Hard Call: Least-Bad Decision and Delivery
For choices where every option hurts: pick on survivability, size the cut once, then plan who hears what, when, and how.
Before & after
Same prompt, same agent — the only difference is the skill.
Both options have trade-offs worth considering. Shutting down saves costs but might disappoint existing customers and lose revenue. Modernizing keeps revenue flowing but ties up engineering resources. You'd want to think about how many customers rely on the legacy product, what the modernization would actually cost, and whether there are other priorities. It's also worth considering how your team would feel about either decision. What does your current financial runway look like?
HARD-CALL FRAMEWORK: Shutdown vs modernize THE 10/10/10 LENS: If we shut down TODAY: In 10 days, relief (crisis over). In 10 weeks, customers migrated, support tickets drop 30%. In 10 months, regret: legacy revenue gone ($240k/year), team morale hits spike as cutover chaos settles. If we modernize: In 10 days, team anxious (4-month crunch). In 10 weeks, beta ship, customers nervous. In 10 months, problem solved, but engineering burned out, missed 2 new feature launches, customer acquisition slowed 22%. REGRET MINIMIZATION: Shutdown regret scenario (worst case): Largest 3 customers (18% of revenue) churn within 30 days to competitor. Cost: $180k lost ARR + $45k in refunds. Learning: should have offered migration incentive (-$12k). Regret score: 7/10 (recoverable, but painful 6 months). Modernize regret scenario (worst case): Scope creeps, takes 7 months not 4. Ship is late. Customer churn happens anyway as they lose confidence. $45k wasted engineering spend. Regret score: 9/10 (worst of all worlds). RECOMMENDATION: Shutdown path is lower-regret, but ONLY if executed with 60-day customer migration plan (offer 20% discount on new product for 12 months). Cost: $60k discount liability, but prevents $180k churn. DECISION: Announce sunset. 90-day sunset period. Offer migration path. Reallocate engineering to 2 new feature launches. Revenue impact: net negative $120k first year, positive by year 2.
About this skill
When every option hurts, ordinary decision frameworks mislead and most of the damage comes from how the decision is delivered. This skill helps you pick the least-bad option on survivability and then deliver it with care.
What it does
- Checks whether it is really lose-lose: smaller versions, sequencing, third parties, and the monthly cost of doing nothing
- Eliminates options that risk ruin, then compares what remains afterward and what can be undone
- Sizes cuts once, against a downside case, so there is no second round
- Plans delivery: legal and HR prep to verify with counsel, board first, affected people individually, then team, customers, and follow-through
- Starts with a direct conversation when the call is about one person
What you get
A committed call with the reason, why not the others, the size, what would change it, and a delivery table: when, who, by whom, format, key message.
Best for
Founders and leaders facing layoffs, down rounds, product shutdowns, customer cuts, wind-downs, or letting a loyal person go.
SKILL.md preview
---
name: hard-call
description: Make and deliver a decision where every option hurts - layoffs vs a down round, shutting a product customers use, cutting a big but unprofitable customer, winding down, letting a loyal early employee go - by checking whether it is truly lose-lose, choosing on survivability first, sizing the cut once, and planning who hears what, when, and how. Use when the user says "there's no good option here", "layoffs or a down round?", "do we shut this product down?", "I have to let someone go and I dread it", "we might have to wind down", "how do I tell the team?", or "which is the least bad choice?".
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# Hard Call
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