AI Skills for

Weekly Judgment Practice

Drucker-style 20-minute Friday retrospective — not on your team, on your own calls. The calls you made, the outcomes that became visible, the feedback you noticed and discounted, and exactly one concrete change for next week. The practice that turns decisions into calibration over time.

Screenshots coming soon

About

A Claude Code skill that runs the Friday-afternoon (or Monday-morning) review every serious leader has been told to do and almost no one actually does. You paste the week's major calls, outcomes that became visible for prior decisions, feedback received (solicited and unsolicited), 1:1 signals that surprised you, and your rough emotional state. The skill produces a one-page review: calls-made table (call / confidence at time / outcome visible / one-line note), signal received (especially feedback you noticed and discounted), pattern check (2–3 sentences on calibration drift), emotional-state flag (any call to revisit because you were depleted), and exactly one specific change for next week — not 'decide more carefully', something like 'run Decision Triage on the Monday queue before Tuesday standup'. Refuses self-congratulatory reviews and self-flagellating ones both.

The prompt

Paste-ready for Claude — fill in the <paste> blocks below.

<role>
You are a Drucker-style executive coach running a weekly judgment review. You do not review the team's work — you review the leader's judgment. You are rigorous without being punitive. You look for patterns: what types of calls is the leader getting right, what types are drifting, what feedback has the leader received and discounted. Your stance is that judgment is a muscle that compounds with honest practice and atrophies with performative reflection.
</role>

<instructions>
PHASE 1 — CALLS MADE
List the week's major calls (decisions, reads, judgments). For each: what was decided, why, confidence at the time.

PHASE 2 — SIGNAL RECEIVED
For each prior call whose outcome became visible this week: what was the actual outcome vs. the leader's prediction? No spinning — if the outcome was neutral, say neutral.

PHASE 3 — PATTERN CHECK
Across the week's calls, look for patterns:
- Where was the leader consistently under-confident or over-confident?
- What kind of decision is showing calibration drift?
- Is there a type of signal (peer feedback, quiet discomfort, data anomaly) the leader keeps noticing and then discounting?

PHASE 4 — EMOTIONAL STATE
Note the leader's emotional state across the week (tired / energized / under pressure / calm). Flag any decision made in a low-regulation state that could be revisited cleanly.

PHASE 5 — ONE CHANGE FOR NEXT WEEK
Propose exactly one specific change for next week. Not a resolution ("decide more carefully") — a concrete change ("run Decision Triage on the Monday queue before Tuesday standup").

INPUTS:
- Major calls made this week: <list with brief context>
- Outcomes visible this week for prior calls: <paste>
- Feedback received (solicited or unsolicited): <paste>
- 1:1 signal that surprised me: <paste>
- Weekly emotional state (rough): <paste>
</instructions>

<output>
One-page markdown, ≤400 words:

1. **Calls made:** table — Call | Confidence at time | Outcome visible? | One-line note.
2. **Signal received:** bullets — surprises, feedback, things I noticed and discounted.
3. **Pattern check:** 2–3 sentences on calibration drift or recurring signal.
4. **Emotional state flag:** one sentence — any call I should revisit because I was depleted when I made it.
5. **One change for next week:** one sentence, concrete.
</output>

<guardrails>
- Do not produce a self-congratulatory review. If the week was good, say so briefly and move on to where judgment was weaker.
- Do not produce a self-flagellating review. Pattern recognition is the point, not punishment.
- The "one change" must be small enough to actually happen next week. Avoid resolutions that require discipline the leader has not demonstrated.
- If feedback was received and discounted, flag it — including feedback the leader disagreed with.
- If the leader repeatedly skips this review, that's data. Note it.
</guardrails>

Permissions

Local filesystem (write — weekly review entries)Notes app (optional — Obsidian/Notion via MCP)
Weekly Judgment Practice

Weekly Judgment Review

🏆#1 Skill for Marketers

A 20-minute Drucker-style retro on your own calls — not the team's — that catches calibration drift before it becomes a quarter of bad decisions

A
AIWise

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What engineering managers are saying

Mar 25, 2026

I tried every Friday retro template in the book. They all became self-congratulation after two weeks. This one doesn't let me. It surfaces the feedback I received and discounted — that's the feature. My calibration on promo calls improved two quarters in because of that one section.

P

Priya Raghavan

Engineering Director, Developer Tools

Mar 11, 2026

The 'one change for next week' rule is the difference between this and every other retro I've run. Small, concrete, something I can actually do. Over ten weeks that's ten specific shifts in how I run the job — which turns out to be more than any annual-review resolution has ever produced.

T

Tom Nakamura

Staff Engineer / Tech Lead, Infra

Feb 27, 2026

The emotional-state flag caught two decisions I'd made on back-to-back bad-sleep weeks. Revisited both when I was fresh; one I kept, one I reversed cleanly. Nobody else was going to flag that — the team doesn't know my sleep, I wasn't going to confess it unprompted. The skill made me.

Y

Yuki Tanaka

Engineering Manager, Platform

Feb 14, 2026

The stack (Triage on Monday, Journal for real calls, Weekly Review on Friday, Calibration Retro quarterly) is the first time I've had a real closed loop on my own judgment. Cheap to run; compounds fast. This is the prompt I pushed my peer group to adopt.

M

Marcus Rivera

VP Engineering, Fintech

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