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

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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!

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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.

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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!

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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)

As a professional in today’s working environment, you are constantly bombarded by things that demand your attention, your action, the very limited moments in your finite life. (wow, heavy).

OK, so there are infinite demands on our time, but finite time. How do we balance those? SWOT analysis?! Of course not!

To help us understand how to effectively prioritize in today’s crazy world,  Kate and Kim are joined by James Louttit, author of Leading Impactful teams. We talk about prickly pears, paw-paws, and practical ways to prioritize in today’s demanding world. Spoiler: It’s not SWOT, MoSCoW or the Eisenhower matrix ;-) 

About our amazing guest, James Louttit

James Louttit knows what it’s like to have to deliver complex projects under pressure, and what it costs when we get it wrong. In 2016 he ended up in hospital because he was trying to run his projects with effort rather than IMPACT. That story, which forms the introduction to his book “Leading Impactful Teams”, inspired him to figure out how to deliver projects better. He learned everything he could around the subject, from the PMP and Agile worlds that we all know and love, to Design Thinking, Facilitation Techniques, Psychology and Human Nature and everything that might be useful to people delivering projects. His career took off. He became the Head of Project management Competency at a large Bank and then Chief Information Officer of a major PLC in Ireland.

What he learned, and put into practice made a huge difference to the effectiveness and stress levels in his teams. People kept asking him for help, so he found an artist and started drawing cartoons to explain the concepts in more human, memorable and fun ways. He wrote “Leading Impactful Teams” to help anyone who is managing any type of work or project that involves real, imperfect people in real, imperfect organizations. 

Now he works with the biggest companies in Ireland to help their teams cut through the noise, and build a toolbox of practical techniques and approaches that reduce stress, improve outcomes and help people face the challenges of project delivery with confidence and positivity.

You can connect with James and check out all his amazing content and the knowledge he shares at the links below: 

James’ book Leading Impactful teams: 

https://www.audible.co.uk/pd/B0DN7GP2XB?source_code=ASSGB149080119000H&share_location=pdpv 

And on Amazon:  https://a.co/d/9rFmDwt 

James Linkedin:  https://www.linkedin.com/in/james-louttit/ 

His website:  https://www.impactfulpm.com/ 

The Brilliant Beaver Guidebook - https://a.co/d/hM4gfz7 

The Brilliant Beaver Audiobook (😊) - https://www.audible.co.uk/pd/The-Brilliant-Beaver-Guidebook-Audiobook/B0DKZ7G93J?source_code=ASSGB149080119000H&share_location=pdp 

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AUDIO QUALITY NOTICE!  Apologies, we have a little static on one of the mics during our recording - sorry for the occasional audio issue.  As a project manager, an organizational structure that will have a big impact on your life is the PMO. But if you aren’t used to working with a PMO, what should you expect? Are they going to make your life and projects easier, or crush you with red tape? If you are interviewing for a job where they have a PMO, what questions should you ask to get a better understanding of how they work? And, what should you expect from a PMO - and what are they expecting from you? 

With all these questions, we thought we should reach out to a couple of the most well known minds in PMO: Lindsay Scott and Eileen Roden. Their UK based “House of PMO” organization does some great things in the PMO space (plus they are a lot of fun!) so we feel very fortunate that Linsay and Eileen agreed to join us and help us understand a bit more about whether PMO’s are our friends or foes. 

About our amazing guests, Lindsay Scott and Eileen Roden

Lindsay has worked in and around project management and PMO for over 20 years and is a Director at PMO Learning, a training company focused on PMO.  She is Co-Founder of the House of PMO, a professional membership organisation for PMO practitioners.

Lindsay is the co-author of the PMO Competency Framework and editor of the Handbook of People in Project Management. She speaks regularly on project management and PMO career topics – and provides 1-2-1 coaching for those looking to advance their careers in PMO.

Eileen has 15 years practitioner experience in a variety of project management roles (predominantly PMO management) along with IT and functional HR roles, with a variety of UK, EMEA and global responsibilities. 

Her practical experience is supported by both academic and professional certifications including a Masters in Applied Project Management (with distinction), AIPMO-E, PRINCE2®, MSP®, MoP®, Managing Benefits®, Better Business Cases®, Programme and Project Sponsorship®.  She is now a Consulting Director of PMO Learning and co-founder of the House of PMO.

She is the author of P3O® Best Management Practice and lead author of the PMO Competency Framework, co-author of Knowledge Management in a Project Environment, along with contribution to many APM publications.  She is a frequent conference speaker throughout UK and Europe.

You can learn more about all the amazing things that Lindsay and Eileen are doing around PMO and even join their great community at https://houseofpmo.com/ 

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In this episode, Kat and Kim talk to Erik Rueter about design thinking in our projects. 

What’s design thinking, you may be thinking? Design thinking is a methodology that focuses on the end users of a system when we are problem solving. Erik will share 5 different design thinking methods for understanding user needs in a way that not only helps your project provide better deliverables but can also help build a better project team.

About our amazing guest, Erik Rueter

Erik K. Rueter, PMP, PMI-ACP, has over 20 years of experience in diverse industries, including tech startups, academia, healthcare, and entertainment. Currently, he serves as a senior project manager at the American Marketing Association and has held multiple senior staff positions at various organizations. Erik holds a BA in neuroscience from Wesleyan University, with further education in digital design, Irish studies, and MicroMasters in Design Thinking and Project Management from the Rochester Institute of Technology. He is also certified in diversity and inclusion by Cornell.

Erik's contributions to the field include co-authoring papers on health inequity, lecturing at Boston and Emerson Colleges, and advocating for diversity and inclusion with organizations like Medtronic, VSP, and the San Antonio Spurs. He has spoken, in person and virtually, at PMI Greece, PMI Michiana, and PMI Western Michigan, among others. He has appeared on podcasts such as “Confessions of a Higher Education CMO”; and “I Wanna Work There!” and contributed to “The Evolution of the PMO”, a key resource for project managers. He founded Human-Centered Success LLC to promote inclusive leadership which is National Gay and Lesbian Chamber of Commerce certified as an LGBTQIA+-owned business.

Residing outside Pittsburgh with his husband and two dachshunds, Erik enjoys marathons, gaming, and sharing his insights. Contact: [email protected].

To learn more about the amazing things Erik is up to: 

Check out his website at: www.humancenteredsuccess.com

Learn about solution delivery: Mastering Solution Delivery

Erik’s Upcoming Speaking Engagement:

PMI Global Summit 2024

Rock Lobster Leadership: Lessons from The B-52s

Resilience and Relatability: A New Paradigm for Project Leadership (With Jake McGaffin and Olivia Montgomery)

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STUMP THE PM’S!

We love to hear about your tough PM issues, so please hit us up at [email protected] or on Linkedin and we’ll see if we can help you. If we use your question, we’ll send you a PM Happy Hour coaster you can enjoy at your next happy hour.