103 - Lessons not Learned: State of Maine HR System Project Debacle
Release Date: 06/04/2025
113 - Top Shelf Replay: Stage direction in the boardroom
Project Management Happy Hour
What happens when you drop a senior project manager into a room full of attorneys, tribal leaders, political operators, and massive personalities? In this Top Shelf Replay, Kate & Kim revisit one of the most beloved—and re-listened—episodes in PM Happy Hour history: “Stage Direction in the Boardroom” featuring master facilitator Sheila Morago. If you’ve ever wondered how elite leaders steer complicated, high-stakes conversations without losing their cool (or losing six months of work with one careless comment), this episode is your new playbook. Sheila shares the tools, tactics,...
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112 - Burnout: when a 500k job isn't worth it, with Norlander Wilson
Project Management Happy Hour
Kate didn’t plan to measure their burnout by the number of bags of pink-and-purple Mother’s animal cookies consumed at their desk…but here we are. Kim’s clue was a rotating cycle of stomach aches and “maybe these aren’t panic attacks but the room is definitely spinning.” And our guest, Norlander Wilson, talks about showing up to work without showering or brushing her teeth for days because she literally couldn’t. This one is about burnout at work — not the “I need a weekend off” kind, but the kind that rewires your nervous system and convinces you you’re the problem....
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111 - Top Shelf Replay: How do you start a hard conversation?
Project Management Happy Hour
Ever freeze up in a tough project conversation? Or worse—blow it up? In this episode of Project Management Happy Hour, Kim and Kate revisit their all-time favorite: Crucial Conversations by the team at VitalSmarts (now Crucial Learning). This book completely changed how they lead, negotiate, and manage conflict. Learn how to spot when a conversation turns “crucial,” stay in dialogue instead of defensiveness, and use “don’t-do statements” and “start with heart” to navigate conflict like a pro. We’re not sponsored—just obsessed. If you lead projects or people, this book will...
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110 - Are you defining project success wrong? Most PM’s do! With PMI’s Dave Garrett
Project Management Happy Hour
Are you defining project success the wrong way? Most project managers are — at least according to PMI’s Dave Garrett. Project Management Happy Hour hosts Kim Essendrup and Kate Anderson sit down with Dave — Senior Advisor at the Project Management Institute (PMI) and co-founder of ProjectManagement.com — for a frank and real conversation about PMI’s new definition of project success to talk about how realistic it is, and what it means for the future of our profession. For decades, project success was judged by the “iron triangle” — scope, schedule, and budget. But PMI has...
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109 - Top Shelf Replay: The Wolf - how to take over broken projects
Project Management Happy Hour
Ever been dropped into a troubled project that’s already gone off the rails? Welcome to life as “The Wolf.” Inspired by the fixer from Pulp Fiction, Kim and Kate revisit one of our most popular episodes—now a PMI Global talk! —and break down how to step in, take charge, and rescue a broken project without losing your cool. Kim shares his new 3-part formula for project recovery: People first – You aren’t just fixing a plan, you’re fixing an organization. Calm – Calm is contagious, and you can only control yourself. Clarity & Courage – Seek out misalignment, bring...
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108 - Why Risk Management? Future You Will Thank You
Project Management Happy Hour
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...
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107 - Top Shelf Replay: The Closer - Avoiding Project Acceptance Exception
Project Management Happy Hour
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...
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106 - Finish Strong: Why the End of Your Project Matters Most
Project Management Happy Hour
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. ...
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105 - Top Shelf Replay: How to Deal with Stupid Executive Asks
Project Management Happy Hour
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,...
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104 - The one meeting that will make or break your project
Project Management Happy Hour
“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...
info_outlineThink 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.)
đź‘‹ 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
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