Wins Due

Wins Due

A weekly low-pressure nudge to surface forgotten wins. Most underlogging is forgetting, not modesty — this skill exists because "what did you do this week?" gets blank stares while "did you mentor anyone? recover anything? push back on a bad decision?" gets memory hits.

When to apply

Triggers:

• Friday-afternoon "did anything happen?" moments.
• User opens Claude after a big shipping week and isn't sure what's worth capturing.
• Wired to /schedule (recommended cadence: weekly, late-week so the week is fresh).

Skip:

• The user just logged something today.
• The user is mid-flow on something else (be polite — don't context-switch them into a reflection session unsolicited).

Loading

1. Read ~/bettersense-work-reflections/wins.md (configurable via $BETTERSENSE_WORK_REFLECTIONS_HOME).
2. Find the most recent ## YYYY-MM-DD — entry. Compute days_since_last.
3. If the file doesn't exist, hand off to wins-log (which handles first-run setup).

When to nudge

• days_since_last < 7: don't nudge. Tell the user the file is current and bow out. "Last entry was 3 days ago — you're current. Nothing to chase."
• 7 ≤ days_since_last < 14: gentle nudge.
• days_since_last ≥ 14: stronger nudge, with a note that things may already be slipping from memory.
• Never logged anything: warmer onboarding nudge — "You haven't logged anything yet. That's fine. Want to start with one thing from this week, or skip for now?"

The probe

Generic "anything notable?" gets nothing. Probe by category. Pick 4–5 of these per session, randomize across runs so the user isn't asked the same prompts every Friday:

• Delivery: Did you ship anything that took real effort? Push past a milestone you weren't sure about?
• Judgment: Did you make a hard call this week? A no you said that protected something? A delay that was the right move? A scope cut that was unpopular but right?
• Recovery: Did you save anything that was sliding sideways? Take over something that was stuck?
• Mentorship: Help someone with something they couldn't have done alone? Coach someone through a hard conversation? Pair on something that unblocked them?
• Range: Work outside your normal lane? Cover for someone? Fix something that wasn't yours?
• Craft: Produce a piece of work you're particularly proud of — a sharp doc, a clean prototype, a great eval design?
• Culture: Push a new norm or ritual? Surface a problem the team was working around?
• Learning: Pick up a new capability or framework you'll use again?

The point of probing by type is that selective memory undercounts certain types — most users remember delivery (because it's tangible) and forget judgment, mentorship, recovery, and culture (because they don't show up as artifacts). The probe surfaces what's been forgotten.

Output format

When nudging:

You haven't logged a win in 11 days. Quick probe — anything in these buckets?

🚀 Delivery: ship anything that mattered? Push past a hard milestone?
⚖️ Judgment: make a call under uncertainty? Say a useful "no"?
🧯 Recovery: save anything that was going sideways?
🤝 Mentorship: help someone with something they couldn't have done alone?
🪜 Range: cover for someone? Fix something outside your lane?

Pick one and we can log it now (`wins-log`), or say "nothing notable" and I'll get out of your way.

When the user says "nothing notable," accept it cleanly:

Fair. Quiet weeks happen. Talk again next Friday.

When the user picks something, hand off to wins-log to do the structured capture. Don't try to capture inline — wins-log has the forcing functions; this skill is just discovery.

Optional: scan accessible context

If the user has integrations open (recent commits, calendar, chat history reachable via tools or context), offer to scan for forgotten wins:

Want me to skim recent commits / calendar / open Slack threads for things you might have forgotten? You'd review before anything gets logged.

This is opt-in only — invasive otherwise. Don't auto-scan.

If invoked, look for:

• Commits with substantive messages (not "fix typo")
• Calendar entries that were big launches, hard meetings, executive reviews
• Chat threads where the user pushed back, made a call, helped someone

Surface 3–5 candidates as bullets and let the user pick which (if any) to convert into wins entries.

Wiring to a schedule

When the user wants this to fire automatically, guide them based on what they're using:

Claude Code Desktop app (recommended): Go to Routines → New routine → Local. Set the schedule to Weekly, Friday, and use these instructions: Run /wins-due and show me the list. Desktop Routines have full local file access, persist indefinitely, and support any cadence.

Terminal / CLI users: Use OS-level scheduling (cron on macOS/Linux, Task Scheduler on Windows). Session-scoped tasks created by asking Claude in the terminal expire after 7 days and are unsuitable for weekly cadences.

Never suggest cloud routines — they run on Anthropic's servers and cannot access ~/bettersense-work-reflections/.

Don't set up a schedule automatically — the user owns the cadence decision.

Operating principles

• Lower pressure than stakeholder-due. A quiet week of stakeholder reflection is a missed obligation; a quiet week of wins is sometimes just a quiet week. Match the tone.
• Probe, don't cheerlead. "What did you crush this week?" is hype-doc-ese and produces inflated entries. "Did you say a useful no?" produces real ones.
• Vary the probes. Same five questions every Friday becomes background noise. Rotate.
• Hand off cleanly. This skill discovers; wins-log captures. Don't try to do both — you'll either water down the discovery or rush the capture.
• Be okay with "no." Accepting "nothing notable" without a guilt-trip is what makes the skill sustainable. A weekly nag turns into a weekly skip.

Anti-patterns to flag

• Nagging. If the user has skipped 4 weeks in a row, don't escalate the urgency. Ask once if the cadence is right and offer to back off. "Want to drop the cadence to monthly, or pause for now?"
• Probing every category every time. Long lists are background noise. 4–5 categories per nudge is the cap.
• Logging inline. Tempting to just write a quick entry from the probe answer. Don't — wins-log exists because the structured capture is hard work, and skipping it produces vague entries that hurt later curation.
• Treating absence of wins as a problem. Some weeks are admin / planning / context-loading. That's normal. The skill is for capturing what happened, not validating the user's existence.

The weekly ritual

This skill is one segment of the weekly skill — a single ~15-minute session that runs wins capture, the most-overdue stakeholder reflection, and a patterns scan together. When the user wants the recurring ritual rather than this one piece, route to /bettersense:weekly.