The AI Frontier Playbook

Samuel Boulanger

AI Frontier Playbook exists because the real conversations about enterprise AI deserve to be heard. The guests here are the practitioners, researchers, and executives actually making decisions inside organizations, not summarizing trends from the sidelines. Every episode is a front-row seat to how AI is reshaping work, leadership, and business strategy in real time. Whether you are leading an AI initiative, advising your organization, or just trying to cut through the noise, this is your space to think clearly, lead confidently, and stay ahead.

  1. 15h ago

    The REAL Reason AI Gets the Attention But Trust Gets the Purchase Order

    AI gets the attention, but trust gets the PO. The coolest demo in the world means nothing if an enterprise does not believe you are safe, compliant, and serious about data. In this episode of The AI Frontier Playbook, I sit down with Tom Davis, Partner at Microsoft for Startups, who founded Solair in 2011, built it on Azure, and sold it to Microsoft in 2016. Tom has spent the last several years helping thousands of founders turn AI and cloud innovation into real business outcomes, and he brings a rare perspective: he has built and sold a company, and now he sits on the other side helping the next generation of startups scale. We talk about why speed to a working product stopped being the advantage it used to be, why plugging into something like Microsoft Copilot can matter more than the product itself, when a founder should build a tool in house instead of buying one off the shelf, and the one mistake that quietly kills startups that looked incredible in the demo. Tom also shares how his own son is building a two person startup powered by AI agents, and why he believes trust, not technology, is what closes enterprise deals. You'll learn: Why time to MVP has collapsed and what that means for founders competing on speed aloneHow to decide whether to build your own tool or buy something off the shelfWhy distribution through platforms like Microsoft Copilot can matter as much as the product itselfWhat enterprises actually check before they trust a startup with their dataWhy technical founders often overbuild and lose sight of what customers actually wantHow AI agents are changing the size and structure of a modern startup teamWhat founders should build into their architecture from day one to avoid costly rework laterHow to test an idea with a proof of concept before committing months of runway to itWhether you are a founder building your first AI powered product or an operator trying to understand how enterprise buying decisions really get made, this episode gives you a practical framework for the next 90 days. Quick thanks to our sponsor OS4 Techno Services, a Quebec based IT firm helping organizations navigate infrastructure, cybersecurity, cloud, and AI with strong Microsoft expertise. Learn more about OS4 Techno Services: https://www.os4techno.com/ 📌 Resources & Links Tom Davis on LinkedIn: https://www.linkedin.com/in/tom-davis-startups/ 📬 Enjoyed this episode? Subscribe to the AI Frontier Playbook: https://theaifrontierplaybook.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit the website: https://frontierplaybook.ai

    The REAL Reason AI Gets the Attention But Trust Gets the Purchase Order

  2. Aug 5

    MS Copilot Studio CVP: Why Most AI Projects Are Solving the Wrong Problem From Day One

    AI projects stall when nobody names the real business bottlenecks first. In this episode of The AI Frontier Playbook, I sit down with Ryan Cunningham, Microsoft CVP of Copilot Studio and Power Platform, to talk about why, and what actually separates a good AI use case from a wasted one. Ryan leads agents, apps, and automation across the entire Microsoft stack, and in this conversation we get into why most AI projects stall before they even start, whether apps and low code still matter now that you can generate almost anything from a chat window, how to actually choose between pro code, low code, and vibe coding, and how Copilot Studio's credit based pricing is reshaping the way teams think about cost. Ryan shares the real story behind a customer who turned a 36 hour quote generation process into a 2 hour one, and why that is the model for a good AI use case. Quick thanks to Kezber, a Microsoft partner, for sponsoring this episode. You'll learn: Why most AI projects fail because nobody defined the outcome before picking a toolHow to turn a vague business problem into a measurable AI use case with a clear ROIWhy apps and structured interfaces are not going away even as chat based AI expandsWhat actually happens to custom software and SaaS as vibe coding becomes mainstreamHow to decide between pro code, low code, and vibe coding for a given problemWhy credit based consumption pricing is replacing flat per user licensing for AIHow Power Apps turning into MCP servers changes what agents can do with your dataWhat governance and oversight look like once agents start operating with less human involvementWhether you are a business leader trying to justify your first AI investment or a developer deciding which tool fits the job in front of you, this episode gives you a practical framework for making that call. Thanks to Kezber for sponsoring this episode. Learn more about Kezber: https://kezber.com/ 📌 Resources & Links Ryan Cunningham on LinkedIn: https://www.linkedin.com/in/rycu 📬 Enjoyed this episode? Subscribe to Mastering AI for Productivity: https://samuelboulangerai.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit my website: https://frontierplaybook.ai

