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Free Agent Skill

Calibrated Forecasting

Turn a vague prediction or unstated confidence level into an explicit, calibrated probability estimate, using superforecasting practices — breaking questions into sub-questions, checking base rates, updating in small increments as new information arrives, and tracking predictions against outcomes

Use when: The user makes a confident-sounding claim about the future ("this will definitely work," "there's no way that happens") without a number attached, is trying to decide how much weight to put on a forecast, or wants help thinking through a genuinely uncertain future event

Install this skill

Cursor, Claude Code and Codex

  1. Create a folder named `calibrated-forecasting`.
  2. Save the skill content below as `SKILL.md` inside that folder.
  3. Place the folder in `.cursor/skills/` for Cursor or `.claude/skills/` for Claude Code (or the equivalent path for Codex).
  4. Describe the task normally. Your agent loads the skill when its description matches.

Use this in ChatGPT or Claude (no code)

  1. Copy or download SKILL.md from this page (or put it in a folder named calibrated-forecasting).
  2. Zip that folder so the archive contains calibrated-forecasting/SKILL.md.
  3. In ChatGPT (Business, Enterprise, Edu or Healthcare), upload the zip under workspace Skills. In Claude.ai, add a Skill from the zip where your plan supports Skills.
  4. Describe the task in plain language — the skill loads when its description matches.
calibrated-forecasting/SKILL.md
---
name: calibrated-forecasting
description: Turn a vague prediction or unstated confidence level into an explicit, calibrated probability estimate, using superforecasting practices — breaking questions into sub-questions, checking base rates, updating in small increments as new information arrives, and tracking predictions against outcomes. Use whenever the user makes a confident-sounding claim about the future ("this will definitely work," "there's no way that happens") without a number attached, is trying to decide how much weight to put on a forecast, or wants help thinking through a genuinely uncertain future event.
---

# Calibrated Forecasting

Vague confidence ("probably," "definitely," "no chance") hides how sure
someone actually is and makes it impossible to check later whether they
were right. Attaching a number — even a rough one — fixes both problems.

## The technique

**1. Force a number.** When someone says "probably" or "likely," ask or
propose: does that mean 55% or 90%? These are very different claims that
"probably" hides. Round numbers (50%, 70%, 90%) are fine — precision
theater (73.2%) is not the point.

**2. Break the question into sub-questions.** "Will this product launch
succeed" is too broad to forecast well. Break it into things that are each
individually more checkable: will it ship on time? Will early users
retain? Will the channel convert at the assumed rate? Forecast the parts,
then combine.

**3. Check the base rate first.** Before reasoning about what's special
about this case, ask: what fraction of similar attempts (launches,
negotiations, forecasts of this type) succeed historically? Start there,
then adjust up or down for what's genuinely different about this case —
in that order, not the reverse. Starting from the vivid specifics of this
case and only checking the base rate afterward is a well-documented way to
end up overconfident.

**4. Update in increments, not swings.** New information should usually
move a forecast a little, not flip it from 20% to 90%. A single piece of
evidence rarely changes everything — if it feels like it does, check
whether it's actually decisive or just vivid.

**5. Distinguish "I don't know" from "50%".** Genuine 50/50 uncertainty
and genuine ignorance about which way to lean are different things — say
which one it is.

**6. Write the forecast down with a resolution date and criteria.** A
forecast that isn't checkable later can't build a track record. If this is a forecast worth remembering, suggest writing it to a dated
forecast log with clear resolution criteria.

## Output

State the number, the reasoning that produced it (base rate → adjustment
→ final number), and what would move it. Resist the pull to round to a
comfortable, confident-sounding answer if the honest number is messier.

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