Build a Plan That Survives Contact With Reality

STEP 1 — LEARN THE BUSINESS (THE INTERVIEW) This is the longest step. Interview the user to build the raw material for their plan. Ask these questions ONE AT A TIME, waiting for each answer before moving on: 1. "What does your business do, in one sentence a stranger would understand?" 2. "Who is your ideal customer? Be specific — not 'everyone,' but the person who gets the most value from what you do." 3. "How do customers find you today? (Referrals, Google, social media, walk-ins, etc.)" 4. "What do you charge, and how? (Per project, hourly, monthly retainer, per unit, etc.)" 5. "Roughly what was your revenue last month? Last year? (Ballpark is fine.)" 6. "What are your biggest expenses? (Materials, labor, rent, tools, software, etc.)" 7. "What is the ONE thing you want this business to look like in 12 months that it doesn't look like today?" 8. "What's the biggest risk to your business right now? The thing that keeps you up at night?" 9. "Do you have employees or contractors? If so, how many and what do they do?" 10. "What have you tried that didn't work? (Marketing channels, pricing models, services, partnerships — anything.)" After each answer, acknowledge what they said and ask the next question. Do NOT rush through these. STEP 2 — BUILD THE PLAN DOCUMENT Once you have all the interview answers, tell the user: "I'm going to create your business plan as a file called business-plan.md in your project folder. This is a living document — we'll update it as your business evolves." Create a file with these sections: 1. **Business Overview** — What you do, who you serve, how you deliver value 2. **Target Customer** — Specific profile, how they find you, what they care about 3. **Revenue Model** — How you charge, average deal size, revenue targets 4. **Cost Structure** — Fixed costs, variable costs, margins 5. **Growth Strategy** — How you plan to get from here to your 12-month goal 6. **Competitive Position** — What you do better, what others do better, your gap 7. **Risks and Assumptions** — Every assumption the plan depends on, stated explicitly 8. **Key Metrics** — 3-5 numbers that tell you if the plan is working 9. **Action Items** — The next 3 things to do, with deadlines Keep it under 3 pages. Use plain language, not MBA jargon. Write it in the user's voice, not a template voice. STEP 3 — SET UP THE "UPDATE PLAN" SKILL Have the user tell Claude: "Save a skill called 'update-plan'. When I say 'update my plan', read business-plan.md and ask me what's changed. Then update the relevant sections, add a dated changelog entry at the bottom, and show me what you changed." Explain: the plan should be updated whenever something meaningful changes — a new service, a price increase, a lost client, a new marketing channel. Monthly at minimum. STEP 4 — SET UP THE "SUGGEST IMPROVEMENTS" SKILL Have the user tell Claude: "Save a skill called 'plan-suggestions'. When I say 'what should I change?', read business-plan.md and think about everything you've learned working with me — my invoices, my leads, my email patterns, my market research, my month-end numbers. Then suggest 3-5 specific improvements to my business plan, with evidence from what you've actually seen." Explain: this is where the plan becomes smarter over time. Claude isn't guessing — it's drawing from real operational data. If the plan says "target 10 new clients per month" but the lead capture data shows 3 per month, Claude should flag that. STEP 5 — SET UP THE "STRESS TEST" SKILL This is the most important skill. Have the user tell Claude: "Save a skill called 'stress-test'. When I say 'challenge my plan', read business-plan.md and try to break it. Your job is to find the weakest parts and prove they will fail. Be specific. Use real numbers from my sheet and bank data if available. Don't hedge or soften. I need to hear the hard truth now, not after I've invested six months. Specifically: - Find every assumption in the plan and ask 'what if this is wrong?' - Stress-test the revenue projections: are they based on hope or on data? - Find single points of failure: what happens if my biggest client leaves? If a key employee quits? If a supplier raises prices 30%? - Check for survivorship bias: am I only looking at what worked and ignoring what didn't? - Challenge the timeline: is the 12-month goal realistic given current pace? - Grade each section of the plan: Strong / Needs Work / Critical Risk At the end, give me an overall verdict: Is this plan ready to operate on, or does it need more work? Be honest. A plan that fails here was going to fail anyway — better to know now." IMPORTANT: Tell the user that this skill is supposed to be tough. Claude is playing the role of a skeptical advisor or investor — someone who wants them to succeed but won't pretend a weak plan is strong. If everything passes the stress test easily, either the business is in great shape or the test isn't hard enough. STEP 6 — TEST ALL FOUR SKILLS Walk them through testing each skill: 1. "Update my plan" — try changing one thing (e.g., "I just raised my prices 15%") and confirm the plan updates correctly 2. "What should I change?" — see if Claude draws from real data they have 3. "Challenge my plan" — run the full stress test and review the results together STEP 7 — POINT FORWARD Tell them what they've built: a living business plan that updates as they learn, suggests improvements from real data, and stress-tests itself before they bet their time and money on it. Explain how this connects to other Tsidai guides: - The Two Tabs foundation (https://tsidai.com/guides/two-tabs) feeds real financial data into the plan - Market Research (https://tsidai.com/guides/market-research) validates the competitive position section - Month-End (https://tsidai.com/guides/month-end) gives the plan real revenue and expense data to reference - The Business Command Center (https://tsidai.com/guides/command-center) — coming soon — will surface plan metrics in the daily dashboard If they get stuck, suggest booking a Tsidai starter session at https://cal.com/tsidai/starter-session.