How to Know If Your Team’s Ready for AI in PM Software

When AI enters the enterprise, the work isn’t just about the tech—it’s about culture, collaboration, and courage. In this episode, Galen chats with Deborah Ketai, a program and change management leader who helped a Fortune 5 healthcare organization align its people, systems, and culture around AI. Together, they unpack how she built a community of practice that broke down silos, reduced knowledge debt, and created space for cross-training, collaboration, and smarter risk management.From talent strategy to trust and transparency, Deborah shares what it really takes to sustain AI-driven change inside complex organizations—and what PMs need to learn now to stay ahead as their roles evolve.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Deborah on LinkedIn

AI has the potential to revolutionize healthcare—but it’s not just about smart algorithms or automated diagnoses. It’s about earning trust in high-stakes environments where lives are on the line. Galen sits down with David Doan, Director at Kyndryl and former registered nurse, to explore how delivery leaders can navigate the clinical, technological, and ethical challenges of implementing AI in healthcare.From preserving human judgment and connection to aligning regulators, executives, and frontline clinicians, this conversation digs into the realities of AI-powered healthcare delivery—and what project leaders can do to make it actually work.Resources from this episode:Subscribe to the newsletter to get our latest articles and podcastsConnect with David on LinkedInCheck out Kyndryl

The AI hype in project management software is real—but is everyone ready for it? In this episode, Galen sits down with returning guest Olivia Montgomery, Associate Principal Analyst at Capterra, to explore the findings from her 2025 Project Management Software Trends Survey. They unpack the real reasons behind the surge in demand for AI-enhanced PM tools and the foundational work teams need to do before expecting AI to deliver real ROI.Together, Galen and Olivia dig into what "AI readiness" actually looks like—technically and culturally. They discuss how competitive FOMO, billion-dollar marketing campaigns, and shifting economic investments are driving decision-making at the executive level, while the realities of adoption, data governance, and employee empowerment are playing out on the ground. They also take a thoughtful look at how PMs can avoid common pitfalls (like AI hallucinations) and begin to build workflows that align with both human and machine strengths.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Olivia on LinkedInCheck out CapterraOlivia’s report, AI & Security Are Top Concerns in Capterra’s 2025 Project Management Software Trends Survey 

The entry-level project management job isn’t what it used to be. With AI automating many of the classic coordinator tasks, the ground floor seems to have disappeared—leaving aspiring PMs wondering how to even get started. In this episode, Galen Low sits down with Benjamin Chan, Founder of CLYMB Consulting, to unpack what this shift really means for junior PMs, hiring managers, and the next generation of project leaders.Together, they explore how AI is reshaping the role of the project coordinator, what skills and traits are most valuable in today’s job market, and how organizations can reimagine career paths to make sure talent isn’t left behind. Whether you’re breaking in, hiring, or mentoring, this conversation is full of real-world perspective and actionable ideas for navigating the new career landscape.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Ben on LinkedInCheck out CLYMB Consulting

Experimenting with AI is exciting—but how do you make the leap from tinkering to transforming agency operations at scale? In this conversation, Galen Low brings together Melissa Morris (Agency Authority), Kelly Vega (VML), and Harv Nagra (Scoro) to talk about how agencies can carve out space for experimentation, align AI use to business goals, and actually implement the good ideas that emerge.The panel shares stories of saving hours on PM tasks, setting up accountability frameworks, and creating safe spaces for knowledge-sharing. They also surface the tough stuff—fear of job replacement, cultural resistance, governance challenges—and how to navigate it with clarity and empathy.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Melissa, Kelly, Harv on LinkedInCheck out Agency Authority, VML, Scoro and The Handbook: Agency Ops podcast

When is the right time to hire an AI leader, and what do they actually do once they’re in the door? In this episode, Galen Low sits down with Tim Fisher, VP of AI at Black & White Zebra, to unpack the real-world impact of AI leadership roles. Together they explore the tension between hype and practicality, the mix of skills needed to bridge tech, business, and people, and why AI leadership is less about flashy experiments and more about building trust, change readiness, and operational maturity.Tim shares candid insights from his own path into the role, offering a grounded look at how organizations can approach AI without losing sight of their business goals—or their people. If you’ve ever wondered whether a VP of AI is a made-up job, or how AI leadership can actually smooth project delivery, this conversation is for you.

