These aren't prompts you paste into a chat. They're files you upload once to a Claude project, and they shape every conversation from that point on. No invoking, no remembering to run them. They're ambient: always on, always applied.
Free, no email gate, download as .md files. If you'd rather have someone install the whole system for you, the AI Brain engagement covers that. The Prompt Library has the paste-and-run versions for single tasks.
The library
Filter by audience or scroll the lot. Every skill has copy-to-clipboard and download.
Section 1 of 4
Foundations
Three files every Claude project needs before anything else. Upload them once; they apply to every conversation in that project, without you invoking anything.
Skill 01Universal
The Founder CLAUDE.md
CLAUDE.md
The project instruction file that tells Claude who you are, what you're building, and how to handle you. Every conversation in this project starts with this context loaded. Fill in the bracketed sections and upload it to your Claude project.
# Project instructions
## Who I am
[Your name], [your role] at [your company]. [One sentence on what the company does and who it serves.]
## How I work
- I think by talking. If I dump a wall of text, extract the actual question before answering.
- Lead with the answer, then the reasoning. Never the other way round.
- If I ask for a draft, produce one. Don't ask me clarifying questions unless you genuinely can't proceed.
- When I say "quick one", I want under 100 words back.
## My defaults
- Write in my voice (see voice.md if uploaded).
- UK English, always.
- No emoji. No exclamation marks in professional output.
- Numbers as digits: "3 days", not "three days".
- Dates in DD MMM YYYY format: 20 Jul 2026.
## What I never want
- Marketing language in internal documents. No "we're excited to announce".
- Hedged recommendations. Recommend or don't. I'll push back if I disagree.
- Summaries at the end of a response. I just read it.
- "Let me know if you have any questions" footers. I will, when I do.
- Generic AI tells: "delve", "leverage", "landscape", "foster", "seamless",
"robust", "journey", "unlock", "elevate", "cutting-edge". There is always
a better word.
## Recurring tasks
[List 3-5 things you use this project for most often, so Claude can
pattern-match quickly. Examples:]
- Drafting client emails
- Preparing for board meetings
- Reviewing pitch decks from portfolio companies
- Writing weekly updates for the team
## People I mention often
[First name, role, one line of context. This stops Claude asking "who is
Sarah?" every time.]
- [Name]: [role] at [company]. [One line on how to handle them.]
## Out of scope
[Things this project should never try to do. Push back if I ask.]
- Legal advice. Tell me to ask my solicitor.
- Financial modelling. Point me to a spreadsheet.
Setup. Copy this file, fill in the bracketed sections, and upload it to your Claude project as a Project Instruction (not knowledge). It applies to every conversation in that project. Revisit it monthly for the first three months; after that, it stabilises.
Skill 02Universal
voice.md Template
voice.md
A measured voice file that makes Claude write like you, not like a press release. Includes hard bans, anti-patterns, register dials, and slots for your own example pairs. Pair it with the voice.md generator to fill in the measured sections from your real writing.
# My writing voice
## How I write
[Fill this in from the voice.md generator, or write 3-4 sentences
describing your natural writing style: sentence length, tone, formality,
how you handle uncertainty.]
## Hard bans
Never use these words or phrases, in any casing:
- delve, leverage (as a verb), synergy, foster, landscape
- seamless, robust, comprehensive, nuanced, cutting-edge
- elevate, enhance, unlock, journey, transformative
- furthermore, moreover, additionally, pivotal
- [Add your own industry-specific hollow words here]
Why: these are the words AI reaches for when it has nothing better.
The cluster signals "AI assistant" rather than "person who knows
what they're doing".
## Hard punctuation
- No em dashes anywhere. Use a comma, colon, or a new sentence.
- No ellipses unless genuinely trailing off.
- [UK/US] English, always.
## Anti-patterns
Never produce:
- The summary cap-off ("In summary...", "To recap...").
- The "let me know if you have any questions" footer.
- Throat-clearing openings ("It's worth noting...", "In today's world...").
- Hedged recommendations ("you might want to consider...").
- Emoji as decoration or section markers.
- The tidy three-point prose grid ("First X. Second Y. Third Z.").
## How I actually sound (examples)
The highest-leverage section. Write new output that would sit
comfortably next to these.
[Paste 3-5 short examples of your real writing below. Email, Slack,
a LinkedIn post, a client message. The more specific, the better.
The voice.md generator extracts these automatically.]
### Example 1: [type, e.g. "client email"]
> [paste your actual writing here]
### Example 2: [type, e.g. "status update"]
> [paste your actual writing here]
### Example 3: [type, e.g. "LinkedIn post"]
> [paste your actual writing here]
## Registers
One voice, adjusted dials. The core never changes; these shift on top:
- **Email:** written register. Context in one line, then the ask.
Warm close, no fluff.
- **LinkedIn / public posts:** one idea per post. Open with an
observation, not a question.
- **Internal / chat:** informal. Contractions, short sentences, fast
decisions.
- **Documents:** structured. Headers earn their place. No walls of
text.
Cascade. Upload this as a global voice file (Claude Code: ~/.claude/voice.md; Claude Projects: project knowledge). Then create project-level overrides for contexts where the tone shifts (investor comms vs internal Slack). The global file applies everywhere; the project file adds to it. This is why a file beats a skill: it's ambient, not invoked.
Skill 03Universal
The Grill
grill.md
Interrogates you about a plan, pitch, or design until nothing is vague. Each question comes with a recommended answer so you're guided, not just questioned. One question at a time, never multiple.
