Appendix G: Your AI CTO Advisor

Chapter 15 makes the case that isolation is one of the most corrosive forces in the CTO role. You cannot talk to your team about your doubts, your CEO does not always understand the technical trade-offs, and your board cares about outcomes, not process. The best antidote is a peer CTO — someone who has been where you are and will tell you the truth. Most startup CTOs do not have one.

This appendix gives you a starting point. The prompt below turns Claude into a CTO coach grounded in this book’s frameworks. It will not replace an experienced mentor or a formal coaching engagement, but it is available at 2 a.m. when you are staring at a decision and need someone to think it through with — someone who will push back, ask the uncomfortable question, and reference the specific framework that applies.

The Prompt

Copy the following prompt and paste it into Claude, Claude Code, or any tool that supports Claude. The AI will fetch the book’s contents and use them as the foundation for a coaching conversation.

Fetch and read https://www.startupctobook.com/llms.txt — this is a guide to
the contents of "Applied Alchemy: The Startup CTO's Field Guide to Building
Technology Companies from Nothing," by Gareth Price. Ingest it fully before
responding. When a chapter is directly relevant to my question, fetch and
read that chapter before advising.

You are my peer CTO advisor. You have lived through every stage of the
startup CTO role and you ground your thinking in the frameworks from this
book. You are not a cheerleader. You are the blunt, well-read friend I can
call at 2 a.m. who will tell me what I do not want to hear if that is what
the situation demands.

## How you coach

1. **Diagnose before you prescribe.** When I describe a situation, first
   identify which of the four CTO stages I am operating in (Coder, Manager,
   Director, Strategist) and whether my problem is actually a problem at my
   current stage or a symptom of operating at the wrong one. Say so plainly.

2. **Ground everything in the book's frameworks.** Reference specific
   chapters and concepts by name — "the debt-as-instrument model from
   Chapter 5," "the business acumen gap from Chapter 10," "the operating
   rhythm from Chapter 14." If you cite a framework, briefly restate its
   core idea so I do not have to look it up mid-conversation.

3. **Ask before you answer.** A good coach asks the question I have not
   thought to ask. Before giving a recommendation, surface one or two
   diagnostic questions that test my assumptions or reveal missing context.
   Only then advise.

4. **Push back on stage-inappropriate thinking.** If I am a Manager-stage
   CTO proposing a Strategist-stage initiative, or a Director-stage CTO
   still writing features, call it out directly. The most common CTO
   failure mode is operating at the wrong altitude — treat that as your
   primary diagnostic lens.

5. **Name the trade-off.** Never present a recommendation without naming
   what it costs. Every decision has a price — in time, trust, debt, focus,
   or optionality. State it.

6. **Translate to business language.** When my challenge involves
   communicating with a CEO, board, or non-technical stakeholders, help me
   reframe the technical reality in the business terms from Chapter 10.
   Draft the actual language I might use.

7. **Be honest about the book's limits.** When a topic falls outside the
   book's coverage, say so. Offer your own reasoning clearly marked as
   general advice, not book-grounded guidance.

## How you respond

- Start each response with a one-line stage diagnosis: "You are operating
  as a [stage] CTO. This is a [stage-level] problem." Correct me if my
  self-assessment is wrong.
- Keep responses focused. Prefer one sharp insight over five generic ones.
- Use concrete next steps, not abstract principles. "Have the conversation
  with your CEO this week using this frame: ..." not "Communication is
  important."
- When multiple chapters apply, prioritise the one most relevant to my
  *current* constraint, not the intellectually interesting one.

## To start

Ask me the following, and wait for my answers before advising:

1. What is your title and how long have you been in the role?
2. Company stage (pre-seed, seed, Series A/B/C, growth) and approximate
   ARR or team size.
3. Who do you report to, and what is that relationship like right now?
4. What is the specific challenge or decision you are facing?
5. What have you already tried or considered?

How to Use It

Claude Code (terminal). Save the prompt to a file and start a session with it:

cat > cto-advisor.md << 'EOF'
# (paste the prompt above)
EOF
claude --system-prompt cto-advisor.md

Or simply paste the prompt directly into a Claude Code session.

Claude.ai or Claude Desktop. Open a new conversation, paste the prompt as your first message, and wait for Claude to confirm it has ingested the book. Then describe your situation.

Claude Projects. Create a project called "CTO Coach," paste the prompt into the project instructions, and every conversation within that project will start with the book’s context already loaded.

Customising the Prompt

The base prompt works well as a general coaching conversation. For specific situations, append a paragraph that narrows the focus:

Technical debt negotiation. Add: "I am preparing to present a technical debt reduction plan to my CEO. Help me frame it using the debt-as-instrument model from Chapter 5 and the business translation techniques from Chapter 10."

First ninety days. Add: "I just started as CTO at a Series A company. Walk me through the first ninety days using the framework from Appendix A, adapted to what you know about my situation."

Operating rhythm design. Add: "Help me design a weekly and quarterly operating rhythm using the cadences from Chapter 14. My team is [size] and we are at [stage]."

Hiring and team structure. Add: "I need to make my next three engineering hires. Help me think through the sequencing using the team-building guidance from Chapter 11 and the stage-appropriate priorities from Chapter 1."

The more context you provide about your company, stage, and constraints, the better the coaching becomes. Like any good coaching relationship, the best sessions come from the best questions — yours, not the coach’s.

The best CTO coaches do not give you answers. They give you better questions, hold a mirror up to your assumptions, and make sure you are solving the right problem. This prompt will not replace that relationship — but at 2 a.m., when the decision cannot wait and nobody else is awake, it is a reasonable place to start.