The AI Grok Moment: Why Most Companies Miss It | Stacey Mulcahy Microsoft Senior Director

The AI Grok Moment: Why Most Companies Miss It | Stacey Mulcahy Microsoft Senior Director

Why does AI adoption fail in business? In this episode of The AI Frontier Playbook, an AI podcast for enterprise leaders, I sit down with Stacey Mulcahy, Senior Director of the Microsoft Garage, to break down the real AI adoption challenges companies face and how Microsoft solves them with curiosity, hackathons, and hands-on AI skilling. Stacey leads the team behind the Microsoft Global Hackathon and the Skill Up AI program, engaging over 70,000 employees in grassroots AI learning and employee enablement across the company. We go deep on why formal learning paths are not enough, why curiosity and exploration drive real behavior change, and what Stacey calls the grok moment: the point where AI stops being a search engine and starts changing how you work. She also shares why leadership modeling makes or breaks adoption, how she runs learning in the open by streaming her own experiments, and why the GitHub Copilot CLI has completely changed her daily workflow. You'll learn: 1. Why AI adoption gets stuck even when the tools and programs are good 2. How to create the grok moment that turns skeptics into adopters 3. Why leadership modeling matters more than any champion program 4. What community skilling looks like and why learning with others beats learning alone 5. How creativity and play outperform productivity use cases as an entry point to AI 6. Why durable skills like adaptability, delegation, and taste matter more than tool knowledge 7. How Stacey uses the GitHub Copilot CLI, custom agents, and MCP integrations to run her day 8. What the future of work looks like when everyone manages a team of agents Whether you are a leader driving AI transformation in your organization or an individual contributor trying to build AI literacy on your team, this episode gives you a practical playbook for making adoption actually stick. 📌 Resources & Links Stacey Mulcahy on LinkedIn: https://www.linkedin.com/in/staceymakes/ [https://www.linkedin.com/in/staceymakes/] 📬 Enjoyed this episode? Subscribe to Mastering AI for Productivity: https://samuelboulangerai.substack.com/ [https://samuelboulangerai.substack.com/] Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ [https://www.linkedin.com/in/samuelboulanger/] Visit my website: https://samuelboulanger.com [https://samuelboulanger.com] #AI #FutureOfWork #AIAdoption #Microsoft #AILiteracy

Beyond the Prompt: Finding Authenticity in AI Work | Jack Rowbotham Microsoft PMM

How to use AI for content creation without losing your voice. Jack Rowbotham earned 7.5 million LinkedIn impressions in a year at Microsoft, and in this episode of The AI Frontier Playbook he breaks down his exact AI content workflow. The real skill in the AI era is not creating more. It is having the judgment to ignore almost all of it. I sit down with Jack Rowbotham, Senior Product Marketing Manager for Copilot Studio at Microsoft, who built a personal brand of over 90,000 followers while working full-time and was named a Microsoft Frontier Trailblazer for FY26. We unpack the line between using AI tools to amplify your voice and letting them replace your thinking. You'll learn: * How to use AI tools for content creation without sounding like a robot or losing your voice * Why leading with your own perspective before touching AI is what protects authenticity * How Jack runs AI evals on his own LinkedIn posts to keep AI-generated content accurate * What separates using AI to amplify your voice from outsourcing your thinking * How the agentic AI agent boss model reshapes work for marketers, creators, and knowledge workers * Why prioritization and judgment are the new edge once AI removes the execution barrier * What a personal brand agent built in Microsoft Copilot Studio can actually do for you * How to turn event photos, whiteboards, and slides into usable notes with AI in minutes 📌 Resources & Links Jack Rowbotham on LinkedIn: https://www.linkedin.com/in/jackrowbotham/ [https://www.linkedin.com/in/jackrowbotham/] Jack's LinkedIn Learning course, How to be an Agent Boss: https://www.linkedin.com/learning/how-to-be-an-agent-boss-leading-ai-agents-at-work [https://www.linkedin.com/learning/how-to-be-an-agent-boss-leading-ai-agents-at-work] Enjoyed this episode? Subscribe to the newsletter: https://samuelboulangerai.substack.com/ [https://samuelboulangerai.substack.com/] Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ [https://www.linkedin.com/in/samuelboulanger/] Visit my website: https://frontierplaybook.ai [https://frontierplaybook.ai]

