Rita Dory: Beyond the Model, Why Experience Decides Enterprise AI Adoption (1:2)

Episode SummaryIn Part 2 of this deep dive into enterprise AI adoption, James Caton continues his conversation with Microsoft Principal UX Researcher Rita Dory. They unpack why simply deploying AI agents into an organization doesn't guarantee adoption and how enterprises can bridge the gap between technological capability and real human value. Rita breaks down the importance of pre-launch evaluation sets (evals), the shift from manual prompting to intent-driven agent orchestration, and why successful AI transformations must prioritize a human-first approach over flashy feature releases.Key Takeaways & TimestampsBreaking Through Enterprise ComplexityLaunching powerful agents doesn't guarantee adoption. Organizations face complex internal tools, risk tolerances, and cultural hurdles. To succeed, AI experiences must active-orchestrate or surface suggested prompts that meet users directly within their daily workflows.Enablement vs. Change ManagementBecause AI products evolve so rapidly, change management is non-negotiable. Successful rollouts rely on internal "AI champions," proactive enablement, and continuous product iteration to shorten the distance between trial and value.Designing the Path to Value & Pre-Launch EvalsRita explains the role of model evaluations (evals)—testing agents against real end-user expectations before deployment to ensure they reliably perform the tasks employees actually need.The Shift to Intent-Driven Agent OrchestrationThe burden of knowing which agent, plugin, or skill to invoke shouldn't fall on the user. The future of enterprise UX moves from manual copy-pasting across tools to system-level orchestration based on natural human intent.Partner & Enterprise Strategy: Test Before You DeployA major takeaway for technology partners and IT leaders: don't just "plug the machine in" and walk away. Engage employees early as internal testers to identify common work patterns, uncover friction, and iterate before a full rollout.Rapid Fire: Deliver the "Wow" (or "Huh?") MomentProving Payoff: Agents must deliver immediate, noticeable value over existing methods to retain users.Product vs. Expectations: Expectation-setting is part of the product experience.Pattern to Stop: Stop building tools just because they are technically possible; focus on transforming how work actually gets done.Advice for Enterprise Leaders: Human-First AIInstead of focusing solely on "human-in-the-loop," adopt a human-first mindset. Start small, target repetitive or low-meaning tasks, and design AI to collaborate alongside employees to augment their thinking.

Why do people try AI agents once and never return? In this episode, host James Caton sits down with Rita Dory, Principal UX Researcher at Microsoft, to explore why model capability is no longer the main bottleneck for enterprise AI adoption. Rita breaks down why the value payoff must happen almost instantly, how system orchestration is reshaping user experience, and why enterprise leaders must prioritize change management, employee testing, and human-first design over simple feature launches.Key TakeawaysIntroduction & The Role of UX in AIRita Dory introduces her work representing user pain points and needs across Microsoft’s AI experiences (Copilot, agents, plugins, and MCPs), framing why the core momentum in AI is shifting from raw model quality to usability and productivity.The Enterprise Adoption ProblemA look at how enterprise environments differ from consumer AI due to existing workflow complexity, exposing the "dirty little secret" of AI: high initial excitement rarely translates to long-term adoption without an immediate payoff.Managing User Expectations & Prompting ChallengesAddressing the friction of moving users from generalist LLMs to specialized agents, and how suggested prompts, clear capability descriptions, and targeted UX education can effectively narrow the trial-to-value gap.

Generate Now is rebranded to Diffusion AI - Why? Because the story isn't AI pilots anymore. It's how AI spreads across the business.So… welcome to Season 3. Exciting new episodes . . . First up: why do people try an agent once… and never come back?Why more agents may not lead to more intelligence- context matters. Then… what if your buyer is a machine? and not the people surfing the internet?

