108 - Why Risk Management? Future You Will Thank You

Why bother with risk management when you can just deal with problems as they happen? In this episode, Kim and Kate dig into the heart of that question—and the answer might just save your future self a world of pain. You’ll hear: Hard-hitting stats: 1 in 6 projects go 200% over budget (Harvard Business Review), 17% of major IT projects threaten company survival (McKinsey), and why 69% of projects don’t succeed. Firefighting vs. fire prevention: why controlled burns (boring, thankless prep) prevent disasters while the “heroes” just put out fires. ROI of risk management: the surprising 20:1 return on time spent planning versus cleaning up issues later. Language hacks: how swapping “risks” for “obstacles” (credit to Dr. Josh Ramirez) can get your team—and executives—on board. Practical techniques: from whiteboarding failure points to slicing your project into risk categories, simple ways to start risk management without drowning in templates. Whether you’re a seasoned PM or just tired of project disasters, this episode shows why risk management isn’t about doom and gloom—it’s about giving future you a fighting chance. JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

Please. Let it end. PLEASE! A defining characteristic of a project is that it ends. Finally. Just finish it, right? If it were only that easy!  In another Top Shelf Replay, Kate and Kim revisit one of their classic past episodes, “The Closer.” We play highlights from the original Closer episode as they talk about how to build up to a crisp conclusion to your project, making it a win for everyone. Then, Kate and Kim talk through their revised perspectives and learnings since the original airing of the Closer - and some of their hard learned lessons since then!    JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

Projects aren’t remembered for how they started—they’re remembered for how they ended. In this PM Happy Hour episode, Kim Essendrup and Kate Anderson unpack why finishing strong is critical to your reputation and your project’s legacy. Drawing on real project stories, they explore the axiom that people will remember your project the way it ended—and two key corollaries every project manager needs to know: Corollary 1: People naturally forget past wins and focus on the most recent problems. Corollary 2: People will redefine success to fit the outcome—if it gives them a win. You’ll learn practical practices to keep your stakeholders focused on value, even when things get bumpy, including: How to keep your team and sponsors aligned on the value proposition Why PMI has redefined project success around value delivered (not just the triple constraints) How to reframe challenges as wins without whitewashing reality Why a strong finish can redeem a rocky project—and a weak finish can ruin a good one If you’ve ever had a project limp across the finish line, this episode will give you tools to finish strong and leave stakeholders with the story you want them to remember. JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

Ah, executives. They fund your project, cheer you on, and sometimes… ask for things that make you want to slam your head into your Gantt chart. Like: “The project’s almost done—let’s change everything!” “I read about [X] in CIO Magazine—can we bolt that on?” “Why are we doing it this way? Let’s redo it completely differently… and badly.” In this Top Shelf Replay, we revisit the best parts of this classic episode, then Kate & Kim reflect on what they’ve learned since—especially now that they're the execs making the asks (hopefully less stupidly). Oh, and yes—this is the episode where we try to talk Darth Vader out of building an infinity pool on the Death Star.  JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership  

“Well begun is half done”  — Aristotle (or Mary Poppins, depending who you ask) The beginning of a project is a time when all stakeholders THINK they know what they want, and maybe the team thinks they know what they are supposed to do. Or maybe they are just wondering, “what the heck is this new madness that I’m getting drug into?!”   Regardless, it’s a near certainty that your team, your stakeholders and your sponsors - someone is NOT on the same page. And if you launch your project with that misalignment, you are lighting the fuse on project troubles. Enter the Kickoff meeting, one of the goals of which is to try to bring everyone’s expectations of the project into alignment.    Join Kate and Kim as they talk about how to approach this most critical meeting, and ensure your project is off on the right step. Be the Aristotle (or Mary Poppins) of your project!  🎯 What you’ll learn in this episode: How to structure your kickoff meeting Key questions to ask your stakeholders Tips for getting your team engaged from the start How to align goals, roles, and expectations JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership  

