Most founders running £1m to £20m businesses either can't afford a Chief of Staff, or think they shouldn't have one yet. They run their executive operating system out of their own head and a Notion board nobody updates. By the time they finally hire, they've already paid the cost in dropped balls, missed follow-ups and decision drift.
And if you already have a Chief of Staff, even better. Walk them through this exact playbook to upskill them, unlock their precious time, and free them up for the non-repetitive, high-judgement work that actually moves the business forward.
Claude Cowork is the workaround for everyone else. Used well, it gives a single founder the leverage of a small executive team: priorities, decisions, projects, communications, all maintained continuously. Below is the 9-step playbook I use to set one up.
One caveat first: this is not a like-for-like replacement for a great human Chief of Staff. A real one sits in rooms, reads body language and handles politics no AI can touch. What you are building here is the operating system layer of the role: continuous context, decision tracking, document production, project memory. You get most of the leverage at none of the cost.
Step 1: Define the mandate and operating principles
Before you build anything, decide what your Chief of Staff actually owns. What stays on your plate, what they take. How they think, escalate and communicate.
Step 2: Create the two core files
Two markdown files become your Chief of Staff's memory and source of truth. They go in every Project you create from here on.
company-context.md
- Mission, strategy, priorities
- Key people and their roles
- Active projects
- Personal preferences and style
- Metrics that matter
cos-playbook.md
- How you actually work
- Decision rules and frameworks
- Communication style and cadence
- Escalation paths
- What you never want to be asked twice
The richer these files, the smarter your Chief of Staff. Update them whenever your strategy shifts, you hire someone senior or a process changes. Treat them like a living onboarding doc.
Step 3: Build a Project for each core function
Claude Cowork lets you set up Projects so different work streams stay clean and don't bleed into each other. One Project per function:
- Strategy: market, OKRs, roadmap, competitive intel
- Operations: processes, tools, automations, SOPs
- People: hiring, performance, culture, org design
- Finance: reporting, cash, forecasts, board updates
- Communications: internal updates, board packs, investor comms
Each Project carries the two core files and develops its own working memory over time.
Step 4: Run an executive operating system in Artifacts
Artifacts are living, shareable outputs your Chief of Staff maintains for you. Six to set up first.
Executive Brief
Top updates, risks, decisions needed and current blockers, refreshed daily.
Priority Scorecard
Live view of your top priorities, status, and what the next move is on each.
Decision Log
Key decisions with rationale, owner, and date. Stops you re-litigating things.
Meeting Hub
Agendas, notes, follow-ups and pre-reads, all in one place per meeting.
Project Tracker
Milestones, owners, progress, risks and dependencies across active projects.
Knowledge Base
Key docs, guides, playbooks and the company memory you keep losing in Slack.
Claude updates these in real time as you work and keeps everything linked. Your weekly executive review becomes scrolling through six Artifacts instead of reconstructing context from memory.
Step 5: Write your systems, scripts and outreach
Codify how things actually get done so your Chief of Staff runs them the same way every time. The point is consistency, not creativity.
- Meeting agenda and pre-read templates
- Decision frameworks and prioritisation models
- Status update and escalation scripts
- Stakeholder update templates (team, board, investors)
- Onboarding checklist for new projects
Step 6: Connect your tools with Connectors
Connectors plug Claude into the systems you already use, so your Chief of Staff has live data and can take action instead of relying on you to copy-paste.
- Slack for updates and summaries
- Google Drive or Notion for docs
- Gmail to draft and send on your behalf
- Google Sheets for dashboards and data pulls
- Calendar to manage your time and prep meetings
Path: Settings → Connectors → Browse → Add. Once connected, Claude becomes the operating layer across your entire stack.
Step 7: Graduate to Cowork to produce real outputs
Cowork is where context becomes deliverables. Not chat answers; actual files you can send.
- Board update decks with charts and insights
- Process docs and SOPs your team can follow
- One-pagers for projects and initiatives
- Hiring briefs and interview scorecards
- Reports that answer the actual question, not adjacent ones
The difference from chat: Cowork reads your real files, produces polished outputs in the formats you use, and saves them where you'll find them.
Step 8: Use Claude Code to automate and extend
When work is genuinely repeatable, move it to Claude Code. Anything you do every week, on a schedule, or in a clear pattern.
- Recurring reports and data pulls
- Internal tools and simple dashboards
- Alerts and weekly digests
- Workflows that run on a schedule without you
Non-technical founders often skip this step. You don't need to learn to code to use Claude Code, but you do need to set it up once. If that step feels like a wall, hire one technical person for a day to wire it up.
Step 9: Run a daily Chief of Staff rhythm
A simple loop keeps the system aligned and useful, rather than slowly drifting back into chaos.
- Morning brief: priorities, plan, risks for the day
- Triage: what genuinely needs your attention today
- Unblocks: remove friction fast, before it compounds
- Delegate: clarify outcomes and owners on anything you hand off
- End of day: recap, decisions, plan tomorrow
- Weekly review: what worked, what to change
£20 a month replaces six months of onboarding, £90k to £200k in salary and the friction of a human handoff. And if you already have a Chief of Staff, this playbook frees them from the repetitive work so they can focus on the high-judgement calls only humans can make. The ceiling on a founder is no longer how much they can hold in their head. It is how well they can build the system that holds it for them.