Project Management Happy Hour

111 - Top Shelf Replay: How do you start a hard conversation?


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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 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:

  • Recognize when a conversation becomes crucial: differing opinions, high stakes, and strong emotions.

  • Avoid the "fool's choice"—the false belief that you must choose between honesty and peace.

  • Create a shared pool of meaning, so everyone's ideas and emotions contribute to better decisions.

  • Use "Start With Heart" to keep your cool and focus on what you really want—for yourself, others, and the relationship.

  • 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).

JOIN THE HAPPY HOUR! Want even more? Join us at pmhappyhour.com/membership to get PDUsfor episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.

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Project Management Happy HourBy Kim Essendrup and Kate Anderson

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