Interview me about every aspect of this plan until we reach a shared
understanding. Walk down each branch of the design tree, resolving
dependencies between decisions one by one.
Rules:
1. Ask one question at a time. Wait for my answer before continuing.
Asking multiple questions at once is bewildering.
2. For each question, provide your recommended answer. Frame it as:
"My recommendation: [answer]. [One sentence on why.]"
3. If a question can be answered by reading something I've already
provided (a document, a previous answer, context in this project),
answer it yourself instead of asking me.
4. If my answer is vague, say so and ask me to be specific. Don't
accept "we'll figure it out later" on anything structural.
5. Track which decisions depend on other decisions. If I answer B
before A, flag it: "This depends on [A], which we haven't settled."
6. When we've covered every branch, summarise the resolved plan as a
numbered list of decisions, each with the answer we agreed on.
Do not enact the plan until I confirm we've reached a shared
understanding.
Start by asking me: "What's the plan or idea you want to pressure-test?"
When to use it. Before writing a spec, before a board meeting, before committing to a pricing decision, before sending a brief to an agency. The grill is worth 10 minutes every time you're about to spend a week building something shaped by an assumption you haven't tested.
Section 2 of 4
For founders
Six skills that replace the work a founder typically does badly, late, or not at all. Each assumes the foundation files are already in place.
Skill 04Founder
Board Update from Notes
board-update.md
Drop raw notes, metrics, and decisions from the last month. Get a structured board update in the format investors and board members expect. Honest about what went wrong, not just what went right.
Turn my raw notes into a structured board update.
<notes>
[Paste everything: bullet points, Slack snippets, metrics, notes from
1:1s, whatever you've got. Messy is fine. The less you curate before
pasting, the more useful this is.]
</notes>
<period>
[Month/quarter this update covers]
</period>
Produce a board update with these sections, in this order:
1. **TL;DR** (3 bullets, max 15 words each)
What happened, what changed, what needs attention. No spin.
2. **Key metrics** (table: metric, last period, this period, direction)
Only include metrics I actually provided. Don't invent or estimate.
If I didn't give you a number for something important, flag it
as missing.
3. **What went well** (3 bullets)
Specific outcomes, not activity. "Closed X deal at Y value" not
"had productive sales conversations".
4. **What didn't** (2-3 bullets)
Things that went wrong or stalled. Be honest. Board members
spot omissions faster than founders think.
5. **Decisions made** (numbered list)
Each: the decision, the reasoning in one line, and what changes
as a result.
6. **Asks** (numbered list, or "None this month")
Intros, advice, approvals, whatever I need from the board.
Each with enough context that a board member can act without
a follow-up question.
7. **Next month** (3 bullets)
What I'll be focused on. Commitments, not aspirations.
Constraints:
- Under 600 words total. Board members skim.
- No marketing language. This is an internal document.
- If my notes are thin in any section, say "insufficient data"
rather than padding.
- Apply voice.md if present.
Frequency. Run this the last Friday of every month. The first one takes 20 minutes to gather the notes. By the third month you'll have a rhythm and it takes 5. The board members who get a consistent, honest update every month are the ones who help you when you need it. Depends on: CLAUDE.md (skill 01) so the output matches your context, and voice.md (skill 02) so it sounds like you wrote it.
Skill 05Founder
Technical Brief Writer
technical-brief.md
Describe what you want built in plain English. Get a spec an engineer can estimate from, scope, and build against. Includes the questions they'll ask on day one, so you can answer them before the brief lands.
I want to describe what I need built, in plain English, and get back
a spec that an engineer or agency can estimate from.
<what-i-want>
[Describe the feature, system, or change you want. Use your own words.
Don't try to be technical. "I want customers to be able to reschedule
their own appointments without calling us" is better than "build a
rescheduling API".]
</what-i-want>
<context>
[Anything relevant: what exists today, what tools/platforms you use,
who the users are, any constraints (budget, timeline, regulatory).]
</context>
Produce:
1. **What this is** (2-3 sentences)
Restate what I asked for in clearer terms. If my description was
ambiguous, pick the most likely interpretation and flag the
assumption.
2. **What's in scope** (bulleted list)
The specific things this build includes. Be concrete: "email
notification when rescheduled", not "notifications".
3. **What's out of scope** (bulleted list)
Things a developer might reasonably assume are included but
aren't. Name them so nobody builds them by accident.
4. **Acceptance criteria** (numbered list)
The conditions that mean "this is done". Testable statements:
"a customer can reschedule up to 24 hours before the appointment",
not "rescheduling works".
5. **Questions the dev will ask on day one** (numbered list)
The decisions I haven't made yet. For each, include a recommended
answer with one line of reasoning, so I can either accept it or
make a different call before the brief lands.
6. **Estimated complexity** (one line)
Small (a few hours), medium (a few days), or large (weeks). Not
a quote, just a rough shape so I can set expectations.
Constraints:
- Total length under 500 words.
- Plain language. If a technical term is necessary, define it in
parentheses.
- Apply voice.md if present.
Who this is for. Non-technical founders sending briefs to freelancers, agencies, or in-house engineers. The "questions the dev will ask" section is the most valuable part: it surfaces the decisions you'd otherwise discover mid-build, when changing course is expensive. Depends on: CLAUDE.md (skill 01) for project context and voice.md (skill 02) for tone.
Skill 06Founder
Investor Q&A Prep
investor-qa-prep.md
Paste your deck or one-pager. Get the follow-up questions a sharp investor would ask in the first meeting, with draft two-sentence answers. Calibrated for UK/EU VC, Seed to Series A.
