Sara Gallagher is President of The Persimmon Group and a recognized expert in strategy execution, PMO leadership, and project portfolio management. For more than 15 years, she has helped organizations—from Fortune 500s to fast-moving startups—untangle the real barriers to execution, from siloed teams and shifting priorities to PMOs that have lost their purpose.
A frequent speaker, author, and instructor, Sara has contributed to PMI’s global standards and delivered international keynotes and whitepapers on strategy execution, organizational change, and high-performing teams. Her consulting portfolio spans industries including energy, finance, manufacturing, pharmaceuticals, and technology, with projects ranging from industrial mega-projects to enterprise transformations.
Sara is also the author of Big Dumb Questions, a LinkedIn newsletter for PMO leaders and executives who want to see strategy move off PowerPoint and into the real world.
Sara Gallagher, President of The Persimmon Group and creator of the Big Dumb Questions newsletter on LinkedIn. Sara is an expert in executive leadership, agility, and strategy execution—helping leaders get strategy off PowerPoint and into the real world. As a speaker, consultant, and coach, she works with organizations of all sizes—from Fortune 500 companies to fast-moving startups—to unstick clogged project pipelines and turn big ideas into real progress.
Most organizations know the “rules” for getting things done—dedicated teams, formal progress reports, clear meeting agendas, and structured oversight. Yet most struggle to follow these proven practices, not because of resistance or lack of knowledge, but because something about these “universal” best practices doesn’t quite fit. This provocative session challenges our assumptions about best practices themselves, revealing how rigid adherence to conventional wisdom can actually prevent us from seeing what comes next.
Learn why organizations consistently struggle to adopt practices they know are valuable and discover when this resistance signals a need to dig deeper rather than push harder. Through real-world examples, explore how to distinguish between organizational resistance that needs to be overcome and resistance that’s revealing legitimate gaps in our frameworks.
Walk away with practical approaches for knowing when to drive best practice adoption and when to envision what “best” could look like for your unique context.
Traditional change management assumes we can carefully plan, explain, and train our way through transformation—but what happens when change is constant and overlapping? Rapidly evolving technology, market disruptions, and organizational restructures rarely arrive as isolated events. This provocative session explores why conventional approaches are breaking down as multiple change initiatives collide, creating complex (and often unpredictable) ripple effects throughout organizations. Learn why treating change as a series of discrete initiatives rather than a continuous flow of forward motion may be creating more organizational whiplash than progress.
You’ll discover fresh frameworks for leading change, focused on building understanding, connectedness, and adaptability at every level.
You’ll walk away with practical insights on how to shift mindsets from “managing change” to cultivating adaptability as a core competency, turning what most people see as disruption into powerful competitive advantage.
In an age of unprecedented data access, why do organizations struggle more than ever to make timely, effective decisions? This thought-provoking session explores the counter-intuitive relationship between information and action, revealing how our attempts to reduce uncertainty often lead to organizational paralysis. Through compelling examples and research, you’ll see how the pursuit of “complete information” actually increases risk by delaying action and allowing problems to compound while teams search for perfect clarity that rarely exists.
Learn why traditional approaches to decision-making can backfire in complex environments and discover practical approaches for making robust decisions with imperfect information. You’ll explore how high-performing organizations adjust their decision speed to match their situation and gain specific techniques for accelerating organizational decision-making without sacrificing quality.
Walk away with fresh insights about the relationship between uncertainty and risk, and a practical toolkit for transforming your team’s decision effectiveness even in rapidly changing conditions.
Like an invisible current beneath calm waters, leadership behaviors create powerful forces that can pull strategic initiatives off course—often without executives even realizing it’s happening. While most project post-mortems focus on team execution, methodology failures, or resource constraints, the real catalyst for strategy execution success frequently traces back to subtle patterns in executive behavior and decision-making.
This provocative session reveals how well-intentioned leadership practices—from how you structure governance to the questions you ask in status meetings—can inadvertently create organizational resistance, strategic confusion, and execution paralysis.
Discover why adding more oversight, increasing status checkpoints, or tightening controls often makes things worse, not better. Learn to identify and correct these hidden leadership patterns, transforming your influence from an invisible drag on progress into a genuine catalyst for strategic success.
Sara Gallagher is a captivating speaker whose keynotes and executive workshops empower leaders and teams to think strategically, lead confidently, and execute with discipline—all while strengthening culture and the human side of transformation.
