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The Missing Step in Implementation Planning
Why listening to educators, understanding school rhythms, and designing for readiness matter more than a launch date. Every school year has a rhythm. There is the beginning of the year, when educators are learning names, building relationships, understanding classroom dynamics, and discovering what their students need. It is the bouquet of freshly sharpened pencils time of year. When notebooks are crisp, markers all have their caps, and every possibility still feels open. The
Winnie O'Leary
Jul 234 min read


The Conversations That Make My Brain Sparkle
There are conversations that move work forward. Then there are conversations that move our thinking forward. The first kind fills our calendars. The second kind is much harder to find. I was reminded of that recently after spending an hour talking about emerging trends, challenging assumptions, and asking questions that didn't have immediate answers. Nothing needed to be decided. There wasn't a project plan waiting at the end of the discussion. Yet when the conversation was o
Winnie O'Leary
Jun 263 min read


When Work Feels Different
A few years ago, I wrote a heartfelt ode to educators and the struggle we had been having with the recommendations for self-care. At the time, I was writing about teachers. Looking back, I think I was really writing about something larger. We often talk about Social-Emotional Learning as something students need, but adults are navigating their own emotional landscapes every day at their work. The challenge is that adult SEL rarely announces itself as a social-emotional issue
Winnie O'Leary
Jun 175 min read


Before We Can Help, We Have to Notice
Learning is never the only thing happening in a classroom. Every day we ask students to focus, solve problems, collaborate, create, read, write, and think critically. We may be focused on teaching fractions, analyzing literature, solving equations, or developing reading skills, but students arrive carrying far more than backpacks and notebooks. Some are excited. Some are worried. Some are grieving. Some are lonely. Some are navigating challenges at home. Some are struggling w
Winnie O'Leary
Jun 123 min read


Data-Rich, Insight-Poor: Why Teachers Stopped Trusting Educational Data
We have spent twenty years asking teachers to be data literate. What if we finally asked the data to be teacher-friendly? That is not a rhetorical reframe. It is the design question the education and edtech communities still have not answered honestly. And artificial intelligence — used carefully, ethically, and with real guardrails — may be the first tool capable of helping us answer it. But first, we need to admit how we got here. Most teachers are not avoiding data. They a
Winnie O'Leary
May 266 min read


The Most Important Part Wasn’t the Scale
Lately I’ve been thinking back on an educator learning network I helped build, especially as it’s come up in conversations and interviews. It’s one of those periods that stays with you—not because of a single outcome, but because of what it required and what it revealed about how educators learn when they’re connected to each other in real time. Looking back now, I don’t think of it as a single initiative so much as a learning community that kept evolving as the conditions ar
Winnie O'Leary
May 84 min read


Gift or Gap?
We tend to talk about unemployment in extremes. It is framed as a crisis to escape as quickly as possible. Less often—and usually more quietly—it is also described as a hidden opportunity. A stretch of time that opens up possibilities that working life does not always allow. Both narratives are incomplete. Because in my experience, there has been something here that feels like a gift—but calling it that, without qualification, feels incomplete at best and misleading at worst
Winnie O'Leary
May 13 min read


Behavioral Assessments Are Not Valuable Because of What They Say — But Because of How They Are Used
The Misuse of Behavioral Insight Behavioral assessments are not valuable because they describe people well.They are valuable because of how they are used—by both individuals and organizations. And that is where most systems break down. Organizations take a working model of behavior and turn it into a fixed identity profile. Individuals do the same internally. A tool meant to surface patterns becomes a label. A lens becomes a conclusion. You end up with language like mine: Yo
Winnie O'Leary
Mar 285 min read


The Momentum of Making:
What Research Tells Us About How Creativity Actually Works Creativity rarely begins with clarity. Many people assume it begins with inspiration—the idea arrives, energy follows, and the work unfolds. Research suggests something far less romantic and far more useful: creativity usually begins with action. Not a lightning strike, but a practical process. Creativity generates momentum. Or more specifically, fake it till you make it. Psychologist Mihaly Csikszentmihalyi, known
Winnie O'Leary
Feb 264 min read


