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

“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.”
“What were the highest ROI decisions I made last year? What made them high leverage, and what should I repeat?”
“Identify the 5 projects that consumed the most time. For each: what the true payoff was, and whether that payoff justified the cost.”
“What did I personally enable that would not have happened without me—and why was I the constraint or catalyst?”

Tradeoffs & opportunity cost

“What did I say yes to that I should have declined? What did those ‘yeses’ cost me (time, reputation, team focus, momentum)?”
“What high-impact opportunities did I miss because my time and attention were occupied? What were the early signals?”
“Where did I over-invest (perfection, over-analysis, over-communication)? What minimum level would have produced the same result?”

Systems, not stories

“What patterns repeatedly created friction for me: meetings, unclear ownership, inconsistent data, approvals, vendor constraints, trading partner delays, dependencies, unclear scope?”
“Which failures were preventable with better governance, better guardrails, or earlier stakeholder alignment?”
“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

“What leadership behaviors consistently created momentum, clarity, and trust? Give 5 examples and the mechanism behind each.”
“When was I at my best last year? What conditions (people, environment, type of work) enabled that?”
“Which of my strengths became liabilities under stress? What was the cost?”

Delegation & leverage

“Where was I a bottleneck for my team? Identify the decision points I held too tightly and why.”
“What should I delegate earlier this year to increase throughput and reduce burnout? Define what ‘good enough’ looks like for each.”
“What are 3 roles or capabilities I need to strengthen in the team so I’m not the default solution?”
“Which problems did I solve personally that could have been solved with a checklist, a template, or a repeatable process?”

Trust, influence, and stakeholder management

“Which stakeholders gained confidence in me last year, and why? Which stakeholders did I not move, and what would have been more effective?”
“Where did I communicate too late, too much, or too vaguely? What communication pattern would have prevented rework?”
“Where did I rely on informal influence instead of governance—and did that create hidden risk?”

3) Last Year: Execution & Delivery (How well did I deliver?)

This segment improves throughput and predictability—especially relevant in multi-dependency environments.

Delivery excellence

“What were my best 3 deliveries? Why did they work? Identify the repeatable recipe (scope control, stakeholder alignment, standards, testing, data readiness, etc.).”
“Where did project timelines slip the most? For each slip: root cause, early warning sign, and mitigation that should be built in this year.”
“What work was blocked by external dependencies (vendors, trading partners, approvals)? What should be redesigned to reduce dependency risk?”

Governance and prioritization

“What were the top 5 priority conflicts I faced? How did I choose? In hindsight, what was the correct prioritization?”
“Where did I lack a clear ‘definition of done’? What would it have looked like?”
“If I had to cut 30% of work last year while preserving value, what would I cut and why?”

4) Personal Sustainability & Focus (How did I manage energy, attention, identity?)

This is critical if you tend to take on too much and want to protect your reputation without burning out.

Time and attention economics

“What 20% of tasks created 80% of my stress last year? What structural changes reduce or eliminate them?”
“Where did I sacrifice strategic work for reactive work? What commitments or boundaries would protect strategic time?”
“What ‘always on’ behaviors are unsustainable? What is a realistic operating model for me this year?”

Reputation and identity

“What did people come to depend on me for last year? Is that dependency healthy or risky? How should I redefine my role?”
“Where did my desire to be helpful create misalignment, overload, or scope creep?”
“What reputation do I want this year: strategic leader, execution powerhouse, coach, innovator, process architect? What behaviors must change to earn it?”

5) This Year: Strategy & Direction (What matters most?)

These prompts drive clarity in priorities and help prevent “too many initiatives.”

North Star

“What are the 3 outcomes that must be true by Dec 31 for this year to be considered a success?”
“What is the single highest-leverage problem I can solve this year that makes other problems easier?”
“What should I stop doing to create space for the above outcomes?”

Portfolio thinking

“List every active initiative I’m involved in. Classify each as: must-do, should-do, could-do, stop-doing.”
“What are the top 5 initiatives that best align with business strategy and measurable impact? Rank them.”
“What is the minimum viable portfolio that preserves value while protecting team capacity?”

Risk and dependency planning

“What are the top 10 risks to my goals this year? For each: likelihood, impact, leading indicators, and mitigation plan.”
“What dependencies are likely to delay delivery again this year? Propose ways to decouple or create parallel paths.”
“Where do we need clearer governance (decision rights, escalation paths, approval SLAs) so work doesn’t stall?”

6) This Year: Execution Model (How will I actually run the year?)

These prompts force you to translate vision into operations.

Operating system

“Design a simple execution operating system for me: weekly rhythm, priority checks, stakeholder updates, and team empowerment. Make it lightweight and repeatable.”
“What metrics should I track weekly to ensure I’m moving priorities forward (not just staying busy)?”
“What are my ‘kill criteria’ for initiatives—signals that a project should stop or be re-scoped?”

Team development

“What capabilities must my team develop this year to increase speed and quality? Provide 3 training/investment areas and measurable indicators.”
“How do I design work so developers and analysts can own outcomes rather than waiting for direction?”
“What work should I standardize (templates, playbooks, checklists) to reduce rework and improve consistency?”

Communication & alignment

“Create a communication plan that prevents surprises: weekly update format, stakeholder mapping, escalation rules, and meeting hygiene.”
“What are the top 3 narratives I must communicate this year (strategy, why, what success looks like), and how should I tailor each narrative by audience?”

7) For High Performers with Too Many Ideas (Focus prompts built for you)

This section is specifically designed for “high-capacity, high-ideas, high-responsibility” leaders.

Scope control and intentionality

“List my top 15 ideas. For each: urgency, strategic fit, ROI, complexity, dependency risk. Then choose only 3 to pursue and justify the cuts.”
“What am I doing because I can, not because I should?”
“What is the smallest version of each priority that still produces meaningful value?”

Boundary setting without reputational damage

“Write a ‘strategic no’ script for me to protect focus while maintaining trust and service leadership.”
“What are three commitments I must consistently honor this year so people trust me—without overcommitting?”
“Design a delegation and decision-rights model that keeps me informed but not overloaded.”

A simple way to use these (fast but powerful)

If you want a structured exercise, do this:

Step 1 — Last Year (45 minutes)

Answer prompts 1, 5, 8, 14, 21, 27, 30.

Step 2 — This Year (45 minutes)

Answer prompts 33, 34, 36, 39, 42, 44, 50.

Step 3 — Ask ChatGPT to synthesize

Use this final prompt:

“Based on my answers, summarize: (1) my top 5 wins, (2) my recurring bottlenecks, (3) what I should stop doing, (4) my highest leverage focus for this year, (5) the 90-day plan, and (6) the operating system I should use weekly. Make it realistic and measurable.”

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