AI is not eating all the jobs—but the story is more nuanced than the headlines suggest. In this episode, Galen Low sits down with Jim Iyoob (President of ETS Labs, CCO at Etech Global Services) and Manu Dwievedi (AVP at ETS Labs) to cut through the noise around large-scale AI transformation in customer experience. Together, they unpack what’s really happening in call centers worldwide, why AI is more about augmentation than replacement, and how organizations can implement AI without breaking the customer or employee experience.From pragmatic strategies to leadership-level insights, this conversation tackles the real challenges of AI change management: how to start small, get quick wins, and bring people along for the journey. Whether you’re leading a CX transformation or navigating an AI project in any industry, you’ll leave with concrete strategies to make AI work for your team instead of against them.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Jim and Manu on LinkedInCheck out ETS Labs and Etech Global Services

How do you know if you’re tracking the right project metrics—or if you’ve been chasing the wrong numbers all along? In this episode, Galen sits down with Lior Gerson, Co-founder & CEO of TargetBoard.ai, to unpack how AI is reshaping KPI management and why aligning metrics with business strategy is the real game-changer.Together, they explore how project leaders can move beyond legacy metrics like velocity and utilization to focus on measures that truly drive impact. From tackling cultural mismatches around KPIs, to building real-time forecasting models, to leveraging AI for smarter, faster reporting—this is a conversation about cutting through the noise and making metrics meaningful.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Lior on LinkedInCheck out TargetBoard.aiWhen the Old, and the New Metrics Fail – Jim Highsmith

In this episode, Galen Low sits down with Brian Kessman of Lodestar Agency Consulting to tackle a big question: is AI finally the deathblow to billable hours? Brian argues yes—and not because AI “broke” the model, but because it’s exposed just how misaligned hourly billing has always been with the real value agencies deliver. Instead of rewarding efficiency and innovation, time-based pricing incentivizes dragging things out and commoditizes expertise. The real shift, Brian says, isn’t just about swapping billing methods—it’s about fundamentally rethinking what you sell, how you position it, and how you prove its impact.They dig into the Agency Value Model—a framework for moving from selling time to selling outcomes. Brian explains how to define your best-fit clients, identify their high-value problems, and design structured solutions that command higher prices while delivering measurable impact. Along the way, they unpack how to navigate the “race to the bottom” fueled by AI, nearshoring, and automation; why confidence in your positioning can help you turn away misaligned clients; and how to operationalize repeatable, scalable value delivery without falling back into chaos.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Brian on LinkedInCheck out Lodestar Agency ConsultingValue Model AssessmentAgencies building business models around AI offerings:Go Supergood — an AI-native creative agencySilverside.ai — an AI innovation labSkeptic™ by Known — uses machine learning and artificial intelligence to deploy rapid scientific experimentation and persistent optimizationJellyfish — social media AI agentsMagnolia by Newfangled — is an AI-powered strategic plannerContent Symphony

AI is transforming the creative workflow—but not in the ways we first expected. In this conversation with Galen Low, creative and PM leaders Sara Fisher, Sara Doubleday, and Greg Storey talk through the practical and philosophical implications of AI’s growing role in creative work. This isn’t about flashy tools or end-to-end automation. It’s about realigning how teams work, communicate value, and preserve the human essence in their process.From misinformed client expectations to the strategic reframing of creative outputs, the panel explores how project leaders and creatives can use AI to amplify their strengths rather than replace them. Spoiler: there’s still no shortcut for trust, authenticity, or thoughtful strategy.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Sara Fisher, Sara Doubleday, and Greg Storey on LinkedInCheck out Vye and Seer InteractiveCheck out Greg’s book – “Creative Intelligence: Don’t Ask AI, Think With AI”