Tired of swinging the “compliance hammer” and hitting people until they submit to you? Would you rather be influential, and not dictatorial? Let's find out how you can with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

See our previous episode on the subject of "buy-in" with our guest Michael Gregg, the CISO of North Dakota -- https://cr-map.com/podcast/171/

When a hospital's systems go down, care does not stop. It goes back to pen and paper, and the first sign is quiet, because the alerts stop. Physician and CISSP Mark Yoffe explains clinical compensating controls: the steps clinicians take to keep patients safe during downtime. He covers who owns the clinical workflow, how to make controls workable and tested, how to recover information lost in the "memory hole," and what leaders should demand as proof. Paper is not the same as proof. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/mark-yoffe-md-cissp-a9927956/

"Fire Doesn't Innovate" by Kip Boyle: https://a.co/d/0bYatohy

LinkedIn post:

Questions:

Here are audience engagement questions for this episode, organized by segment:

Segment 1 – When the Hospital Goes Analog

• Have you ever worked through a system outage — at a hospital or anywhere else? What was the first thing that broke down?
• Does your organization have any setting where "no news is bad news" during downtime — where information stops coming to you and you don't immediately notice?

Segment 2 – Ownership

• Who owns your clinical downtime workflow right now — not IT, but the clinical side? Can you name them?
• If your systems went down tonight, is there a single person accountable for whether patient care workflows hold up — or would people be figuring it out as they go?

Segment 3 – Workability

• Does your downtime policy actually get used, or does it live in a binder somewhere? When did anyone last open it?
• What's one task your team assumes staff can improvise during downtime — that they probably can't?

Segment 4 – The Memory Hole

• After your last outage, how confident are you that everything documented on paper actually made it into the record? Did anyone check?
• Has a gap in documentation during downtime ever affected a patient's care — or nearly did?

Segment 5 – Leadership Oversight

• If your CEO asked today, "Can you show me that our clinical downtime controls actually work?" — what would you hand them?
• When did your organization last run a tabletop exercise specifically for clinical downtime — not just IT recovery?

Closing poll question:

Does your organization have a named, clinically credible owner for downtime workflows — yes, no, or "I genuinely don't know"?

After a breach, you either pay the fine, or fight the regulator and lose. There's a third path. It comes down to one word: reasonable. A method called DoCRA turns that question into something a court can use. DoCRA is short for Duty of Care Risk Analysis. Our guest Chris Cronin of HALOCK Security Labs helped build it. Now it's in standards and law. And it shaped a real case where a breached company spent its money on cybersecurity, not fines. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/chris-cronin-351416/

"Fire Doesn't Innovate" by Kip Boyle:

https://a.co/d/0bYatohy

Learn more about DoCRA: https://docra.org

There's a popular new playbook for running an "AI-native" company. Record everything, put all your data in one place, and let an AI agent reach all of it. The productivity story is real. New hires ramp up in days, and the whole company can ask questions it never could before. But the same moves that create the speed also switch off safeguards that some businesses are not allowed to switch off. So, which controls are we turning off to get this speed, and are we allowed to? Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Y Combinator's AI native playbook video -- https://youtu.be/B246K_G7mHU

AIR-MAP website -- https://air-map.io/

Your cybersecurity tools were built for people: a login, a single sign-on, an email address. But the AI agents now showing up inside your company don't work that way, and most of them slip right past your controls. So how do you find the "Shadow AI" already running in your business, and get a handle on it? Let's find out with our guest Nancy Wang, Chief Technology Officer at 1Password, who works at the front edge of how machines get access to systems. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile profile: https://www.linkedin.com/in/wangnancy/

1Password: https://1password.com/

Would you know if the AI tools your team is buying are actually trustworthy to use? Who gets to decide what trustworthy AI even means? Let's find out with our guest Jim Reavis, CEO of the Cloud Security Alliance, the group that helped the world learn to trust the cloud and is now building the standards for trusting AI. Jim explains how AI is changing what attackers, defenders, and governments can do, and walks through the tools his team built so you can adopt AI without guessing. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Cloud Security Alliance: https://cloudsecurityalliance.org/

Anthropic, the company that built Claude, just accidentally published the full source code of their most important product. And it was their second data exposure in five days. What does this teach every organization buying AI tools right now? Kip Boyle shares the best takeaways from CRO's AI governance training and explains why the risk of AI isn't the AI itself. Your host is Kip Boyle, CISO with Cyber Risk Opportunities.

Subscribe to Inflection Point -- https://cr-map.com/inflectionpoint/

SecureWorld AI Security PLUS course -- https://www.secureworld.io/events

"Gears Don’t Guess: The Executive’s Practical Guide to Thriving in the Face of AI Hype and Risk" (forthcoming book, Fall 2026)

AIR-MAP AI Risk Assessment -- https://air-map.io

In August 2024, a ransomware attack shut down baggage systems, flight displays, and Wi-Fi at Sea-Tac Airport. What did it reveal about how executives think about cyber investment? And why is “how much more security do we need?” the wrong question to ask after a major incident? Let’s find out with our guest Stephanie Warren, Assistant Director of Information Security at the Port of Seattle, who lived through that attack and came out the other side with hard-won lessons about executive decision-making under pressure. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile – https://www.linkedin.com/in/stephanie-warren-0746343/

What does the generative AI conversation actually sound like inside a boardroom? Is the board ready to govern it? And what do board members wish CISOs understood about how they make decisions? Let’s find out with our guest, Vanessa Pegueros, former CISO at Docusign and U.S. Bank, and current board member at LivePerson and BECU. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn profile – https://www.linkedin.com/in/vanessapegueros

Website – https://vanessapegueros.com

Anthropic released Claude Mythos Preview. The headline is "AI can now find zero-days." Yes, but the real story is the gap between what AI finds and what organizations can fix. About 99 percent of Mythos findings are still unpatched. We cover what Mythos is in plain English, why the patching gap matters most, what duty of care means when your board knows these tools exist, where AIR-MAP fits, and why most advisors skip data sovereignty. Hosts: Kip Boyle, CISO, Cyber Risk Opportunities; Jake Bernstein, Partner, K&L Gates.

Anthropic Claude Mythos Preview

https://red.anthropic.com/2026/mythos-preview/

AISLE / Stanislav Fort, "AI Cybersecurity After Mythos: The Jagged Frontier"

https://aisle.com/blog/ai-cybersecurity-after-mythos-the-jagged-frontier

AIR-MAP overview

https://air-map.io/