You are a partner at a top-quartile UK/EU venture fund evaluating an
early-stage deal. Read my materials and produce the questions I need
to prepare for.
<materials>
[Paste your deck content slide by slide, your one-pager, or your
executive summary. Attach a PDF if you have one.]
</materials>
<context>
Stage: [pre-seed / seed / Series A]
Raising: [amount, e.g. £750k]
Use of funds: [one line, e.g. "hire two engineers and run paid acquisition for 6 months"]
</context>
Produce:
1. **The 10 questions** (numbered list)
In the order an investor would ask them, not grouped by category.
Start with the one they'd open the meeting with. End with the one
they'd ask as you're packing up.
For each question:
- The question itself, as the investor would phrase it (direct,
not softened)
- A two-sentence draft answer I can use as a starting point
- One line on what the investor is really testing with this question
2. **The gap** (one paragraph)
The single biggest thing missing from my materials that would
make an investor pause. Not a list. The one thing.
3. **The strongest card** (one paragraph)
The single most convincing thing in my materials, and the best
way to lead with it.
Constraints:
- Don't soften the questions. Investors don't.
- The draft answers should be honest, not polished. If the honest
answer is "we don't know yet", say so, then add what we'd need
to find out.
- Under 800 words total.
- Apply voice.md if present.
Pair this with The Grill. Run Investor Q&A Prep first to surface the questions, then run The Grill on your answers. The prep gives you the questions; the grill stress-tests whether your answers hold up under follow-up pressure. Depends on: CLAUDE.md (skill 01) for company context and voice.md (skill 02) so the draft answers sound like you.
Skill 07Founder
Founder Advisory Panel
advisory-panel.md
Simulate a panel of five named advisors, each with a specific expertise and decision framework. Present a decision; get five structured perspectives, including a mandatory dissenter who names the assumption everyone else is underweighting.
Simulate a panel of five named advisors. Each has a specific expertise
and a documented decision framework. I'll present a decision or
challenge, and each advisor responds from their specialism.
The panel:
1. **The Technical Architect** evaluates system design, scalability,
and technical debt. Their question: "Does this simplify or
complicate the system in 18 months?"
2. **The Commercial Operator** evaluates unit economics, pricing,
and go-to-market fit. Their question: "Who pays for this, how
much, and why now?"
3. **The Talent Strategist** evaluates hiring, team structure, and
capability gaps. Their question: "Can the current team build and
maintain this?"
4. **The Investor Lens** evaluates from a board seat: risk, capital
efficiency, and narrative. Their question: "Does this make the
next raise easier or harder?"
5. **The Devil's Advocate** is the mandatory dissenter. Their job is
to find the weakest assumption in the room and pressure-test it.
They are not contrarian for sport: they name the specific risk
the others are underweighting.
Ground rules:
- This is a SIMULATION. The advisors are named roles, not real
people. Do not present their opinions as expert advice.
- Each advisor answers in 2-3 sentences, grounded in their framework.
No padding, no "great question" openers.
- The Devil's Advocate speaks last, after hearing the others.
- If two advisors conflict, surface the conflict explicitly. Don't
resolve it: that's my job.
- If an advisor doesn't have a useful perspective on this specific
question, they say "No strong view on this one" instead of forcing
a take.
- Never fabricate credentials, data, or case studies. The value is
the structured thinking, not fake authority.
- Apply voice.md if present.
After all five have spoken, close with:
**The split**: where the panel agrees and where it doesn't, in two
sentences.
Start by asking me: "What decision or challenge do you want the
panel to weigh in on?"
When to convene the panel. Before any decision that commits you for more than a quarter: a new hire, a platform choice, a pricing model, a partnership. The panel is most useful when you're leaning one way and haven't stress-tested the lean. Run it, read the Devil's Advocate's take, then decide. Depends on: CLAUDE.md (skill 01) for company context and voice.md (skill 02) for tone.
Skill 08Founder
Launch Playbook
launch-playbook.md
Describe what you're launching and what channels you own. Get a three-phase launch plan (pre-launch, launch week, post-launch) with owned/rented/borrowed channel allocation, a day-by-day schedule, and the kill-or-scale decision criteria. Built for one person, not a marketing team.
Build a launch plan for what I'm about to ship.
<what-im-launching>
[Describe the product, feature, service, or content you're launching.
What it does, who it's for, and when you want it live.]
</what-im-launching>
<what-i-have>
[What channels do you already own? Email list size, social following,
existing customers, partnerships, anything you can reach without
paying. Be honest about the numbers.]
</what-i-have>
Produce a launch plan across three phases:
## Phase 1: Pre-launch (2-4 weeks before)
Build anticipation using OWNED channels only (your email list, your
existing audience, your current customers). No spend.
- **The hook**: one sentence that makes the right person stop
scrolling. Not a tagline. The sentence you'd say in a conversation.
- **Validation checklist**: 3-5 things to confirm before launch day
(pricing tested, landing page live, payment flow working, one
person has gone through the full journey end to end).
- **Warm-up sequence**: 3 touchpoints with dates, channel, and
content angle for each.
## Phase 2: Launch week
Coordinate across three channel types:
- **Owned** (your list, your profile, your site): what you post,
when, where.
- **Rented** (platforms where you have a presence but don't control
distribution: LinkedIn, Twitter, communities): what format works
on each, timing.
- **Borrowed** (other people's audiences: guest posts, podcast
appearances, cross-promos, partner emails): who to ask, what to
offer them, the ask template.
Day-by-day schedule for launch week. Keep it doable for one person.
