Generate problem-solving questions for this situation: [PROBLEM]. I need to decide or accomplish [DECISION OR OUTCOME] by [DEADLINE], within these constraints [CONSTRAINTS]. The facts, data, and assumptions I currently have are [CURRENT INFORMATION]. The people affected and the decision-maker are [STAKEHOLDERS AND AUTHORITY]. Create a question set that helps me reduce uncertainty before jumping to solutions. Do not answer the questions unless a fact I supplied directly answers one. Organize 18-24 questions into these labeled groups: 1. Frame the problem: questions that distinguish the observed symptom, desired state, scope, and cost of inaction. 2. Establish facts: questions that identify baseline, timing, variation, data quality, and the difference between observed evidence and interpretation.
3. Test causes: questions that generate alternative explanations and ask what evidence would support or weaken each one. 4. Surface constraints and stakeholders: questions about authority, incentives, dependencies, capacity, policy, and people who bear the consequences. 5. Choose action: questions that compare options against success criteria, reversibility, downside, and implementation feasibility. 6. Learn after acting: questions that define leading indicators, review timing, and stop or scale triggers. For each question, add a brief note explaining why it matters and identify the answer type: fact to collect, judgment to make, or stakeholder input. Put an asterisk next to the five questions most likely to change the decision. Include 3 questions specifically designed to challenge my current assumptions. Keep questions neutral and answerable; avoid vague prompts such as “What can we do?” or compound questions that contain two decisions. Do not invent facts, authority, or stakeholder views. Ask up to 3 clarifying questions only if a required input is missing. Before answering, check that every question is relevant to the stated outcome and that the set includes at least one plausible explanation other than the obvious one. Flag any constraint that makes the requested outcome unrealistic.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [PROBLEM] | Describe the issue or decision in concrete terms. | A neighborhood nonprofit’s volunteer shifts are regularly unfilled |
| [DECISION OR OUTCOME] | State what must be decided or achieved. | Choose changes that raise shift fill rate to 90% |
| [DEADLINE] | Enter the date or time window for action. | Before the winter meal program begins in six weeks |
| [CONSTRAINTS] | List fixed limits, risks, policies, and available resources. | No paid coordinator; volunteers receive schedules by email; weekend shifts cannot move |
| [CURRENT INFORMATION] | Provide known facts, data, and assumptions separately where possible. | Fill rate is 68%; cancellations cluster within 48 hours; weekday morning shifts fill fastest; we assume reminders are the main issue |
| [STAKEHOLDERS AND AUTHORITY] | Name affected groups and who can approve or implement a change. | Volunteers, meal recipients, site captains; the board can approve scheduling changes |
How to use
- Paste the situation as it exists today, including inconvenient facts and limits.
- Answer the starred questions first, using records or stakeholder input where the answer is factual.
- Turn the answers into a short problem statement and success criteria before brainstorming solutions.
- Follow up with: "Here are my answers. Sort them into confirmed facts, assumptions, and open questions, then name the next three checks in priority order."
Variations
Team workshop
Use when a group needs questions to structure a short problem-solving meeting.
Design a [MEETING LENGTH]-minute problem-solving workshop for [TEAM] on [PROBLEM]. The decision needed is [DECISION], known facts are [FACTS], and boundaries are [CONSTRAINTS]. Provide 10 questions in agenda order, a timebox for each section, and a written artifact the group should produce. Include prompts that separate evidence from opinions and prevent the loudest participant from setting the diagnosis. Do not provide solutions. Ask up to 3 clarifying questions only if needed. Check that the agenda ends with a named decision owner and next evidence-gathering step.
Executive questions
Use when preparing concise questions for a leader who must make a decision.
I need to brief [DECISION-MAKER] on [DECISION] regarding [PROBLEM]. The available evidence is [EVIDENCE], the choices are [OPTIONS], and the decision deadline is [DEADLINE]. Write 8-10 executive-level questions in priority order, each with why it affects the decision. Cover strategic fit, financial or operational impact, execution capacity, downside risk, and what information would reverse the recommendation. Do not invent metrics. Ask up to 3 clarifying questions only if inputs are missing. Check that no question merely repeats a detail already answered by the evidence.
Personal decision
Use for a personal choice with competing priorities and incomplete information.
Help me formulate questions for a personal decision about [DECISION]. My options are [OPTIONS], priorities are [PRIORITIES], limits are [LIMITS], and unknowns are [UNKNOWNS]. Give 15 neutral questions grouped into values, practical constraints, evidence to gather, downside protection, and commitment. Mark questions that require outside information versus personal reflection. Do not make the decision for me or assume facts about my finances, health, or relationships. Ask up to 3 clarifying questions only if necessary. Check that the questions do not frame one option as the default without evidence.
Tips
- Questions about timing and variation often reveal more than questions about averages; ask when the problem does and does not occur.
- Make assumptions visible in the question list so the team can test them rather than defend them.
- Separate a question for data from a question for a decision; “What is the fill rate?” and “Is 90% enough?” require different answers.
- Limit a workshop to questions that could alter the next action, not every question that is intellectually interesting.
FAQ
How many problem-solving questions should I start with?
Eighteen to twenty-four gives breadth for diagnosis, but you should prioritize the few answers most likely to change the decision.
What makes a question actionable?
It has a clear answer type, relates to a decision, and can be answered by evidence, a stakeholder, or an explicit judgment within the available time.
Should questions include possible solutions?
Keep diagnosis questions separate from solution questions at first. Naming a solution too early can make people seek confirming evidence.