Designing Early Literacy as Infrastructure
Why a Small Book Can Change a Life Long before a child walks into kindergarten, the foundation for literacy is already under construction. Brain development is most rapid in the first five years of life, forming more than one million neural connections per second in the earliest years. During this window, language exposure, shared reading, and access to print-rich environments shape not only vocabulary development, but cognitive growth, executive function, and social-emotiona
Winnie O'Leary
Feb 124 min read


When Learning Only Looks Like Learning
Understanding Grows Through Use, Not Exposure In professional learning, we often behave as though exposure equals understanding. Slides are shared. Concepts are explained. Time is spent. And when learning doesn’t show up in practice, the explanation is often simple: the content was delivered, and the responsibility is assumed to be complete. But understanding does not come from being told.It comes from use. A persistent assumption in professional learning is that teaching is
Winnie O'Leary
Jan 94 min read


Adults Don’t Learn on Cue—They Learn on Purpose
Adult learning rarely happens in a vacuum. Every adult learner walks into a learning space carrying decades of experience, layered identities, professional pressures, and a well-developed sense of what feels worthwhile. They bring successes and failures, confidence and skepticism, urgency and fatigue. They are often willing—even eager—to invest in learning, but only when it honors who they are and what they bring. This is where many professional learning experiences fall shor
Winnie O'Leary
Dec 16, 20253 min read


The Human Work of Teaching: How EdTech Can Use AI Without Losing Its Soul
Every generation of educators faces a wave of innovation that challenges what it means to teach and learn. It’s generative AI’s moment — a moment filled with both excitement and unease. AI promises personalization, instant feedback, and limitless information. Yet it also raises the question that anchors every educational era: How do we keep what is uniquely human in the act of teaching and learning? For educators, that question is not philosophical — it’s practical. And for E
Winnie O'Leary
Nov 17, 20256 min read


We Can Measure What Matters — If We Stop Measuring What’s Easy
Rethinking Assessment in the AI Era There’s a line I keep coming back to: we can measure what matters—if we stop measuring what’s easy. For decades, we’ve used tests as our shorthand for progress. They gave us numbers, charts, and accountability. They made data visible. But they also made learning small—flattened into bubbles and benchmarks. The irony is that we’ve built a system that rewards efficiency, not understanding. It measures compliance and timing, not curiosity and
Winnie O'Leary
Nov 17, 20259 min read


From Data to Wisdom: Letting the Noise Fall Away
Data has long been our mirror—reflecting progress, performance, and patterns of use. But too often, that reflection is blurred by noise: multiple systems, competing measures, and the constant chase for real-time results. Somewhere between collection and clarity, the wisdom we seek gets lost. Data promises clarity. Dashboards, metrics, and indicators are designed to show what’s happening in schools and classrooms. Yet too often, the story data tells is flat. Static. A mirror r
Winnie O'Leary
Nov 17, 20253 min read


When Inclusion Leads Innovation
Blurring the Lines: What AI Can Learn from Special Education The most effective strategies in education share a common origin story: they began by designing for the edges. When educators focused on students with the most complex challenges, they developed tools that proved more flexible, responsive, and powerful for everyone. From differentiated instruction to adaptive technologies, practices once built for access became the blueprint for excellence. hen focused on students
Winnie O'Leary
Nov 5, 20258 min read


How do we stem the exodus?
In the ever-evolving realm of education, there exists a growing concern that beckons our attention with increasing urgency: educators are...
Winnie O'Leary
Sep 20, 20236 min read


CRPE and the Critical Points
The report from the Center on Reinventing Public Education (CRPE) titled "Teaching Recovery: Addressing Instructional Losses Three Years...
Winnie O'Leary
Aug 10, 20234 min read


Why do you want to work HERE?
I get this question all the time. Most recently from Modern Classroom. I have been following their program for years, since it was in...
Winnie O'Leary
Jul 27, 20232 min read


Safe Space and Think Tank
Once upon a time I was asked what educators needed most, the answer was more time in the day. No matter how hard I tried, getting 26...
Winnie O'Leary
Jul 27, 20233 min read
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