Join us for a compelling conversation with Sara Gallagher, President of The Persimmon Group and creator of the popular "Big Dumb Question" newsletter. A recognized expert in PMO leadership and strategy execution, Sara helps leaders and teams translate ambitious strategies from PowerPoint into real-world results.
In this episode, Sara shares her unique approach to unsticking clogged project pipelines, detailing how she helps companies diagnose and overcome execution challenges. She explains why many brilliant strategies fail (it's often a prioritization problem!) and offers actionable advice for project managers to transform PMOs from "project police" into true enablers of innovation. Sara also dives into the practical, non-hype ways project leaders can leverage AI, the crucial skills for future PMs, and her personal framework for making high-stakes decisions under extreme uncertainty – a skill honed while becoming a CEO just weeks before the pandemic. You'll also get an inside look at her "Big Dumb Questions" newsletter, exploring the underexamined questions that derail tech teams.
In this episode, you’ll discover:
· What it truly means to get strategy "off PowerPoint and into the real world."
· Why brilliant strategies often fail, and how to address the root causes (hint: prioritization).
· How PMOs can transform from "project police" into enablers of innovation and execution.
· Practical, non-hype ways project leaders can start using AI right now to improve execution.
· The most valuable skills for project managers and technical leaders in the next five years.
· Sara's personal framework for making high-stakes decisions under extreme uncertainty.
· An inside look at her "Big Dumb Questions" newsletter and the power of exploring "obvious" questions.
· One underexamined question that frequently derails tech teams: "Why do smart people miss what later seems obvious?"
· A 30-minute exercise to get a stuck project or struggling product launch back on track.
· Sara's definition of innovation: the uncomfortable intersection of creative and useful ideas.
This episode is a must-listen for executives, project managers, technical leaders, and anyone looking to improve strategy execution, foster innovation, and navigate complexity in their organizations.
Connect With Sara Gallagher:
· LinkedIn: https://www.linkedin.com/in/saraegallagher/
· Big Dumb Questions Newsletter: https://www.linkedin.com/newsletters/7335309583109828609/
· The Persimmon Group: https://thepersimmongroup.com/about/sara-gallagher/
Chapters:
00:00 Intro: Sara Gallagher - Strategy Execution Expert
00:58 Getting Strategy from PowerPoint to Reality
03:19 Tangible Steps for Strategy Execution on the Ground
05:49 Why Brilliant Strategies Fail (It's a Prioritization Problem)
09:54 PMOs: From Project Police to Innovation Enablers
13:30 Practical AI for Project Leaders: Beyond the Hype
16:12 Future Skills for Project Managers in the AI Era
20:00 Decision-Making Framework for Extreme Uncertainty
24:21 The "Big Dumb Questions" Newsletter Explained
27:01 Underexamined Question Derailing Tech Teams
28:26 Getting a Stuck Project Back on Track: A 30-Minute Fix
31:01 What Innovation Truly Means to Sara Gallagher
33:14 How to Connect with Sara Gallagher
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