    MS Copilot Studio CVP: Why Most AI Projects Are Solving the Wrong Problem From Day One

  3. Jul 8

    AI Expert: Stop Automating Your Entire Department — Do This Instead

    Learn how to automate sales and back-office processes with AI for business, without overwhelming your team. In this episode of The AI Frontier Playbook, I sit down with Eric Murray, Director of Innovation at Kezber, a Microsoft partner in Quebec, to break down AI implementation and business workflow automation with Microsoft Copilot, Power Platform, and Copilot Studio. Many companies fail when they try to automate an entire department at once. Eric's approach starts instead with repetitive tasks that are low risk for your business, owned by a champion who knows every exception. We dig into how to identify the right processes to automate first, why most AI projects stall before delivering anything, and what it really takes to move from a working prototype to a secure production system. Eric brings a practitioner's view shaped by real client deployments. We walk through a full accounts payable automation scenario, from the invoice landing in a shared mailbox to the data reaching the ERP, and break down which steps should be plain deterministic automation with Power Automate and which ones genuinely need AI reasoning in the loop. We also cover human-in-the-loop design, exception handling, data residency under Quebec's Law 25, governance with tools like Microsoft Purview and Agent 365, and why a single model swap took one of his AP solutions from 50 dollars a month to 5 dollars a month. You'll learn: Why deploying Copilot licenses is the starting line, not the finish lineHow to spot a strong first automation candidate: repetitive, low risk, and owned by a championWhat red flags signal a process is not ready to automateHow to slice a process like accounts payable into small chunks that deliver value in weeks, not monthsWhen to use straight automation versus AI reasoning inside the same workflowHow to design human-in-the-loop escalation so people trust the system instead of working around itWhy security, access control, and data residency are the real work behind any AI agentHow to measure ROI after launch and diagnose whether the problem is the tool or adoptionWhether you are a business leader wondering where to start with AI automation or a Power Platform and Copilot Studio builder taking prototypes into production, this episode gives you a concrete framework for picking the right first project and scaling it without losing trust. 📌 Resources & Links Eric Murray on LinkedIn: linkedin.com/in/eric-murray-ing-18851a6Kezber: https://kezber.com/en/ 📬 Enjoyed this episode? Subscribe to The AI Frontier Playbook Newsletter: samuelboulangerai.substack.comConnect with me on LinkedIn: linkedin.com/in/samuelboulangerVisit my website: samuelboulanger.com #AI #FutureOfWork #MicrosoftCopilot #PowerPlatform #Automation

    AI Expert: Stop Automating Your Entire Department — Do This Instead

  4. Jun 10

    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: Why AI adoption gets stuck even when the tools and programs are good How to create the grok moment that turns skeptics into adopters Why leadership modeling matters more than any champion program What community skilling looks like and why learning with others beats learning alone How creativity and play outperform productivity use cases as an entry point to AI Why durable skills like adaptability, delegation, and taste matter more than tool knowledge How Stacey uses the GitHub Copilot CLI, custom agents, and MCP integrations to run her day What the future of work looks like when everyone manages a team of agentsWhether 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/ 📬 Enjoyed this episode? Subscribe to Mastering AI for Productivity: https://samuelboulangerai.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit my website: https://samuelboulanger.com #AI #FutureOfWork #AIAdoption #Microsoft #AILiteracy