If you can't execute it solo, say so and flag what needs delegating.
## Phase 3: Post-launch (weeks 2-4)
- **What to measure**: 3-5 metrics that tell you whether the launch
worked, with the threshold for "good enough" vs "needs rethinking".
- **The follow-up sequence**: what to send to people who showed
interest but didn't convert.
- **The kill/scale decision**: at what point you double down, and at
what point you cut it.
Constraints:
- This is for a founder doing the launch themselves, not a marketing
team. Keep the plan realistic for one person with limited time.
- No vanity metrics. "Impressions" is not a success metric for a
founder.
- If my audience is too small for a real launch (under 500 reachable
people), say so and adjust the plan to a soft launch instead.
- Apply voice.md if present.
Launch vs ship. Shipping is getting the thing live. Launching is getting the right people to notice. Most founders ship well and launch badly, or the other way round. This playbook is the launch half. If you haven't finished building yet, use the Technical Brief Writer (skill 05) first. Depends on: CLAUDE.md (skill 01) for business context and voice.md (skill 02) for consistent messaging.
Skill 09Founder
The Unstick Protocol
unstick.md
For the task you have been carrying for three weeks without starting. Four stages, run in order: name the feeling under the avoidance, shrink the entry point, attach the work to a cue that already fires, and write the re-entry plan before you need it. Built on the research that says the anticipation is the painful part, not the task.
You are my unstick advisor. I use you when I have been avoiding
something and the avoidance has started to cost me.
Trigger this whenever I say I am stuck, overwhelmed, drowning, behind,
avoiding something, or that I keep meaning to start a thing and haven't.
I will rarely call it procrastination. "I keep meaning to" is the tell,
and so is a task that has moved to next week three weeks running.
## What you know that I don't
Avoidance is not a discipline problem. In people anxious about maths,
the brain's pain network activated when they anticipated doing maths,
not while they were doing it (Lyons and Beilock, 2012). The dread is
front-loaded. It settles once the work is actually underway, usually
inside the first 20 minutes.
Two consequences, and they run this whole file:
1. Any plan that depends on me wanting to start is a plan that fails.
Design around the first 20 minutes instead.
2. What I am avoiding is a feeling, not a task. Until that feeling is
named, every plan built on top of it is aimed at the wrong thing.
Never tell me to be disciplined, to want it more, to remember my why, or
to think about how good I'll feel afterwards. Motivation is not the
mechanism and you are not my cheerleader.
## Stage 0: pick one (only if I bring you several)
If I arrive with a list, or with "everything", do not process the list.
Overwhelm is what a pile of avoided tasks feels like from the inside,
and triage is the wrong tool: I will spend the session ranking work
instead of starting any of it.
Ask one question: which of these, if it were done, would make the others
smaller or matter less? Take my answer. Park the rest by name, out loud,
so I can stop holding them. Then run stages 1 to 4 on the one task only.
## Stage 1: name what I am actually avoiding
Find the feeling, not the task.
- Locate the precise moment resistance peaks. Usually it is not the work.
It is opening the file, or the second before I would have to type the
first line.
- Separate the task from what it triggers: fear of doing it badly,
fear of what the answer will be, boredom, the size of it, having to
ask someone for something, or having to admit something is behind.
- Test whether the same feeling shows up in the other things I avoid.
A pattern is more useful than an incident.
- Name it in one sentence, plainly.
Rules for this stage: do not accept "laziness" or "no time" as an answer,
because neither is a feeling. Do not soften the name once you have it.
If what I have told you is not enough to name it, ask me one question
and wait. Do not guess.
## Stage 2: shrink the entry point
Find the smallest first action, then make it smaller.
- Reduce the task to something so small that refusing it takes more
effort than doing it. Not a scaled-down version of the work. The
first physical move.
- Define what the first 20 minutes look like. Only the 20 minutes.
Not the whole task, and no plan for finishing it.
- Name one signal that tells me the resistance has passed and I am
working properly.
- Say what happens immediately after the 20 minutes, so the momentum
has somewhere to go.
Rules for this stage: if the first action still has a decision inside
it, it is too big. Cut again. Never propose willpower as the mechanism.
## Stage 3: kill the decision about when
Every time I have to decide when to start, I get a fresh chance to
avoid it. Remove the decision.
- Find a cue that already exists in my week and fires reliably without
me arranging it. An existing meeting ending, the school run, the
first coffee, Monday's standup. Not a new habit, and not an alarm I
will learn to dismiss.
- Attach the task directly to that cue with nothing in between. If
there is a step between the cue and the work, that step is where I
will escape.
- Say what to do if the cue fires and I still do not want to start.
Usually: do the stage 2 action anyway and stop after 20 minutes if
it is still awful. It almost never is.
Rules for this stage: the cue must already happen without me. Never
build the plan on remembering.
## Stage 4: write the re-entry plan now
I will miss a day. That is not the failure. Abandoning the system on
the day I miss is the failure, and it happens because there was no
plan for it, so the miss gets read as proof the whole thing does not
work for me.
- Name what a slip actually looks like for me: one skipped day, a
skipped week, or dropping it altogether without saying so.
- Define the re-entry action. It must be smaller than the stage 2
action, not the same size. Catching up is banned. Whatever I missed
is gone and re-entry does not include it.
- Name what usually causes the slip, so it can be handled directly next
time rather than discovered again.
- Give me one signal that says I am properly back in, not just having
done it once.
Rules for this stage: never frame a slip as a personal failure, and
never let me build a repayment plan for missed days.
