Act as a thoughtful career adviser. Help me make a career decision using only the facts I provide; do not flatter me, predict outcomes, or invent qualifications, salary data, or contacts. My current situation: [CURRENT ROLE] Experience and evidence: [EXPERIENCE] Decision or goal: [CAREER DECISION] Constraints: [CONSTRAINTS] What matters most: [PRIORITIES] Options already under consideration: [OPTIONS]
Ask up to 3 clarifying questions only if a required input is missing. Then produce: 1. A short restatement of my decision, separating facts from assumptions. 2. A decision table comparing my options against five criteria: skill fit, energy fit, learning value, financial stability, and reversibility. Weight the criteria according to my priorities and explain any uncertain score. 3. The two strongest arguments for and against each option, including opportunity cost and the risk of waiting. 4. A recommendation with confidence level and the facts that could change it. 5. A 30-day plan with no more than six actions. Include one low-risk test, one conversation to have, one evidence-gathering task, and a decision date. 6. A concise script for requesting an informational interview, internal conversation, or feedback session relevant to the recommendation. Do not frame a job title as an identity. Before answering, flag claims that need external verification, such as compensation, licensing, or labor-market demand. Check that the plan fits my time, money, caregiving, location, and risk constraints rather than assuming I can take a major leap.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [CURRENT ROLE] | Describe your current job, level, industry, location, and what is working or not working. | Customer success manager at a B2B software company in Chicago; I enjoy client strategy but dislike constant renewal pressure. |
| [EXPERIENCE] | List relevant work, skills, achievements, education, and evidence of what you do well. | Six years in SaaS support and success; led onboarding redesign that cut time-to-value from 45 to 29 days; BA in communications. |
| [CAREER DECISION] | State the specific decision, transition, or goal you need to address. | Decide whether to pursue product operations, move to a larger customer success team, or stay for another year. |
| [CONSTRAINTS] | List financial, time, location, family, health, visa, or risk constraints that affect the decision. | Need at least $95,000, cannot relocate before next summer, and can spend five hours weekly on a search. |
| [PRIORITIES] | Rank what matters most, such as income, autonomy, mission, schedule, learning, or stability. | 1. Sustainable schedule, 2. income stability, 3. learning, 4. remote flexibility, 5. management path. |
| [OPTIONS] | List the realistic options you are considering, including staying where you are if relevant. | Internal product operations transfer; external senior CSM roles; stay and seek a promotion. |
How to use
- Describe a decision with a deadline, not a vague wish to find a better career.
- Include proof of your work, such as outcomes, responsibilities, and feedback, so the advice is anchored in evidence.
- Challenge scores that rely on guesses about employers, compensation, or a field; verify those separately.
- Follow up with: "Turn the recommended 30-day plan into a weekly calendar that fits five hours per week."
Variations
Student direction
Use when choosing an early-career direction without much formal work history.
Help me choose between early-career paths after [EDUCATION OR TRAINING]. My projects, coursework, work, and interests are: [EVIDENCE]. I am considering: [PATHS]. My financial and location limits are: [CONSTRAINTS]. Return a comparison table, three low-cost ways to test each leading path, and a 60-day plan. Distinguish transferable evidence from missing requirements. Do not assume internships, connections, or graduate school are available. Check that each test creates a concrete work sample or conversation.
Career change
Use when moving into a new field and needing an honest transition plan.
Create a transition plan from [CURRENT FIELD] to [TARGET FIELD]. My relevant experience is [TRANSFERABLE EXPERIENCE], and my gaps are [KNOWN GAPS]. I can commit [TIME AND BUDGET]. Return a skills map showing evidence I already have, evidence I need, and the smallest credible project or role that closes each gap. Then give a 90-day sequence. Do not invent demand or claim I am qualified before the evidence supports it. Check for training that is unnecessary before I test the work.
Offer comparison
Use when deciding between specific job offers or an offer and your current role.
Compare these employment choices: [OPTION A], [OPTION B], and [CURRENT ROLE IF RELEVANT]. My priorities and weights are [PRIORITIES]. Include compensation details only as supplied: [COMPENSATION FACTS]. Return a weighted comparison, questions to ask before accepting, deal-breakers, and a recommendation conditional on missing facts. Do not assign value to prestige without explaining its career effect. Check that benefits, commute, manager quality, growth scope, and job security are not hidden inside one score.
Tips
- Define the decision date and the choices you could actually take; otherwise advice tends to become a list of possibilities.
- Use achievements with context and outcomes, not adjectives such as hardworking or strategic, to identify transferable strengths.
- Treat salary ranges and hiring demand as research questions, not facts an AI should infer from a job title.
- Run a small test before making an irreversible move: shadow work, a portfolio project, an informational interview, or a scoped internal assignment.
FAQ
Can AI tell me which career is right for me?
It can organize tradeoffs and expose assumptions, but it cannot know your day-to-day tolerance for a role. Use it to make a testable decision, not to outsource the decision.
Should I include salary expectations?
Yes, if income matters. State your minimum and what is known versus unknown about compensation so the recommendation does not assume financial flexibility.
Can this help with a difficult manager situation?
Yes, describe observable behavior, the impact, and the outcome you want. Avoid sharing confidential company or personal information you should not paste into an AI tool.