111 - Top Shelf Replay: How do you start a hard conversation?
Release Date: 10/29/2025
Project Management Happy Hour
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,...
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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....
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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...
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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...
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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...
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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...
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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! JOIN THE...
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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. ...
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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,...
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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...
info_outlineEver 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:
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Recognize when a conversation becomes crucial: differing opinions, high stakes, and strong emotions.
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Avoid the “fool’s choice”—the false belief that you must choose between honesty and peace.
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Create a shared pool of meaning, so everyone’s ideas and emotions contribute to better decisions.
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Use “Start With Heart” to keep your cool and focus on what you really want—for yourself, others, and the relationship.
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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).
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