Think your project’s on fire? 🔥 Come hear how Maine tried to swap a 30‑year‑old COBOL HR/payroll system for something cloud‑friendly … and wound up with six years, two vendors, and ± $35 M spent—with no live system to show for it. (Psst—Love this kind of real‑world PM talk? Join our member community for templates, monthly problem‑solving Happy Hours with us, and coaching: PMHappyHour.com/membership.)   👋 Your Hosts Kim Essendrup – PM coach, speaker, project‑failure super‑fan Kate Anderson – coffee‑powered realist & co‑host of Project Management Happy Hour   What We Cover Why Maine’s 2016 “$15 M, 2‑year” vision looked reasonable on paper Vendor #1: Infor hired for $13.5 M … then fired after two years with nothing working Vendor #2: Workday lands a $15 M deal—hope (briefly) restored 2019–2020 red flags: missing staff, test cycles where 50 % of paychecks were wrong, “rosy” status decks Feb 2021: Maine’s 30‑day ultimatum & $22.16 M demand letter to Workday (spoiler: lawyers ensue) Project culture bombs: 400 % team turnover, a toxic manager, and a “rescue PM” married to the sponsor Independent audit slide‑deck gold: zero items “ready for go‑live,” chaotic configs, no data owner Accenture steps in (another $10.9 M) while employees still depend on the 1980s mainframe   5 Brutal Lessons You Can Use Tomorrow 1) Write it down or write a check – fuzzy requirements = infinite rework. 2) Freeze configs, then test – moving targets make every cycle worthless. 3) Own the data – bad source data means bad payroll, period. 4) Toxic leadership kills progress – harassment & turnover wipe out continuity. 5) Audit early, not post‑mortem – an external sanity check at first failure could have saved millions.   You Might Be in Trouble If … Your payroll test run is half wrong but the go‑live date stays. A core requirement (e.g., labor‑cost distribution) is “coming later”—after all testing. Status decks stay green while teammates are crying in their cars. The new “fix‑it” PM just happens to be married to the exec in charge. Nobody can explain entrance‑/exit‑criteria, yet QA keeps restarting. Ad‑hoc reports only work if you strip every security role. Steering committee = five‑minute victory lap + fifty‑five minutes of blame ping‑pong. Backup plan is still “keep the COBOL mainframe running indefinitely.”   If any of those hit home, open your RAID log—now—before your $15 M idea turns into headline fuel.   Why listen? Rolling out HRIS, ERP, or Workday? Spot the landmines first. Tired of sanitized “success stories”? We tell it like it is—with a dash of salt. Exec or sponsor? See how weak governance detonates budgets—and morale.   👉 Subscribe for more Lessons Not Learned, salty PM rants, and practical tips. 💡 Grab our free RAID Log template & on‑demand training at https://PMHappyHour.com   Sources & References Maine Legislature. Government Oversight Committee Report on Workday Implementation (2021). Maine Legislature. IJA Strategies Independent Assessment (2020). Portland Press Herald. “System failure: Inside Maine’s $35 M HR software meltdown” (Jun 20 2021). Sun Journal. “Maine hires new contractor to complete long‑delayed software upgrade” (Jun 7 2022). The Register. “Maine threatens to terminate Workday contract over delays” (Mar 31 2021). The Register. “No accountability for Workday’s HR system failure, officials claim” (Apr 14 2021). Views are the hosts’ own. Brand names belong to their respective owners. #ProjectManagement #LessonsNotLearned #Workday #ProjectFailure #PMHappyHour   JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

Our D&D-style project role play was such a hit, we did it again - in a different universe. One far, far away… This time, it’s Kim’s first day as a project manager working on a secret government project for the Empire. As he shows up, he finds that his predecessor… well, let’s just say he didn’t get-on well with his exec sponsor. Kim’s new project is behind schedule, roadblocked with supply chain issues and is out of funding. Can he get the “RTDU” project back on track by the end of the day, or will he have to give an awkward project update to his black-cloaked project sponsor? You can bet Game Master Kate has some fun in store! And… you can get the mug! For a limited time, you can go to https://pmhappyhour.com/merch and get a commemorative PM Happy Hour mug with an image of the “RTDU” in use! JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership  