In this episode of Generate Now!, host James Caton sits down with Jason Baumgarten, a senior partner at the leadership advisory firm Spencer Stewart. As a consultant who works directly with C-suite executives, CEOs, and board members, Jason provides a unique perspective on how the world's top leaders are—and aren't—adapting to the AI revolution.The conversation explores his three-phase roadmap for leaders to move from AI novices to visionary evangelists. Jason explains why the biggest hurdles to AI adoption aren't technical, but cultural, and why every leader must personally get on the keyboard to understand the future of their business.The AI Adoption Gap: Why many executives are still using AI as a basic search engine rather than a transformative productivity tool.The "Steno Pad" Parallel: Comparing today's AI hesitancy to the 1980s transition when some executives resisted using PCs.Red Teaming Your Leadership: Using AI agents to create "digital twins" of a board of directors to predict questions and refine strategy.Data Swamps vs. Strategic Data: How to identify the "fumes" of your business—the unique data assets that actually create a competitive moat.Culture Over Code: Why AI initiatives fail when rigid corporate cultures penalize the "trial and error" required for learning.Start with low-stakes, high-impact tasks to become familiar with the technology:Evaluate Communications: Use AI to audit the tone and receptivity of your emails from various stakeholder perspectives.Audit Time Allocation: Analyze your calendar data to see if your schedule actually aligns with your strategic priorities.Automate a Workflow: Move beyond simple prompting to automating a daily task, such as competitive landscape monitoring.Move beyond the surface to understand the "how" and "why" of the technology:Find an AI Mentor: Partner with someone—even a junior employee or "AI native"—who uses these tools to transform their daily work.Master the Core Areas: Gain literacy in machine learning, model architecture, data engineering, and responsible AI governance.Transition from personal use to organizational leadership:Set the Ambition: Determine if your goal is 5% efficiency in customer service or a 50% shift in work product generated by agents.Manage the Change: Foster a "typing class" mentality where employees are given the time and safety to learn without penalty."If you put the lawyers in the room first to talk about governance, you're probably not going to get to a good end state view of what this can do because you'll spend all the time talking about what it shouldn't do." — Jason Baumgarten"This is not about delegating it to a team. This is about your personal journey of learning where the future is headed... get on the keyboard." — Jason BaumgartenJason Baumgarten is a leader at Spencer Stewart, specializing in CEO and board advisory services for companies ranging from high-growth startups to the Fortune 10. He is a leading voice on how AI is redefining the "what" and "how" of modern leadership.Unlock the C-suite AI roadmap with Spencer Stewart’s Jason Baumgarten. Learn how CEOs use "digital twins" and personal sandboxes to lead the AI revolution.

Genzeon CEO Ilanko Kumaresan, is transforming healthcare with AI. Industry estimates are that up to 11% of all claims are underpaid - James and Ilanko discuss REVA, the intelligent agent based on Microsoft copilot. We also discuss Patient Engagement, using Microsoft Nuance technology, and Health Intelligence, and the power of the Microsoft ecosystem.* Youtube @ https://youtu.be/ED-xa6vF1mU* Spotify @ https://open.spotify.com/show/43XcU8A1dsNfW3YGT8KXhp?si=7fc7caf95f764cfe* Apple @ https://podcasts.apple.com/us/podcast/generate-now/id1566458654Connect with* Ilanko @ https://www.linkedin.com/in/ilanko/* James @ https://www.linkedin.com/in/jmcaton/

Most organizations struggle to balance building their own AI infrastructure with leveraging reliable, scalable solutions. Oded Sagie and Perry Krug reveal how partnering with Pinecone transformed their approach—turning complex infrastructure challenges into seamless, "boringly reliable" systems. Discover how this shift unlocked faster innovation, lower operational overhead, and the peace of mind to focus on delivering real customer value.In this episode, you'll break down the core architectural innovations behind Pinecone’s platform, including its adaptive indexing and serverless design, which support workloads from low-latency high-throughput applications to massive multi-tenant environments. Oded shares real-world lessons on choosing build vs. buy—highlighting the long-term costs of ownership versus operational simplicity and scalability. Perry dives into how Pinecone's managed vector database facilitates rapid deployment on cloud platforms like Azure, helping teams focus on their core product, not infrastructure.If you're navigating the complexity of deploying AI at scale—especially in industries demanding high reliability and performance—this episode is your game plan. Perfect for data engineers, AI leaders, and CTOs ready to ditch operational headaches and embrace "boringly reliable" technology that accelerates innovation while minimizing risk. Tune in to discover how to build smarter, scale faster, and focus on what truly matters—your customers.Apple @ https://podcasts.apple.com/us/podcast/generate-now/id1566458654Spotify @ https://open.spotify.com/show/43XcU8A1dsNfW3YGT8KXhp?si=62e09c6df65b4dc9&nd=1&dlsi=e9e6a138e7064929Youtube @ https://www.youtube.com/@generatenowpodcast/featuredConnect with Oded @ https://www.linkedin.com/in/odedkal/Perry @ https://www.linkedin.com/in/perrykrug/James @ https://www.linkedin.com/in/jmcaton/

