#shifthappens in the Digital Workplace Podcast

Hosted by Dux Raymond Sy

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Episodes

138

Latest episode

Oct 2026

Language

EN-US

About the show

#shifthappens is the podcast for leaders navigating the frontier of AI, security, and digital trust in the modern workplace. Hosted by Dux Raymond Sy, Chief Transformation Officer at AvePoint, each episode goes beyond the buzzwords to explore the real strategies, hard decisions, and lessons learned at the frontier of business transformation. Conversations span artificial intelligence, digital transformation, the future of work, information security, leadership, and real-world implementation — with guests who are actively shaping how enterprises adopt AI responsibly, defend against modern threats, and build trust at scale. Built for CEOs and business leaders, CISOs and security practitioners, technology decision makers, digital transformation leaders, and entrepreneurs. Ranked in the top 10% of podcasts globally by Listen Score, with 100% year-over-year listener growth and an audience spanning the Americas, EMEA, and Asia & Oceania. New episodes drop regularly. Subscribe and follow #shifthappens wherever you get your podcasts.

Listen to episodes

60 recent

October 22, 2026Episode 13943 min

Ep. 139: AI Won’t Fix What’s Already Broken: Rethinking the Operating Model for Scale

Most enterprises are applying AI to ways of working that were never designed for it. In this episode of #shifthappens, Giovanni Piccirilli, Founder of Pepper Technology and former CTO of RTL Nederland, explains why AI cannot compensate for a broken operating model — and what leaders need to fix before AI can scale. Giovanni walks through what holds organizations back as AI moves from experimentation into day-to-day operations. He breaks down why treating AI as an automation layer increases complexity, how more autonomous systems change the decisions leaders need to make, and what it takes to move from isolated pilots to repeatable results. The conversation focuses on the work behind scaling AI: aligning strategy, rethinking how processes are designed, and building an operating model that supports how AI actually works.

October 8, 2026Episode 13834 min

Ep. 138: Why Most Enterprise AI Training Fails — and How Learning Design Turns Use Into Real Adoption

Most organizations measure AI adoption by who attended training and how many licenses got activated. That's not adoption — that's logistics. In this episode of #shifthappens, Dr. Samson Tan, Chief AI Officer at the Institute for Adult Learning (IAL) Singapore, explains why most enterprise AI upskilling fails: leaders confuse attendance with adoption, and access with application. He argues that learning design, not tools or workshops, is the engine that moves AI from abstract concept to daily practice. Drawing from IAL's work with curriculum designers and adult educators, Samson breaks down how learning design embeds AI into real workflows, why "Tech Thursdays" outperform generic courses, and how leaders can replace fear with confidence through psychological safety, innovation sandboxes, and protected professional judgment. He also reframes what enterprises should measure to know adoption is real: not prompts and logins, but reasoning, iteration, and assisted performance.

September 24, 2026Episode 13742 min

Ep. 137: Automation and Augmentation Are Not the Same Strategy

Most AI strategies treat every initiative as the same kind of project. Ori Marom, program manager innovation at the Port of Rotterdam, argues that’s where strategy breaks down. In this episode of #shifthappens, Ori shares what three decades of operational AI looks like at Europe’s largest port, where over 30,000 vessels pass through each year, and failure affects critical national infrastructure. He makes the case that automation and augmentation are not interchangeable; each demands a different approach to workforce engagement, risk, and stakeholder buy-in. He also explains how connected data and digital twin platforms are enabling real-time, multi-agent orchestration, and why starting with purpose – not enthusiasm – is what separates lasting impact from expensive experimentation.

September 10, 2026Episode 13629 min

Ep. 136: When the Patient Owns the Agent: The Case for Individual-First AI Governance

Healthcare organizations say patient data is secure. Paul Swider, CEO and Chief AI Officer of RealActivity, argues that security and patient control are not the same thing. In this episode, he explains why centralized healthcare systems remain attractive ransomware targets, why patients often have limited visibility into how their data is used, and why the next phase of AI governance starts when the patient owns the agent. He also explores why the 21st Century Cures Act has already redrawn the perimeter, and what that means for AI hasn't fully landed in most governance conversations yet. Paul walks through how he granted an AI agent access to his medical record, why a single-patient agent has a smaller attack surface than a centralized electronic health record (EHR) system, and why healthcare leaders should evaluate AI against today's care outcomes rather than on the expectation of perfection.

