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Project Management Happy Hour

Project Management Happy Hour

By: Kim Essendrup and Kate Anderson
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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!2026 | Project Management Happy Hour, LLC. Career Success Economics
Episodes
  • 132: Why Your Most Supportive Stakeholder is Ruining your Project, with Dawn Mahan

    132: Why Your Most Supportive Stakeholder is Ruining your Project, with Dawn Mahan
    Aug 25 2026

    Projects rarely fail from a lack of templates — they fail because of people. Author Dawn Mahan reveals the animal avatars that help you spot the cheerleader, the finicky fan, and the saboteur before one of them bites you in the ankle.

    Why do projects really fail? Not, as guest Dawn Mahan argues, from a shortage of templates or Gantt charts — but from the people around them. In this episode, Kim and Kate dig into the human side of project delivery: the stakeholders who love your project, the ones who quietly want it dead, and the "style under stress" that surfaces when the pressure cooker of Projectland heats up. If you've ever been blindsided by a saboteur or tripped up by an over-eager cheerleader, this conversation on stakeholder management, risk, and project leadership is for you.

    Kim and Kate welcome Dawn Mahan, author of the bestselling Meet the Players in Project Land and co-editor of Project Land Goes to the Movies: 22 Blockbuster Strategies for Project Success. Dawn's premise is refreshingly human: projects rarely fail because the paperwork is wrong — they fail because the people involved aren't set up for success. Using animal avatars to make stakeholder behavior easier, and safer, to talk about, she gives project managers and leaders a practical vocabulary for the messy, political, feelings-driven reality of getting work done inside real organizations.

    Grab a drink and join us.

    Quotes from the Episode

    "If you're skipping through the meadow of project land toward your goal, one might just jump up and bite you in the ankle when you least expect it…" — Dawn Mahan "You've got a style under stress." — Kate Anderson "Instead of being a cheerleader, she accidentally became a saboteur." — Dawn Mahan "I believe PMs are in the pain prevention business." — Dawn Mahan "Any of us can sabotage our own lives, relationships, projects, even." — Dawn Mahan Practical Takeaways
    1. The three stakeholder archetypes — the cheerleader (happy dog), the finicky fan (flamingo), and the saboteur (snake), and how each one engages with or endangers a project.
    2. "Style under stress" — how both stakeholder and team behavior shifts under pressure, and why leaders should plan for those reactions in advance.
    3. Stakeholder analysis as a scheduled activity — running it privately with the sponsor, casting a wide net, documenting decisions, and coding the stakeholder register discreetly.
    4. The "Feel" question — asking "How do you feel about this?" instead of "What do you think?" to surface fear and identify project risk early.
    5. Managing cheerleaders with soundbites — the Stakeholder Gabby lesson on why enthusiastic champions can accidentally become saboteurs, and how to channel their energy constructively.
    Closing Reflection

    Perhaps the most human insight of the episode is Dawn's reminder that any of us can sabotage our own projects. Sabotage isn't always evil; more often it's fear, miscommunication, or a stakeholder who simply doesn't understand how Projectland works. The leadership question worth sitting with: who on your project is operating from fear right now — and what could you do to change that?

    🔗 Links & Resources Mentioned
    • PM Happy Hour Membership: pmhappyhour.com/membership
    • PM Happy Hour Facebook Page
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    52 mins
  • 131: Don't be the PM everyone hates, with Rachel Losser

    131: Don't be the PM everyone hates, with Rachel Losser
    Aug 12 2026

    Your worst project management habit might also be your superpower — the trick is knowing which one you're wielding, and when.

    What actually separates a great project manager from the one everyone dreads seeing on their calendar? It's rarely a certification or a prettier Gantt chart — it's behavior. This episode of Project Management Happy Hour digs into project leadership, accountability, team dynamics, and the everyday habits that quietly undermine project delivery. The uncomfortable truth running through the whole conversation: our worst project management habits are usually just our genuine strengths turned all the way up, with no dial to turn them back down.

    Kate and Kim are joined by Rachel Losser, founder and managing partner of Losser Consulting Solutions, a delivery-focused firm known for its get-stuff-done philosophy. Together they walk through five "bad PM personas" — the versions of ourselves that colleagues quietly avoid — and, crucially, the more skilled counterpart each one can grow into. Rachel sets the tone early with a bit of grace: we're talking about these "with love and reverence," because everybody starts somewhere and most of us have been every one of them at some point.

    The practical throughline is nuance. Every strength becomes a liability when it's your only mode. Great PMs read the moment: when to slow down and build consensus, and when to say "we're going this way." They tell hard truths early, manage handoffs rather than just dates, and treat relationships and communication as the real currency of the job. As Kate puts it, the only way out of a struggling project is through it — not around the color of the status.

    Which persona are you under stress? That self-awareness, the hosts suggest, is where better project leadership actually begins.


    Grab a drink and join us.