In this episode, James Caton (Microsoft) interviews Srinivasaa HG (Wipro) to discuss the advancements and challenges in Data and AI. They explore the important of Wipro being a finalist for Partner of the Year for Data and AI, the impact of integrated offerings like Foundry IQ and Work IQ, and Wipro's strategies for distinguishing itself across industries. Conversation topics include Wipro's venture investments, acquisitions, and the importance of data readiness for AI value realization.Connect with Srinivasaa at https://www.linkedin.com/in/srinivasaahg/?originalSubdomain=ukand with James at https://www.linkedin.com/in/jmcaton/

James Caton hosts Pavan Ganugapati, EMEA Leader at Accenture for the Microsoft Alliance, discusses the historic 20th consecutive Partner of the Year award, and the impact strategic partnership with Microsoft. The episode explores AI transformation, sovereign cloud, and leveraging sovereignty as a strategic advantage. Pavan emphasizes that sovereignty is not just about compliance but also a driver for value creation, with Microsoft technology supporting a full-stack sovereign architecture to adapt to evolving regulations.

In this episode, James Caton interviews Christoph Wollersheim from Egon Zehnder, discussing the impact of AI on organizational structures and leadership. They explore how AI is reshaping traditional pyramid structures into rectangles, the roles of AI builders and transformers, and the importance of cultural adaptation in AI transformations.Apple @ https://podcasts.apple.com/us/podcast/generate-now/id1566458654Spotify @ https://open.spotify.com/show/43XcU8A1dsNfW3YGT8KXhp?si=62e09c6df65b4dc9&nd=1&dlsi=e9e6a138e7064929Youtube @ https://www.youtube.com/@generatenowpodcast/featuredConnect with Christoph @ https://www.linkedin.com/in/christoph-wollersheim-a4b58744/Connect with James @ https://www.linkedin.com/in/jmcaton/

Most companies overlook a game-changing secret behind their AI success — but KPMG's Cherie Gartner reveals how strategically embedding Microsoft's AI tools has transformed their entire operation. Imagine leveraging AI not just for clients, but first for your own teams, creating a ripple effect of innovation and efficiency that competitors can’t match. This episode uncovers the real partnership behind KPMG’s industry-leading AI adoption, offering insights you won’t hear anywhere else.See how KPMG's "Client Zero" approach harnesses Microsoft 365 Copilot, Azure AI Foundry, and new toolkits like Agent 365 to embed AI deeply into audits, tax, advisory, and legal services. You’ll discover the frameworks and best practices that are setting new standards for enterprise AI. Learn how this internal "test kitchen" accelerates client-ready solutions — with real-world examples from Telstra and Vodafone demonstrating the tangible results of their AI journey.We break down the evolving role of platforms like KPMG Workbench, a unified, secure engine built on Azure that manages AI agents at scale. Cherie Gartner shares how this platform is revolutionizing professional services, enabling seamless AI deployment across industries and geographies. Plus, get a glimpse into the future of the Microsoft-KPMG alliance, where trust, transparency, and innovative co-creation are powering a new era of client transformation.Why does all this matter? Because in the race for AI dominance, the difference isn’t just technology — it’s strategic internal adoption, relentless experimentation, and a partner ecosystem that fosters rapid evolution. This episode is essential listening for leaders eager to embed AI deeply, scale securely, and stay ahead in a competitive landscape.Whether you're a C-suite executive, a tech innovator, or an AI enthusiast, you’ll come away with proven frameworks, inspiring examples, and a clear vision of how to unlock your organization’s full AI potential. The future belongs to those who act first — don’t miss your chance to learn how KPMG and Microsoft are shaping that future today.Connect with Cherie at https://www.linkedin.com/in/cherie-gartner/Connect with James at https://www.linkedin.com/in/jmcaton/Video at https://youtu.be/tMdNTnJIp1cOn Apple at https://podcasts.apple.com/us/podcast/generate-now/id1566458654