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

  5. May 28

    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 voiceWhy leading with your own perspective before touching AI is what protects authenticityHow Jack runs AI evals on his own LinkedIn posts to keep AI-generated content accurateWhat separates using AI to amplify your voice from outsourcing your thinkingHow the agentic AI agent boss model reshapes work for marketers, creators, and knowledge workersWhy prioritization and judgment are the new edge once AI removes the execution barrierWhat a personal brand agent built in Microsoft Copilot Studio can actually do for youHow to turn event photos, whiteboards, and slides into usable notes with AI in minutes📌 Resources & LinksJack Rowbotham on LinkedIn: 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 Enjoyed this episode? Subscribe to the newsletter: https://samuelboulangerai.substack.com/Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/Visit my website: https://frontierplaybook.ai

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

  6. May 6

    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/ 📌 Resources & Links Pam Maynard on LinkedIn: https://www.linkedin.com/in/pam-maynard/ ITI Microsoft 365 Copilot solutions: 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 📬 Enjoyed this episode? Subscribe to the AI Frontier Playbook Newsletter: https://samuelboulangerai.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit my website: https://frontierplaybook.ai #ArtificialIntelligence #FutureOfWork #Leadership #EnterpriseAI #DigitalTransformation

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

  7. Apr 23

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

    The AI Frontier Playbook - Meaghan Platt Episode DescriptionMicrosoft 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: Why dignity is the missing word in every accessibility and AI conversation How GenAI removes friction that most of us never even notice but that stops others completely What it looks like to build a custom voice model so a child can use speech-to-text in her own pronunciation Why AI adoption fails when leaders treat it like a software rollout instead of a people strategy How a trilingual team with no shared language built real collaboration using Microsoft Copilot When AI shifts from adapting people to technology, to technology adapting to people What parents and teachers can do right now to prepare kids for an AI-native worldWhether 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/ 📌 Resources and Links Meaghan Platt on LinkedIn: https://www.linkedin.com/in/meaghanplatt/ 📬 Enjoyed this episode? Subscribe to the AI Frontier Playbook newsletter: https://samuelboulangerai.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit my website: https://frontierplaybook.ai #MicrosoftCopilot #AIAccessibility #FutureOfWork #ArtificialIntelligence #AIAdoption

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

  8. Apr 8

    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 Why organizational structures designed for human decision-making become liabilities in an AI-enabled workplace. How generative agents are shifting Dynamics 365 and business applications from rigid tools to flexible, adaptive systems. What it means to evaluate AI systems beyond technical accuracy to include human qualities like empathy and voice authenticity. How the future of work requires flatter organizations with fluid project-based team assignments rather than static org charts. Why user researchers and design leaders are becoming the primary voices defining what makes AI assistance trustworthy and effective. What the ethical and transparency challenges are when deploying AI agents in organizations alongside human teams. How to balance using cutting-edge AI tools daily while maintaining security and ethical boundaries around sensitive data. 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 Resources & Links Steve Gustavson on LinkedIn: https://www.linkedin.com/in/stevegustavson/ Microsoft Agent 365: https://www.microsoft.com/en-us/microsoft-agent-365Enjoyed this episode? Subscribe to the AI Frontier Playbook Newsletter: https://samuelboulangerai.substack.com/ Connect with me on LinkedIn: https://www.linkedin.com/in/samuelboulanger/ Visit my website: https://samuelboulanger.com

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

AI Frontier Playbook exists because the real conversations about enterprise AI deserve to be heard. The guests here are the practitioners, researchers, and executives actually making decisions inside organizations, not summarizing trends from the sidelines. Every episode is a front-row seat to how AI is reshaping work, leadership, and business strategy in real time. Whether you are leading an AI initiative, advising your organization, or just trying to cut through the noise, this is your space to think clearly, lead confidently, and stay ahead.

Information

  • Creator
    Samuel Boulanger
  • Years Active
    2024 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Samuel Boulanger
  • Show Website
    The AI Frontier Playbook