Long Story Short
A playbook that works isn’t documentation, it’s culture. The magic is in who writes it, how people get trained on it, and whether anyone’s actually watching when reality hits the beautiful plan. Check out Chris’s Playbook Toolkit if you want a head start.
How to Jump!
There is VERY often an enormous gap between “we have a vision” and “everyone in this organization actually knows how to do the work.” There are so many ways to try to close it, but how do you actually build strategy into the soul and the day-to-day of an organization? How do you bring forward the HOW?
Shockingly, (giggling over here!) it is NOT more planning, or clearer goals, or writing better OKRs. Those things matter, but what does any of it look and feel like on a Tuesday morning in the middle of a quarter? What do you do when a difficult funder calls, a new hire asks how things work around here, or something just breaks?
When we had new research teams in the field at Think of Us and when we were expanding SO fast at Revolution Foods, we kept trying to write it all down — to have experienced people be there to train and share, but it never quite stuck.
I don’t think you can just TELL someone how to do something. I think they need to learn it and breathe it and immerse themselves in it. Then figure out how THEY will live it. AND I think we’re rarely successful by just throwing someone into something without grounding, support, or clarity.
So what’s the middle ground? How do you build something that looks and feels consistent? That embodies culture? That is owned across the org, not just by the leader or one long-time human who holds all the institutional knowledge in their head?
I still don’t have a perfect answer, but I learned about Playbooks from Chris O’Brien, and I think they have the capacity to be pretty powerful. They are SO detailed and SO specific, and in giving that grounding framework, they give people a way to bring plans and practices to life. Then from there, folks can have fun and build and be creative. What a beautiful gift to give your organization, your teams, and your work. When you create that backbone of expertise first, people can actually improvise and innovate from a place of confidence rather than chaos.
You don’t need a hundred plays. You need to define your core of what you do and how you drive excellence.
(Full disclosure: I don’t know that I would ever have the discipline to execute this AND I love that the Chris’s of the world do!)
Quick note before we dive in: Chris’s approach is especially powerful for organizations doing repeatable work with humans: schools, workforce development programs, ongoing training, regular convenings, research coordination, community organizing. If you ever find yourself saying “I wish everyone did this the same way” or “we need more consistency here” — you’re going to love what Chris figured out.
The person who turned “executing plans into real life” into an art form
I met Chris O’Brien when he reached out about using Helia’s OKR template. When he told me his favorite compliment of all time came from a city education official who called him “the best executor,” I knew I was talking to my kind of person.
Chris is going into his 27th year in education. He started as a third grade teacher in Cleveland (he still apologizes to the third grade class of 1999), spent years coaching high school football, became the founding principal of a charter school, and eventually served as Managing Director of Schools at Breakthrough Schools where he oversaw ten schools across five campuses. That’s where the playbooks were born.
His boss handed him a challenge on Day One: everything was institutional knowledge. People knew how things worked, but it wasn’t written down, so it wasn’t teachable, and there was no record of it. Sound familiar?
So, he took a lesson from his coaching days and built playbooks.
Chris’ aha moment? Playbooks aren’t documentation. They’re culture codifiers. When done right, they’re not a Google Doc living on a shelf but the backbone of how your organization works, what it believes, and how a brand-new person can walk in and just… see it happening.
Lai is now the Senior Director of IT at Uncommon Schools, leading a team of 20. When I asked how often we should be using her delegation process, her answer was simple: “I have never regretted spending the
time on creating a delegation AND I have often regretted not having the delegation.”
So, well, basically, JUST DO IT!!!!
The Key Takeaway
Here’s what makes this different from every “we should write down our processes” conversation you’ve had: the playbook is just the enabling condition. It’s pre-game. Writing it is Step One of maybe fifteen.
Most people think the work is done when they hit “save” and export to PDF. Chris would say that’s when the real work starts. The magic is in who writes it, how people get trained on it, who monitors it, and whether leaders are actually present when reality starts punching the beautiful plan in the face.
Done right, playbooks get you to what Edgar Schein calls “level three culture” — where your newest team member can show up and not just read about how you do things, but watch it happening around them. “This really is the culture. This really is how we work.”
Chris’s Playbook Process
If you’re a “just give me the tool” kind of person (aka Helia’s COO, Libby), check out Chris’s Playbook Checklist in our toolkit. It walks you through the whole approach step by step.
