The Digital Project Manager

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 [https://thedigitalprojectmanager.com/membership/] * Subscribe to the newsletter [https://thedigitalprojectmanager.com/subscribe/] to get our latest articles and podcasts * Connect with Ben [https://www.linkedin.com/in/pmcoachben/], Mackenzie [https://www.linkedin.com/in/mackenziedysart/], and Elizabeth [https://www.linkedin.com/in/elizabethharrin/] on LinkedIn * Check out Thoughtworks [https://www.thoughtworks.com/] and Rebel’s Guide to Project Management [https://rebelsguidetopm.com/] * Organized Chaos Café [https://open.spotify.com/show/5Mr9Fo04GHdmJo2gsjuuCx] – Ben’s podcast * Managing Multiple Projects [https://elizabeth-harrin.com/managing-multiple-projects-online-resources/] – 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 [https://thedigitalprojectmanager.com/membership/] * Subscribe to the newsletter [https://thedigitalprojectmanager.com/subscribe/] to get our latest articles and podcasts * Connect with Mukhtar [https://www.linkedin.com/in/m-kadiri/], Pam [https://www.linkedin.com/in/pambutkowski/], and Elaina [https://www.linkedin.com/in/elaina-martinez-csm-b9408136/] on LinkedIn * Check out WorkTipsPro [https://www.worktipspro.com/] and Horizontal Digital [https://www.horizontaldigital.com/]

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 [https://thedigitalprojectmanager.com/membership/] * Subscribe to the newsletter [https://thedigitalprojectmanager.com/subscribe/] to get our latest articles and podcasts * Connect with Kayla on LinkedIn [https://www.linkedin.com/in/kayla-quijas/] * Check out Kayla’s website [https://www.kaylaqcareercoaching.com/]

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 [https://thedigitalprojectmanager.com/membership/] * Subscribe to the newsletter [https://thedigitalprojectmanager.com/subscribe/] to get our latest articles and podcasts * Connect with Devin on LinkedIn [https://www.linkedin.com/in/devinmahoney/] * Check out QTalo [https://www.qtalo.com/]

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 [https://thedigitalprojectmanager.com/membership/] * Subscribe to the newsletter [https://thedigitalprojectmanager.com/subscribe/] to get our latest articles and podcasts * Connect with Kelly [https://www.linkedin.com/in/kelly-suter/], Matthew [https://www.linkedin.com/in/matthewfox/], and Marcel [https://www.linkedin.com/in/marcelpetitpas/] on LinkedIn * Check out Parakeeto [https://parakeeto.com/]