## Output format
Keep the whole thing under 400 words. Use these headings, in order,
and nothing else. No preamble, no encouragement, no closing summary.
**What I'm really avoiding:** [the feeling, one sentence, named plainly]
**The pattern:** [where else it shows up, or "one-off" if it is]
**First action:** [small enough to do now]
**The first 20 minutes:** [exactly what happens in them]
**The cue:** [the existing thing it hangs off]
**If the cue fires and I resist:** [what to do]
**When I slip:** [the re-entry action, smaller than the first action]
**Back on track when:** [the signal]
Apply voice.md if present. Do not congratulate me at any point.
Use it on one thing, not the pile. Stage 0 exists because founders bring this a list, and a list is how the session turns into another hour of prioritising. Run stage 4 while things are going well, not on the day you slip: the re-entry action is much smaller when you write it before you need it. Depends on: CLAUDE.md (skill 01), so it knows what you are actually working on. Pairs with the Decision Journal (skill 11) if the thing you keep avoiding turns out to be a decision rather than a task.
Section 3 of 4
For teams
Two skills for the operational gaps that appear when a team doesn't have a CTO or chief of staff making sure decisions and actions don't leak.
Skill 10Team
Meeting Actions Extractor
meeting-actions.md
Paste a transcript or messy notes. Get actions with owners, deadlines, and the one decision that was made but nobody said out loud. Catches the commitments that leak between meetings.
Extract the actions and decisions from this meeting.
<transcript>
[Paste the transcript, voice-note transcription, or your own notes.
Messy is fine. If multiple people spoke, include names where you can.]
</transcript>
<meeting-context>
Meeting: [name or topic]
Date: [date]
Attendees: [who was there]
</meeting-context>
Produce:
1. **Decisions made** (numbered list)
Each: what was decided, and by whom. If a decision was implied
(everyone moved on as if it was settled, but nobody said "we've
decided"), flag it as "implied decision" and name it anyway.
These are the ones that cause arguments later.
2. **Actions** (table: action | owner | deadline | depends on)
- If no deadline was mentioned, write "none stated" (don't invent)
- If ownership was vague ("someone should..."), write "unowned"
- "Depends on" captures blockers: "after the contract is signed",
"once Sarah confirms budget"
- Use the verb the person actually used. "Look into" and "do" are
different commitments.
3. **Open questions** (bulleted list)
Things that came up but weren't resolved. For each, name who
raised it and who's expected to follow up, if that was clear.
4. **The one thing nobody said**
The decision, tension, or commitment that was present in the
conversation but not stated explicitly. If there isn't one, say so.
Don't manufacture one.
Constraints:
- Don't add context I didn't give you. If ownership is unclear, say so.
- Under 400 words total.
- Plain language. No corporate meeting-minutes tone.
- Apply voice.md if present.
Make it routine. Run this after every meeting where decisions happen. Paste the output into a shared document or Slack thread within an hour. The value isn't the extraction itself: it's that everyone sees the same list of commitments before memory starts drifting. Depends on: CLAUDE.md (skill 01) for team context and voice.md (skill 02) for consistent tone across extractions.
Skill 11Team
Decision Journal
decision-journal.md
Captures every material decision with the reasoning, the alternatives, and what would make you change your mind. Builds a searchable log across conversations, so six months later you can find why you chose X, not just that you did.
I've made a decision I want to log properly.
<decision>
[Describe the decision you made. One or two sentences.]
</decision>
<context>
[What prompted this decision? A meeting, a metric, a customer complaint,
a gut feeling? Be honest about the trigger.]
</context>
<alternatives>
[What else you considered, even briefly. Include "do nothing" if that
was on the table.]
</alternatives>
Log it as a structured decision record:
1. **Decision** (one sentence, starting with a verb)
"Switch from Stripe to GoCardless for recurring billing" not
"billing platform decision".
2. **Date**: [today's date]
3. **Decided by**: [who made the call]
4. **Context** (2-3 sentences)
What was happening that forced this decision now.
5. **Options considered** (bulleted list)
Each: the option, one line on why it was attractive, one line on
why you didn't pick it.
6. **Why this option** (2-3 sentences)
The actual reason, not the rationalisation. "It was cheaper" is
fine. "The CEO preferred it" is also fine. Be honest.
7. **What would make us revisit this** (bulleted list)
The specific conditions under which this decision should be
reopened. "If churn exceeds 5%", "if the vendor raises prices
above £X", "after the first quarter of data".
8. **Depends on** (bulleted list, or "nothing")
Decisions that need to hold for this one to stay valid.
Constraints:
- Under 250 words total.
- Don't editorialise. Log it as it happened.
- Format consistently so entries are searchable across months of logs.
- Apply voice.md if present.
After producing the record, append it to the running log below the
line. If no log exists yet, start one with a "# Decision Journal"
heading.
---
Why a journal beats a memory feature. ChatGPT and Claude both remember things across chats, but that memory is a black box: you can't read what it stored, audit whether it captured the reasoning correctly, or hand it to a co-founder when the context needs sharing. A file you can read, search, and hand over is worth more than a vendor's best guess at what you decided. Depends on: CLAUDE.md (skill 01) for project context and voice.md (skill 02) for consistent formatting across entries.
Section 4 of 4
CTO decision frameworks
Five frameworks from real client engagements. These are the decision structures I install first when I start with a new founder: build vs buy, first hire, due diligence, architecture decisions, and scaling readiness.
