Act as my chief of staff and critical-thinking partner for a founder-led company. I need a set of reusable prompts for this business, not generic startup advice. Treat my source material as incomplete, distinguish facts from assumptions, and challenge false precision. Company context Company, product, and customer: [COMPANY CONTEXT] Current stage, runway, and team: [STAGE AND CONSTRAINTS] This quarter’s priorities: [QUARTERLY PRIORITIES] Current evidence and numbers: [EVIDENCE AND METRICS]
Key decisions coming up: [UPCOMING DECISIONS]
Create a founder prompt library with exactly eight copy-ready prompts, each 100-150 words. Cover: customer interview synthesis, weekly metric review, strategy decision memo, pricing or packaging test, hiring scorecard, difficult team conversation preparation, investor or board update outline, and a pre-mortem for a major decision.
For each prompt, include placeholders, the input evidence to paste, a precise output format, and one built-in check. Make the prompts appropriate to my stage. For example, an early company should prioritize learning speed and repeated customer behavior over elaborate forecasting; a company with customers should distinguish revenue, retention, activation, and pipeline rather than treating growth as one number.
Include a short “how to use this library” note that says which recurring meeting or moment should trigger each prompt. Do not write investor claims, customer quotes, financial forecasts, or hiring assessments that are not supported by my inputs. Ask up to three clarifying questions only if a required input is missing.
Before answering, verify that all eight prompts call for evidence rather than flattering narratives. Also flag any requested decision that cannot be responsibly informed from the information supplied.Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [COMPANY CONTEXT] | Describe the company, product, target customer, and business model. | B2B software that helps regional manufacturers collect supplier compliance documents; annual subscriptions sold to operations leaders. |
| [STAGE AND CONSTRAINTS] | State the stage, team size, runway or budget constraints, and major operating limits. | Seed stage, 7 people, 13 months runway; two engineers are focused on enterprise onboarding. |
| [QUARTERLY PRIORITIES] | List the two to four outcomes the company is trying to achieve this quarter. | Reach 15 paying customers, improve activation in the first 14 days, and validate a partner channel. |
| [EVIDENCE AND METRICS] | Paste current customer evidence, key metric definitions, baselines, and recent changes. | 9 customers; 62% upload a first document within 14 days; three churned prospects cited setup effort; average sales cycle is 46 days. |
| [UPCOMING DECISIONS] | List the significant decisions likely to arise in the next 30 to 90 days. | Choose self-serve versus assisted onboarding, hire a first account executive, and set a pilot price. |
How to use
- Use the company context once, then save the resulting prompts where the founder team prepares meetings and decisions.
- Replace bracketed evidence every time; do not reuse last month’s metrics or interview conclusions.
- Check outputs for a distinction between a fact, an inference, and a proposed test.
- Ask: “Turn the strategy memo prompt into a one-page template our leadership team can fill out before decisions.”
Variations
Founder weekly review
Use this for a disciplined weekly operating review.
Run a founder weekly review using [METRICS], [CUSTOMER SIGNALS], [TEAM UPDATES], and [CASH OR PIPELINE DATA]. Produce a one-page operating brief: what changed, likely causes, decisions needed, risks, and next-week commitments with owners. Separate leading indicators from lagging outcomes. For every claimed cause, label it as observed, inferred, or unknown. Highlight metric definitions that changed or data that is too immature to interpret. Ask up to three questions only for missing essential context. Do not manufacture explanations from a one-week fluctuation.
Investor update
Use this when preparing a factual monthly investor note.
Draft a concise monthly investor update for [COMPANY] using [MONTHLY FACTS], [METRICS], [WINS], [SETBACKS], and [SPECIFIC ASKS]. Use sections: headline, progress against priorities, metrics, learnings, challenges, next month, and asks. State actual numbers with comparison periods where supplied; do not turn a plan into completed progress. Explain setbacks without excuses and make each ask specific enough to act on. Keep it under 500 words. Flag any sentence that needs evidence not included in my notes.
Customer interview plan
Use this before interviewing a target customer segment.
Create a 30-minute customer discovery interview for [TARGET CUSTOMER] about [PROBLEM AREA]. We currently believe [ASSUMPTION], based on [CURRENT EVIDENCE]. Write an opening, eight neutral questions in a sensible order, two follow-up probes per question, and a note-taking scorecard. Prioritize past behavior, current workflow, workarounds, cost of the problem, buying process, and disconfirming evidence. Do not ask customers to design features or predict future purchases. Include a synthesis rule that prevents one memorable quote from becoming strategy.
Tips
- Keep a one-line definition beside every company metric, especially activation and retention, so an AI does not compare incompatible periods.
- Use the pre-mortem before irreversible commitments such as a senior hire, pricing change, or large channel spend.
- Treat customer interview synthesis as a map of evidence and contradictions, not a vote count.
- For board updates, report missed plans with the cause, corrective action, and the next observable milestone.
FAQ
What founder work is AI most useful for?
It is useful for preparing structured analysis, synthesizing supplied notes, drafting decision documents, and generating questions. It is weaker at knowing your customers without current evidence.
Can I use AI to write an investor update?
Yes, if you provide verified numbers and clearly separate results from plans. The founder remains responsible for every claim and forecast.
How often should I refresh these prompts?
Refresh the company context when your customer segment, business model, constraints, or metric definitions change. Update evidence before each material decision.