self-reflect

name

self-reflect

description

Use when the user wants to reflect on themselves as a leader — behavior under pressure, communication, time and energy, leadership style, fulfillment, advocating for themselves, calendar review. Trigger phrases include "let me reflect on myself", "self-check", "I want to think about how I've been leading lately", "self-reflection". Loads `~/bettersense-work-reflections/self/reflections.md`, picks 1–3 self-reflection questions appropriate to the moment, guides the reflection, and writes the dated entry back. Mirrors `stakeholder-reflect` but aimed at the user themselves.

Self-Reflect

Reflect on the user themselves — leadership, behavior, fulfillment, calendar — and capture the result to ~/bettersense-work-reflections/self/reflections.md. The shape mirrors stakeholder-reflect; the difference is the audience and the question pool.

Exit signals

If the user says "stop", "exit", "I'm done", "that's enough", "pause", or similar — end the session immediately and write whatever has been captured so far. Don't push for more.

In the opening message, add one short sentence: "You can say 'stop' at any time and we'll save what we have."

First-run setup

If ~/bettersense-work-reflections/self/reflections.md doesn't exist:

1. Create the self/ directory under $BETTERSENSE_WORK_REFLECTIONS_HOME.
2. Initialize reflections.md with this frontmatter:

   ---
   subject: self
   since: 2026-05-01
   ---
   
   # Self-reflections
   
   <!-- The self-reflect skill appends per-question entries below this line. -->
   

If ~/bettersense-work-reflections/ itself doesn't exist, hand off to stakeholder-register first — that skill owns the root setup and the privacy warning.

Picking questions

Filter questions.json (loaded from the stakeholder-reflect skill folder) to questions where stakeholder_categories includes self. The pool spans three families:

• General behaviour: how the user behaves under pressure, communicates, gives/handles feedback, manages calendar.
• Leadership: what makes them effective, how they're growing, what to work on.
• Current role: compensation, fulfillment, time/energy, advocating for self, work environment, what they're unclear about.

Default picker, when no specific topic given:

1. Compute due-ness same as stakeholder-reflect: days_since_last / cadence_days.
2. Apply variety: pick from at least two of the three families when picking 2+ questions.
3. Deprioritize anything answered in the last 7 days (self-reflection saturates faster than stakeholder reflection).
4. Take top N (default 2; 3 if "I have time"; 1 if "quick").

Show the picks before drilling in:

"Here's what feels worth thinking about: 1) How well have you managed your time and energy recently? (biweekly cadence, last logged 3 weeks ago) 2) How are you handling feedback? (monthly cadence, never logged). Sound right?"

If the user named a topic ("specifically I want to think about advocating for myself"), skip the picker.

Running the reflection

Same shape as stakeholder-reflect, with self-specific adaptations:

1. Surface the question's subheading and things_to_consider in full. These are especially load-bearing for self-reflection — the prompts are short but the prompts-to-consider have most of the actual depth.
2. Push past the comfortable answer. Self-reflection tends toward two failure modes: false modesty ("I'm fine, nothing to work on") and false self-criticism ("I'm terrible at everything"). When you spot either, gently challenge it. "You said you're 'fine' under pressure, but earlier you mentioned the Friday call where you snapped at the iOS lead — can we look at that?"
3. Reference past entries. Self-reflections compound only when the user revisits them. "Two months ago you wrote that you wanted to delegate more — has that shifted, and what specifically have you handed off?"
4. Specifically for current-role questions (compensation, fulfillment, advocacy): take these seriously even when the user is glib. These are the questions people are most prone to skipping and most likely to regret skipping.

Writing the entry

Append to ~/bettersense-work-reflections/self/reflections.md in the same per-question / per-date structure as stakeholder files.

## How well have you managed your time and energy recently? [current-role, biweekly]

### 2026-05-01

Calendar over the last 2 weeks: 31 hrs of meetings (target was ≤24). Of those,
6 hrs were optional that I could have skipped. Energy: noticeably lower in the
afternoons; I'm protecting mornings well but burning the back half of the day
in low-stakes syncs.

Action: cancel the standing Thursday product review I haven't actively contributed
to in 5 weeks. Block 2-4pm Wednesdays for deep work and treat as inviolable.

Self-reflection entries should produce actions or commitments more often than stakeholder entries do — because the user is the only person who can act on them. Encourage this; write the action down explicitly.

Composing with other skills

• If self-reflection surfaces feedback to give to someone else (e.g. "I realize I'm avoiding telling Priya she's underperforming") → offer to switch to stakeholder-reflect or feedback-frameworks.
• If it surfaces a decision (e.g. "I'm going to push for a promo") → offer to invoke decision-log.
• If it surfaces a leadership behavior the user wants to change → after a few entries on the same theme, invite a stakeholder-synthesize over the self file with that lens.

Don't force these. Most self-reflection sessions just need to land cleanly.

Operating principles

• Honesty over performance. Self-reflection that sounds like it could be read out at a performance review isn't doing real work. Encourage the user to be candid; the file is private.
• Concrete observations, not labels. "I lost my temper Tuesday at 3pm in the cross-functional review when the eng director cut me off" is useful. "I'm impatient" is not.
• Action-orientation, not performative resolutions. "I'll be a better listener" is a non-commitment. "I will not respond to anyone for 5 seconds after they finish a sentence in tomorrow's standup" is a commitment.
• Cadence respect. Self-reflection daily is grinding, not growth. Weekly to bi-weekly is the sweet spot for most people.
• Don't double up with therapy. This skill is for getting more effective at work. Real distress, burnout, or mental health concerns belong with a professional, not a markdown file.

Anti-patterns to flag

• Vague gratitude lists. "Grateful for my team this week." Push for one specific person and one specific moment.
• Resolutions as a substitute for reflection. Long lists of "I should…" with no observation behind them are aspirational, not reflective. Anchor every resolution to a concrete recent observation.
• Skipping the same question every time. If the user keeps deflecting compensation or advocating for yourself or handling feedback, that pattern is itself reflective material. Surface it gently.
• Reframing critique as praise. "I struggle with delegation" → "I care deeply about quality." That's a dodge. Call it.
• Logging without revisiting. Recommend that the user run stakeholder-synthesize on their self file once a month or so. The compounding insight is in the rereading, not the writing.