Planning

What I optimize for

Outcome-based roadmaps that are honest about risk.
Cross-functional alignment with explicit tradeoffs.
Fast, reversible decisions anchored to metrics.

My default approach

Start with the problem and the measurable outcome.
Split bets (strategic) from backlog (tactical).
Make dependencies and capacity explicit.

Roadmap stance

A roadmap is a hypothesis with confidence ranges, not a promise.

Tools and artifacts I produce

Quarterly operating plans with leading indicators.
Risk registers and dependency maps.
Decision memos for high-impact bets.
Narrative updates for exec and customer audiences.

Examples

txt

Bet vs backlog
- Bet: 3-5 outcomes tied to top metrics
- Backlog: tactical items with owner + next review date
- Risks: top 3 risks with mitigation owners
- Confidence: high / medium / low with evidence

txt

Operating plan template
- Outcome: what changes for the customer
- Leading indicators: early signals we are winning
- Dependencies: teams, vendors, or contracts
- Risks: top 3 with mitigations
- Decision checkpoints: when we re-evaluate

Decision memo outline One page, five sections.

Context, options, tradeoffs, recommendation, and next review trigger.

Tradeoffs

Speed vs alignment: align only the needed stakeholders.
Precision vs adaptability: use ranges and revisit assumptions.
Strategy vs execution: protect time for both or you get neither.

Signals I look for

Teams can explain the “why” behind every roadmap item.
Stakeholders know what changed and why.
Plans include risk and capacity, not just wishlists.

Anti-patterns

Roadmaps that are date-only and impact-free.
Hidden dependencies and surprise resource asks.
Strategy without execution owners.