Skill 12Founder
Build vs Buy Analysis
build-vs-buy.md
The decision tree for whether to build internally, buy a tool, or adapt an existing platform. Covers total cost (not just licence fees: integration, maintenance, hiring, opportunity cost), lock-in risk, and the trigger conditions that should reopen the decision. This is the analysis I run with every CTO client before they commit to a platform or start building.
I need to decide whether to build, buy, or adapt for a specific
capability. Walk me through the analysis.
<capability>
[Describe the capability you need. What does it do? Who uses it?
What happens if you don't have it?]
</capability>
<current-state>
[What exists today? Are you doing this manually, using a workaround,
or starting from nothing? What tools and platforms are already in
your stack?]
</current-state>
<constraints>
[Timeline, budget, team size, regulatory requirements, anything
that narrows the options before the analysis starts.]
</constraints>
Produce:
1. **The three options** (one paragraph each)
For each of Build, Buy, and Adapt:
- What this looks like concretely (not abstract: name the likely
tool, or describe what you'd build)
- Time to first value (when does the team start using it)
- Who does the work (existing team, new hire, contractor, vendor)
2. **Total cost comparison** (table over 12 months and 36 months)
Columns: option | upfront cost | monthly run cost | integration
cost | maintenance/support cost | opportunity cost | total 12mo |
total 36mo
Rules for the cost table:
- Integration cost is the work to connect this to your existing
systems. It's never zero for Buy.
- Maintenance cost for Build includes the ongoing engineer time
to keep it working. Be honest: it's always more than you think.
- Opportunity cost for Build is what those engineers would ship
instead. Name the specific thing they won't build.
- If I didn't give enough information to estimate a line, write
"[need input: what I need to know]" instead of guessing.
3. **Lock-in assessment** (one paragraph per option)
How hard is it to switch away from this choice in 18 months?
What data gets trapped? What integrations break? What contracts
bind you?
4. **The recommendation** (one paragraph)
Which option, and why. Be direct. If it's close between two,
say so and name the single factor that tips it.
5. **Revisit triggers** (bulleted list)
The specific conditions under which this decision should be
reopened. "When we hit 10k users", "if the vendor raises prices
above X", "when we hire a second engineer". Not vague.
Constraints:
- Don't default to Build because it feels more "startup". Most
pre-Series A companies should buy more than they think.
- Don't default to Buy because it's faster. If the capability is
your core differentiator, building it is probably right.
- No marketing language. This is an internal decision document.
- Under 800 words total.
- Apply voice.md if present.
When to run it. Before committing to any platform, tool, or internal build that will take more than a week of effort. The opportunity cost line is where most founders get surprised: the engineers who spend three months building an internal tool aren't shipping product during those three months. Depends on: CLAUDE.md (skill 01) for company and team context.
Skill 13Founder
First Technical Hire Brief
first-technical-hire.md
For non-technical founders hiring their first engineer, tech lead, or fractional CTO. Covers what to look for (and what to ignore), the JD, interview questions that test real competence, red flags, and 90-day success criteria. Calibrated for startups pre-Series A where the first technical hire shapes everything.
I'm hiring my first technical person. Help me get it right.
<role>
[What role are you hiring? Engineer, tech lead, CTO, fractional CTO,
technical co-founder? If you're not sure, describe what you need
them to do and I'll tell you which role that is.]
</role>
<company-stage>
[What stage are you at? Idea, prototype, live product, revenue?
How many people on the team now? How much runway?]
</company-stage>
<what-exists>
[What's been built so far, and by whom? Agency, no-code, a friend,
nothing yet? What's the tech stack, if you know it?]
</what-exists>
<budget>
[Salary range or day rate you can afford. Be honest. An unrealistic
budget is the fastest way to hire the wrong person.]
</budget>
Produce:
1. **What you actually need** (one paragraph)
Based on your stage and what exists, the role you should hire
for. This might not match what you asked for. If you said CTO
but you need a senior engineer, I'll say so.
2. **What to look for** (bulleted list, max 6 items)
The specific skills and traits that matter at your stage.
- Prioritise by what matters now, not what matters at scale
- Include at least one non-technical trait (communication,
autonomy, comfort with ambiguity)
- Mark which ones are non-negotiable vs nice-to-have
3. **What to ignore** (bulleted list, max 4 items)
The things that look impressive on a CV but don't predict
success in this specific role at this specific stage. FAANG
experience at a pre-seed company is one example. Name the
others.
4. **The job description** (ready to post)
Under 400 words. No jargon the candidate won't use themselves.
Include:
- What they'll do in the first 90 days (specific, not "help
shape the technical vision")
- What success looks like at 6 months
- What the company is and what stage it's at (honest)
- Salary range or day rate (founders who hide this waste
everyone's time)
5. **Five interview questions** (numbered list)
Each with:
- The question, worded as you'd say it in conversation
- What a good answer sounds like (one sentence)
- What a red-flag answer sounds like (one sentence)
The questions should test:
- Can they build the thing you need right now?
- Can they make decisions without you holding their hand?
- Do they communicate clearly with non-technical people?
- Will they challenge you when you're wrong?
- Have they worked at this scale before (or can they adapt)?
6. **Red flags in the hiring process** (bulleted list, max 5)
The signals during interviews that predict a bad hire, specific
to early-stage technical roles.
7. **90-day success criteria** (numbered list, max 5 items)
Concrete, testable conditions. "Deployed the first feature to
production", not "integrated into the team".
Constraints:
- This is for a non-technical founder. Explain any technical term
in plain language.
- Be honest about what this hire can and can't do. One engineer
doesn't replace a team.
- If the budget doesn't match the role, say so directly and
suggest what the budget can get.
- Apply voice.md if present.
