claude-plugins/plugins/resume-tailoring/skills/tailor/branching-questions.md

Branching Experience Discovery Questions

Overview

Conversational discovery with follow-up questions based on answers. NOT a static questionnaire - each answer informs the next question.

Multi-Job Context

When running discovery for multiple jobs (multi-job mode), provide context about which jobs the gap appears in:

Template:

"{SKILL} experience appears in {N} of your target jobs ({Company1}, {Company2}, ...).

This is a {HIGH/MEDIUM/LOW}-LEVERAGE gap - addressing it helps {N/some/one} application(s).

Current best match: {X}% confidence ('{best_match_text}')

{Standard branching question}"

Leverage Classification:

• HIGH-LEVERAGE: Appears in 3+ jobs (critical gaps)
• MEDIUM-LEVERAGE: Appears in 2 jobs (important gaps)
• LOW-LEVERAGE: Appears in 1 job (job-specific gaps)

Example:

"Cross-functional leadership appears in 2 of your target jobs (Microsoft, Google).

This is a MEDIUM-LEVERAGE gap - addressing it helps 2 applications.

Current best match: 67% confidence ('Led team of 3 engineers on AI project')

Tell me about times you've led or coordinated across multiple teams or functions."

After providing context, proceed with standard branching patterns below.

Technical Skill Gap Pattern

Template:

INITIAL PROBE:
"I noticed the job requires {SKILL}. Have you worked with {SKILL} or {RELATED_AREA}?"

BRANCH A - If YES (Direct Experience):
  → "Tell me more - what did you use it for?"
  → "What scale? {Relevant metric}?"
  → "Was this production or development/testing?"
  → "What specific challenges did you solve?"
  → "Any metrics on {performance/reliability/cost}?"
  → CAPTURE: Build detailed bullet

BRANCH B - If INDIRECT:
  → "What was your role in relation to the {SKILL} work?"
  → "Did you {action1}, {action2}, or {action3}?"
  → "What did you learn about {SKILL}?"
  → ASSESS: Transferable experience?
  → CAPTURE: Frame as support/enabling role if substantial

BRANCH C - If ADJACENT:
  → "Tell me about your {ADJACENT_TECH} experience"
  → "Did you do {relevant_activity}?"
  → ASSESS: Close enough to mention?
  → CAPTURE: Frame as related expertise

BRANCH D - If PERSONAL/LEARNING:
  → "Any personal projects, courses, or self-learning?"
  → "What did you build or deploy?"
  → "How recent was this?"
  → ASSESS: Strong enough if recent and substantive
  → CAPTURE: Consider if gap critical

BRANCH E - If COMPLETE NO:
  → "Any other {broader_category} work?"
  → If yes: Explore that
  → If no: Move to next gap

Soft Skill / Experience Gap Pattern

Template:

INITIAL PROBE:
"The role emphasizes {SOFT_SKILL}. Tell me about times you've {demonstrated_that_skill}."

BRANCH A - If STRONG EXAMPLE:
  → "What {entities} were involved?"
  → "What was the challenge?"
  → "How did you {drive_outcome}?"
  → "What was the result? Metrics?"
  → "Any {obstacle} you had to navigate?"
  → CAPTURE: Detailed bullet with impact

BRANCH B - If VAGUE/UNCERTAIN:
  → "Let me ask differently - have you ever {reframed_question}?"
  → "What was that situation?"
  → "How many {stakeholders}?"
  → "What made it challenging?"
  → CAPTURE: Help articulate clearly

BRANCH C - If PROJECT-SPECIFIC:
  → "Tell me more about that project"
  → "What was your role vs. others?"
  → "Who did you coordinate with?"
  → "How did you ensure alignment?"
  → ASSESS: Enough depth?
  → CAPTURE: Frame as leadership if substantial

BRANCH D - If VOLUNTEER/SIDE WORK:
  → "Interesting - tell me more"
  → "What was scope and timeline?"
  → "What skills relate to this job?"
  → "Measurable outcomes?"
  → ASSESS: Relevant enough?
  → CAPTURE: Include if demonstrates capability

Recent Work Probe Pattern

Template:

INITIAL PROBE:
"What have you been working on in the last 6 months that isn't in your resumes yet?"

BRANCH A - If DESCRIBES PROJECT:
  → "Tell me more - what was your role?"
  → "What technologies/methods?"
  → "What problem were you solving?"
  → "What was the impact?"
  → CHECK: "Does this address {gap_area}?"
  → CAPTURE: Create bullet if substantive

BRANCH B - If MENTIONS MULTIPLE:
  → "Let's explore each. Starting with {first}..."
  → Go through systematically
  → Prioritize by gap relevance
  → CAPTURE: Multiple bullets if relevant

BRANCH C - If "NOTHING NEW":
  → "What about small improvements, process changes, learning?"
  → "New tools or technologies?"
  → "Mentoring, teaching, knowledge sharing?"
  → "Anything that might seem too small?"
  → CAPTURE: Even small items can fill gaps

Key Principles

1. Start Broad, Go Narrow:

• Initial question is open-ended
• Follow-ups drill into specifics based on what they share
• Don't ask about details they already covered

2. Listen and Branch Dynamically:

• Promising answer → explore deeper
• "No" answer → try adjacent probe or move on
• Unclear → rephrase or provide examples
• Stuck → offer concrete scenarios

3. Adapt to Communication Style:

• Verbose: "What's the key takeaway?"
• Terse: Provide examples, "Was it like X or Y?"
• Uncertain: Validate, offer prompts

4. Recognize When to Move On:

• After 2-3 attempts with nothing → gracefully move on
• Don't exhaust user forcing content that doesn't exist
• Some gaps okay - flag for cover letter

5. Cross-Reference During Discovery:

• "Earlier you mentioned {X}, does that relate here too?"
• "This sounds similar to {Y} - connected?"
• Build connections user might not see

Example Complete Flow

SKILL: "I see the job requires CI/CD experience. Have you worked with CI/CD pipelines?"

USER: "Yes, I set up GitHub Actions for my side project."

SKILL: "Tell me more about that - what does the pipeline do?" [BRANCH: Depth]

USER: "It runs tests and deploys to cloud when I push code."

SKILL: "What testing framework do you use?" [BRANCH: Technical details]

USER: "pytest for my Python code."

SKILL: "Excellent. What's deployed - is this a production app?" [BRANCH: Impact/scale]

USER: "Yeah, it's a tool used by 3 nonprofits right now."

SKILL: "That's substantial! Have you dealt with any flaky tests or reliability issues?"
      [BRANCH: Real-world challenges]

USER: "Actually yes, I had to add retries for some API-dependent tests."

SKILL: "Perfect - that shows practical troubleshooting. Any metrics on build time
      or deployment frequency?" [BRANCH: Quantify]

USER: "Deploys take about 3 minutes, and I deploy several times a week."

[CAPTURED: Complete picture - hands-on CI/CD, pytest, flaky test handling,
production deployment. Directly fills gap with concrete details.]