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Project Management Happy Hour

Kim Essendrup and Kate Anderson
Project Management Happy Hour
Último episodio

135 episodios

  • Project Management Happy Hour

    126: "What's your AI Strategy?" Handling the Executive who wants AI in everything

    03/06/2026 | 39 min
    You know the moment.
    Your project plan is solid. The scope is defined. The team is ready. Then an executive walks by and casually asks:
    "Can we just make this AI?"
    Suddenly you're no longer managing a project. You're managing expectations, buzzwords, corporate excitement, and whatever article someone just read on the flight home from a conference.
    In this episode, Kim and Kate tackle the question nearly every project manager is hearing right now: What's your AI strategy?
    They discuss why this isn't the first technology hype cycle we've lived through, how to respond when leaders want AI without knowing what they actually want AI to do, and why saying "yes" doesn't mean committing to anything.
    Along the way, they unpack executive AI buzzwords, governance concerns, AI productivity myths, vibe coding, project management tools, and where AI genuinely helps versus where it's mostly creating noise.
    Most importantly, they share practical ways to stay credible, keep your projects grounded, and avoid getting swept up in the latest technology frenzy.
    So grab a drink, pull up your RAID log, and let's talk about surviving the AI gold rush without losing your mind.
    🎙️ Spicy Quotes from the Episode
    "My eyes actually fell all the way out of my head and are rolling down the street. I actually can't see anything anymore." — Kate
    "Your project cannot be more mature than the organization." — Kim
    "AI is not like magic pixie dust you sprinkle on your project and suddenly magical things happen, right?" — Kim
    "AI is not better than you at project management. And it probably never will be." — Kate
    Key Concepts & Takeaways
    AI Hype Cycles Are Not New
    The technology changes, but the executive behavior doesn't.
    Before AI there was cloud. Before that there was blockchain. Every generation gets its must-have technology that promises massive transformation. Project managers shouldn't panic when AI becomes the topic of every conversation. The important skill isn't becoming an AI expert overnight. It's understanding enough to have an informed conversation.
    Other key concepts covered: 
    Learn the Language Without Drinking the Kool-Aid

    Don't Let Projects Outrun Governance

    Ask "How?" Before You Ask "Why Not?"

    AI Is Only As Good As Your Data

    AI Helps More With Starting Than Finishing

    Closing Reflection
    The next time someone asks, "What's our AI strategy?" maybe the better question is:
    "What problem are we actually trying to solve?"
    Because the organizations that benefit most from AI probably won't be the ones chasing every new buzzword—they'll be the ones that stay focused on outcomes while everyone else is getting distracted by the hype.


    🔗 Links & Resources Mentioned
    Project Management Happy Hour Website 

    PM Happy Hour Membership
  • Project Management Happy Hour

    125: How to survive the AI landscape as a PM with PMI's Dr Kelly Heuer

    20/05/2026 | 58 min
    AI is changing work fast enough to give every project manager emotional whiplash. New tools, new workflows, new expectations… and somehow you're still expected to hit deadlines, manage stakeholders, and explain for the fifth time why the project scope changed after leadership changed the entire business strategy.
    In this episode, Kim and Kate sit down with Kelly Heuer from Project Management Institute to talk about the skills that actually survive industry shifts, changing technology, and whatever shiny new buzzword LinkedIn is obsessed with this week.
    They unpack why "soft skills" are actually the hardest skills in project management, how business acumen separates strategic PMs from task trackers, and why learning to navigate ambiguity matters more now than memorizing formulas from the PMP exam.
    The conversation also dives into the uncomfortable reality that project success is rarely about perfectly following the original plan. Sometimes the real job is realizing the plan should change in the first place.
    Along the way, they cover durable vs. perishable skills, why varied career experience is secretly a superpower, how PMs can become more effective strategic partners, and why "say the thing" might be the most important career advice you'll hear all year.
    Grab a drink, question your project charter, and let's get into it.

    Guest Bio
    As Vice President of Learning at the Project Management Institute (PMI), Dr. Kelly Heuer brings over two decades of experience in higher education to lead PMI's Learning division. She oversees a global portfolio including professional standards, publications, live and enterprise training, and digital learning products that equip project professionals worldwide to drive project success.
    Kelly holds multiple degrees in philosophy, including an AB from Harvard and an MA and PhD from Georgetown University. She began her career at Georgetown, helping launch the university's first Massive Open Online Course (MOOC) in bioethics and co-founding its ethics and social innovation lab. She most recently served as Vice President of Learning Experience at edX, driving learning strategies and digital innovation across the company's portfolio.
    As the first in her family to pursue higher education, Kelly is passionate about mentoring first-generation students, coaching formerly incarcerated individuals, and supporting colleagues exploring alternative career paths. She lives in Brooklyn with her partner, Arjun, and their two children, chess enthusiast Kiran and aspiring explorer Ryan.


    🎙️ Quotes from the Episode
    "If you're thinking the thing, if you're wondering the thing, if you're confused about the thing, say the thing." — Kelly
    "Human skills are more important than artificial intelligence skills." — Kate
    "Soft skills are the hardest part of project management." — Kate
    "Comfort with ambiguity. It's acknowledging change as a constant, not as something you're going to design around or manage your way away from." — Kelly


    📌 Key Concepts & Takeaways
    Durable Skills vs. Perishable Skills
    Technical skills expire faster than most PMs want to admit. Tools change. Platforms die. Entire workflows disappear. But communication, business acumen, stakeholder management, adaptability, and decision-making under uncertainty keep paying dividends across every phase of a career.
    "Say the Thing"
    One of the biggest career mistakes is staying quiet because you don't want to sound inexperienced, difficult, or slow the room down. Asking the uncomfortable question early often prevents much bigger problems later.
    Business Acumen Is the Real Career Multiplier
    Technical project management skills are still important—but they're table stakes now. The PMs who move into larger, more strategic work understand value, organizational priorities, market shifts, and executive decision-making.
    Varied Experience Builds Better PMs
    Working across industries, teams, and business problems creates stronger long-term judgment. Diverse experience teaches pattern recognition, adaptability, and strategic thinking in ways repetitive specialization sometimes doesn't.
    Learning Happens in the Field
    Courses, books, and certifications matter—but they're only part of the equation. Real growth happens when people practice skills, make mistakes, reflect, adapt, and try again in live environments.


    Discussion Highlights
    One of the strongest threads throughout the conversation was the idea that project managers are being forced to rethink what makes them valuable. Kelly talked about how rapidly technical skills are expiring, referencing research showing that the "half-life" of professional skills has dropped dramatically over time. The implication wasn't that technical knowledge no longer matters—it absolutely does—but that technical expertise alone is no longer enough to sustain a long career.
    Kate pushed hard on the idea that so-called "soft skills" have always been the hardest part of the job. Not the formulas. Not the software. The real challenge is learning how to navigate people, power dynamics, ambiguity, and shifting business priorities without becoming either invisible or terrifying.
    The conversation also got surprisingly honest about career growth. Kate talked about how asking "dumb questions" early in a career feels different than asking them after twenty years of experience. Early on, vulnerability makes you non-threatening. Later, the exact same question can suddenly feel like a high-level strategic critique because people assume expertise from seniority alone.
    Kim brought up another tension a lot of PMs quietly experience: organizations wanting project managers who have done the exact same project fifteen times already. That led into a larger conversation about how difficult it can be for experienced PMs with varied backgrounds to communicate the value of transferable skills during hiring processes.
    And naturally, because this is PM Happy Hour, the conversation eventually circled back to the reality that no amount of theory replaces getting kicked by the metaphorical horse yourself.
    Sometimes literally.


    Practical Takeaways
    Stop treating stakeholder communication as a "soft" secondary skill. It's one of the highest leverage parts of the job.

    When joining a new project or industry, focus first on understanding how the business creates value—not just how the process works.

    Ask questions earlier, especially when something feels unclear or inconsistent. Waiting usually makes problems more expensive.

    Revisit project success criteria regularly during long initiatives. The business environment may have shifted even if the project plan hasn't.

    If your background is varied, learn how to frame it as strategic adaptability rather than lack of specialization.

    Build learning habits that fit into real work. Continuous learning matters more now because many technical skills become outdated quickly.

    Don't confuse sticking to the original plan with leadership. Sometimes leadership means recognizing the plan itself needs to evolve.


    Closing Reflection
    Project management used to reward the people who could control complexity.
    Now it increasingly rewards the people who can navigate uncertainty without freezing, adapt without losing direction, and keep delivering value even while the ground underneath the project keeps moving.
    That's a very different skill set.
    And honestly? Probably a much more human one.
    🔗 Links & Resources Mentioned
    Project Management Institute (PMI)

    PMI Learning Resources

    The Five Dysfunctions of a Team

    Death by Meeting

    PM Happy Hour Membership

    PM Happy Hour Website

    Kelly Heuer on LinkedIn
  • Project Management Happy Hour

    124: Drowning in Tasks: How Successful PMs Organize the Chaos

    06/05/2026 | 56 min
    If your to-do list is 47 items long, your Slack won't shut up, and you ended the day thinking, "Cool… but what did I actually accomplish?"—welcome. You're among friends.
    In this episode, Kim and Kate take on the very real, very unsexy side of project management: figuring out how to manage your own work when everything (and everyone) is demanding your attention.
    This isn't about finding the perfect tool or building a prettier dashboard. It's about surviving—and actually functioning—in an interrupt-driven world where emails breed overnight, notifications multiply, and every task somehow feels urgent.
    They get into what actually works: setting a North Star for your week (yes, only a few priorities), getting tasks out of your brain before they haunt you at 10 PM, and why some tasks are secretly just traps that create even more work (looking at you, boomerang tasks).
    Also: a gentle reality check—you're not supposed to do everything.
    Grab a drink, ignore your inbox for a bit, and let's figure out how to organize the chaos without losing your mind.
     
    🎙️ Spicy Quotes from the Episode
    On chaos: "If you have no North Star point, the rest of your week is going to feel like chaos." — Kate
    On overwhelm: "The human brain can't really process all of that. We can process having three priorities." — Kate
    On modern work life: "Notifications trying to notify you about notifications." — Kim
    On control: "Manage your tasks—don't let your tasks manage you." — Kim
    On reality: "There has to be things you can stop doing." — Kate

    📌 Key Concepts & Takeaways
    The North Star Rule (a.k.a. calm down, it's not 47 priorities):
    Pick 2–3 things that actually matter this week. Everything else? It either supports those—or it waits.
    Get It Out of Your Head (your brain is not a storage system):
    If you're trying to remember everything, you've already lost. Write it down somewhere reliable so your brain can stop yelling at you.
    Boomerang Tasks (aka "this will take 5 minutes" lies):
    Some tasks look small but come with hidden side quests. Know the difference before you commit.
    Interrupt-Driven Work Is the Default—Act Accordingly:
    You're not bad at focusing. Your environment is designed to destroy it. Filter, batch, and control when you engage.
    Physical Lists Still Work (and no, it's not just nostalgia):
    Sometimes the best productivity hack is using something that doesn't ping, buzz, or open 12 tabs.
    Reflection Beats Hustling Harder:
    End your day or week by asking: what actually mattered? Not what felt urgent—what mattered.
    Not Doing Things Is a Skill:
    You don't need a better system. You probably need fewer things on your list.
     
    🔗 Links & Resources Mentioned
    PM Happy Hour Website: https://www.pmhappyhour.com
    Scripts & Resources: https://www.pmhappyhour.com/scripts
    Books Mentioned:
    Essentialism by Greg McKeown

    Getting Things Done by David Allen

    Conquer the Chaos by Clate Mask

    Tools Referenced: Notion, Evernote, OneNote, Smartsheet, Jira, Monday
  • Project Management Happy Hour

    123 - Hungry Hungry HPPOs - managing loud personalities with Evan Unger

    14/04/2026 | 1 h
    If your weekly calendar looks like the loser in a state fair quilt competition - just solid blocks of mismatched colors with no room to breathe - this episode is for you. Today, we're joined by facilitation expert Evan Unger to talk about a topic that Kate and Kim geek out over: meetings. Specifically, why most of them are terrible, how they drain organizational productivity, and exactly what you can do to fix yours.
    We also tackle one of the most delicate situations in project management: how to handle the HIPPO (Highest Paid Person's Opinion) when they barge into your meeting and try to completely take over the flight controls. Grab a drink, settle in, and let's get into it.
    🎙️ Spicy Quotes from the Episode
    On owning your time: "If you don't own your calendar, you don't own your life." – Kim

    On the true cost of bad meetings: "If you're spending 50% of your time in meetings [that are less than 50% effective], you're literally going to spend a year's worth of your life and hours in meetings in under a decade. How organizations tolerate this, I have no idea." – Evan

    On visibility: "Every meeting is a leadership moment." – Evan

    On career survival: "We don't want to make hippos wrong because there's career limiting interventions. I mean, let's be honest, they have power and authority over us." – Evan

    On meeting math: "Nine things on an agenda in a 40-minute meeting is 4.44 minutes per agenda item. That's just not possible. It is better to end early than to run over." – Kate

    📌 Key Concepts & Takeaways
    The Meeting Metaphor (Flying the Plane): Every meeting needs three phases. Takeoff (getting aligned), the Flight (the process/agenda), and Landing (saving 5-10 minutes at the end to secure next steps and accountability). Do not run out of fuel and crash. Leave time to land the plane.

    The POPRA Model for Meeting Prep: Don't accept or run meetings without knowing these five things:

    Purpose: Why are we here?

    Objectives: What are the specific deliverables or decisions needed?

    Process: What is the agenda?

    Roles: Who is the ultimate decision-maker? Who is the SME?

    Agreements: How will we interact and handle disagreements?

    The AREA Model for Taming the HIPPO: When a senior leader tries to bulldoze the process:

    Acknowledge: Validate their right to a point of view without necessarily agreeing.

    Reframe: Tie the conversation back to the project's purpose or objectives.

    Engage: Ask neutral questions to open the floor ("Would you be willing to listen to other perspectives on this?")

    Align: Bring the group's feedback back to the leader to help them make a better, more informed decision.

    The Power of Simultaneous Chat: To break the dominance of the loudest voices (and the HIPPO), ask a question and have everyone type their answer in the chat without hitting enter. On the count of three, everyone submits at once. This holds space for introverts, junior staff, and non-native English speakers to contribute without getting run over.

    Process is Your Shield: If a leader has a strong opinion, use process structure to ensure all sides are heard. Force the group to list "Pros" before "Cons," or use a timer to keep long-winded talkers (even the boss) in check.

    🔗 Links & Resources Mentioned
    Connect with Evan Unger: Find Evan on LinkedIn (look for the blue/black check shirt and the impish grin, not the doctor!). Note: Evan is generously offering $2,000 off a seat in his training program for PM Happy Hour listeners!

    Books Mentioned: The Five Dysfunctions of a Team and Death by Meeting by Patrick Lencioni.

    Join the Conversation: Want to geek out about project management with us? Check out the PM Happy Hour membership site at https://www.pmhappyhour.com/membership.

    Say Hello: Hit us up on Facebook at PM Happy Hour or find our contact info on the website under "About Your Hosts."
  • Project Management Happy Hour

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

    03/04/2026 | 1 h 14 min
    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 because it's true.
    "My dice are green like all of my status reports."
    The setup is playful. The meeting pain is not.
    Kim tries to survive a kickoff with distracted leaders, a giant update meeting nobody needed, a build-versus-buy conversation where nobody wants to own the decision, and a phase gate where "close enough" suddenly becomes everyone else's problem. As the dungeon gets worse, you hear what experienced project managers actually do under pressure: reset the room, cut through noise, force clarity, and keep momentum when everyone else is drifting.
    "This is how Kim would operate in a meeting."
    That's what makes this episode so fun - and insightful. The dice are a toy. The project management is real.
    If you've ever had a sponsor with a hard stop in ten minutes, a technical lead who gets defensive the second testing reveals a problem, or a leadership team that turns every decision into one more meeting, this episode will feel painfully familiar.
    "We survived that near miss. It's okay. Next time we'll be okay."
    A lot of bad meeting habits stick around because teams get used to surviving them. This episode turns that reality into entertainment—and into a sharp reminder that surviving dysfunction is not the same as managing well.
    And because it's PM Happy Hour, the whole thing is loaded with lines that hit for PMs immediately.
    "We can't food bribe our way out of every meeting disaster."
    "I need you to do a speed run of a project."
    "It is 2 hours long."
    That last one might be the most terrifying quote in the whole episode.
    What you'll hear in this episode
    a kickoff already heading off the rails

    a giant status meeting from hell

    executive indecision in full view

    a technical lead bringing equal parts talent and chaos

    a release decision that gets messy fast

    Key project management takeaways
    Get to purpose fast.

    Push for the real decision.

    Keep updates short and relevant.

    Make the cost of delay visible.

    Manage the room, not just the agenda.

    Don't let technical defensiveness hijack the issue.

    Find the compromise that keeps momentum.

    If your work depends on steering messy rooms, stubborn stakeholders, and overloaded calendars toward an actual outcome, this episode will feel like both comedy and continuing education.
    Love our content? Then join the PM Happy Hour membership at pmhappyhour.com/membership
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Acerca de Project Management Happy Hour
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!
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