Project Management Happy Hour

Have you ever gotten feedback that made you want to flip a table because it was both insulting and totally useless? In this Top Shelf Replay, we revisit "They Told Me I'm Too Nice" and break down what that kind of vague feedback is really doing (sometimes gendered, almost always inactionable), why it hits so hard, and how to respond without spiraling - or people-pleasing your way into a personality transplant. Then we go beyond the original episode with practical, real-world tactics: how to ask better follow-up questions, how to force examples without sounding defensive, how to "prime" your manager before a meeting so you get usable feedback, and how to figure out whether your boss is actually trying to coach you… or just dumping drive-by advice from a book they skimmed on a flight. If you lead people, we also flip the lens: how to avoid giving your team confusing feedback that basically translates to "please be a different person," and how to coach toward outcomes instead of vibes. Key actionable insights Treat vague feedback as a starting point, not a conclusion. Thank them, then ask them to say more until you have something observable and specific. Ask for examples on demand. Use: "Can you tell me about a time I did that well?" or "Who does that really well?" This forces specificity and gives you a model to study. Match your effort to their effort. If it was a drive-by comment, don't burn three weeks of anxiety trying to decode it. If they clearly invested in you, invest back proportionally. Prime your manager before a meeting so they know what "good" looks like. Tell them your goal (scope agreement, signature, commitment, decision) so their feedback anchors to outcomes, not vibes. If you want feedback, specify what kind you want. "I'm not looking for grammar edits—I want alignment on strategy" is a transferable skill for stakeholder reviews and exec comms. For managers: don't "coach" people who don't want coaching. Find out what they want first, or you'll waste time and damage trust. Key Quotes - "I don't need you to be my Grammarly when you review this document. I need to know if we are strategically aligned." "Below the line? You just crossed the line, buddy." Love our content? Then join the PM Happy Hour membership at pmhappyhour.com/membership

"Three PMs walk into a bar: a business PM, an IT PM, and a Vendor PM…" Sounds like a bad joke, but if you don't get it right - the joke will be your project. In this Top Shelf Replay episode, Kim and Kate revisit an episode that was originally inspired by one of their listeners. Very often, you aren't the "one PM to rule them all" - you may have other PMs involved in your project that you need to work with. But how do you decide who is what, and how do you prevent turf wars from turning your project into a slow-motion train wreck? In this episode, we ditch the corporate fluff to dive into the messy reality of projects with "too many cooks". We discuss how to navigate the friction between different project management roles, how to handle "useless" vendor PMs who won't manage their own resources, and what to do when an executive buyer bypasses you to talk directly to the vendor. You'll learn how to look "one level up" in the hierarchy to identify what actually drives your counterparts and how to draw professional boundaries that keep you in the driver's seat. In this episode, you'll learn: How to use the "Hierarchy Hack" to uncover your counterparts' hidden motivations. Strategies for handling a vendor PM who refuses to do their job. Why a high-level human conversation beats a technical tool every time. The "Time and Materials" pivot to force vendor accountability. How to professionally block an executive from undermining your role. From this episode: "The first thing to do is to have a conversation and, honestly, call it out in the open." — Kate "One of the ways I like to think about situations like this is one level up in the hierarchy." — Kim "I've been like, 'No, you can talk to me. Shut up, talk to me.'" — Kate "If I and my team are going to be held accountable... I have to be able to plan what we're accountable for." — Kim Love our content? Then join the PM Happy Hour membership at pmhappyhour.com/membership

