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Project Management Happy Hour

Kim Essendrup and Kate Anderson
Project Management Happy Hour
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  • 106 - Finish Strong: Why the End of Your Project Matters Most
    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
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  • 105 - Top Shelf Replay: How to Deal with Stupid Executive Asks
    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  
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  • 104 - The one meeting that will make or break your project
    “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  
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  • 103 - Lessons not Learned: State of Maine HR System Project Debacle
    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
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  • 102 - Kim's first day working for the Empire: Kate runs another Project Management role-play
    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  
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About Project Management Happy Hour

PM Happy Hour is the place for frank and honest discussion about real world issues in project management. We do it in a way that’s not too dry, though it may get a bit salty from time to time. Each episode, your hosts Kim Essendrup and Kate Anderson cover a problem faced in project management today, and share practical advice, real-life examples and the occasional project horror story. Not only that, but every podcast is also an online class! Our host is a PMI Registered Education Provider, who has structured each podcast as an easy-to-listen-to lesson. To get credit, go to our web site at PMHappyHour.com, purchase your class, take the test (based on the content from our podcast) and you get your PDU certificate instantly!
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