The Hard Truth About Your AI Strategy | Pam Maynard, Microsoft Chief Transformation AI Officer

AI strategy stuck in pilot purgatory? In this episode of The AI Frontier Playbook, I sit down with Pam Maynard, Microsoft's first ever Chief AI Transformation Officer, on artificial intelligence adoption, organizational change, leadership, automation, and the future of work. Pam led Avanade as CEO across 60,000 employees before taking on this pioneering role at Microsoft. We unpack the four-layer metrics framework that prevents pilot purgatory, the Manulife $1 billion AI value example, why middle managers decide whether AI adoption sticks, and the McKinsey research showing companies with AI led from the top perform 3x higher than those without. A big thank you to ITI for sponsoring this episode. ITI is a proudly Canadian company that has spent over 30 years helping organizations bring their IT projects to life by making technology accessible, meaningful, and human. Whether you are a C-suite leader trying to scale AI across your enterprise or a manager closing the adoption gap on the ground, this episode delivers a practical framework you can put into action this quarter. Learn more about ITI: https://iti.ca/en/microsoft-365-copilot/ [https://iti.ca/en/microsoft-365-copilot/] 📌 Resources & Links Pam Maynard on LinkedIn: https://www.linkedin.com/in/pam-maynard/ [https://www.linkedin.com/in/pam-maynard/] ITI Microsoft 365 Copilot solutions: https://iti.ca/en/microsoft-365-copilot/ [https://iti.ca/en/microsoft-365-copilot/] Episode with Meaghan Platt from ITI on AI, accessibility and inclusion: https://www.youtube.com/watch?v=v5ydmRrYXnQ [https://www.youtube.com/watch?v=v5ydmRrYXnQ] 📬 Enjoyed this episode? Subscribe to the AI Frontier Playbook Newsletter: https://samuelboulangerai.substack.com/ [https://samuelboulangerai.substack.com/] Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ [https://www.linkedin.com/in/samuelboulanger/] Visit my website: https://frontierplaybook.ai [https://frontierplaybook.ai] #ArtificialIntelligence #FutureOfWork #Leadership #EnterpriseAI #DigitalTransformation

The Shift Nobody's Talking About: AI and Human Independence | Meaghan Platt, ITI

The AI Frontier Playbook - Meaghan Platt Episode Description Microsoft Copilot, AI accessibility, and dignity: what most GenAI conversations completely skip. Meaghan Platt from ITI joins The AI Frontier Playbook to explore what real inclusion looks like in the age of AI. Most people talk about AI and productivity. Meaghan Platt talks about AI and dignity. As a Copilot Sales and Adoption Specialist at ITI and a mom navigating the daily reality of raising a daughter with PCDH19, a condition that causes epilepsy, seizures, cognitive delays, and significant communication challenges, Meaghan sees GenAI through a lens most enterprise conversations never touch. We go deep on what most AI conversations completely skip: dignity. The moment a child realizes the world was not built for how she communicates. The confidence that erodes every time a tool fails her. And why Copilot, used intentionally, starts to flip that. We also talk about language barriers, neurodivergence, burnout, and what it actually means to lead AI adoption with people at the center. You'll learn: 1. Why dignity is the missing word in every accessibility and AI conversation 2. How GenAI removes friction that most of us never even notice but that stops others completely 3. What it looks like to build a custom voice model so a child can use speech-to-text in her own pronunciation 4. Why AI adoption fails when leaders treat it like a software rollout instead of a people strategy 5. How a trilingual team with no shared language built real collaboration using Microsoft Copilot 6. When AI shifts from adapting people to technology, to technology adapting to people 7. What parents and teachers can do right now to prepare kids for an AI-native world Whether you lead AI adoption at an enterprise level or you are a parent, educator, or anyone who navigates the world a little differently, this episode will change how you think about what inclusion actually means in the age of AI. Learn more about ITI: https://iti.ca/en/microsoft-365-copilot/ [https://iti.ca/en/microsoft-365-copilot/] 📌 Resources and Links Meaghan Platt on LinkedIn: https://www.linkedin.com/in/meaghanplatt/ [https://www.linkedin.com/in/meaghanplatt/] 📬 Enjoyed this episode? Subscribe to the AI Frontier Playbook newsletter: https://samuelboulangerai.substack.com/ [https://samuelboulangerai.substack.com/] Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ [https://www.linkedin.com/in/samuelboulanger/] Visit my website: https://frontierplaybook.ai [https://frontierplaybook.ai] #MicrosoftCopilot #AIAccessibility #FutureOfWork #ArtificialIntelligence #AIAdoption

