114 - Happy Hour Chatter: What PMs Really Do, Fear in Decision-Making, and Lessons from Going solo
Release Date: 12/09/2025
Project Management Happy Hour
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:...
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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...
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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. ...
info_outlineKim 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.
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