The importance of Writing in business: the Stripe playbook

I found this document where is summarized Stripe's internal communication and writing playbook (as told by former employee Brie Wolfson)

I came across this incredibly interesting document.

It’s about how Stripe¹ built a culture where writing is not just for mere documentation, but rather the backbone of decision-making, deep thinking, and cross team alignment.

The Collison brothers are Stripe’s founders and they simply love writing (photo: Pamela Littky)

Much of this insight comes from Brie Wolfson, who spent five years at Stripe (including launching Stripe Press²).

I’ve always believed writing is a powerful tool for clarifying thoughts, but I never knew a company made it essential to its operating model.

I found this document so fascinating that I had to share it with you all.

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Here's exactly what Stripe did differently and how other companies can copy it.

Writing Before Speaking: Pre-Writing for Clearer Thinking

• Pre-meeting memos were mandatory. Before key discussions, the organizer had to circulate a structured written doc explaining the problem, proposed solution, and open questions. No meeting happened without this.

• No brainstorming before writing. Stripe discouraged real-time ideation in meetings. Instead, everyone wrote down their thoughts independently first to ensure deeper insights.

• Decisions required written summaries. Any strategic shift or major initiative had to be documented before implementation.

Founders Modelled Exceptional Writing

• Patrick & John Collison (the founders) set the tone. They were exceptional writers and sent long, detailed emails to the company, which influenced the entire team's approach.

• Leaders were expected to write. Senior execs and managers weren't exempt from writing - any major update, decision, or change was shared in writing.

• Emails were designed to be compelling. Writing had to be engaging, not just functional. Patrick Collison's emails were known for being packed with insights and sharp reasoning.

Documentation As a Competitive Advantage

• Every team had a 'living document'. Instead of scattered knowledge, each team maintained a central doc summarizing its strategy, key decisions, and lessons learned.

• New hires got a 'How We Operate' guide. Stripe's onboarding doc was packed with thinking frameworks (e.g. trapdoor decisions), references to intellectual figures (Tyler Cowen, Richard Feynman), and company principles.

• Nothing important lived only in Slack. Major conversations and takeaways were moved from Slack to structured documents so they wouldn't get lost.

Standardized Writing Rituals for Every Team

• Kickoff memos for every project. Before launching any initiative, a written doc outlined the goal, risks, assumptions, and metrics for success.

• Retrospectives were written, not just discussed. After completing projects, teams documented what worked and what didn't to ensure learnings were captured.

• Weekly written updates, no unnecessary status meetings. Instead of syncing in meetings, teams sent structured updates covering progress, blockers, and next steps.

Radical Email Transparency

• CC lists instead of private conversations. Employees were encouraged to CC internal email lists rather than siloing knowledge in one-on-one messages.

• Decisions were documented in email threads. If a key decision was made in Slack or a meeting, someone summarized it in an email to ensure visibility.

• Employees could opt into knowledge streams. Instead of pulling everyone into meetings, people could follow relevant email lists to stay informed.

Writing Was a Habit, Not a Burden

• Frequent, informal writing was encouraged. Writing wasn't reserved for strategy memos - employees were expected to write often, even for small updates.

• Templates reduced friction. Stripe used pre-made templates for kickoffs, retros, and updates, making structured writing the default.

• No perfectionism - just write. Employees were told to write first drafts quickly, then refine them. The act of writing mattered more than getting it perfect immediately.

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See you all on Sundays 🗓️
Thanks,
Giacomo

1. Stripe, founded in 2010, is a financial infrastructure platform for businesses of all sorts. It processed $1.4 trillion in total payment volume in 2024, around 1.3% of global GDP.

2. In Brie Wolfson’s words: “Stripe Press publishes books about economic and technological advancement. I brought the imprint and its first four books to life.”