From Strategic Plan to Daily Reality: Chris O'Brien's Playbook Method
Summary
You don't have to choose between being strategic AND operational. Chris O'Brien's playbook approach transforms your organizational vision into teachable, repeatable actions that create culture — not just documentation. His secret? Playbooks that create a foundation for excellence — then give people permission to innovate and make it their own.
What’s in it for you:
You're doing repeatable work + for humans — running programs, trainings, convenings, research projects, or any work where people need to do similar things consistently
You're tired of beautiful strategic plans that sit in your Google Drive (or even worse, printed on your shelf!)
You want to scale what works without losing quality or creating chaos
You need systems that work with real humans, not perfect robots
You're looking for a way to build culture with real humans - it’s time to go beyond hope and vibes!
Helia’s Perspective
I met Chris when he reached out about using Helia's OKR template. When he told me his favorite compliment was being described by a city education official as "the best on executing plans into real life," I knew he was a doer! He's spent 10 years developing his playbooks—his method for HOW organizations operationalize and bring to life all the strategy and planning and culture—and ways of making things happen that are in continuous use (not living on Google Drive) and part of the fabric of the organization. Collectively built, collectively updated, collectively monitored.
Quick note before we dive in: Chris's approach is magic for organizations doing repeatable work + for humans — schools, workforce development, ongoing training programs, regular convenings, community organizing, research coordination. If you're creating brand-new technology or writing novels, this might feel like overkill. But if you ever find yourself saying 'I wish everyone knew how to do this the same way' or 'we need more consistency in how we handle this,' you're going to love what Chris figured out.
What struck me is the brilliance in giving folks what they need as a foundation so they can know it and then, from there, give them permission to have fun and build and be creative— such a beautiful gift to give your organization, the teams, and the work. When you create that backbone of expertise first, people can actually improvise and innovate from a place of confidence rather than chaos. (Full disclosure: I don’t know that I would ever have the discipline to execute this AND I love that the Chris’ of the world do!)
Chris's Story
"I started off as a third grade teacher here in Cleveland. Apologies to the third grade class in 1999," Chris laughs. He spent his first 12 years in education as a football coach, honing his skills on development, culture building, and executing when the stakes mattered most. His path took him from working in suburban schools to teaching in urban charter schools, where he quickly realized he needed to level up. "For as good as I thought I was, I wasn't that good, and I had a really hard time making an impact." This led him to Doug Lemov's work on repeatable teaching techniques.
The real breakthrough came when Chris became managing director at Breakthrough Schools, overseeing ten schools total. "One of my first major priorities was identifying what was working and replicating it. My boss said to me, 'We have to figure out how to codify everything. Everything is institutional knowledge right now. People know the way we do things, but it's not teachable, it's not written down.'"
That's when he remembered Philip Garza's rule: "If it's not on paper, it doesn't exist."
So, he took a lesson from his football coaching days and built playbooks. "My path towards an equity floor, an excellence floor, was through playbooks," Chris explains. "We had to first define great student culture. Where do we win and how do we win?" They started with basics — arrival, dismissal, lunch — then tackled the harder question: "How do you translate student culture into repeatable plays?"
That was almost a decade ago. The playbook Chris shared looks "vastly different than it did 10 years ago, but that's because our beliefs and behaviors changed. And so therefore, so did our playbooks." You'll now see "connect before correct" throughout the latest version — something influenced by his recent learning about developmental appropriateness.
Today, Chris is Executive Director of GEO Academies Cleveland - and will use these playbooks as the cornerstone for their launch in Fall 2026.
Proudly wearing what I get to build every day — GEO Academies
What this looks like in practice
Chris's approach to playbooks follows a specific sequence that ensures they actually get used instead of gathering digital dust. (Again, this works best when you're doing repeatable work + for humans — but when it fits, it's transformational.)
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What Chris did: "You start with your vision, your values, your OKRs, your big objective. Who are we? What do we believe? What are our intended outcomes?" Then he asks two critical questions: "How do we win?" and "Where do things typically break down? These are the two questions for which you develop your plays. Everything that falls under “How do we win?” become your everyday plays; the stuff that goes under “Where do things typically break down?” are the plays you run when a wrench gets thrown into your everyday.”
