Webinar Recap: From Legacy to Leading Edge – Harmonizing Risk Assessment Approaches

In our recent sponsored webinar with the FAIR™ Institute, Ostrich Cyber Risk teamed up with FAIR™ experts to discuss how businesses can transition from legacy assessments to a smarter, more effective risk management strategy while aligning with industry standards like NIST Cybersecurity Framework (NIST CSF).

What We Covered

Moderated by Adam Lamantia, Director of Business Development and Cyber Risk Quantification at Ostrich, the panel featured insights from John Feezell and Penny Longman. They covered a lot of ground, including:

• When to assess risk in-house versus bringing in outside experts

• How to make risk insights resonate across different audiences

• Finding the right balance between qualitative and quantitative risk assessments

• How to turn risk analysis into real, actionable decisions

• How frameworks like NIST CSF and FAIR™ complement each other

Key Takeaways from the Discussion

One of the biggest themes was the shift away from outdated red-yellow-green heat maps toward more data-backed risk assessments. While qualitative assessments are familiar and easy to understand, adding quantitative insights through Cyber Risk Quantification (CRQ) helps teams tell a clearer, more persuasive story.

As John put it, “Even if you never run a Monte Carlo simulation, FAIR™ gives you a structured way to think about risk and communicate it more effectively.”

Penny echoed this, emphasizing that data needs to be framed in a way that leadership understands. “We are creatures of narrative—data is valuable, but if you can’t tell a story with it, you won’t drive action,” she said.

Blending Qualitative and Quantitative Approaches

The panel agreed that organizations don’t have to ditch qualitative risk assessments altogether. Instead, a hybrid approach—one that integrates quantitative insights where it makes the most impact—is the best way forward.

So where should organizations start if they’re new to CRQ?

• Focus on high-impact use cases. Not every risk needs deep quantification—start with the risks leadership is already paying attention to.

• Use industry data. Ostrich Cyber Risk integrates cyber insurance claims data and other industry benchmarks to help teams quantify risks without starting from scratch.

• Align with frameworks like NIST CSF. Combining FAIR™ with NIST CSF controls helps organizations build a structured, repeatable approach to cyber risk management.

• Leverage automation. Managing risk quantification manually (think Excel spreadsheets) is time-consuming and tough to scale. Tools like Ostrich simplify the process.

Overcoming Challenges: Shifting the Culture

One of the biggest hurdles in adopting CRQ is the cultural shift—especially for executives used to traditional risk assessments. Many security leaders still rely on heat maps and gut instincts, making it essential to bring them along for the journey.

How do teams make CRQ adoption easier?

• Educate leadership on the benefits. Position CRQ as an enhancement, not a replacement, for existing assessments.

• Start small and scale gradually. Find a meaningful early use case, demonstrate value, and build from there.

• Make insights actionable. Decision-makers need risk data that helps them allocate resources, not just numbers on a report.

How Small Organizations Can Get Started

For smaller teams with limited resources, CRQ can feel overwhelming. The good news? It doesn’t have to be. The panel emphasized that FAIR™ is flexible and scalable—you don’t need complex modeling to see value.

John’s advice? “FAIR™ changes how you think about risk. Even if you don’t go deep into modeling, just applying its principles improves how you communicate risk.”

Why the Right Tools (and Support) Matter

Wrapping up, the panel stressed the importance of using the right tools and expert guidance to speed up the process. A platform like Ostrich Cyber Risk helps organizations streamline risk assessments, integrate industry data, and build a defensible risk management strategy without the heavy lift.

Q&A Highlights

The webinar wrapped up with an engaging Q&A session where attendees had the chance to dig deeper into the topics discussed. Some of the standout questions included:

• How can smaller organizations apply FAIR™ if they don’t have in-house expertise?

  • The panel emphasized starting small, leveraging external data, and using tools like Ostrich to streamline processes.

• What’s the best way to get executive buy-in for CRQ?

  • Focus on how CRQ supports business objectives, makes decision-making easier, and provides a clearer picture of risk.

• How do you balance qualitative assessments with quantitative data?

  • Penny highlighted that it’s not an either-or decision—quantification enhances qualitative insights rather than replacing them.

Final Thoughts

Cyber Risk Management is shifting, and organizations need to move beyond outdated risk assessments toward a more data-driven, strategic approach. The combination of FAIR™ and NIST CSF provides a powerful framework for assessing cyber risk, improving decision-making, and ensuring compliance with industry standards.

For businesses looking to modernize their approach, integrating CRQ with established security frameworks like NIST CSF and leveraging industry data will be key. Whether you’re just starting with FAIR™ or refining an existing program, the goal is clear—empower teams with actionable risk intelligence that drives real-world impact.

Missed the webinar? You can watch the full session on demand through the FAIR™ Institute Resource Library.

Want to learn more about Ostrich Cyber Risk and how we can help your organization enhance its risk assessment strategy? Let’s talk!