Why 70% of Digital Transformations Still Fail (And How AI Can Help)

Digital transformation has been a business buzzword for decades—but despite years of experience, most enterprise transformation initiatives still fail. Why? And can AI finally help organizations break the cycle?In this episode, Galen Low sits down with Rick Catalano, founder and CEO of AMIGO and author of The AI Project Manager, to unpack why large-scale transformation projects continue to struggle, what AI can (and can't) solve, and why the future of project leadership is less about replacing people and more about helping them make better decisions.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Rick on LinkedInVisit AMIGOCheck out Rick’s book – “The AI Project Manager: The Framework for Successful AI-Enabled Enterprise Transformation”

Project management in construction is often dismissed as traditional, but when it comes to AI and data, the industry may be further ahead than many people realize. In this conversation, James Garner, Head of AI and Data at Gleeds and founder of Project Flux, shares why construction is becoming a proving ground for AI adoption—and what project professionals in every industry can learn from it.From overcoming resistance to new technology to navigating career shifts and building AI literacy, James offers a refreshingly balanced perspective on the future of project management. Whether you're leading digital initiatives or considering a career pivot, this episode explores why judgment, curiosity, and creativity will become even more valuable in the age of AI.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with James on LinkedInVisit Gleeds and Project Flux

AI is starting to reshape project management—but its biggest impact isn't replacing project managers. It's removing the operational overhead that keeps them buried in admin so they can focus on the work that actually moves projects and client relationships forward.In this conversation, Tim Fisher sits down with Bernarda Vrbat from Productive to explore how AI is evolving beyond chatbots into skills and autonomous agents. They discuss where AI is already delivering practical value for professional services businesses, what teams are (and aren't) comfortable delegating to AI, and why the future of project management is less about doing repetitive work and more about making high-value decisions.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Bernarda on LinkedInVisit Productive

Some people see AI as a threat to creativity. Others see it as the next evolution of the creative toolkit. In this episode, Galen Low sits down with Tom Brown and Eric Oldrin, co-founders of Original Model, an AI-native creative agency, to explore what happens when creative thinking—not AI—stays at the center of the process. Together, they unpack how agencies can embrace AI without sacrificing originality, storytelling, or quality.Broadcast live from the Cannes Lions International Festival of Creativity, this conversation explores why so much AI-generated work falls flat, how thoughtful agencies are integrating AI across strategy, ideation, and production, and why the future of creative work may depend less on mastering tools and more on strengthening human judgment.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Eric and Tom on LinkedInVisit Original Model Creative Agency

Remote and hybrid work is no longer a temporary adjustment—it’s how many project teams operate every day. But while we've become better at working asynchronously and using AI to boost productivity, it's worth asking whether we've unintentionally lost some of the human elements that make collaboration truly effective.In this conversation, Galen Low sits down with Karen Chong to explore what remote teams are missing, why intentional collaboration matters more than ever, and how project leaders can recreate the trust, creativity, and learning that once happened naturally in shared office spaces. They also dive into AI's growing role in team collaboration—and why efficiency alone isn't enough to build high-performing teams.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Karen on LinkedInVisit Abracademy & The Mind Blend podcast

Project management often gets framed as a career path, but increasingly it's becoming a skill that professionals across every function need to develop. As organizations navigate AI-driven transformation, cross-functional initiatives, and constant change, more people are finding themselves responsible for leading projects—whether or not "project manager" appears in their job title.Galen Low sits down with Stuart Taylor, founder of Influential PMO and author of Becoming The Project Manager, to explore what separates effective project leaders from accidental coordinators. They unpack common misconceptions about project management, the leadership and communication skills that matter most when plans don't go as expected, and why learning to lead projects may become a defining career milestone for professionals at every level.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Stuart on LinkedIn and YouTubeVisit Influential PMOCheck out Stuart’s book: “Becoming The Project Manager”

AI is forcing every function to reevaluate what creates value—and project management is no exception. In this conversation, Alla Tarasenko, Principal Technical Program Manager at Gusto, shares why building AI agents isn't about replacing program managers. It's about reclaiming capacity for the work that matters most: coaching teams, improving processes, and driving cross-functional alignment.Alla walks through the practical realities of building an AI-powered intake and triage system that serves more than 1,000 internal stakeholders, the unexpected challenges that emerge after the first successful prompt, and why change management may become one of the most important leadership skills in the AI era. More importantly, she offers a thoughtful perspective on how AI could break down silos and create stronger collaboration across technical teams—if leaders are intentional about how they implement it.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Alla on LinkedInVisit Gusto

Public speaking is often framed as a stage skill—but for project leaders, it’s really a leadership skill. In this episode, Galen Low sits down with fractional PM, consultant, and award-winning Toastmaster Megan Cotterman to explore how communication, audience awareness, active listening, and adaptability show up in the everyday realities of project work. From project kickoffs and stakeholder updates to difficult conversations and team alignment, they unpack why strong communication is becoming even more valuable in an AI-powered world.They also dive into practical ways introverted and ambiverted project managers can build confidence, develop resilience, and strengthen their ability to think on their feet—without becoming the loudest person in the room.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Megan on LinkedInVisit Managed By Megan

In a marketing landscape shaped by lean teams, rising expectations, and an ever-expanding stack of AI tools, many leaders are asking the same question: do agencies still have a role to play? In this episode, Galen Low sits down with Tammy Valentine, President of LuckyTamm Marketing Group, to explore how boutique agencies are evolving in the age of AI—and why human expertise, trust, and collaboration still matter.Together, they unpack where AI genuinely adds value, where it falls short, and how marketing leaders can build stronger agency partnerships that help them achieve more with less. Along the way, they share practical lessons on experimentation, brand trust, onboarding, and the fundamentals that continue to drive marketing success regardless of technology shifts.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Tammy on LinkedInVisit LuckyTamm

What happens when AI stops being a tool you type into and starts becoming something you talk to? In this episode, Galen Low sits down with Oliver Shoulson, Agent Design and Engineering Lead at PolyAI, to unpack the surprisingly human problem at the heart of conversational AI: most AI conversations still feel weird.From clunky chatbot scripts to overly polite “LLM voice” personas that sound like they were trained by a committee of HR robots, Oliver explains why good conversational design is less about mimicking humans perfectly and more about removing friction. The conversation explores the psychology of trust, the mechanics of social presence, and why the future of AI interfaces may depend less on visual design and more on understanding how people naturally speak, interrupt, hesitate, clarify, and collaborate.Resources from this episode:Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Oliver on LinkedInCheck out Oliver’s websiteVisit PolyAI