Project managers are constantly told they need to "learn how to say no." But in the real world—especially when the ask comes from a sponsor, executive, or important customer—just saying no often isn't productive, strategic, or even possible. In this Top Shelf Replay episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson revisit one of the show's earliest "Appetizer" episodes: Say No by Saying Yes, originally aired in 2017. Short, deceptively simple, and still painfully relevant, this episode breaks down a technique that helps project managers protect scope, schedule, cost, and sanity—without sounding combative or inflexible The core idea is straightforward: Instead of responding to tough requests with a flat "no," you respond with "yes—but" or "yes—and here's what that would require." "Yes, we can do it faster—but it will require triple the resources." "Yes, we can release both languages at once—but we'll need more budget or a delayed launch." "Yes, we can remove that resource—but you'll need to help me explain the downstream impact to the sponsor." This approach reframes the conversation away from emotion and into trade-offs, which is where real project leadership lives. As the conversation unfolds, Kim and Kate explore why this technique works so well psychologically. Leaders—especially busy executives—often don't have full context. Their "ridiculous asks" aren't always malicious; they're frequently driven by incomplete information, pressure from above, or a misunderstood business constraint. Saying "yes" first acknowledges their goal, signals partnership, and keeps them engaged long enough to hear reality The episode also connects this technique to a broader leadership pattern the hosts have refined over the years: what they now describe as "affirm, caution, query." You affirm the request. You surface the risk or constraint. You return the decision to the person who actually owns it. In other words, you stop absorbing problems that don't belong to you—and you stop shielding leaders from the consequences of their own decisions. The replay discussion expands the idea further, touching on burnout, executive presence, and why many project managers get stuck in a defensive "control mindset" around the triple constraint. Kim and Kate argue that stepping back—mentally taking off the project manager hat and putting on the sponsor's hat—makes these conversations easier, calmer, and more strategic. When you focus on outcomes instead of guarding boundaries, you stop reacting and start partnering. There's also an unexpected but memorable parallel: gentle parenting. The same structure used to redirect an emotional five-year-old ("I see what you want—but here are your options") turns out to work remarkably well with stressed executives, difficult customers, and unrealistic stakeholders. You don't remove agency; you structure it. Ultimately, this episode is about more than saying no politely. It's about changing the power dynamic—from executor to partner. From order-taker to decision facilitator. From "blocking progress" to helping leaders make informed choices. If you've ever been handed an impossible deadline, an under-funded scope change, or a request that made your stomach drop, this episode gives you language, structure, and confidence to respond without burning trust—or yourself.

Thinking about going contractor? Kate and Kim share how they each left corporate and made the leap—two very different stories (burnout vs acting early) with the same core truth: contracting is built on relationships, reputation, and value… not job boards and commodity rates. We cover how to know if you're ready, why sales is part of the job, what to watch out for (hello, 2008), and how to avoid racing to the bottom. Want us to teach the full process with scripts + steps? Head to http://pmhappyhour.com/be-free.

As project managers, we spend a lot of time talking about tools, processes, and delivery frameworks—but far less time talking about the invisible structure that holds projects together: trust. In this Top Shelf Replay episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson revisit one of the show's earliest and most enduring concepts: Trust Bricks. Originally recorded in 2018, this short but powerful episode explores how trust is built—not through grand gestures or heroic saves—but through consistent, everyday actions that compound over time. The core idea is simple: trust is predictability. When you repeatedly do what you say you'll do—whether that's sending meeting notes on time, honoring estimates, or showing up prepared—you lay one small Trust Brick at a time. Over weeks, months, and years, those bricks form a structure strong enough to withstand missed deadlines, bad news, or the occasional broken promise. Kim and Kate break down why Trust Bricks matter so much in project environments: Teams are more honest with you when they trust you Estimates improve when people believe they won't be punished for telling the truth Difficult conversations become easier when everyone believes you're on the same side Sponsors give you more latitude when your track record is consistent The conversation also explores what happens when trust breaks—and how the same Trust Brick approach can be used to rebuild credibility. Rather than trying to restore trust with a single "big win," the hosts argue that rebuilding starts small: partial deliverables, frequent check-ins, and deliberately meeting micro-commitments until confidence is restored. In the replay commentary, Kim and Kate reflect on how their thinking has evolved since the original recording. They discuss: The role of showing up consistently, even when no explicit promise was made How trust operates differently in virtual and remote teams Why strong performers can accidentally set expectations that lead to burnout How leaders vary widely in how much "trust damage" they tolerate before overreacting The episode also revisits the journey of Trust Bricks beyond the podcast, including Kim's experience delivering a TEDx talk on the topic and refining the framework into three enduring lessons: You are always building or breaking Trust Bricks—whether you realize it or not Missed expectations don't pause trust building; they actively tear it down Unspoken expectations are the fastest way to accidentally destroy trust This episode is a reminder that trust isn't soft, vague, or optional—it's a core delivery skill. If you want stakeholders who back you, teams who tell you the truth, and projects that don't require constant firefighting, it starts with sweating the small commitments. The next time you make a commitment—big or small—ask yourself: Am I laying a brick… or cracking one? Check out Kim's TEDx talk at trust-bricks.com or on the TED youtube channel Want more PM reality without the fluff? Join the PMHH membership for courses, templates, community, and direct access to Kate and Kim. https://pmhappyhour.com/membership

