What am I missing?
The gaps between what I've said I'm doing and what I'm actually doing.
Unlocked
01 · QUESTION
02 · QUESTION
03 · QUESTION
04 · QUESTION
05 · QUESTION
01 · THE FIVE QUESTIONS
02 · FRIDAYS
03 · BEFORE A DECISION
04 · QUARTERLY
The five questions
They only work if Claude knows your business first. With your context loaded, these are the questions I'd ask a very good COO if I could afford one.
Where's the money I'm not collecting?
Past enquiries never followed up. Clients with no next step. Offers with nothing after them.
What have I decided that contradicts something earlier?
The plan from three weeks ago that this week's decision undoes without anyone noticing.
What should I be worried about?
Based on everything it knows: risk, overload, the thing I keep putting off.
Can this year's plans still be made in the time left?
The one that stings. It does the arithmetic I've been avoiding.
The six documents it reads
Boring. Load-bearing. The reason the answers are about your business and not a business.
- Voice: how you write and speak, your sign-offs, the phrases you overuse, the words you'd never use
- Role: what you do, what you're accountable for, what success is measured on
- Business: what you sell, to whom, at what price, how it works, the team, the constraints
- Brand: colours, fonts, the rules, examples of what looks right and wrong
- Objectives: what you're working on this quarter and this year, and why
- Stakeholders: the people you communicate with most, and how each likes to receive things
Set it up in six steps
- Have Claude Cowork set up with a project. You need the Claude desktop app, a project, and that project pointed at one folder on your computer. If that isn't done yet, the Starter Pack walks you through it: tuitiv.ai/free/setup.
- Build your six context documents. The free plugin in the Starter Pack builds them with you through a guided interview: tuitiv.ai/free/setup. Allow an hour. Talk rather than type; the rambling is where the good stuff is.
- Add what you've built lately. Proposals, plans, notes on this month's big decisions. Save them in the project folder. The more it can see, the more it catches.
- Run prompt 01, and sit down before you read it. Go through the answers one at a time. For each, decide: act on it, park it, or tell it why it's wrong.
- Schedule it for Friday afternoon. Scheduled tasks, new task, Fridays at 3pm, paste prompt 02. It'll be waiting when you close the week.
- Refresh the objectives every quarter. The questions are only as good as the objectives file. Prompt 04 does the refresh.
The prompts
01 runs the five questions. 02 schedules them. 03 is for before a big decision. 04 keeps the objectives honest.
Run the Chief of Staff check
Paste into a new task in your project.
With everything you know about my business, my objectives and what I've built recently, answer these five questions. Be specific, name the files or decisions you're drawing on, and don't soften it. 1. What am I missing? 2. Where's the money I'm not collecting? 3. What have I decided this month that contradicts something I decided earlier? 4. Based on everything you know, what should I be worried about? 5. Can the plans I've made for this year still be made with the time that's left? Show the arithmetic. Finish with the one action you'd take first if you were me.
The scheduled version
Paste into a scheduled task for Fridays at 3pm.
Every Friday at 3pm, read my context documents, objectives.md, and anything added or changed in this project folder this week. Answer the five Chief of Staff questions: what am I missing; where's the money I'm not collecting; what have I decided that contradicts something earlier; what should I be worried about; can this year's plans still be made with the time left. Lead with anything that's changed since last Friday. One page. Save it to my Outputs folder as chief-of-staff-YYYY-MM-DD.html.
The contradiction check
Run before you commit to something new.
I'm about to decide [decision]. Before I do, check it against everything you know: my objectives, my recent decisions, what I've promised people, and my capacity. Tell me what it conflicts with, what it would push out, and who I've already promised something to that this affects. Then tell me whether you'd still do it, and why.
Refresh the objectives
Once a quarter, so the questions stay honest.
Read objectives.md and what's happened in this project over the last quarter. Tell me which objectives are on track, which have stalled, and which I should drop. Then interview me, one question at a time, to write next quarter's objectives. Stop at three. Save the new version as objectives.md and move the old one to my Archive folder.
Downloads
When it's not quite right
The answers are generic
It doesn't know enough yet. Check the six context documents exist and are more than a line each. The business and objectives files do most of the work.
It keeps raising something I already know about
Tell it, and tell it what you're doing about it. It'll stop raising it and look for the next thing.
It's harsh
It's meant to be. You can ask it to be kinder. I'd ask it to be clearer instead.
Should I put client information in the context?
No names or identifying details. Describe clients by type ("a 40-person consultancy"), and scrub any transcripts first. The scrubber is in the free resources: tuitiv.ai/free/scrub.