Why this mattered: "You don't need a hundred plays. You need to define your core of what you do, how you drive excellence, and what you do when things get tough. If you're going to write a playbook, they should be things that are repeated actions — things that happen weekly or monthly or quarterly, and the things that happen under high stakes."
How to replicate: Before writing anything, get clear on your organization's non-negotiables and biggest failure points. Chris recommends focusing on "the 20 that drives the 80" — the core processes that actually make or break your success.
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What Chris did: "I did not author these alone. Key players were involved. For the culture playbook, there were people from different departments that helped author and give their perspective." This included the operations person who knew busing and food service, the dean who understood behavior interventions, even building differences like "doors are in different places for arrival and dismissal."
Why this mattered: "Authoring playbooks in isolation is a recipe for failure. When playbooks fail, they fail twice. They fail on the design side if the author does not bring in the real-life users to help create the playbook. Don't think because you're the CFO that you can write the playbook for accounting processes, because I bet you can't. The people on the ground know the processes better and have thoughts on how to make them better. The playbooks fail again when people aren’t trained well by the people who wrote them. Who’s going to be a better trainer: the CFO that spends their time at the strategic level or the Controller who runs these plays day in and day out? Writing a playbook without involving your team almost always ensures failure."
How to replicate: For each section of your playbook, involve the person who actually does that work daily. Have them write it with you, not just review what you've written. (Oh! This is why so many strategic plans fail — they're written BY leadership FOR everyone else!)
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What Chris did: "I was really intentional on making sure the author of the playbook — me or any of those who author things — can do the things that the playbook tells them to do." He literally stood in different parts of the school during arrival and dismissal; between classes he practiced using the lesson internalization protocol he had developed himself. "Turns out my first draft didn't make sense. By practicing, I figured out I had to flip the order."
Why this mattered: "I think playbooks fail when they fail to get to the nitty-gritty—when they stay lofty, they stay general. If you look at the tools I've made, it is very specific. There's even quotation marks with how to say something or parenthetical that really gets into the details if someone needs more guidance."
How to replicate: Test every single step yourself. If you can't follow your own playbook successfully, neither can your team. Include actual scripts, time stamps, and specific language — not just concepts.
The goal is NOT to create robots — it's to build that foundation of expertise so people can then innovate, adapt, and make it their own with confidence.
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What Chris did: "As the authors of the playbook, it is your duty and obligation to run those trainings, to be present. I'm going to keep using football analogies — when I was a football coach and we wrote our playbook, we practiced our plays in August before the season started."
Why this mattered: "Most people think the work is done when they print to a PDF and now it is done. If you’re the coach, that's actually just your preparation for practice – you’re not even at the pregame yet. A written playbook is just the enabling condition to allow you to do the work. The practice is the work."
How to replicate: Plan extensive rollout training run by the people who wrote each section. Start with your most foundational processes first and practice them regularly. And plan to be present during those first few weeks when reality hits your beautiful plan. As Mike Tyson said, "Everyone has a plan until you get punched in the face.”
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What Chris did: "Initially, I as the Managing Director (analogous to a superintendent) did the culture audit all by myself with my little notepad. I took copious notes and shared my reports broadly. People were like, 'I don’t like. This feels judge-y and terrible.' So I made up a rule: No solo walkthroughs. First, I publicly shared the look-for criteria BEFORE the walkthrough so everyone knew what mattered most. Then, I created systematic monitoring every six weeks with different combinations of people — principal + dean, instructional coach + grade team leader, ops person + principal. Then came the evolution: "The third evolution was that I stopped going and I had school leaders review each other. An ops person and a principal and a dean go to a different school, review it, and then they flip."
Why this mattered: This created peer learning, not just accountability. "Not only did they help monitor and they held a high bar, they started just noticing other cool stuff and sharing it. 'I saw this thing at Baltimore and that was awesome.' They just started sharing good ideas, which was an unintended consequence." Plus, "it wasn't my feedback. It was their feedback to their own people. So I would put it all together and report, but it was like from Teraca, from Hana — that was like their leader speaking to them, not random Chris."