Hands-On or Left behind : The new reality of AI fluency | Steve Gustavson, Microsoft CVP

What if the biggest obstacle to AI in your business isn't the technology, but the organizational structures built for humans to be the bottleneck? In this episode of the AI Frontier Playbook, I sit down with Steve Gustavson, CVP of Design and Research at Microsoft, leading the Business Apps and Agents division with a 350-person team spanning design, research, and content. We explore how organizational transformation, AI agents, and user experience converge to reshape how companies build and run their business processes. Steve brings 20+ years of experience from Adobe, ServiceNow, and now Microsoft, where he leads the design thinking behind Copilot Studio, Agent 365, and the broader agentic ecosystem. What makes this conversation different is how concrete it gets. We go deep on why rigid org charts become liabilities when AI teammates start handling workflows at scale, what it actually takes to evaluate agents beyond technical accuracy, and why generative UX is forcing a complete rethink of how business applications get built. If you want to understand where the future of work is heading across agent ecosystems, this is the conversation. What You'll Learn 1. Why organizational structures designed for human decision-making become liabilities in an AI-enabled workplace. 2. How generative agents are shifting Dynamics 365 and business applications from rigid tools to flexible, adaptive systems. 3. What it means to evaluate AI systems beyond technical accuracy to include human qualities like empathy and voice authenticity. 4. How the future of work requires flatter organizations with fluid project-based team assignments rather than static org charts. 5. Why user researchers and design leaders are becoming the primary voices defining what makes AI assistance trustworthy and effective. 6. What the ethical and transparency challenges are when deploying AI agents in organizations alongside human teams. 7. How to balance using cutting-edge AI tools daily while maintaining security and ethical boundaries around sensitive data. 8. Why the next generation of agents will be customizable by end users, PMs, and other non-engineers using plain-language markdown specifications. Whether you are an enterprise leader grappling with legacy systems or a designer thinking about human-centered AI, this episode challenges conventional thinking about how technology and people will work together. Sponsored by Talan Learn more about Talan's AI Commerce Agent for B2B Buyers: https://bit.ly/4kZRDTj [https://bit.ly/4kZRDTj] Resources & Links * Steve Gustavson on LinkedIn: https://www.linkedin.com/in/stevegustavson/ [https://www.linkedin.com/in/stevegustavson/] * Microsoft Agent 365: https://www.microsoft.com/en-us/microsoft-agent-365 [https://www.microsoft.com/en-us/microsoft-agent-365] Enjoyed this episode? * Subscribe to the AI Frontier Playbook Newsletter: https://samuelboulangerai.substack.com/ [https://samuelboulangerai.substack.com/] * Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ [https://www.linkedin.com/in/samuelboulanger/] * Visit my website: https://samuelboulanger.com [https://samuelboulanger.com]