“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!

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