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114 - Happy Hour Chatter: What PMs Really Do, Fear in Decision-Making, and Lessons from Going solo

Project Management Happy Hour

Release Date: 12/09/2025

122 - Kate puts Kim through the worst meeting hells our listeners could dream up: a PM HappyHour role play show art 122 - Kate puts Kim through the worst meeting hells our listeners could dream up: a PM HappyHour role play

Project Management Happy Hour

Boss fights and boardrooms. Kate puts Kim through meeting hell in this tabletop roleplay episode. Kate: “Help me torture Kim.” That was the prompt. What followed was a meeting dungeon built from listener-submitted horror stories, tabletop chaos, and the exact kinds of project meetings that make smart people question their career choices. In this April Fool’s episode of Project Management Happy Hour, Kate becomes game master and throws Kim into a gauntlet of cursed kickoffs, bloated status meetings, executive dodging, and stakeholder nonsense. It’s funny because it’s absurd. It lands...

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121 - Top Shelf Replay: Embracing the Escalation show art 121 - Top Shelf Replay: Embracing the Escalation

Project Management Happy Hour

Escalation: it’s a word that can make even experienced project managers tense. But what if you approached it as a tool rather than a threat? In this Top Shelf Replay of Project Management Happy Hour, we revisit the classic episode “Embracing De-escalation,” exploring how savvy project managers use escalation to enhance visibility, make informed decisions, and navigate risk—without losing their cool. Hosts Kim and Kate dive into the nuances of escalation, showing how the best project leaders balance assertiveness with thoughtful communication. Far from being a reactive panic button,...

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120 - How smart teams talk themselves into Failure, with Dr. Bill Brantley show art 120 - How smart teams talk themselves into Failure, with Dr. Bill Brantley

Project Management Happy Hour

Why do smart teams still deliver failed projects? Most project failures don’t begin with a catastrophic mistake. Instead, they begin with small deviations—minor compromises that seem harmless in the moment. A warning sign gets ignored. A shortcut becomes acceptable. A risk is acknowledged but tolerated because “nothing bad happened last time.” Over time, those deviations quietly become the new normal. In this episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson sit down with Dr. Bill Brantley to explore one of the most dangerous patterns in project leadership:...

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119 -  TSR: They told me I’m ‘too nice’?? show art 119 - TSR: They told me I’m ‘too nice’??

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...

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118 - PM Turf Wars: Sharing your projects with other Project Managers show art 118 - PM Turf Wars: Sharing your projects with other Project Managers

Project Management Happy Hour

"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. Very often, you aren't the "one PM to rule them all" on your project - you may have other PMs involved that you need to work with. But how do you decide who does 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...

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117 - Top Shelf Replay: Say No by Saying Yes show art 117 - Top Shelf Replay: Say No by Saying Yes

Project Management Happy Hour

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,...

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116 - How to quit your job and completely fail as a PM contractor show art 116 - How to quit your job and completely fail as a PM contractor

Project Management Happy Hour

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.  

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115 - Top Shelf Replay: Trust Bricks show art 115 - Top Shelf Replay: Trust Bricks

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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114 - Happy Hour Chatter: What PMs Really Do, Fear in Decision-Making, and Lessons from Going solo show art 114 - Happy Hour Chatter: What PMs Really Do, Fear in Decision-Making, and Lessons from Going solo

Project Management Happy Hour

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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113 - Top Shelf Replay: Stage direction in the boardroom show art 113 - Top Shelf Replay: Stage direction in the boardroom

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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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.
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