alexe-ev Prioritize Strategic Bets
Purpose
Help teams make structured decisions about which strategic bets to invest in, sequence, or deprioritize — with explicit trade-off reasoning and risk awareness.
Skill type
Conceptual skill
Use this skill when
- Multiple large initiatives are competing for limited resources
- The team is unsure which bets align with strategy and which are distractions
- A planning cycle requires deciding between core investments and exploratory bets
- Stakeholders disagree on strategic priorities and need a structured framework
Do not use this skill when
- Feature-level prioritization is the goal (use apply-prioritization-framework)
- The goal is roadmap sequencing within a known portfolio (use build-portfolio-roadmap-strategy)
Required inputs
- List of strategic bets or initiatives under consideration
- Business goals or strategic objectives
- Rough resource constraints
Optional inputs
- PMF assessment per bet
- Competitive context
- Risk tolerance framing from leadership
- Time horizon
Upstream context
Works best when:
- Vision and strategy are defined
- Portfolio map exists
If upstream context is missing
Cannot prioritize bets without knowing what the strategy is. Produce a framing of the question and list what must be clarified first.
Downstream handoff
Output can feed:
- build-portfolio-roadmap-strategy (prioritized bets shape portfolio)
- build-business-case (each funded bet needs a business case)
Instructions
- List all bets and describe each in terms of: goal, hypothesis, investment required, potential payoff.
- Assess each bet on: strategic alignment, potential value, probability of success, reversibility.
- Classify each bet: core (high confidence), growth (medium confidence), explore (high uncertainty).
- Identify the right portfolio balance for the current stage and risk tolerance.
- Recommend which bets to fund, pause, or stop — with rationale.
- Identify key decisions or milestones that should trigger a re-evaluation.
Output
Provide:
- Bet inventory with: goal, hypothesis, investment, payoff potential
- Assessment matrix: alignment / value / confidence / reversibility
- Portfolio classification per bet
- Prioritization recommendation with rationale
- What is being deprioritized and why
- Review triggers and milestones
Risks / caveats
- Sunk cost bias distorts bet prioritization — evaluate forward-looking, not backward-looking
- Explore bets must have defined kill criteria, or they become zombie projects
- A portfolio with only safe bets doesn't generate strategic growth