Risk Never Sleeps Podcast – Episode #189

Title: "If Your AI Program Ignores Security You Are Already Behind"
Host: Ed Gaudet
Guest: Will Conaway (Healthcare Technology Executive & AI Advisor)
Date: January 14, 2026

Overview

This episode features a vibrant and insightful conversation between Ed Gaudet and returning guest Will Conaway, a seasoned healthcare technology executive and AI advisor. The episode probes deeply into the intersections of AI, cybersecurity, and governance in healthcare, with a focus on protecting patient safety amidst rapid technology change. Outside the technical discourse, Ed and Will share personal stories (from Grateful Dead encounters to guitar building), bringing warmth and personality to the conversation.

Key Discussion Points & Insights

1. Will’s Career Evolution: From Corporate Executive to Consultant

• Will provides an update since his last Risk Never Sleeps appearance. He’s transitioned from a senior VP role at a large company to full-time consulting, AI advising (via Ascent Business Partners and his own Tuxedo Cat Consulting), and continued academic work at Cornell.
• He describes the realities of consulting:
  • Quote: “When you work for a large corporation, there’s people to help you… When you go into kind of working on your own… you have none of that. You find yourself wearing all hats.” (06:19)
• Consulting lets him focus on unique projects (including AI hallucination reduction and cybersecurity), more speaking engagements, and media opportunities.

2. AI Strategy vs. IT Strategy in Healthcare

• Will distinguishes the need for a formalized AI strategy separate from traditional IT. He predicts:
  • Quote: “Within the next couple years there will be AI officers at all healthcare organizations.” (08:10)
• Advice for Healthcare Leaders:
  • Define what you want AI to do before engaging consultants.
  • Set measurable, realistic metrics: “People call me all the time with unreasonable thoughts of what AI can do… they’re thinking 500-fold.” (08:10)
  • Know your organization’s history and pain points, and focus improvement efforts on patient-centered care.
  • Emphasize continuous improvement in organizations running slim margins: “Healthcare organizations… running below dollar or zero or 2% EBITDA, that’s a hard thing to do.” (09:37)
• AI is a "game changer," with $394B in global spending projected for 2025.

3. Common Mistakes in AI Implementation

• Dirty Data: Organizations assume their data is clean—usually a false assumption.
  • Quote: “Use your data and your metrics and have them clean. I keep seeing people not… use benchmark of the industry. Use your own data.” (10:44)
• Vision Deficit: Many organizations lack a compelling, clear vision for AI’s role, leading to unfocused, IT-driven projects instead of business transformations.
  • Quote: “The vision points the way for your people… these are paradigm shifts.” (11:32)
• Low-hanging Fruit: HR, finance, and contact centers are ripe for rapid AI impact, but security is critical.
  • Quote: “If you’re not talking to people around security… you’re missing the boat. That is one of the most serious things we have.” (12:34)
  • Healthcare breaches average $4.4 million per incident; records are highly valued on the black market.

4. Trends & Playbook for AI Adoption (2026 Outlook)

• Ed and Will discuss the shift from AI concept to implementation, focusing on rapid wins before scaling.
• Will highlights:
  • Agency AI (tailored applications)
  • Domain-specific models
  • Robust AI security measures
  • The converging roles of payers and providers

5. AI Governance: Building Effective Committees

• Committees need cross-functional representation—not just IT.
• Five essential pillars: Fairness, Transparency, Privacy, Accountability, and Trust
  • Quote: “Good governance says… you need to make sure you’re looking at fairness… it should be inclusive, accessible, not discriminate, not amplify existing biases.” (14:59)
  • Transparency (“black box” problem) and clear accountability are touchy but non-negotiable, especially when patient harm is possible.
• On patient/family involvement:
  • Patient and family voices are increasingly included; families often provide fuller perspective on care episodes.

6. Security and Patient Safety: The Core Message

• Cybersecurity is non-optional in AI-enabled healthcare.
• Senior leaders must collaborate with CISOs to address the unique vulnerabilities and high-value stakes of health data.

7. The Human Side: Faith, Fears, and Philosophy on AI

• Will and Ed explore the philosophical and spiritual dimensions of AI, including the specter of job loss and "playing God" (resurrecting personas, etc.).
  • Quote: “You are a creator. You could create life... Very Star Trek.” (25:34)
• Will is working on another book exploring AI from a faith-based perspective.

8. How Will Uses AI Day-to-Day

• As a thought partner: generating feedback for students, brainstorming for writing, and even personal advertising via avatars.
• Quote: “I’m not beyond… writing out my ideas and saying, ‘What did I miss here?’ It’s a thought partner.” (23:54)
• He creates content for courses, consults for clients, and uses AI avatars for communication.

Notable Quotes & Memorable Moments

• On data and metrics:
  “Metrics… tell you where you’ve been, where you are today, and if you’re going to hit things. People tend to measure what makes them look good, not what makes them better.” (11:00, Will Conaway)

• On security and AI programs:
  “Healthcare is probably the weakest… they need to really lock that down.” (13:26, Will Conaway)

• On the existential risks of AI:
  “People are worried about an asteroid hitting the earth and that’s going to be the end of things. Maybe it could be AI, maybe that’s in how we do things.” (20:58, Will Conaway)

• On “playing God” with AI:
  “You are a creator. You could create life. You could create people who have already been here. Very Star Trek.” (25:34, Will Conaway)

• On AI as creative inspiration:
  “I have my own avatar … my wife seems to like him better … they actually asked me to bring the avatar over for Thanksgiving.” (24:03, Will Conaway)

Timestamps for Key Segments

| Timestamp | Topic/Quote | |------------|----------------------------------------------------------------------------------------| | 01:22 | Will’s career changes since last podcast | | 06:19 | Consulting vs. big corporate experiences | | 08:10 | “There will be AI officers at all healthcare organizations.” | | 10:44 | The importance of clean, organization-specific data and measurable metrics | | 11:32 | On vision and organizational transformation with AI | | 12:34 | Security as the most pressing AI concern in healthcare | | 14:59 | Building fair, accountable, and transparent AI governance committees | | 17:18 | Including patients and families in AI committees, survey limitations | | 20:45 | AI’s potential downsides—job loss, existential risk | | 23:18 | How Will uses AI as a day-to-day thought partner | | 24:03 | “I have my own avatar … my wife seems to like him better.” | | 25:34 | Discussing “playing God,” AI personas, faith, and philosophical implications | | 27:52 | Personal life—Will’s cat stories; conversation about pets, music, and guitars | | 31:49 | Session playing stories; favorite rock albums, musical influences | | 34:56 | Lightning round: decisions to change, bucket list, and travel anecdotes |

Tone and Language

• The tone is candid, energetic, and often humorous, with both host and guest openly sharing insights and personal anecdotes.
• Will is particularly direct when discussing healthcare’s failings (“healthcare is probably the weakest… with their security”), but also empathetic regarding leaders’ challenges.

Closing Thoughts

• The key message is clear: AI in healthcare without security is reckless. Data hygiene, measured goals, inclusive governance, and unflinching attention to security are the table stakes.
• Will’s humanistic, even philosophical, perspective on AI runs throughout, reminding listeners that these are not just technical challenges, but societal ones.

Resources & Further Reading

• Will's Book: “The AI Universe” (Published Oct 31, 2025, available on Amazon)
• Censinet — Risk and security resources
• For music enthusiasts, Led Zeppelin’s “Presence” and “Achilles Last Stand” get particular mention as all-time favorites.

End of Summary