How to replicate: Design your key look-fors and share them out ahead of time. Create a structured schedule where peers monitor each other's work every six weeks throughout the year. They learn from seeing other approaches AND the feedback feels collegial rather than top-down. The key is making it systematic — "It was on my calendar every six weeks. Cultural audit, half a day per school. Boom boom boom boom boom."
Secret Sauce & Takeaways
If there's one thing you should do, it's: Write the playbook with the people who will use it. "Don't hire a consultant to write a playbook about your own organization. Don't do it." The expertise is already in your building — you just need to capture it systematically.
Common pitfalls to avoid:
Writing playbooks in isolation then expecting people to follow them
Staying too high-level instead of getting into the specific details
Thinking the work is done when the document is finished (that's when the real work starts!)
Creating monitoring systems that feel punitive instead of supportive
The real work begins after it’s written: “The secret isn’t just writing the playbook. It’s running the plays yourself, fixing the gaps, and coaching the team live when the lights are on. A coach would never hand the players the playbook and then stay back in the coach’s office while the game was being played”
What makes this work well: "When done right, playbooks create the backbone that lets people be creative and responsive. New team members get the foundation, experienced folks can build on it, and everyone can innovate from a place of expertise rather than chaos. This is literally just how we do things. A new person comes in, here's the playbook, but also they can just see it. They can just watch people do the thing that's in the playbook. It feels like, 'Oh, this really is the culture.'"
This is often how my face looks when I’m contemplating what I moves I need to make next – or what to make for dinner.
Questions to ask yourself
Where can your trainings/teachings/human-based programming benefit from more consistency? (Think programs, services, convenings — anything where you're saying "I wish everyone did this the same way.")
Who in your organization actually knows how to do the most important work really well? (Those are your co-authors!)
If someone brand new walked into your organization tomorrow, what would they need to know to be successful — and where would they find that information?
Are you monitoring the things you say matter most? And does that monitoring feel supportive or scary?
Want to Try This?
Templates & Guides:
Chris’ secret sauce is the Playbook Checklist - everything you need to know about creating and building your playbook.
Design learning that moves your playbook from paper to practice and culture with Chris’ Training Checklist
Great trainings start with great assessments of what is truly needed
Follow Chris’ Instructional Walkthrough Tool to identify what’s needed on classroom instruction
Consider foundational culture - including leaders, systems, teachers and more) through this culture rubric
A real, anonymized, example of a student culture roll-out from Chris to help you launch clearly and intentionally!
A real, anonymized example of a Late-Hire onboarding presentation also from Chris! Ensure your new hires are oriented thoughtfully to policies and culture.
Recommended Reads:
Teach Like a Champion by Doug Lemov is the foundation for Chris's approach to making excellence teachable
Managing to Change the World by Alison Green and Jerry Hauser has been a guide for Chris throughout his journey
Get inspired to get things right in your essential work with the Checklist Manifesto by Atul Gawande
The Advantage by Patrick Lencioni for great info on achieving the greatest competitive advantage - organizational health
Another great read on org health - Organizational Culture and Leadership by Edgar Schein for continuous improvement in the face of our very real modern challenges
Connections
Libby Fischer, in addition to producing amazing content as a Helia Collective member, is available for jump-right-in strategy sessions and other help from day-to-day operations and process optimization (i.e., chaos reduction) to building/improving organizational culture. Book time with her today!
The Management Center - for many great and related tools on systems and accountability
For comprehensive professional development designed to equip educators - Chris recommends Relay GSE
About the Contributor
Chris O'Brien is a father of five, hack cook, and equally hack gardener who's obsessed with college football and pickling vegetables. He's also the kind of leader whose favorite compliment of all time came from the city’s education official who called him "the best executor." Going into his 27th year in education, Chris believes deeply in finding the beautiful synergy between systems and people — building things that work with real humans, not perfect robots.
If you’re not having fun while you’re totally exhausted, you’re doing it wrong.
This article comes from a coffee chat with Chris in September 2025. These conversations form the heart of the Helia Library – because I've learned the most from doing and from talking with other doers willing to share their wisdom. We don't need to start from blank pages or do everything alone.
As always, take what's helpful, leave what's not, and make it your own.
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