If you’re a “tell me why this matters” kind of person (aka Founder Jess), read on. Here’s what we’re going to cover:
- Step 1 — Start with identity and where things break down (not with the document)
- Step 2 — Write WITH the experts, not for them
- Step 3 — Get specific enough that a brand-new person could execute it
- Step 4 — Train it like the game depends on it, because it does
- Step 5 — Build monitoring into your rhythm, and make it peer-to-peer
How Chris’s Process Works
1. Start with who you are and where things fall apart
Before you write a single word, get clear on two questions: How do we win? And where do things typically break down? These are the two questions for which you develop your plays.
The “how we win” plays become your core protocols, the repeated actions that drive results on a good week. The “where things break down” plays are what you run when something goes sideways.
“You don’t need a hundred plays. You need to define your core of what you do and how you drive excellence. If you’re going to write a playbook, they should be things that are repeated actions. Things that happen weekly, monthly, or quarterly, and the things that happen under high stakes.”
Chris calls it the 20 that drives the 80. What are the core processes that actually make or break your success? Start there.
You never walk-through alone. It’s literally pointless. You might as well not even do it. It doesn’t benefit anybody.
2. Write WITH the experts, not for them
This is the number one place playbooks fail, and Chris is clear about why.
“Playbooks fail on the design side because the author does not take the position of the user. Don’t think because you’re the CFO 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.”
When Chris built the student culture playbook at Breakthrough, it wasn’t just him. The operations person who knew bus schedules and food service delivery had to be in the room. The dean who understood behavior interventions had to write her piece. Even building-by-building differences — “doors are in different places for arrival and dismissal” — had to be informed by the people who stood in those spaces.
This led to one of Chris’s golden rules: do not hire a consultant to write a playbook about your own organization. The expertise is already in your building. Your job is to capture it.
(Oh! And this is also why so many strategic plans fail because they’re written BY leadership FOR everyone else, without the people who have to actually live inside them.)
3. Get specific enough that a brand-new person could execute it
Most playbooks stay too lofty and lose their usefulness right here.
“I think playbooks fail when they don’t get to the nitty-gritty. If you look at the tools I’ve made, they are very specific. There are even quotation marks with how to say something, or parentheticals that really get into the details if someone needs more guidance.”
Chris tests every protocol himself. He stood in the spaces during arrival and dismissal to make sure the timing actually worked. He ran through the lesson internalization protocol on his own and discovered the steps were in the wrong order. “Turns out my first draft didn’t make sense. I had to flip the order.”
The test is simple: if you can’t follow your own playbook successfully, neither can your team. Include actual scripts, timestamps, specific language, not just concepts.
And the important framing: the goal is NOT to create robots. Chris instructs his team: “Do it this way first — get fluid with it — and then you can start to play around with it.” Build the foundation of expertise so people can adapt, innovate, and make it their own from a place of confidence rather than chaos. A surgeon follows the SOP until they’ve done it enough times that their skillset actually adds something new. Same idea.
Do not hire a consultant to write a playbook about your own organization. The expertise is already in your building. Your job is to capture it.
4. Train it like the game depends on it, because it does
The most common mistake: finishing the playbook and thinking the work is done.
The playbook is your August prep. Training is your practice season. And the real pressure-testing happens when reality shows up. As Mike Tyson famously noted, everyone has a plan until they get punched in the face.
And who does the training really matters. “The second place playbooks fail is when people aren’t trained 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.”
“As the authors of the playbook, it is your duty and obligation to run those trainings, to be present to see what happens.”
The person who wrote the arrivals section runs the arrivals training. The dean who wrote the behavior intervention piece runs that session. You don’t hand it to someone else to present on work they didn’t author and, you absolutely don’t install the plays and then stay in your office while the season starts.
“Can you imagine if a football coach sat in the coach’s office while the team played?! That’s bananas.”
When things don’t go perfectly in those first weeks — and they won’t — that’s coaching data. Call a timeout, regroup, model the technique again. Simplify if you made it too complex. The game surfaces what practice couldn’t.
5. Build monitoring into your rhythm, and make it peer-to-peer
Here’s where the magic compounds.
