Why Security Teams Are Being Asked to Do Three New Jobs - and What to Do About It

Guest: Rob Lee, Chief AI Officer and Chief of Research at SANS Institute

Host: Seth Earley, CEO at Earley Information Science

Published on: March 27, 2026

In this episode, Seth Earley speaks with Rob Lee, Chief AI Officer and Chief of Research at SANS Institute, about why AI governance is broken in most organizations - and what it actually takes to fix it. They explore why security teams are being asked to simultaneously govern, adopt, and defend AI, why the default framework of no is driving shadow IT rather than preventing risk, and what a practical reset of AI governance actually looks like. Rob also shares why agents should be treated like workers rather than software, and why executives cannot afford to outsource their understanding of AI to anyone else.

Key Takeaways:

• Security teams are now being asked to do three new jobs at once - evaluate AI tools for the organization, drive their own AI transformation, and manage governance and regulatory compliance.
• The default framework of no does not prevent AI use - it drives it underground, creating shadow IT that is far harder to monitor and control than sanctioned tools.
• Governance needs a stoplight model - green means experiment freely, yellow means involve security as a lifeguard, red means stop - with the default answer being yes unless there is a clear reason to say no.
• AI governance documents written before generative AI arrived are already outdated - most say nothing about agentic workflows, human-in-the-loop requirements, or connector permissions.
• Agents should be treated like workers, not software - they reason, improvise, and operate 24-7, which means they require the same zero-trust principles, oversight structures, and ethical guardrails as human employees.
• Executives cannot outsource their understanding of AI to security teams - AI literacy at the C-suite level is a competitive requirement, not an optional capability.
• Good governance is not about documenting every possible bad outcome - it is about establishing overarching goals and building a culture of trust with enough guardrails to prevent the truly stupid risks.

Insightful Quotes:

"The framework security teams are using is a framework of no. And that framework of no is causing people to use AI secretly, regardless of what the security team says." - Rob Lee

"An agent in the future - and some organizations are already treating it this way - is a worker. Everything you ask about governing agents, replace that with a human who just got hired. The same rules apply." - Rob Lee

"You can't automate what you don't understand - and with agents, the stakes are even higher. An agentic mistake isn't a wrong paragraph, it's a blocked critical system." - Seth Earley

Tune in to discover how security and executive leaders can move from a governance posture of restriction to one that enables innovation, manages real risk, and keeps organizations competitive in the age of agentic AI.

Links:

LinkedIn: https://www.linkedin.com/in/leerob/

Website: https://www.sans.org

Sponsor: Vector - https://www.vktr.com/

Thanks to our sponsors:

• VKTR
• Earley Information Science
• AI Powered Enterprise Book

Accuracy, Trust, and the Interface Revolution: How AI is Transforming Legal Workflows

Guest: Mike Anderson, Chief Product Officer, Filevine

Host: Seth Earley, CEO at Earley Information Science

Published on: March 20, 2026

In this episode, Seth Earley speaks with Mike Anderson, Chief Product Officer at Filevine, about what it takes to bring AI into one of the most demanding and high-stakes environments in the enterprise - legal operations. They explore why AI will not replace attorneys but will dramatically extend what legal professionals can accomplish, how real-time deposition analysis is transforming courtroom preparation, and why information architecture remains the critical foundation beneath every AI capability. Mike also shares why the interface - not the model - is the biggest unlock AI offers the legal industry.

Key Takeaways:

• AI will not replace attorneys or paralegals - legal services are already severely undersupplied, and AI's role is to extend what existing professionals can accomplish.
• The billable hour model is evolving, but the bigger opportunity is eliminating non-billable administrative burden so attorneys can focus on higher-order legal thinking.
• Real-time deposition analysis - live transcription cross-referenced against case files - is one of the most powerful and practical AI applications in legal today.
• Boolean search cannot be replaced in legal because accountability for document populations requires transparent, auditable logic that external parties can evaluate.
• Effective AI in legal requires three information retrieval lenses: semantic search, Boolean search, and attribute-based filtering - all three are necessary.
• Information architecture - defining the is-ness and about-ness of legal objects like matters, contracts, depositions, and clients - remains the foundation for AI to work accurately.
• The interface is the single biggest unlock AI offers legal professionals - the ability to ask a question in natural language rather than navigate complex click paths changes everything.

Insightful Quotes:

"The demand for legal services already outpaces supply, and it has for some time. We should be talking about the productivity and extensibility of legal professionals - not obsolescence." - Mike Anderson

"If only I had this analysis of the deposition during the deposition. That one customer comment kicked off an entire depositions platform for us." - Mike Anderson

"You still need the is-ness and about-ness. The interface changes, but the underlying information architecture is still what makes AI work correctly." - Seth Earley

Tune in to discover how legal teams are moving past AI skepticism and building the foundations that make AI accurate, trustworthy, and transformative in practice.

Links

LinkedIn: https://www.linkedin.com/in/michael-anderson-374299163/

Website: https://www.filevine.com

Thanks to our sponsors:

• VKTR
• Earley Information Science
• AI Powered Enterprise Book

From Vision to Value: How Leaders Can Close the Gap Between AI Ambition and Operational Reality

Guest: Brian Stafford, CEO at Diligent

Host: Seth Earley, CEO at Earley Information Science

Published on: March 9, 2026

In this episode, Seth Earley speaks with Brian Stafford, CEO of Diligent, a $700 million global software and AI company focused on governance, risk, and compliance. They explore why most organizations understand that AI is transformative but still struggle with the how of actually getting there, and what it takes to move beyond pilots into real operational change. Brian shares how Diligent is helping clients in compliance, audit, and risk functions do more with less through AI-wired software and agents, and why context, leadership, and process understanding are the real drivers of successful AI transformation.

Key Takeaways:

• Most organizations have crossed from asking what AI can do to struggling with how to actually execute and drive measurable transformation.
• Calling initiatives pilots gives organizations an excuse to fail - framing AI as transformation from the start changes accountability and outcomes.
• AI maturity is less about sector or company size and more about the quality and commitment of executive leadership driving change.
• Compliance, risk, and audit functions face a structural mandate - increasing obligations with flat or shrinking budgets - making AI adoption a necessity, not a choice.
• Agents should be thought of like a smart new associate - trained gradually, checked in with frequently at first, then trusted to operate with more autonomy over time.
• Context is the key differentiator for AI solutions - partners who already understand your domain, regulatory environment, and workflows will deliver faster, better outcomes.
• AI-native employees who are intellectually curious and fluent in modern tools can deliver 5 to 10 times the output of peers who resist adopting new capabilities.

Insightful Quotes:

"I hate the term pilot. Pilot gives organizations the license to call something unsuccessful. You're not piloting a transformation - you're either driving it or you're not." - Brian Stafford

"Most of our clients don't care if I ever said the word agent. They care about an outcome. The technology is just what helps deliver it." - Brian Stafford

"You can't automate what you don't understand. And once you do understand it, agents change everything - but the process clarity has to come first." - Seth Earley

Tune in to discover how forward-thinking leaders are closing the gap between AI ambition and real operational impact across governance, risk, and compliance functions.

Links

LinkedIn: https://www.linkedin.com/in/brian-k-stafford/

Website: https://www.diligent.com

Thanks to our sponsors:

• VKTR
• Earley Information Science
• AI Powered Enterprise Book