Resilient Cyber

- First off, for those not familiar with Containers and Kubernetes, what are they?- Why are organizations increasingly adopting these technologies over traditional forms of compute?- How does Cybersecurity change with Kubernetes and what are some things practitioners should be sure to keep an eye on?- When organizations are adopting Kubernetes they often are faced with options such as rolling their own or using managed Kubernetes offerings, any thoughts there?- I recently read a report that researchers found 380,000 publicly exposed Kubernetes API servers, do you think people simply are spinning up these new technologies with security as an afterthought?- Kubernetes is incredibly complex, do you think this leads to challenges around properly configuring and securing it?- Any thoughts on software supply chain security as it relates to Kubernetes and Containers?- For those looking to learn more about Kubernetes and Container Security, do you have any recommended resources?

- For those unfamiliar with a vCISO, what is it and how is it different than a traditional CISO?- Do you feel like the SMB market is catching on to the necessity of a vCISO and how it is critical to enabling secure business outcomes?- How do organizations go about ensuring they get a qualified vCISO? Any things in particular to watch out for?- For those looking to get started as serving as a vCISO, any recommendations?- You are a great story teller and communicator on LinkedIn. What made you start making your videos?- How important do you think communication is to helping drive secure business outcomes for Cyber professionals?

Chris - Lets start off with discussing what is Purple Teaming exactly, and what is it not?Nikki - The industry can be somewhat siloed between job roles, and purple teaming really breaks down those barriers - do you see purple teaming being adopted more in the industry? Or do you think that too many industry experts hold too closely to their areas of expertise? Chris - People often conflate Red Teaming, Pen Testing and Purple Teaming - how do we help clear up that confusion? Nikki - Purple teaming is supposed to be an iterative continuous process between red teams and blue teams. Do you feel like this continuous flow of information should be consistent between the teams? Do you feel like there is more value in one direction versus another?  Nikki - The purple team concept is centered around blue teams and red teams, but this type of iterative and cooperative concept could be applied outside of red teamers and network defenders. Do you see value between using this type of cooperation between security assessment and audit teams and network defense teams?Chris: You've been someone I have watched who has been really effective at personal branding through platforms like LI. Can you discuss how you approach that and why it is valuable?Chris: For those looking to get into Purple Teaming or more broadly OffSec or even Blue Team, what are some of your primary recommendations resource wise for learning?

Nikki - You have some really awesome content on LinkedIn around Vulnerability management - one of my favorite posts you made recently was asking "Is vulnerability management dead". Can you explain a little bit about what you mean? I'm curious on your take, because there isn't a ton of modern guidance around vulnerability management  Nikki - One of the biggest challenges I think we face around vulnerability identification, and specifically prioritization, is that a lot of emphasis is put around CVSS scores and CVE ID's specifically. And while an incredibly helpful tool, plenty of vulnerabilities are not ID'ed or are not seen in traditional vulnerability scanners. What do you think the industry can do to better use other tools/techniques to identify and remediate vulnerabilities?  Nikki - Can you talk a little bit about where you think we could use more guidance or leadership around vulnerability management? I really don't hear about it when we talk cloud security or AI/ML, but it still incredibly relevantChris - We know another topic you're passionate about is software supply chain security. Can you share your thoughts on where the industry is headed with SBOM, VEX and other efforts to bring transparency and better governance to the SW supply chain?Chris - You've also written and spoken a fair bit about broader Supply Chain Risk, partners, MSP's, CSP's etc. Do you think organizations are just now waking up to the exponential risk due to the interconnected and as-a-Service orientation we've taken as an industry?Chris - As we mentioned, you do a ton of writing on LinkedIn, as well as your substack distro. How do you keep up the pace and what led you to start the substack originally? Where can people follow it and stay informed? 

- For those not familiar with Threat Modeling, what is it? Also, to clear up potential confusion, what is it not? (e.g. Threat Hunting)- You were part of an effort to create the Threat Modeling Manifesto, can you tell us a bit about that project?- We recently saw NIST both define critical software as part of the Cyber EO and also list Threat Modeling as a key activity for critical software. What are your thoughts on that occurring and if you think that will impact the Threat Modeling community?- Some folks have made comments about Threat Modeling being too cumbersome for methodologies/cultures such as DevOps/DevSecOps. Why do you think that is an opinion among some and is it true? - Can Threat Modeling be applied to any sort of architecture or system? Are there any major differences for same on-prem vs cloud systems?- For organizations looking to get started with Threat Modeling, where do you recommend they start? - Moving on from getting started, have you seen large organizations with successful, or unsuccessful Threat Modeling programs, and what were some major themes either way?

