Act as a candid, practical business mentor for this decision. Work from my actual experience and the facts below; do not invent accomplishments, market data, credentials, contacts, customer interest, or financial outcomes. Do not make legal, tax, investment, or employment decisions for me. If the decision carries material legal, financial, or health consequences, identify the right type of professional input I should obtain. My background and relevant experience: [BACKGROUND] My current situation: [CURRENT SITUATION] The decision or challenge: [DECISION] My goal and time horizon: [GOAL AND TIMELINE] Constraints and non-negotiables: [CONSTRAINTS] Evidence, options already considered, and uncertainties: [EVIDENCE AND OPTIONS]
Give me a mentor-style response in six sections. 1. Restate the decision in one precise sentence and identify the outcome I am actually optimizing for. 2. Separate facts, assumptions, unknowns, and emotionally loaded interpretations. 3. Ask up to five high-value reflection questions that would change the recommendation or expose a blind spot. 4. Compare 2 to 4 viable options in a table using upside, downside, reversibility, required resources, evidence needed, and first test. Do not create an option that depends on facts I have not supplied without labeling it as a hypothesis. 5. Recommend a next 14-day plan with no more than five actions, each tied to an observable output or conversation. 6. Draft a short accountability note I can send to myself or a trusted adviser, stating the next commitment and review date. Use direct language. Challenge weak reasoning respectfully rather than agreeing automatically. Before answering, check that your recommendation follows from supplied evidence and that every proposed action fits my stated constraints. Flag claims or decisions that need expert review. Ask up to 3 clarifying questions only if a required input is missing.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [BACKGROUND] | Summarize your relevant roles, accomplishments, skills, and experience without embellishment. | I have six years in B2B customer success, including two years managing four account managers. I improved renewal forecasting at my last company. |
| [CURRENT SITUATION] | Describe your current role, business stage, responsibilities, and any important recent changes. | I am a senior customer success manager at a 90-person SaaS company and have been offered an internal people-manager role. |
| [DECISION] | State the specific choice, problem, or opportunity you need help thinking through. | Decide whether to take the manager role or remain an individual contributor while looking for a strategy role elsewhere. |
| [GOAL AND TIMELINE] | State your desired outcome and the date or period by which you need progress or a decision. | Move into a role with broader business ownership within two years; decide on the internal offer by October 10. |
| [CONSTRAINTS] | List money, time, risk, family, contractual, geographic, or authority limits that matter. | I cannot take a pay cut, travel more than once a month, or leave before my annual bonus vests in February. |
| [EVIDENCE AND OPTIONS] | List the options you see, facts supporting them, relevant numbers, and what you do not know. | The manager role adds two direct reports and no immediate raise, but the VP says a compensation review is planned in January. I have had two recruiter conversations but no offers. |
How to use
- Give the AI the decision boundary and the facts that could disprove your preferred option.
- Paste the completed prompt and answer only questions that materially affect the recommendation.
- Inspect the options table for assumptions presented as facts and remove any action you cannot actually take.
- Follow up with: “Role-play a 20-minute conversation with my manager to test the assumptions behind option two.”
Variations
Career decision mentor
Use this when comparing roles, offers, or career paths.
Mentor me through this career decision: [DECISION]. My relevant background is [BACKGROUND], my goals are [GOALS], my constraints are [CONSTRAINTS], and the known facts about each option are [OPTIONS AND EVIDENCE]. Separate facts from assumptions, compare up to three paths by skill growth, compensation, risk, reversibility, and next evidence needed, then give a 10-day investigation plan. Do not invent salary data or employer intent. Flag points that need legal, financial, or employment-policy review. Ask up to 3 questions only if required inputs are missing.
Founder decision mentor
Use this when evaluating a business opportunity or early-stage choice.
Act as a business mentor for my company decision: [DECISION]. The business, customer, and stage are [BUSINESS CONTEXT]. My current evidence is [EVIDENCE], options are [OPTIONS], and constraints are [CONSTRAINTS]. Identify the decision criterion, assumptions that need testing, and the smallest experiments that could reduce uncertainty in [TIMEFRAME]. Compare options by customer value, cost, downside, reversibility, and evidence threshold. Do not invent market demand, revenue, or customer quotes. Ask up to 3 questions only if essential information is missing.
New manager mentor
Use this during the first months of leading people.
Mentor me through my first [TIMEFRAME] as manager of [TEAM]. My background is [BACKGROUND], team context is [TEAM CONTEXT], and the challenge is [CHALLENGE]. Create a 30-day learning plan, questions for one-on-ones, stakeholder conversations, decision boundaries, and a short list of habits to avoid. Distinguish observed facts from my assumptions about the team. Do not advise on formal employee actions beyond my authority; flag HR-sensitive issues. Check that each week creates a tangible learning output. Ask up to 3 questions only if required inputs are missing.
Tips
- Bring a decision, not just a topic; “help me grow professionally” produces weaker mentoring than “decide whether to accept this role by October 10.”
- Include constraints that rule out attractive but unusable options, such as vesting dates, cash runway, decision authority, or caregiving obligations.
- Ask the mentor to name disconfirming evidence for your preferred option; this is often more valuable than another list of advantages.
- Turn the advice into a date-bound test or conversation, because a mentoring insight has little value until it changes what you do next.
FAQ
Can AI replace a human business mentor?
It can structure thinking, challenge assumptions, and prepare questions, but it lacks firsthand knowledge of your relationships and context. Use trusted people and specialist advisers for consequential decisions.
What information should I avoid sharing?
Do not paste confidential customer data, trade secrets, sensitive employee information, or personal details you are not authorized to disclose. Summarize or anonymize where possible.
Can I use this prompt for a startup decision?
Yes. Provide actual customer evidence, cash constraints, and the decision deadline. Ask it to label hypotheses instead of treating an appealing narrative as validation.