August 27, 2026Episode 13527 min

Ep. 135: Agents, Governance, and the Discipline Behind AI That Actually Ships

Moving AI into production requires clarity on what AI is allowed to do and who is accountable for the outcome. In Part 2 of our two-part series, Luise Freese returns to walk through how organizations can design AI agents with clear boundaries, embed governance directly into delivery, and build the operating model needed to scale. She also shares her 90-day approach for turning an early-stage proof-of-concept into a repeatable, production-ready capability.

August 20, 2026Episode 13429 min

Ep. 134: Escaping Proof-of-Concept Prison: The Path from AI Pilot to Production

Organizations aren't short on AI enthusiasm — they're short on the ability to turn that enthusiasm into anything that actually runs. In Part 1 of our two-part series, Luise Freese, developer, consultant, and author breaks down why so many AI initiatives stall after the demo. She covers how to evaluate use cases with intent, why data readiness shapes everything AI can deliver, and what leaders should be asking to turn early momentum into lasting operational capability.

August 6, 2026Episode 13335 min

Ep. 133: What Is Category Design? How to Stand Out in a Crowded Market

Most companies think they have a messaging problem. In reality, they haven't defined who they are and their place in the market. In this episode of #shifthappens, Mike Damphousse, co-founder of Category Design Advisors and co-author of The Category Creation Formula, breaks down why standing out goes beyond being better than the competition. When you own the category, the market doesn't compare you to others — it chooses you on your terms. He explains how category design moves beyond marketing into company-wide strategy, why AI alone won't differentiate your business, and how the most successful companies shape how the market thinks before competitors can.

July 16, 2026Episode 13227 min

Ep. 132: AI Attacks Move in Minutes. Can Your Response Keep Up?

GenAI has industrialized social engineering. The human entry point is now automated, personalized, and scalable, and that changes how security leaders must defend. In this #shifthappens episode, Andrew Carr, Managing Director and Global Head of Threat Management for Booz Allen Hamilton's Commercial Incident Response team, joins AvePoint Chief Brand Officer Dux Raymond Sy and AvePoint Chief Risk, Privacy, and Information Security Officer Dana Simberkoff to unpack what's genuinely new about AI-driven attacks — and what organizations need to do about it. Drawing on frontline incident response across healthcare, financial services, manufacturing, and more, Andrew explains why attackers no longer need to compromise systems to extract millions, why built-in trust is now a liability, and why the fundamentals that have been ignored for too long – zero trust, data classification, least privilege – are exactly what this moment demands. He also breaks down how AI should be used in defense: not as autopilot, but as a human-augmented layer that triages, prioritizes, and buys decision-makers the time they no longer have.

July 2, 2026Episode 13139 min

Ep. 131: AI Is a Tool, Not a Search Engine

Most organizations gave everyone access to AI — and then watched them use it as a search engine. In this episode of #shifthappens, Marco Galimberti, CEO of Venchi Asia Pacific, explains why the real shift is AI use. Drawing from his experience leading a global premium brand across manufacturing, retail, and consumer engagement, Marco breaks down where AI creates immediate value (process automation, pattern recognition, shift optimization) and where the longer-term opportunity lies: transforming how brands understand and respond to what customers actually want. The conversation covers why data overabundance is more dangerous than data scarcity, why AI currently works better in the hands of experienced professionals who can verify its outputs, why education systems need to prioritize fundamentals over tools, and why leaders who use AI openly and normalize it across their teams are the ones driving real adoption.

June 18, 2026Episode 13027 min

Ep. 130: AI Readiness Starts Before AI: Identity, Endpoints, and Security First

AI readiness doesn't start with AI; it starts with the infrastructure most organizations overlook. In this episode of #shifthappens, Lior Bela, Business Director for Microsoft Intune, breaks down what it actually takes to prepare managed service providers (MSPs) and their customers for AI adoption, and why skipping the foundation creates more risk than it solves. Lior explains why cloud-native environments are the prerequisite, not the afterthought, for AI success — comparing the journey to paving a road before driving a car on it. He discusses how legacy tooling and on-prem comfort create a growth ceiling, why AI agents should be governed with the same guardrails as employees, and what happens when organizations fail to offer sanctioned AI tools: shadow AI fills the gap. The conversation also covers the three-tier path to AI maturity, from baseline alignment to assisted automation to full autonomy, and why building trust in AI follows the same arc as trusting a driverless car. Lior closes with a practical 30-day action plan any MSP can follow: learn, experiment in a sandbox, and deploy on low-risk, high-impact processes.