Navigating a career in project management today means wrestling with more than just Gantt charts and stakeholder standups—it means making high-stakes decisions about your salary, your specialization, and what brings you meaning at work. In this panel episode, Kelsey Alpaio brings together PM thought leaders Ben Chan, Mackenzie Dysart, and Elizabeth Harrin for a candid conversation on how to design your PM career with both pay and purpose in mind.

Together, they unpack fresh data from DPM’s 2025 Salary Guide and tackle some of the most pressing questions PMs are facing right now: Should you specialize or stay a generalist? When do certifications actually help? Is it ever too late to take control of your career? And how do you make confident moves when AI and automation are reshaping the role in real time? This is a jam-packed episode full of tactical tools, honest reflections, and grounded advice for anyone looking to take the reins of their project career.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Ben, Mackenzie, and Elizabeth on LinkedIn
• Check out Thoughtworks and Rebel’s Guide to Project Management
• Organized Chaos Café – Ben’s podcast
• Managing Multiple Projects – Elizabeth’s book

When it comes to getting paid what you’re worth, project managers in 2025 are facing a unique challenge: job switching no longer guarantees a big raise, and most PMs are staying put—even if they feel underpaid. So what now? In this episode, Kelsey Alpaio sits down with Mukhtar Kadiri, Pam Butkowski, and Elaina Martinez to talk real strategies for negotiating a raise where you are—with confidence, clarity, and without burning bridges.

You’ll hear honest takes on why PMs feel undercompensated, how the market has shifted, and what leaders actually want to hear in raise conversations. From mapping your invisible impact to understanding company timing cycles and navigating tough “no’s,” this panel brings practical, actionable insights for anyone ready to make the ask—and get results.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Mukhtar, Pam, and Elaina on LinkedIn
• Check out WorkTipsPro and Horizontal Digital

Navigating job interviews as a project manager can feel like walking through a minefield of unpredictable questions. In this episode of The Retro, Kelsey sits down with Kayla Quijas—a senior PM and certified career coach—to unpack how to tackle curveball questions with poise and purpose. From candy bar hypotheticals to high-stakes stakeholder slip-ups, Kayla shares actionable frameworks that help PMs answer tough questions with clarity, honesty, and a whole lot of confidence.

They dive deep into how interviews aren’t just about your resume—they’re about how you think, lead, and adapt under pressure. Whether you’re pivoting into PM from another field, trying to land your first role, or just looking to sharpen your interview game, this conversation offers the tools to prep smarter, answer authentically, and leave a lasting impression.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Kayla on LinkedIn
• Check out Kayla’s website

There’s no shortage of AI tools for project managers these days—and they can be pretty amazing. But using them? Often a frustrating, disjointed experience. In this episode, Galen Low is joined by Devin Mahoney, CEO and Co-founder of QTalo, to unpack why AI can feel more like a burden than a boost in our day-to-day project work, and how to fix that.

They dive into how AI can truly serve project leaders: from cutting down on context switching to surfacing what actually matters, and building systems that fit into the real workflows of PMs. Devin also shares why privacy matters not just for compliance, but for preserving the creative space we need to do our best work. If you’ve ever felt like AI is both magical and maddening, this one’s for you.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Devin on LinkedIn
• Check out QTalo

Why does time tracking suck—and what can we actually do about it? In this lively and deeply honest panel session, Kelsey Alpaio sits down with agency consultant Marcel Petitpas, PMO leader Kelly Vega, and project operations expert Matthew Fox to get to the root of why time tracking feels so broken. Together, they unpack not just the tactical challenges, but the deeper cultural and strategic dynamics that make time tracking feel like a chore (or worse, a surveillance tool). But this isn’t just a vent session—our panel brings clarity, practical advice, and a few hard truths to help you shift your mindset and your systems.

From rethinking data accuracy and redefining utilization to making smarter tooling choices and harnessing AI (without falling for the hype), this conversation delivers actionable insight for PMs, leaders, and anyone in the messy middle of tracking work. Whether you’re tracking time for billing, planning, or just staying afloat, there’s something here to make it suck a little less—and maybe even become a tool for empowerment.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Kelly, Matthew, and Marcel on LinkedIn
• Check out Parakeeto

Rolling out a new tool or process sounds simple—until you try it. In this episode, Galen Low sits down with Frances Odera Matthews, founder of The Notion Bar, to unpack why change management is so hard, even with the best intentions and the best tools. From shiny object syndrome to culture gaps, they explore why tool adoption often fails and what project leaders can do to set their teams up for long-term success.

Frances shares practical insights from the front lines of Notion implementations, including how phased rollouts, internal champions, and intentional design can make or break adoption. They also dig into the cultural side of change—how open sharing, avoiding silos, and even acknowledging when to rip the band-aid off can help teams navigate tool fatigue and create lasting transformation.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Frances on LinkedIn
• Check out the Notion Bar, The Notion Zeitgeist newsletter, and the Coffee & Oysters podcast

In this episode of The Digital Project Manager podcast, Kelsey Alpaio sits down with Oliver Yarbrough—founder of Not Your Father’s AI and a LinkedIn Learning instructor—to talk about the AI-driven future of project management. With automation creeping into every corner of our workflows, PMs are no longer just task managers; they're becoming AI operators, process optimizers, and digital workforce leaders.

Oliver breaks down what PMs should be doing today to stay ahead: learning to communicate effectively with AI tools, mastering process optimization, and strengthening foundational PM skills. Whether you're just starting to explore AI tools or already dabbling in automation, this episode gives you a roadmap for evolving your skill set and redefining your value as a project manager in an increasingly digital workplace.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Oliver on LinkedIn
• Check out Not Your Father's A.I.

The agency world is undergoing major shifts, with evolving business models, leaner teams, and new demands on project leaders. While disruption can feel overwhelming, it also presents opportunities for growth—if you know how to adapt. As roles blur and responsibilities pile up, resilience and flexibility have never been more essential.

Joining us is Harv Nagra, Head of Brand Communications at Scoro and host of The Handbook: Agency Ops podcast, to break down how operating models are changing and what project managers can do to stay ahead. From navigating uncertainty to leading with a growth mindset, this episode offers actionable insights for anyone facing rapid change in agency life.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Harv on LinkedIn
• Check out Scoro and  The Handbook: Agency Ops podcast
• Range: Why Generalists Triumph in a Specialized World

We’re joined live by Crystal Richards, PMP trainer and founder of MindsparQ, to dive into everything you need to know about passing the challenging Project Management Professional (PMP) exam. With its high failure rate and tough reputation, the PMP remains a highly respected certification that can open significant career doors—but balancing exam prep with work and life can be daunting.

Crystal shares practical strategies to help candidates navigate the exam process with clarity and confidence, drawing on her experience training project managers and her new book, PMP Exam Prep For Dummies. Whether you’re just starting your PMP journey or feeling overwhelmed, this conversation offers valuable tips to help you succeed.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Crystal on LinkedIn
• Check out MindsparQ

Fractional remote job opportunities are growing, offering professionals the chance to break free from the traditional rat race and take on multiple roles, be their own boss, and avoid the transactional nature of full-time work. But how do you get started in this new world of fractional work, and what if it doesn’t work out?

Michael Gold, a fractional project management expert and founder of The Fractional Hub, discusses the growing trend of fractional project management roles. He shares insights on how this model could become just as common as, or even replace, traditional full-time positions in the future, helping you make an informed decision about whether this path is right for you.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Michael on LinkedIn
• Check out The Fractional Hub