Chris used to do culture audits alone. Notepad in hand, walking the schools, taking copious notes, writing intense reports. People hated it. “This feels judge-y and terrible.”
So he made a rule: no solo walkthroughs. Ever.
“You never walk through alone. It’s literally pointless. You might as well not even do it. It doesn’t benefit anybody.”
Instead, he built a rotating schedule: principal + dean, instructional coach + grade team leader, ops person + principal. Always a combination, always tied to specific sections of the playbook. Always publicly shared ahead of time. Here’s what we’re watching for, and here’s what matters most.
Then came the real evolution: he stopped going at all. An ops person, principal, and dean would go to a DIFFERENT school, monitor it, then flip. Peer-to-peer, without Chris in the room.
“Not only did they hold a high bar, they also started just noticing other cool stuff and sharing it. ‘I saw this thing in Baltimore that was awesome.’ The sharing of good ideas was a wonderful unintended consequence.”
And the feedback landed differently: “It wasn’t my feedback. It was their feedback to their own people. From Teraca, from Hana — that was like their leader speaking to them, not random Chris.”
The key is making it systematic. “It was on everyone’s calendar every six weeks. Cultural audit, half a day per school. Boom boom boom boom boom.”
If you’re not going to monitor it, don’t build the process. Monitoring isn’t punitive, it’s coaching infrastructure. It’s how you find out where things are actually breaking down so you can fix them. “It’s an autopsy without blame. Where did we break down? Did we skip something? Let’s just get better at it.”
When to do this Yourself vs Bring Someone in
You can absolutely start a playbook on your own — especially if you start small (one process, one team, one use case).
You might want outside support if:
- You’re building a playbook process from scratch across multiple teams or sites,
- You’ve tried before and stalled at the “beautiful document nobody uses” stage,
- You want someone to facilitate the co-authoring process so leadership doesn’t end up writing it alone,
- You need help building the monitoring infrastructure alongside the playbook itself.
If You Want Help
Chris O’Brien works directly with organizations that are ready to build the infrastructure to make their work actually stick, across teams, sites, and seasons. He specializes in taking what your most experienced people know and turning it into something teachable, trainable, and monitorable. He’s especially good at working with organizations that have tried to document before and ended up with a beautiful Google Doc nobody uses.
He’s a good fit if:
- Your team does important work inconsistently and you want more reliable quality,
- You have great people doing things well but it all lives in their heads,
- You’ve got growth or transitions coming and need to codify before you scale,
- You want someone who will actually train your team on the playbook, not just hand it off.
Connect with Chris !
Try it Yourself
- Chris’s Playbook Checklist — The step-by-step guide to building a playbook that actually works — covering everything from identity and co-authorship to specificity and rollout.
- Chris’s Training + Launch Checklist — The guide to rolling out your playbook so it lands — not just gets emailed out.
- Chris’s Monitoring Plan — The system for keeping your playbook alive after launch — with a schedule template, look-fors framework, and share-out protocol.
- School-Specific Examples — Two real examples of Chris’s playbook approach in action at Breakthrough Public Schools — a student culture roll-out training and a late-hire onboarding session
Recommended reads:
- Teach Like a Champion by Doug Lemov — the foundation for Chris’s approach to making excellence teachable
- Managing to Change the World by Alison Green and Jerry Hauser
- The Checklist Manifesto by Atul Gawande
- The Advantage by Patrick Lencioni
- Organizational Culture and Leadership by Edgar Schein
Connections:
- The Management Center — tools on systems and accountability
- Relay GSE — professional development designed to equip educators
Questions to Sit With
- What are the repeated actions in your organization that desperately need consistency?
- Who actually knows how to do the most important work really well? (Those are your co-authors.)
- If someone brand new walked in tomorrow, what would they need to know — and where would they find it?
- Are you monitoring the things you say matter most? And does that monitoring feel supportive or scary?
- What’s living in people’s heads right now that would be catastrophic to lose?
Not sure Chris ‘s the right fit? Talk to Helia directly!
This article comes from a coffee chat with Chris in September 2025. These conversations form the heart of the Helia Library — because we’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.
About Chris
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 a city education official who called him “the best executor.” In his 27th year in education, Chris believes deeply in the beautiful synergy between systems and people — building things that work with real humans, not perfect robots.
Work with Chris
