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Finding the right freelance project manager can feel like searching for a unicorn. Do you hire someone who knows your industry inside out, or someone who can solve the problem in front of you? And if you're a freelance PM looking to branch into a new industry, how do you know which of your skills will actually transfer? In this episode, host Galen Low sits down with Ashanti Johnson, founder of the Freelance PM Club and owner of Strategy House, to unpack what makes a great freelancer-client match. They explore why industry experience isn't always the deciding factor, how to position your expertise around outcomes rather than job titles, and why the future of freelance project management depends on treating independent professionals as strategic partners, not just extra hands. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsCheck out this episode’s sponsor: FingerprintConnect with Ashanti on LinkedInVisit The Freelance PM Club

AI is changing how software gets built, but does that mean technical program managers (TPMs) and engineering managers should become one role? Not so fast. As engineering teams move faster with AI, the need to manage dependencies, anticipate risks, and keep cross-functional teams aligned isn't disappearing. It's evolving. In this episode, host Galen Low sits down with Satish Menon, a technical program management and engineering operations leader with experience at Google, Dell, and other major software companies. Together, they explore what technical fluency really means for TPMs, how AI is shifting the value of program management, and why the future of the role depends less on tracking work and more on solving problems, earning trust, and orchestrating delivery at scale. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsCheck out this episode’s sponsor: FingerprintConnect with Satish on LinkedIn

AI search is changing discovery, but the playbook isn’t about finding a magic prompt, tag, or shortcut. Matt Slater, founder of Receipts, explains why AEO and GEO still depend on fundamentals: knowing who your brand is for, publishing clear first-party information, and building enough real-world credibility for third-party sources to corroborate what you say about yourself. For project professionals, that shift matters. Stakeholders may want immediate visibility in ChatGPT or Claude, but sustainable results come from consistent, integrated work across brand, content, reputation, and search—not hacks that could disappear with the next update. And as zero-click searches grow, success may increasingly look less like “more traffic” and more like better-informed prospects arriving ready to act. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsCheck out this episode’s sponsor: FingerprintConnect with Matt on LinkedInVisit Receipts

AI’s biggest opportunity in professional services may not be replacing expertise—it’s removing the operational drag that keeps experts from using it. In this conversation, Projectworks CEO Mark Orttung explores how AI can take on the neglected or repetitive work around proposals, resource planning, timesheets, invoicing, and forecasting while keeping human judgment firmly in the loop. The bigger shift is moving beyond using AI for isolated tasks and rethinking entire business processes around it. For consulting firms, that means connecting the journey from winning work to staffing it, delivering it profitably, and getting paid—with better data and fewer administrative handoffs along the way. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Mark on LinkedInVisit  Projectworks

Strategic initiatives rarely stall because teams aren’t working hard enough. More often, the information leaders need to make timely decisions is scattered across Jira, Asana, Slack, spreadsheets, meetings, and everything in between. By the time a risk becomes visible at the executive level, the opportunity to address it early may already be gone. Galen Low sits down with Maria Delgado Oliveros, founder of glidiffy and former program management leader at Uber, Hexagon PPM, and Chime, to unpack what makes strategic initiatives different from ordinary projects—and why better visibility can transform the relationship between program managers and executive sponsors. They explore how PMs can spend less time chasing updates and more time understanding dependencies, surfacing risks, making trade-offs, and becoming trusted operational partners. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsCheck out this episode’s sponsor: FingerprintConnect with Maria on LinkedInCheck out glidiffy

Change is no longer something organizations can neatly package into a transformation initiative. It’s constant—and the real challenge is keeping strategy, decisions, and execution connected while everything around the organization keeps moving. Galen Low sits down with Denise Jarvie, Managing Director of Agile Alliance and Director of Agile Community at PMI, to explore what it takes to build change readiness as an organization-wide capability. They dig into why strategic intent gets lost on its way to delivery teams, how leaders can move decision-making closer to the work without creating chaos, and why AI is making human judgment—not just technical execution—an increasingly valuable skill. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Denise on LinkedInCheck out Project Management Institute (PMI) and Agile Alliance

AI is changing more than how work gets done—it’s changing who gets to make decisions in the first place. And that makes role clarity, decision rights, and organizational design much harder to leave implicit. In this episode, Galen Low talks with Cassie Solomon about why RACI still matters in the age of AI, how it can evolve from a documentation tool into a design tool, and what leaders need to rethink as AI agents take on more work, more judgment, and in some cases, more authority. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Cassie on LinkedInCheck out The New Group Consulting and Cassie’s book — Leading Successful Change: 8 Keys to Making Change WorkPower and Prediction: The Disruptive Economics of Artificial Intelligence

For many project professionals, the job title that once felt like a marker of progress can eventually start to feel like a box. And with AI disruption, shifting responsibilities, and increasingly blurry career paths, figuring out what comes next means looking beyond the label on your LinkedIn profile. Galen Low sits down with career coach and former project professional James Compton to unpack “career dysmorphia”: the disconnect between a career that looks successful on paper and one that feels draining, flat, or directionless in practice. They explore how to recognize when your professional identity has become too tied to your title, create space to rethink what actually energizes you, and use disruption as an opportunity to rediscover the value and purpose underneath the role. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with James on LinkedInCheck out Limitless Leading and The Career Dysmorphia Dossier

When margins get tight, reducing headcount can look like the fastest route to a healthier balance sheet. But in professional services, there’s a catch: your people aren’t just a cost—they’re a big part of what clients are paying for. Cut too deeply, and the short-term savings can quickly turn into overloaded teams, weaker client service, unwanted attrition, and eventually, the cost of hiring people back. In this episode, Michael Gold and James Leigh explore another path: getting more value from the people you already have. They unpack what it means to “activate” human potential, why AI adoption needs more than a stack of new tools, and how organizations can rethink work around people’s actual strengths instead of forcing everyone into the same job-shaped box. The result is a different way of thinking about efficiency—one that asks how you can grow capability before assuming you need to shrink the team. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Michael and James on LinkedInCheck out Aria, Gold Strategic Delivery, Vanberra, and Kintara

Founders are wired to look ahead: spotting opportunities, chasing possibilities, and imagining what the business could become. Project and operations people tend to live closer to today, turning those ideas into something teams can actually deliver. The friction between those two perspectives isn’t necessarily a problem—it can be the engine that moves a business forward. Galen Low sits down with Derek Fredrickson, founder of The COO Solution, to unpack how operators can become the bridge between vision and execution. They explore why trust and clarity matter more than simply “getting things done,” how to challenge a founder without becoming the resident no-machine, and why strong project leaders need to know when to step out of the details and into strategic dialogue. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Derek on LinkedInVisit The COO Solution

AI fluency isn’t about knowing the latest tools, collecting certificates, or casually dropping “agentic” into a meeting. It’s about knowing where AI fits into the work—and where human judgment still matters most. Justin Bateh joins Galen Low to unpack why the real advantage comes from building an operating layer above AI’s increasingly capable execution layer. They dig into what separates genuine AI fluency from familiarity, why hands-on practice and feedback matter, and what employers can do to build capability without turning AI training into homework. They also explore a bigger career question: when technical skills are becoming easier to replicate, what makes a project leader’s career durable? Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Justin on LinkedInVisit AI Operators Lab and Tactical Memo

Projects are, in many ways, a collection of decisions. But when work is moving fast, information is scattered, and the stakes are high, making a well-informed call isn’t always straightforward. AI can pull together more context than any one person could realistically hold in their head—but that doesn’t mean we should hand over the decision-making reins. Galen Low sits down with Cali Collins, Co-Founder and Chief Product Officer of Optimality, to explore how AI can support better decisions without removing humans from the equation. They dig into decision context, bias, traceability, accountability, and why the rise of AI could actually make project leaders more—not less—important. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Cali on LinkedInVisit Optimality

Government projects are often dismissed as slow, bureaucratic, and overly reliant on expensive consultants. But according to William Moroz, that narrative is increasingly outdated. Drawing on experience across both government and consulting, William explains how modern public sector teams are leading ambitious, mission-driven initiatives with a stronger focus on accountability, transparency, and measurable public value. In this conversation, Galen and William explore how AI is reshaping government procurement, why collaboration is replacing traditional vendor relationships, and what it really takes to become a trusted government collaborator. From auditability and AI literacy to balancing innovation with responsible governance, this episode offers a grounded look at delivering technology that serves citizens—not just stakeholders. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with William on LinkedIn

Generative AI is changing how project teams work—but too many professionals are still treating it like a smarter search engine. The result? Generic prompts, generic outputs, and a growing tendency to trust polished responses without applying the critical thinking that makes great project leaders valuable in the first place. In this episode, Galen Low sits down with AI consultant and educator Mashhood Ahmed to explore why curiosity, context, and strategic questioning matter more than ever. Together, they unpack how AI can amplify—not replace—human judgment, and share practical ways leaders can help their teams move beyond surface-level prompting toward more thoughtful, effective collaboration with AI. Resources from this episode: Join the Digital Project Manager CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Mashhood on LinkedIn and TikTokVisit M1 Consultants Inc.

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”