Kim and Kate settle in for a classic PM Happy Hour episode — the kind where the drinks are metaphorical, the conversation is wandering in the best way, and the insights sneak up on you. This one covers three big themes that hit close to home for project managers, leaders, and anyone who's ever had to keep a project — or a career — moving forward despite chaos. It starts with a deceptively simple question: How do you describe what a PM actually does for a living? Kim brings his favorite one-sentence description, and Kate immediately pokes at it (lovingly) to reveal the gaps between a tidy definition and the messy reality of day-to-day PM work. Together they break down the core functions that aren't on the job description: expectation-setting, alignment-building, timeline-translating, political-atmosphere-reading. Yes, PMs manage plans — but they also manage humans, assumptions, ambiguity, and the definition of "done," which shifts more than anyone wants to admit. The conversation hits on why this matters so much for stakeholder alignment, project success, and your own sanity. From there, the discussion pivots to fear in decision-making — specifically, how fear quietly creeps into choices that leaders and teams make every day. Kim shares a general's perspective on why big decisions get stalled ("people won't make hard decisions if it forces them to change"), and Kate adds their own real-world examples of hesitation disguised as caution. They unpack how fear leads to risk-avoidant behavior, analysis paralysis, unnecessary escalations, or decisions that look safe but actually create more work downstream. This part of the conversation digs into the psychology of leadership, the emotional drivers behind "bad" decisions, and how project managers can spot when fear — not logic — is driving a stakeholder's position. Along the way, they also reflect on why PMs sometimes avoid decisions themselves, even when they know the right call. Finally, Kim and Kate open up about what they've learned from going out on their own and being their own boss — the good, the bad, and the "wow, nobody warned me about this part." They talk candidly about leaving stable corporate paths, the discomfort of striking out solo, the thrill of autonomy, and the realities of running a business while also running your own mental health. Listeners get the inside picture of what independence really looks like: the freedom, the discipline, the failures, the self-doubt, and the eventual confidence that comes from owning your decisions and your livelihood. This segment offers honest lessons learned for anyone considering consulting, freelancing, starting a business, or just trying to build a healthier professional life. Through all three topics, the conversation carries the familiar PMHH rhythm: candid laughter, a little self-roasting, and the practical wisdom that comes from having been around the block more times than they're willing to count. It's not a tidy thematic episode — it's better than that. It's a Happy Hour catch-up that turns into real insight about project leadership, stakeholder psychology, career development, and the everyday challenges PMs face. If you've ever struggled to explain your job, watched fear take over a meeting, or wondered what life might look like outside the corporate bubble, you'll find something in this episode that feels uncomfortably familiar — and maybe a little inspiring. Want more PM reality without the fluff? Join the PMHH membership for courses, templates, community, and direct access to Kate and Kim. https://pmhappyhour.com/membership