Ever had a moment where you saw a problem in the world and thought, “Someone should fix that”? What if that someone was you? Mick Ebeling, founder of Not Impossible Labs, joins us to share how he turned a bold promise into world-changing innovation. From helping a paralyzed graffiti artist create art again to launching life-changing tech solutions, Mick’s story is a masterclass in fearless problem-solving. In this episode, we dive into what it takes to commit to the impossible, build the right team, and use project management superpowers to change lives. If you’ve ever doubted your ability to make an impact, this conversation will prove otherwise. Cheers to embracing audacity—tune in now! 🍻🎧   About our amazing guest, Mick Ebeling: Named Fortune’s Top 50 World’s Greatest Leaders and honored with the Muhammad Ali Humanitarian of the Year Award, Mick Ebeling is a groundbreaking innovator dedicated to changing the world through innovation and story.  As the Founder of Not Impossible Labs – an innovation incubator disrupting the status quo and tackling seemingly impossible problems – Mick has spent over a decade driving a movement of positive impact for the sake of humanity.  Through his “Help One. Help Many” approach, Mick and his team have created some of the most internationally celebrated inventions, including The Eyewriter, Project Daniel, and Don’s Voice, as well as their most recent spin-off companies, Bento (formerly Hunger: Not Impossible) and Music: Not Impossible. His work has been recognized as a 3x recipient of TIME’s Best Inventions and Fast Company's World Changing Ideas. Mick continues to inspire, empower, and teach individuals, organizations, and communities to take bold action, so they too can make the impossible, NOT impossible. JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership  

We cannot believe it! It’s been 100 episodes of PM Happy Hour!  In this very special episode, we have a retrospective, looking back at when we first decided to do this crazy podcast, to our highlights, lessons, and favorite episodes.  We are so filled with gratitude for our amazing community who have supported us these 100 episodes, and the many incredible leaders who have joined us as guests over the years.  Note: we recorded this episode as a Linkedin livestream. If you want to watch the video version, it should be out there on Linkedin!  Cheers! JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership  

If you are looking for a PM job or considering doing so, you are definitely not alone! The project management field has always had a good amount of mobility, but it sure seems like change has been accelerating the last couple years.  And if you are in the hunt for a job right now, it can feel like the market is harder than ever!   So what do you do? Focus on getting more certs? Get a recruiter? Submit 500 more applications through Linkedin?  To help understand how to land a great PM job in today’s job market, we talk with Kayla Quijas, practicing project manager and professional Project Manager career coach. Kayla helps her clients develop their profiles and land fantastic PM jobs. Kayla gives us the low-down on today’s PM job market, and shares her own “Iron Triangle” of things to focus on to land that great job.  About our amazing guest, Kayla Quijas After five years as a cake decorator and feeling stuck in a dead-end job, Kayla Quijas made a bold move: she quit after being asked to return to work after a grueling 12-hour shift.  Determined to break into the corporate world, she started as a receptionist at a law firm and rapidly climbed the corporate ladder. Now, Kayla is a senior project manager at a global law firm, overseeing one of its largest accounts.  Realizing the invaluable role her coaches played in her journey to success, she found her true purpose: inspiring others to escape dead-end jobs and pursue fulfilling careers. Now, as a certified Senior Career Coach, Kayla empowers individuals to make intentional career transitions. You can connect with Kayla and get help with your PM career via the links below:    LinkedIn: https://www.linkedin.com/in/kayla-quijas/ Tiktok: https://www.tiktok.com/@thepmcareercoach Website: Kayla Quijas Career Coaching | Project Management Career Coach (kaylaqcareercoaching.com)