This toolkit brings together Chris O’Brien’s complete playbook process — from the checklist that helps you build it right to the training guide that makes it real, to the monitoring plan that keeps it alive six months later.
From the Helia Library — based on the article Playbooks to Build Consistency AND Culture, from our Coffee Chat with Chris O’Brien.
What’s Inside
01 — 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. Use this when you’re starting from scratch, or when you have processes that exist only in people’s heads.
02 — Chris’s Training + Launch Checklist
The guide to rolling out your playbook so it lands — not just gets emailed out. Use this once your playbook is drafted and you’re ready to turn it from a document into a living part of how your team works.
03 — Chris’s Monitoring Plan
The system for keeping your playbook alive after launch — with a schedule template, look-fors framework, and share-out protocol. Use this once your team has launched and you need to build the infrastructure to stay on track. If you’re not going to monitor it, don’t build the process. (Chris’s words, not ours — but we completely agree.)
04 — 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. These are education-specific artifacts, but the bones translate. Use them to see what a real launch training and a real onboarding session actually look like.
When Resources and Templates Aren’t Enough
These tools will get you through the build and launch. What they can’t do is help you figure out which of your processes actually deserve a playbook right now, facilitate the co-authorship process across a team that doesn’t agree on how things should work, or coach you through the first monitoring cycle when the feedback is landing badly. If you’ve tried to document before and ended up with a beautiful Google Doc nobody opens — that’s usually where a thought partner makes the real difference.
If You Want Help With Playbooks
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 a good fit if:
- Your team does important work inconsistently and you want more reliable quality across people and programs
- You have great people doing things well — but it all lives in their heads, and you’re one departure away from losing it
- You’ve got growth, transitions, or new hires coming and need to codify before you scale
- You’ve tried to document before and ended up with a beautiful Google Doc nobody uses
- You want someone who will actually train your team on the playbook — not just hand it off and disappear
Connect with Chris !
Not sure Chris ‘s the right fit? Talk to Helia directly!
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