The mistake I see most. Non-technical founders hire for reassurance, not capability. They pick the candidate who sounds most confident, not the one who asks the sharpest questions. The interview questions in this skill are designed to surface the difference. Depends on: CLAUDE.md (skill 01) for company context.
Skill 14Founder
Tech Due Diligence Prep
tech-due-diligence-prep.md
The checklist a buyer's CTO or investor's technical advisor runs during due diligence. Produces a structured DD pack the founder can prepare in advance so the real DD goes smoothly. This is the framework I ran when Vault Platform was acquired by Diligent.
I need to prepare for technical due diligence. Help me build the
pack before the assessor arrives.
<context>
[What's the DD for? Acquisition, investment round, partnership?
Who's on the other side? What stage is your company?]
</context>
<tech-stack>
[Your current stack: languages, frameworks, cloud provider, key
third-party services, CI/CD, monitoring. List what you know.]
</tech-stack>
<team>
[Engineering team: size, seniority split, tenure, any key-person
dependencies. Include contractors and agencies.]
</team>
<known-issues>
[What you already know is weak. Be honest here: the assessor will
find it anyway, and it's better if you've already documented it
with a remediation plan than if they discover it cold.]
</known-issues>
Produce a DD prep pack covering these seven areas:
1. **Architecture overview**
- System diagram description (major components, how they connect,
where data flows)
- Deployment model (cloud, on-prem, hybrid)
- Key architectural decisions and why they were made
- What you'd change if you started again (assessors respect
self-awareness more than perfection)
2. **Code quality**
- Test coverage: what's tested, what isn't, why
- Code review process (or lack of one)
- Linting, formatting, CI pipeline
- Age of the codebase, major rewrites, migration history
3. **Security**
- Authentication and authorisation model
- Data encryption (at rest and in transit)
- Dependency scanning and update cadence
- Incident history (be honest: "none" is less credible than
"one, here's what we learned")
- Compliance requirements and current status (SOC 2, GDPR, etc.)
4. **Scalability**
- Current load and headroom
- Known bottlenecks
- What breaks first if usage doubles
- Database: size, growth rate, indexing, query performance
5. **Technical debt register**
- Known debt items, each with: what it is, why it exists,
severity (blocks progress / slows progress / cosmetic),
estimated effort to fix
- Which ones you'd fix before an acquisition closes
6. **Team and knowledge**
- Bus factor: who holds critical knowledge?
- Documentation state (honest assessment)
- Onboarding time for a new engineer
- Retention: who left in the last 12 months and why
7. **Dependency and vendor risk**
- Critical third-party services and what happens if they go down
- Contract terms: are you locked in? Can you migrate?
- Open-source dependency health (abandoned projects, licence risk)
For each area, produce:
- **Status**: green (solid), amber (known gaps with a plan), or
red (material risk)
- **Evidence**: what documentation or artefacts exist today
- **Gap**: what's missing and what you need to prepare before DD
- **Talking points**: how to present this area honestly without
underselling
Close with:
**The three things to fix before DD starts** (numbered list)
The highest-impact items you can address in the time available.
Prioritise by what an assessor will flag as a blocker, not what's
technically most interesting.
Constraints:
- Assessors value honesty over polish. Don't hide problems;
document them with remediation plans.
- If I haven't given enough information for an area, tell me
what's missing rather than guessing.
- Total output under 1,200 words.
- Apply voice.md if present.
Timing. Start this the moment DD becomes a possibility, not when the assessor sends the data request. A month of preparation makes a one-week DD feel routine. A day of preparation makes it feel like an audit. Depends on: CLAUDE.md (skill 01) for company and product context.
Skill 15Team
Architecture Decision Record
architecture-decision-record.md
The format for documenting technical decisions so they're findable and reversible. Status, context, decision, consequences, and what would make you revisit. Simpler than the academic ADR format. Designed for startups where decisions happen fast and the reasoning needs to survive staff turnover.
I've made a technical decision I want to document properly.
<decision>
[What did you decide? One or two sentences. "We're moving from
PostgreSQL to DynamoDB for the events table" or "We're keeping
the monolith instead of splitting out the billing service".]
</decision>
<context>
[What prompted this? A performance problem, a new requirement,
a team change, a scaling concern? What was the situation before
this decision?]
</context>
<options-considered>
[What alternatives did you evaluate? Include "do nothing" and
"defer the decision" if they were on the table.]
</options-considered>
Produce an Architecture Decision Record in this format:
**ADR-[number]: [decision title in imperative mood]**
(e.g. "ADR-007: Use DynamoDB for event storage")
1. **Status**: [proposed | accepted | superseded by ADR-XXX | deprecated]
2. **Date**: [today's date]
3. **Participants**: [who was involved in the decision]
4. **Context** (2-4 sentences)
The situation that forced this decision. What problem exists,
what constraint applies, what changed. No preamble.
5. **Options considered** (one paragraph each, max 4 options)
For each option:
- What it is (one sentence)
- The strongest argument for it
- The strongest argument against it
- Rough effort and timeline
6. **Decision** (one paragraph)
What you chose and the primary reason. Be specific. "We chose
X because Y" not "after careful consideration, we decided".
7. **Consequences** (two lists)
- **What improves**: the specific things that get better
- **What gets harder**: the specific trade-offs and new
constraints. Every decision has these. If you can't name
them, you haven't thought it through.
8. **Revisit when** (bulleted list)
The concrete conditions that should trigger reopening this
decision. Measurable where possible: "when write throughput
exceeds 5k/sec", "when the team grows past 4 engineers",
"if the vendor deprecates the API". Not "if requirements
change" (that's always true and therefore useless).
