ADVISORY ARTICLE
By Jeff Oltmann
Oregon, USA
After a difficult milestone, Andy’s team held a thoughtful retrospective. They identified real issues and agreed on what to do differently next time.
It worked—for a while. The next milestone went more smoothly, but the improvement stayed mostly within that team. Similar issues surfaced on other projects, and as team members moved on, what they had learned faded under the pressure of new urgencies. Before long, the same mistakes were being repeated.
The retrospective had limited impact, even though the learning was real. It stayed concentrated in a few people on one team. When they dispersed, it faded because it never changed the organization’s long-term behavior. Its impact would have been broader and more durable if it had been embedded in shared tools, workflows, and processes. The first figure shows this progression.
What It Takes for Learning to Last
Learning isn’t automatically embedded when a retrospective is completed successfully. Changing organizational systems and behavior takes ownership, intentional decisions and hard work. The problem was not Andy’s retrospective. It was what didn’t happen afterward. Figure 2 shows the steps that learning goes through as it spreads from individuals to an entire organization.
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How to cite this article: Oltmann, J. (2026). Why Team Learning Often Fails to Scale, PM World Journal, Vol. XV, Issue VIII, August. Available online at https://pmworldjournal.com/wp-content/uploads/2026/08/pmwj167-Aug2026-Oltmann-why-team-learning-often-fails-to-scale.pdf
About the Author
Jeff Oltmann
Oregon, USA
Jeff Oltmann helps organizations accelerate results through strategy deployment and project portfolio management. He consults, teaches, and leads forums for senior PMO leaders. He is principal at Synergy Professional Services (spspro.com) in Portland, Oregon and is on the faculty of the Division of Management at Oregon Health and Science University. He was previously on executive staff at IBM and is the founder of the Portfolio and Project Leaders Forum, a gathering of senior managers who lead project-based organizations (pplforum.org).
Jeff welcomes your questions and ideas. You can contact him at jeff@spspro.com or read previous articles at www.spspro.com/article-library.
