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 truth to light, and have the guts to ask, “Does this project still make sense?”

Of course, Kate keeps Kim honest, adding the perspective (and laughs) that make the tough lessons go down easy.

If you’ve ever been handed a project that feels unsalvageable, this episode is your playbook.

👉 Want even more? Join us at pmhappyhour.com/membership to get PDU certificates for episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.

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.

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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!

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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.

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“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!

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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

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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