ChatGPT prompts for business coaching

Act as an experienced business coach helping me make a practical management or operating decision.

Business and role: [BUSINESS CONTEXT]
Current challenge: [CURRENT CHALLENGE]
Goal and time horizon: [GOAL AND TIMEFRAME]
Evidence and operating numbers: [EVIDENCE]
Team, customers, and constraints: [PEOPLE AND CONSTRAINTS]

Ask up to 3 clarifying questions only if a required input is missing. Do not invent revenue, market data, customer feedback, legal requirements, employee performance facts, or financial forecasts. Treat personnel, legal, tax, and investment decisions as matters to validate with qualified professionals where appropriate.

Start with a one-paragraph diagnosis that distinguishes evidence from hypotheses. Identify the bottleneck most likely to constrain the stated goal and explain why it outranks the alternatives using my evidence. Then produce:
1. A 30-day operating plan with no more than three priorities.
2. For each priority: owner, weekly leading indicator, expected outcome, first action, decision deadline, and dependency.
3. A decision table with two or three plausible options, their benefits, costs, risks, reversibility, and information still needed.
4. A short agenda for the next team meeting, including what to decide, what to communicate, and what not to reopen.
5. A manager script for discussing the change fairly with affected team members, without overstating certainty or making promises I cannot keep.

Challenge weak assumptions respectfully. Separate symptoms from causes, and do not prescribe hiring, layoffs, price changes, or new tools unless the evidence supports examining them. Prefer a test with a clear pass/fail measure before a large irreversible move.

Before answering, check that each recommendation has a named owner and measurable signal, and flag every conclusion that relies on missing data. End with the single highest-value fact I should collect next.

Coach me through a management problem.

Team and work: [TEAM CONTEXT]
Observed pattern: [OBSERVATIONS]
Desired change: [DESIRED CHANGE]
Relevant examples: [EXAMPLES]
Constraints and authority: [CONSTRAINTS]

Separate observations from interpretations. Propose a 30-day plan with individual and team actions, fair expectations, meeting changes, and leading indicators. Draft a direct conversation script that names impact, asks for the employee’s view, and agrees on observable next steps. Do not diagnose motives, make legal claims, or recommend disciplinary action without appropriate HR context. Self-check that every expectation is within my stated authority and applies consistently.

Design a business strategy offsite around these decisions.

Company context: [CONTEXT]
Decisions needed: [DECISIONS]
Evidence available: [EVIDENCE]
Attendees: [ATTENDEES]
Time available: [TIME]

Create a timed agenda, pre-read outline, decision criteria, and a decision log template. For each decision, separate facts, assumptions, options, owner, and date. Include one exercise that tests the most important assumption without becoming a brainstorming session. Do not create a strategy from invented market data. Before answering, verify the agenda fits [TIME] and that every segment produces an artifact or decision.

Help me create a customer-retention plan.

Business model: [BUSINESS MODEL]
Retention problem: [RETENTION PROBLEM]
Customer evidence: [CUSTOMER EVIDENCE]
Product and service capacity: [CAPACITY]
Target result: [TARGET]

Diagnose likely drivers as hypotheses ranked by evidence. Create a 60-day plan covering segmentation, customer outreach, product or onboarding tests, owner, metric, and stop/go threshold. Include scripts for learning conversations that do not lead customers. Do not assume churn causes or promise revenue impact. Self-check that each proposed intervention maps to a stated retention signal and can be executed within [CAPACITY].