9. **Depends on** (bulleted list or "none")
Other decisions or assumptions this one relies on. If those
change, this ADR needs review.
Constraints:
- Under 400 words total. ADRs that are too long don't get read.
- Technical precision matters here. Don't simplify away the
detail that makes this decision findable in six months.
- No opinion on whether the decision is right. This is a record,
not a recommendation. Log what was decided and why.
- Number this sequentially. If this is the first ADR, it's ADR-001.
Ask me what number to use if I've got existing ADRs.
- Apply voice.md if present.
After producing the record, confirm: "Should I append this to
a running ADR log, or is this standalone?"
Why bother. Six months from now, someone will ask why you chose Postgres over Mongo, or why the billing service is still in the monolith. If the answer lives in someone's head, and that person has left, you're guessing. If it's in an ADR, you're reading. Keep ADRs in a /docs/adr/ folder in your repo, one file per decision. Depends on: CLAUDE.md (skill 01) for project context. Pairs well with the Decision Journal (skill 11) for non-technical decisions.
Skill 16Founder
Scaling Readiness Assessment
scaling-readiness.md
When to re-platform, when to hold steady, and how to tell the difference. Takes your current stack, traffic, team size, and growth trajectory as inputs. Produces a scored assessment across five dimensions with a clear recommendation: hold, prepare, or act now.
Assess whether my current setup is ready for the growth we're
expecting. Tell me what to fix, what to leave alone, and what
to watch.
<current-stack>
[Your tech stack: languages, frameworks, database, hosting/cloud
provider, CDN, key third-party services. Include versions if you
know them.]
</current-stack>
<current-load>
[What does your traffic/usage look like today? Monthly active users,
requests per second, database size, storage, anything you can
measure. Rough numbers are fine.]
</current-load>
<growth-trajectory>
[What growth are you planning for or expecting? "2x users in 6
months", "launching in a new market Q1", "just closed a deal that
adds 500 enterprise seats". Be specific about the timeline.]
</growth-trajectory>
<team>
[Engineering team: size, seniority, what they're currently working
on. Include contractors and agencies.]
</team>
<known-pain>
[What's already hurting? Slow queries, deployment bottlenecks,
on-call burnout, features taking too long? List everything,
even if it feels minor.]
</known-pain>
Produce a Scaling Readiness Assessment:
## Scored assessment
Rate each dimension 1-5 (1 = will break under projected load,
5 = handles 10x current load with no changes). For each:
- **Score** with one-sentence justification
- **What breaks first** at projected load
- **Effort to fix** (hours, days, weeks, months)
The five dimensions:
1. **Infrastructure**
Hosting, compute, networking, CDN. Can the current setup
handle the projected load? What needs to scale, and is it
configured to auto-scale or does someone have to do it
manually?
2. **Data**
Database performance, storage growth, backup/recovery,
data pipeline throughput. Where are the slow queries?
What happens to the database at 5x current size?
3. **Team**
Can the current team build new features and handle
operational load at the projected scale? Where are the
knowledge silos? What's the bus factor on critical systems?
4. **Process**
Deployment pipeline, incident response, monitoring and
alerting, on-call rotation. Does the process work at
current scale? Will it work at 3x?
5. **Architecture**
Service boundaries, coupling, API design, data model.
Which architectural decisions will hold, and which ones
are already creaking?
## The recommendation
One of three verdicts:
- **Hold**: the current setup handles the projected growth.
Invest in features, not infrastructure. Name the 1-2 things
to monitor so you catch problems early.
- **Prepare**: the current setup works today but won't survive
the projected growth. Here's what to start now (with priority
order and estimated effort) so you're ready before the load
arrives.
- **Act now**: something is already at or near its limit.
Here's what to fix first, in what order, and what it costs
in team time and money.
## Scaling roadmap (if Prepare or Act Now)
Numbered list, priority order. Each item:
- What to do (specific, not "improve database performance")
- Why it matters (what breaks if you don't)
- Effort (days/weeks, who does it)
- When to do it (now, next quarter, before [event])
## What not to touch
Bulleted list. The things that look like scaling problems but
aren't, at your current stage. Founders over-engineer here
constantly. Name the things that can wait and why.
Constraints:
- Don't recommend re-platforming unless the current platform
genuinely can't handle the growth. Migration has a cost that
founders routinely underestimate.
- If I haven't given enough data to score a dimension, say
"[need input: what I need]" and score it as "unscored".
- Be direct about what's fine. Not everything needs fixing.
- Under 1,000 words total.
- Apply voice.md if present.
Run this quarterly. Or whenever a large deal, new market, or funding round changes the growth trajectory. The "what not to touch" section saves more money than the roadmap in most cases: founders spend weeks optimising systems that don't need it yet. Depends on: CLAUDE.md (skill 01) for company context. Pairs well with Build vs Buy (skill 12) when the assessment surfaces a component that needs replacing.
How to install a skill
Claude Projects (claude.ai):
Download or copy the skill file.
Open your Claude project.
Go to Project Knowledge and upload the .md file.
Every conversation in that project now has the skill loaded.
Claude Code (CLI or desktop):
Save the file to ~/.claude/skills/[skill-name]/SKILL.md
Add frontmatter: ---\nname: skill-name\ndescription: one line\n---
Invoke with /skill-name in any session.
The foundation files (CLAUDE.md and voice.md) work best as project instructions. The task-specific skills (board update, technical brief, etc.) work as either project knowledge or standalone skills.
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