so, start by cataloging your achievements, skills and the reasons why clients trust you with their cybersecurity. Then, list the unique perspectives and capabilities you bring to each client. This includes metrics on risk reduction, successful initiatives, or strategic recommendations that improved their security posture. Finally, anytime you reach a goal, receive a compliment from a client, or succeed overcoming a difficult hurdle, add these to your list.

2. Seek Peer Support

The vCISO role is growing rapidly, meaning there are others who are walking a similar path. According to “The State of the vCISO 2024” report finds that 39% of MSPs and MSSPs are expected to offer vCISO services by the end of 2024.

Networking with other vCISOs, whether through online forums, industry groups, conferences, or communities can provide a strong sense of solidarity. You’ll find that others share your doubts, and you can exchange tips on navigating client dynamics, discussing approaches to governance, sharing security and compliance resources, advising on tools that can help like vCISO platforms, or handling executive pushback.

3. Embrace a Learning Mindset

Cybersecurity is constantly evolving, and even the most seasoned professionals don’t have all the answers. Shifting from a “know-it-all” to a “learn-it-all” mindset can help reduce pressure. Accepting that you’ll continuously learn and improve allows you to view challenges as growth opportunities rather than tests of your adequacy.

For example, Cynomi vCISO academy is a knowledge base for MSPs, MSSPs, security consultants and CISOs to build and expand their vCISO skills and services. By providing guides, exercises, templates and real-world examples across a wide range of topics, it helps reinforce your understanding of the required skills from vCISOs. The best part – it’s free.

4. Build Your Soft Skills

While not entirely an externally-validated method, building soft skills is a powerful way to tackle imposter syndrome. By focusing on skills like communication, empathy, adaptability and resilience, you can create a toolkit to manage self-doubt and build confidence.

For example, improving communication helps you articulate your thoughts clearly, which not only reinforces your expertise but also helps you connect with others who may share similar struggles. Practicing empathy allows you to recognize that everyone faces insecurities, fostering a sense of shared humanity. Adaptability helps you embrace challenges rather than seeing them as threats to your competence, while resilience enables you to bounce back from setbacks without internalizing them as personal failures.

These skills collectively make it easier to step out of self-critical thinking, engage more meaningfully in your work, and slowly silence the nagging voice of imposter syndrome. In addition, they improve collaboration and trust with your clients, making them feel more secure in your capabilities and more inclined to view you as a true partner in their success. This in turn can build your confidence and help with imposter syndrome as well.

Turn Imposter Syndrome into an Advantage

A bit of imposter syndrome can be an asset. It often drives vCISOs to stay vigilant, continually improve, and be highly adaptable—all valuable traits in cybersecurity. By recognizing this, you can reframe imposter syndrome from a debilitating hurdle to a source of motivation. Key to this is investing in your learning. Multiple available resources, like the vCISO academy, can help turn your imposter syndrome into a unique strength that empowers you as an effective, impactful vCISO.

Check out the vCISO academy now.