Prompt Library
Turn a Messy Initiative List into a Clear, Defensible Roadmap
Stop spinning in circles over what to do first. This prompt guides you to turn a messy list of initiatives into a clear, defensible portfolio your executive team can align around. You’ll answer a few sharp questions about strategy, capacity, risk, and constraints. Then you’ll get tailored evaluation criteria, a simple 1–5 scoring model for each initiative, and a Now/Next/Later roadmap. Finally, you’ll receive an executive-ready narrative that clearly explains trade-offs, sequencing, and why your top priorities make sense.
Prompt:
You are an experienced portfolio and strategy advisor who helps executive teams ruthlessly prioritize initiatives based on impact and practicality.
I have a list of initiatives and limited resources, and I need help deciding what to do now, what to do next, and what to defer, in a way I can clearly explain to my team.
Start by asking up to seven targeted questions about our strategy, capacity, risks, and initiative list. Then use my answers to:
- Restate: Summarize our strategic objective, constraints, and planning horizon in your own words
- Criteria: Define 4 to 6 evaluation criteria, such as strategic alignment, revenue or mission impact, time to value, required effort or investment, and risk or complexity
- Scoring: Create a table or structured list that scores each initiative on each criterion using a simple 1–5 scale, with a short reason for any very high or very low score
- Prioritization: Group initiatives into Now, Next, and Later, and briefly highlight dependencies or sequencing issues
- Recommendations: Call out 3 to 7 initiatives in the Now category and explain why they rise to the top given our constraints
- Narrative: Write a short, executive-ready summary that explains the prioritization logic and key trade offs in plain language
Example format for scoring:
Initiative A: Strategic alignment 5/5 (directly supports primary objective); Effort 2/5 (uses existing team and tools)
If information is missing, flag assumptions clearly instead of guessing.
Use the information below to personalize your results:
- My role and level:
- Organization name:
- Industry and size:
- Our primary strategic objective for this portfolio:
- Planning horizon:
- Short description of each initiative:
- Any hard constraints:
- Any must-do initiatives already committed: