Startup Critical Path Planning

Scenario: Founder with 15 priorities

Trigger: "We're a 6-person B2B SaaS startup, 3 months from running out of runway. Need to raise a Series A. We're working on: the new dashboard redesign, hiring a VP Marketing, a big feature release, onboarding automation, enterprise SSO, the blog we've been meaning to launch, getting on the Salesforce marketplace, rebuilding our pricing page, and a bunch of other things."

Process: (1) Goal: $30k MRR by month-end — the minimum to make an A story credible. (2) Brainstorm: all the items above plus ~8 more. (3) Filter — for each item ask "does this get us to $30k MRR this month?" Results: onboarding automation YES (converts trials faster), Salesforce marketplace MAYBE (takes too long to ship, move to exclusion), dashboard redesign NO (doesn't acquire customers), VP Marketing hire NO (won't ship this month), blog NO (too slow), pricing page NO, SSO NO (enterprise deals don't close this month). Of 15 items, only 3 survive: onboarding automation, closing 4 active trials that are on the edge, and accelerating one enterprise deal already in flight. (4) Order: close the enterprise deal first (biggest lever), accelerate trial closures, ship onboarding automation last. (5) Filter ongoing work: team was spending 40% of time on dashboard redesign — stop. Reallocate to closing the enterprise deal.

Output: critical-path.md with the 3 surviving items, critical-path-excluded.md with 12 items and reasons, immediate reallocation plan.

Scenario: Startup 18 months in, still no focus

Trigger: "Consumer mobile app, 18 months in, $0 revenue, $400k raised. We have a free app with 20k users. Founders disagree on whether to focus on ads, in-app purchases, or a B2B licensing deal."

Process: (1) Force one goal. Ask: "Which of these, if achieved in 6 months, would most change the trajectory?" — founders agree: first $10k MRR. (2) Brainstorm milestones for each of the 3 paths: ad-supported model, IAP, B2B licensing. (3) Filter: ad-supported model requires 500k+ users (can't hit in 6 months) → excluded. IAP requires product changes + payment infrastructure + marketing test → viable. B2B licensing requires 1 deal closure → viable and fastest. (4) Order: pursue B2B first (single deal = goal), IAP as parallel fallback. (5) Filter ongoing work: team was building ad infrastructure — stop, reassign to B2B outreach.

Output: Clear single goal, decisive cut of ad strategy, parallel B2B+IAP path with B2B as primary.

Scenario: DuckDuckGo-style long-arc planning

Trigger: "Privacy-focused product competing with incumbents. We have 10k users. Where do I even start with goals?"

Process: (1) Goal: specific user count that unlocks next phase — "100k monthly active users" as first goal (DDG-style cascade: product/messaging stable → break-even threshold → mainstream adoption). (2) Brainstorm all milestones that might contribute: mobile app, improved messaging, 1 piece of viral PR, API integration with a power user tool, SEO on "privacy" keywords, etc. (3) Filter: mobile app YES (retention driver), SEO on privacy keywords YES (aligned with cause), viral PR YES (one good story could 10x users), API integration MAYBE — moved to exclusion for this phase. (4) Order: SEO foundation first (slowest to compound), then PR preparation, then mobile app launch. (5) Filter proposed features: product team wants to add a new browser extension → apply filter → does this contribute to 100k MAU? Only if it ships in 3 weeks. Otherwise, exclude.

Output: Multi-goal cascade pattern inspired by DuckDuckGo's approach. One current goal with clear milestones. Features that don't serve it are explicitly excluded, reviewable at next goal transition.