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, and emotional intelligence behind managing senior stakeholders, building trust, engineering alignment, and yes…occasionally staging a fight to get everyone to "yes." Get ready—this episode is full of real-world policy drama, tribal gaming insight, negotiation theater, and powerful lessons for any PM trying to move from "task master" to strategic leader. Great Quotes From the Episode "Never ask a question you don't already know the answer to." "These aren't meetings—they're Kabuki theater." "Nothing brings people together like a common enemy." "If you don't let them vent early, they will vent later—and at the worst possible moment." "Policy takes years. Tech takes a week." What You'll Learn (Key Outcomes) 1. How Senior Leaders Actually Negotiate Sheila breaks down what it takes to orchestrate alignment among executives, attorneys, policymakers, and stakeholders—none of whom work for you, all of whom report to someone powerful. 2. The Secret Skill That Makes PMs Into Leaders How listening (really listening) becomes your most strategic tool at the senior level. 3. Managing High-Stakes Meetings Without Losing Control Why should one person guide the conversation? How to posit their positions to draw out quiet or hesitant stakeholders. How to keep the emotional temperature safe but not silent. 4. The Power of the 'Safe Zone' Why must you create a space where stakeholders can speak unfiltered, off-record, and without fear of political consequences. 5. Relationship-Building: The Long Game Happy hours, lunches, hallway conversations—how the "work between the work" makes the boardroom possible. 6. The Art of the Staged Fight Why conflict must be visible. Why letting people "win" (feel like they won) is essential. Why is the real battle scripted before the meeting starts? 7. Using Common Ground—and Common Foes When "we all want the same thing" works. When "the real enemy is over there" works even better. 8. How to Lock Down Decisions So They Don't Backslide Why immediate execution is key. How implementation momentum prevents second-guessing. 9. Lessons Kate & Kim Learned 8 Years Later Why parts of this episode hit harder after a decade of PM leadership. How letting emotions into the meeting leads to better outcomes. What PMs often overlook when they're new to senior-level facilitation. If you want to level up from "planner of tasks" to leader of leaders, this replay is essential listening. Whether you're negotiating policy, driving enterprise transformation, or just trying to get two teams to agree on anything—Sheila's battle-tested tools will help you steer the room, keep your cool, and bring people with you. ABOUT OUR GUEST, SHEILA MORAGO Sheila Morago is the Executive Director of the Oklahoma Indian Gaming Association. OIGA has 30 member tribes and numerous associate members. Oklahoma now ranks third in the United States in gaming revenue, with 118 casinos ranging from small fuel stops to full resort casinos. Prior to working for OIGA, Ms. Morago was Executive Director for the Arizona Indian Gaming Association. She has also served as the Director of Public Relations for the National Indian Gaming Association, based in Washington, D.C. Ms. Morago began her career in tribal gaming in 1994 when she was appointed Director of Marketing for the Gila River Casinos, where she built the marketing department for this...

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. About our guest: Norlander Wilson is an experimental psychologist and an orbit disruptor by calling. She is the founder and CEO of Becoma, an operational strategy firm that helps leaders, creatives, and organizations move from survival mode into clearer systems and healthier energy. Through her work, Norlander blends psychology, strategy, and system design to challenge the patterns that keep people stuck and to create ways of working that don't require self-sacrifice. She's also the host of the podcast "She Don't Work Like That, No More," where she unpacks wounded leadership patterns and reimagines what it means to build, lead, and live without breaking yourself in the process. The theme today: burnout at work, and how project managers — the people everyone counts on — get trapped in it. Norlander doesn't sugarcoat it: "Burnout is a collective conversation, especially in an organization." She calls out how burnout starts at the top. If leadership pushes 100 hours, teams assume they should push 150. If leaders are exhausted, their teams are exhausted. Burnout isn't a personal failing; it's a system failure — and PMs often absorb the blast radius. Kate opens up about their 2024 breakdown: crying daily, losing appetite except for cookies, medical leave, and the creeping belief that if they just tried harder, they could fix everything. Kim shares his own burnout and the helpless feeling of watching teammates slide into it — seeing that "day-five-I-haven't-showered look" on Zoom and wanting to save them. And then there's the half-million-dollar moment. Kate negotiated nearly $500,000/year in compensation and turned it down because walking into the building made them feel sick. Not metaphorically — physically. "I'm not getting on that wheel unless I want to." Norlander validates it: "If it's profound burnout and everything triggers you at that job, yes, it's time to leave." She gives language PMs desperately need: Capacity check-ins, not productivity interrogations Systems that hold boundaries so you don't have to Stop parenting grown adults at work — "You are not an emotional container." Let people fail so they learn the consequence, not you Kim connects it to the "mouse on the wheel" experiment — the difference between choosing to run and being forced to run. The stress chemicals — literally — are not the same. Norlander's tools for burnout prevention and burnout recovery: Audit your systems quarterly Build boundaries into SOPs Protect scheduled joy like you protect deadlines Delegate to the system, not your nervous system Kate shares how protecting Tuesday riding lessons became non-negotiable. Not because horseback riding is magic (although…it kind of is), but because no one else will protect your time but you. Norlander's toast at the end is the line we're all putting on sticky notes: "When you do find your boundary… don't compromise it for anyone." If burnout at work is starting to feel familiar — if you're living on cookies, caffeine, and dread — pull up a chair. You're not lazy. You're not failing. The system is failing you. And if you're tired of carrying the emotional labor for your entire project team, come get some backup and community. Join us at: https://pmhappyhour.com/membership © 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 change your life. 🍸 Pull up a stool at the bar—here's what we're talking about this round: 🍸 Every project manager has been there: a stakeholder meltdown, a team standoff, or that one sponsor meeting where your pulse hits 200. The question is—what do you do when the conversation turns crucial? In this PM Happy Hour throwback, Kate and Kim revisit one of their most popular and enduring episodes—based on the book Crucial Conversations: Tools for Talking When Stakes Are High by the VitalSmarts team (now Crucial Learning). They aren't paid to say this—but this book changed their lives and careers. Seventeen years after Kate's colleague first handed her this book, they still call it "the single most important leadership book for project managers." Forget the PMBOK—start here if you want to build trust, executive presence, and influence. You'll learn how to: Recognize when a conversation becomes crucial: differing opinions, high stakes, and strong emotions. Avoid the "fool's choice"—the false belief that you must choose between honesty and peace. Create a shared pool of meaning, so everyone's ideas and emotions contribute to better decisions. Use "Start With Heart" to keep your cool and focus on what you really want—for yourself, others, and the relationship. Apply "Don't-Do Statements" to set boundaries, de-escalate tension, and build empathy. From team conflicts to sponsor negotiations, this episode gives you practical, human ways to talk about hard things—and actually make things better. Kim and Kate share real-world examples from project meetings, resource battles, and even personal life to show how dialogue beats defensiveness every time. And they're not just quoting theory. Crucial Conversations is built on decades of behavioral research and communication psychology—and it's as relevant today as ever. Whether you manage projects, programs, or entire teams, mastering these techniques can level up your leadership, reduce drama, and get you promoted faster. 📚 Get the Book: Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler Available anywhere books are sold (we're not sponsored—we just love it). JOIN THE HAPPY HOUR! Want even more? Join us at pmhappyhour.com/membership to get PDUsfor episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.

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 officially redefined it: “A successful project is one that delivers value worth the effort and expense.” Dave explains how this updated definition shifts the focus from checking boxes to delivering outcomes that truly matter — and how every PM can start measuring success through value creation instead of rigid constraints. The discussion digs into PMI’s new M.O.R.E. framework — a practical mindset for modern project leaders: M – Manage Perceptions: Build trust and alignment with stakeholders. O – Own Success: Don’t just deliver; ensure the value lands. R – Relentlessly Reassess: Constantly re-evaluate priorities and adapt to change. E – Expand Perspective: See the bigger picture across business strategy, customers, and society. Dave also shares lessons from his early startup days building Gantthead.com, the dot-com crash, and how those lessons apply in today’s AI-driven project world. You’ll hear how the rise of automation is making project management more human, pushing PMs to lead through empathy, influence, and strategic insight rather than process checklists. If you’ve ever struggled with the question, “Was my project really a success?” this episode will give you a fresh, empowering way to answer it. Key Takeaways PMI’s official definition of project success now centers on value, not just time, cost, and scope. The M.O.R.E. mindset helps PMs evolve beyond administrators into strategic leaders. AI will augment, not replace, project managers — freeing them to focus on human connection and business impact. “Success” is contextual: a delayed project that delivers exceptional value can still be a win. Guest Links Learn more about PMI’s Project Success initiative: pmi.org/projectsuccess Connect with Dave Garrett on LinkedIn Explore PMI’s AI resources: pmi.org/ai 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.

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. 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

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 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

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. 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

“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! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

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 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

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 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

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. 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

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! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership