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

What if the reason your project management job search is stalling has nothing to do with your skills? On average, about 300 people apply to a single opening, and the odds of being the one who gets the offer are slim. In that market, strong project leadership isn't enough. Landing a six-figure project management role takes the same things that make projects succeed: clear decision making, a targeted strategy, and the ability to read how an organization really works.

Why "over-communicating" isn't about saying more — it's about knowing exactly what your stakeholders need to hear, and when. What happens when a project manager goes silent? According to this episode of Project Management Happy Hour, nothing good. Left in an information vacuum, stakeholders don't assume the best — they assume the worst. That single insight sits at the center of a conversation about project leadership, stakeholder communication, and the quiet skill that separates good project managers from great ones: knowing exactly what to say, to whom, and when. If you've ever been accused of "running dark" on a project, or been told to simply "communicate more" without any idea what that actually means, this episode is for you. Kate and Kim open up about their own early missteps as project managers — Kim recalling a boss who relentlessly demanded he "over communicate" without explaining what that looked like in practice, and Kate admitting that while she never struggled to talk to her own team, she took years to learn how to communicate effectively up and out to executives and sponsors. Their honest, back-and-forth storytelling style — equal parts practical and funny — turns what could be a dry topic into a genuinely useful conversation about project delivery and leadership communication. Grab a drink and join us. Quotes from the Episode "The human brain is not nice. It takes lots of therapy and or meditation to tell yourself nice stories... if you're in an information vacuum, because our brain wants to protect us from bad things happening." — Kate Anderson "Data is meaningless without context and contrast." — Tim Creasy (as quoted by Kim) "It's not that it's meaningless. It's that it's vulnerable to misinterpretation without context and contrast." — Kate Practical Takeaways The information vacuum effect — In the absence of updates, stakeholders default to negative assumptions rather than neutral or positive ones. Communication baseline calibration — New project managers often start with a communication baseline that is far lower than stakeholders actually need. Bottom-line-up-front (BLUF) messaging — Lead with the specific action or decision needed, then follow with supporting context. Self-service reporting channels — Creating an always-available update source (chat channel, dashboard, bulletin) reduces stakeholder anxiety and unplanned interruptions. Narrative ownership in project leadership — Framing project updates as a story you control, rather than a list of data points, shapes how stakeholders perceive project health. Closing Reflection The episode's real throughline is ownership: the best project managers don't just report facts, they own the narrative of their work. As Kate puts it, data without context and contrast is vulnerable to misinterpretation — and if you don't tell the story of your project, someone else's imagination will tell it for you. 🔗 Links & Resources Mentioned PM Happy Hour Membership: pmhappyhour.com/membership

Projects rarely fail from a lack of templates — they fail because of people. Author Dawn Mahan reveals the animal avatars that help you spot the cheerleader, the finicky fan, and the saboteur before one of them bites you in the ankle. Why do projects really fail? Not, as guest Dawn Mahan argues, from a shortage of templates or Gantt charts — but from the people around them. In this episode, Kim and Kate dig into the human side of project delivery: the stakeholders who love your project, the ones who quietly want it dead, and the "style under stress" that surfaces when the pressure cooker of Projectland heats up. If you've ever been blindsided by a saboteur or tripped up by an over-eager cheerleader, this conversation on stakeholder management, risk, and project leadership is for you. Kim and Kate welcome Dawn Mahan, author of the bestselling Meet the Players in Project Land and co-editor of Project Land Goes to the Movies: 22 Blockbuster Strategies for Project Success. Dawn's premise is refreshingly human: projects rarely fail because the paperwork is wrong — they fail because the people involved aren't set up for success. Using animal avatars to make stakeholder behavior easier, and safer, to talk about, she gives project managers and leaders a practical vocabulary for the messy, political, feelings-driven reality of getting work done inside real organizations. Grab a drink and join us.

Your worst project management habit might also be your superpower — the trick is knowing which one you're wielding, and when. What actually separates a great project manager from the one everyone dreads seeing on their calendar? It's rarely a certification or a prettier Gantt chart — it's behavior. This episode of Project Management Happy Hour digs into project leadership, accountability, team dynamics, and the everyday habits that quietly undermine project delivery. The uncomfortable truth running through the whole conversation: our worst project management habits are usually just our genuine strengths turned all the way up, with no dial to turn them back down. Kate and Kim are joined by Rachel Losser, founder and managing partner of Losser Consulting Solutions, a delivery-focused firm known for its get-stuff-done philosophy. Together they walk through five "bad PM personas" — the versions of ourselves that colleagues quietly avoid — and, crucially, the more skilled counterpart each one can grow into. Rachel sets the tone early with a bit of grace: we're talking about these "with love and reverence," because everybody starts somewhere and most of us have been every one of them at some point. The practical throughline is nuance. Every strength becomes a liability when it's your only mode. Great PMs read the moment: when to slow down and build consensus, and when to say "we're going this way." They tell hard truths early, manage handoffs rather than just dates, and treat relationships and communication as the real currency of the job. As Kate puts it, the only way out of a struggling project is through it — not around the color of the status. Which persona are you under stress? That self-awareness, the hosts suggest, is where better project leadership actually begins.

A $6.9 million estimate. A $1.25 billion catastrophe. How fake deadlines, a rigged bid, and a steering committee allergic to bad news turned a routine payroll migration into one of the biggest project disasters in Australian history. What happens when project leadership treats risk management as optional, decision making gets diffused across committees, and a hard deadline turns out to be completely negotiable? You get one of the most instructive project failure case studies in project management history — and in this episode, Kim and Kate pour it out one painful lesson at a time. The subject is Queensland Health, the public healthcare provider for the Australian state of Queensland, employing roughly 85,000 people across about 300 sites. In 2005, their legacy payroll vendor gave them three years' notice: support ends June 30, 2008. Sounds like plenty of runway — until the organization waited two of those three years to act. By the time a consultant named Terry Burns (remember that name) ran the procurement and IBM signed a contract in December 2007, the original $6.9 million estimate had ballooned to a $98 million contract with just six months to deliver a system covering more than 24,000 unique payroll combinations. Why does this matter for project managers and leaders? Because almost nothing that went wrong here is exotic. Late project intake. Governance where a transition team, a steering committee, and an IT department all had partial authority but no single decision-making structure. Two weeks — total — for requirements gathering on a nine-figure program. A "lift and shift" strategy that preserved every broken process and demanded 2,500 custom software configurations to replicate them. As Kim and Kate walk through it, the episode becomes a masterclass in how ordinary project management failures compound into organizational catastrophe. The discussion highlights are equal parts horrifying and hilarious. There's the program's actual internal slogan, taken straight from the project materials: "Plan A or Die" — no continuity plan, no risk mitigation, no fallback. There's the June 2008 deadline that came and went with a simple change request and some extended support from the legacy vendor, prompting Kate's sharp observation that the date was fake and not fake at once: end-of-life risk is real even when the cliff turns out to be movable. There's the UAT phase in June 2009 that surfaced 2,422 severe defects — after which the steering committee simply reclassified high-severity defects as lower severity so the dashboards would show enough green to proceed. Watermelon project, indeed. And when frontline payroll staff kept failing the system in testing, leadership's answer was to remove the requirement for business sign-off entirely. The go-live in March 2010 delivered the reckoning: 35,000 payroll anomalies, roughly $400 million in accidental overpayments, zero-dollar paychecks for healthcare workers, and government debt collectors hounding nurses for money they never asked to receive. Queensland ultimately hired a thousand staff to manually prop up the new system — a 40 percent increase in labor over the old one — with a projected five-year cost to taxpayers of $1.25 billion. The commission of inquiry that followed, led by the Right Honourable Richard Noel Chesterman, revealed the final twist: Terry Burns, a former IBMer, had leaked a competitor's bid specs to IBM and browbeaten the selection panel into rescoring until IBM won. And when the state sued? A release buried in the fine print of a change order had signed away its right to litigate. Grab a drink and join us.