    Quotes from the Episode

    "The PM has to be the brutal truth-sayer. Because if the PM doesn't say it, who's going to say it?" — Kim Essendrup "The only way out is through." — Kate Anderson "We had to live it to be able to write it." — Rachel Losser "You have no idea what people are motivated by until you implement something like that." — Rachel Losser Practical Takeaways
    1. Every PM strength has a shadow. Each of the five personas is a positive skill (documenting, reporting, follow-through, decisiveness, convening) overused into a liability.
    2. Report status honestly, then own the path back to green. Transparent "highlighter green" reporting builds credibility; greenwashing destroys it.
    3. Accountability beats date-moving. A Task Master probes why a deadline slipped and what will change, instead of silently updating the due date.
    4. Directive leadership works only in moderation. The Hammer is effective in a crisis precisely because they aren't operating at full intensity all the time.
    5. Every meeting needs a goal and buy-in. Confirming the objective at the top of a call is how you avoid becoming the Meeting Vampire.
    Closing Reflection

    Rachel's toast says it best: this is often a thankless job of late nights and "adult babysitting." But the difference between a PM everyone avoids and one everyone wants on their project usually isn't talent — it's the self-awareness to know which persona you default to under stress, and the discipline to reach for its better half instead. Which of the five is your worst habit — and what would its superpower version look like?

    🔗 Links & Resources Mentioned
    • PM Happy Hour Membership: pmhappyhour.com/membership
    • PM Happy Hour Facebook Page
    • Losser Consulting Solutions — Rachel Losser's firm
    • Big Project Energy with Rachel Losser
    • Rachel Losser on LinkedIn
    • Losser Consulting Solutions on LinkedIn
    • Rachel Losser on Instagram: @losserconsultingsolutions
    • Rachel Losser on TikTok: @losserconsultingsolutions
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    51 mins
  • 130: Rigged bids, fake deadlines, and going 181x over budget

    130: Rigged bids, fake deadlines, and going 181x over budget
    Jul 29 2026
    A $6.9 million estimate. A $1.25 billion catastrophe. How fake deadlines, a rigged bid, and a steering committee allergic to bad news turned a routine payroll migration into one of the biggest project disasters in Australian history. What happens when project leadership treats risk management as optional, decision making gets diffused across committees, and a hard deadline turns out to be completely negotiable? You get one of the most instructive project failure case studies in project management history — and in this episode, Kim and Kate pour it out one painful lesson at a time. The subject is Queensland Health, the public healthcare provider for the Australian state of Queensland, employing roughly 85,000 people across about 300 sites. In 2005, their legacy payroll vendor gave them three years' notice: support ends June 30, 2008. Sounds like plenty of runway — until the organization waited two of those three years to act. By the time a consultant named Terry Burns (remember that name) ran the procurement and IBM signed a contract in December 2007, the original $6.9 million estimate had ballooned to a $98 million contract with just six months to deliver a system covering more than 24,000 unique payroll combinations. Why does this matter for project managers and leaders? Because almost nothing that went wrong here is exotic. Late project intake. Governance where a transition team, a steering committee, and an IT department all had partial authority but no single decision-making structure. Two weeks — total — for requirements gathering on a nine-figure program. A "lift and shift" strategy that preserved every broken process and demanded 2,500 custom software configurations to replicate them. As Kim and Kate walk through it, the episode becomes a masterclass in how ordinary project management failures compound into organizational catastrophe. The discussion highlights are equal parts horrifying and hilarious. There's the program's actual internal slogan, taken straight from the project materials: "Plan A or Die" — no continuity plan, no risk mitigation, no fallback. There's the June 2008 deadline that came and went with a simple change request and some extended support from the legacy vendor, prompting Kate's sharp observation that the date was fake and not fake at once: end-of-life risk is real even when the cliff turns out to be movable. There's the UAT phase in June 2009 that surfaced 2,422 severe defects — after which the steering committee simply reclassified high-severity defects as lower severity so the dashboards would show enough green to proceed. Watermelon project, indeed. And when frontline payroll staff kept failing the system in testing, leadership's answer was to remove the requirement for business sign-off entirely. The go-live in March 2010 delivered the reckoning: 35,000 payroll anomalies, roughly $400 million in accidental overpayments, zero-dollar paychecks for healthcare workers, and government debt collectors hounding nurses for money they never asked to receive. Queensland ultimately hired a thousand staff to manually prop up the new system — a 40 percent increase in labor over the old one — with a projected five-year cost to taxpayers of $1.25 billion. The commission of inquiry that followed, led by the Right Honourable Richard Noel Chesterman, revealed the final twist: Terry Burns, a former IBMer, had leaked a competitor's bid specs to IBM and browbeaten the selection panel into rescoring until IBM won. And when the state sued? A release buried in the fine print of a change order had signed away its right to litigate. Grab a drink and join us. Quotes from the Episode "Everyone's in charge, so no one's in charge." — Kate "If you've got a deadline, question the deadline." — Kim "I've heard the term watermelon project where they're green on the outside and red on the inside." — Kim "And you are paying that company that you're hiring to learn." — Kate "But ultimately, if your project options are plan A or die. Maybe sometimes the best option is die." — Kim Practical Takeaways Governance and decision rights — When multiple bodies share authority without a single decision-making structure, accountability evaporates ("everyone's in charge, so no one's in charge"). Deadline validation — Interrogate whether a project deadline is a true constraint or a negotiable date, and what options (like extended vendor support) exist beyond it. The watermelon project pattern — Recognizing status distortion, including reclassifying defect severity and removing sign-off requirements to force green dashboards. Parallel run as cutover risk mitigation — Why replacing a legacy business-critical system requires side-by-side operation and validation before go-live. Procurement integrity and vendor selection — The risks of conflicts of interest in vendor selection, of choosing a vendor with no prior experience delivering the solution, and of unreviewed ...
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    39 mins
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