Nikki - You have a varied background between being a security engineer, consultant, manager, etc. What made you decide to focus more on the compliance aspects of cybersecurity?Chris - It is often said "Compliance doesn't equal Security". Why do you think this phrase has taken hold, do you think its accurate and how do we evolve beyond it? Nikki -  Based on some of your posts about compliance - one specifically about implementing frameworks and guidance from NIST and the CMMC standards - do you think there's a need in the industry to focus more on implementation guides or do you feel like organizations are to complex to create guides? Chris - On the topic of compliance frameworks, we seem to be so reactionary, with new frameworks coming after incidents etc. and organizations struggle to keep up. Do you think we have a framework sprawl problem?Chris - On the topic of 800-171 and CMMC, there's a lot of talk on the topic of affordability and cost and the impact to the small businesses in the DIB, which has already seen massive consolidation. What are your thoughts on this, and how do we balance compliance/security with the need for a robust DIB of suppliers?Nikki -  What do you think the future of compliance looks like? CMMC and otherwise - do you foresee more legislation around compliance coming down the pike?

Chris: We're undoubtedly seeing a growing discussion around Software Supply Chain, with several notable events and also now evolving guidance/legislation such as the Cyber EO, NIST guidance etc. Any thoughts on why this is just now becoming such a focused concern?Nikki: When a lot of people discuss software supply chain security, it can quickly turn into a discussion about SBOM or Log4j and SolarWinds. I think about software supply chain security as being part of a really good threat detection and response program - what are your thoughts on that?Nikki: I also wanted to address, expanding on the topic of threat detection and moving into threat modeling - do you think that with the attack surface expanding through the software supply chain that there are threat modeling techniques that can be used to understand and account for that growing attack surface?Chris: You've been pretty involved in efforts around software supply chain and DevSecOps, most notably sigstore - can you tell us what that is and why it is important or useful? Nikki: In the last couple of years ' technical debt' has become a bigger concern for organizations, but this includes software supply chain, dependencies, EOL or outdated software, etc. How do you think organizations can account for their software inventory better and more efficiently?Chris: As we look to the future of Software Supply Chain, with efforts such as SBOM, VEX, Sigstore, SLSA and more, where do you think we're headed? What does the state of software supply chain look like in say 3 years?

Chris - We know there's a massive Cyber workforce challenge, what role do you think academia plays there and how can it improve to close the gap?Nikki - Speaking of the young professionals in cybersecurity, what do you think are some of the in-demand skillsets and career paths available for individuals interested in pursuing a career in cybersecurity?Chris - There's often a debate between academics and practitioners, why do you think that is, and do you think we're seeing that gap dissolve with new degree programs and more practitioner focused curriculum?  Nikki - On the subject of academia - do you feel like there is enough focus on research in cybersecurity fields? Do you think that research is getting to private and public partners or is there something we can be doing to strengthen those relationships?Chris - What do you think the future of Cybersecurity education looks like? What role does non-traditional education such as certifications, bootcamps, online courses and content etc. play in the hiring qualifications of the future?

Chris: So let's start with how we've gotten here. With digital systems accounting for 60% of global GDP, how do we still not have requirements or adoption of cyber expertise on public board?Nikki: You mention in your article about the SEC mandating cyber leadership into board rooms - do you think that the type of experience expected on boards should be geared specifically to risk management, or a mix of highly technical and governance experience?Chris: For those looking to fill some of those upcoming board opportunities, what recommendations do you have?Nikki: For your book the Great Reboot - you recommend that not only leadership but employees read it as well - do you think there's a gap in knowledge or maybe awareness of how risk impacts the business from a practitioner level? Would you encourage junior and senior personnel to read this book?Chris: On the flip side, for boards and publicly traded companies looking to bring cyber expertise into the fold, what competencies and skills should they be looking for? Where do they start?Nikki: Risk is bigger than one vulnerability or one misconfiguration but can have a number of definitions - how do you define risk management and do you think there's a need to define 'risk' more aptly in organizations?Chris: You often speak about systemic risk. Do you think the modern digitally driven economy and ecosystem is inherently insecure and vulnerable?