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Insight-dense prompts you can use to evaluate last year with clarity and honesty, and (2) architect this year with focus, measurable impact, and better personal sustainability.
1) Last Year: Strategic Retrospective (What actually happened?) These prompts help you surface reality—outcomes, causality, and constraints—without getting lost in “activity.” Outcomes & impact 1. “List my top 10 outcomes from last year that created durable value. For each: who benefited, what changed, and how we can measure that change.” 2. “What were the highest ROI decisions I made last year? What made them high leverage, and what should I repeat?” 3. “Identify the 5 projects that consumed the most time. For each: what the true payoff was, and whether that payoff justified the cost.” 4. “What did I personally enable that would not have happened without me—and why was I the constraint or catalyst?” Tradeoffs & opportunity cost 5. “What did I say yes to that I should have declined? What did those ‘yeses’ cost me (time, reputation, team focus, momentum)?” 6. “What high-impact opportunities did I miss because my time and attention were occupied? What were the early signals?” 7. “Where did I over-invest (perfection, over-analysis, over-communication)? What minimum level would have produced the same result?” Systems, not stories 8. “What patterns repeatedly created friction for me: meetings, unclear ownership, inconsistent data, approvals, vendor constraints, trading partner delays, dependencies, unclear scope?” 9. “Which failures were preventable with better governance, better guardrails, or earlier stakeholder alignment?” 10. “What are the 3 systemic bottlenecks in my environment (process, tools, people, approvals, vendors), and what would remove or reduce each one?” 2) Last Year: Leadership & Team Effectiveness (How did I lead?) These prompts reveal how you show up as a leader—how your strengths help, and where they create drag. Strengths you should double down on 11. “What leadership behaviors consistently created momentum, clarity, and trust? Give 5 examples and the mechanism behind each.” 12. “When was I at my best last year? What conditions (people, environment, type of work) enabled that?” 13. “Which of my strengths became liabilities under stress? What was the cost?”
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