upskill

name	upskill
description	Use to turn the jobs someone is chasing into a concrete learning plan — "what should I learn", "where are my skill gaps", "how do I become competitive for X roles", "make me a study plan". Aggregates the tracked pipeline (or a single posting) against the profile, builds a prioritized gap heatmap, and produces a learning plan with real, web-searched resources.
tools	["careercoach_list_applications","company_researcher"]

Upskill

Two-pass gap analysis adapted with credit from Mads Lorentzen's ai-job-search (MIT), upskill/SKILL.md.

Two modes:

• Aggregate (default) — analyse the whole tracked pipeline (careercoach_list_applications).
• Targeted — analyse a single posting the user gives you (fetch it with fetch_url).

Step 1 — Load

Read the candidate profile (Settings › Career Coach + anything shared in the conversation). In aggregate mode, pull the tracked applications and their fit_scores (lower fit = the role exposed more gaps → weight it heavier). In targeted mode, fetch and parse the one posting.

Step 2 — Pass 1: hard-skill diff

Extract required + preferred technical skills from each source. Build a frequency map; in aggregate mode weight each skill's contribution by (100 - fit_score) / 100. Diff against the profile and be generous — if the profile shows a skill in any form ("Python" covers "Python scripting"), it's not a gap. What remains is the hard-skill gap list, ranked by score.

Step 3 — Pass 2: synthesis (what the diff misses)

Reason holistically about gaps a keyword diff can't catch, and tag each:

• [domain] — unfamiliarity with the industry/problem space (cybersecurity, quant finance, climate…)
• [soft] — ways of working, communication, leadership expectations the postings emphasize
• [tooling] — frameworks, cloud, methodologies (MLOps, CI/CD, agile-at-scale) recurring across jobs
• [credential] — a certification multiple postings prefer

Don't duplicate Pass 1; only add what it missed.

Step 4 — Gap heatmap (show this before the plan)

Combine both passes into one prioritized table (Critical / High / Medium / Low), and print it:

Priority	Skill / Area	Type	Gap source
Critical	Kubernetes	Hard	4/5 jobs, score 3.2
High	Security domain	Domain	synthesis

Step 5 — Learning plan

For every Critical + High gap (and Mediums if there are fewer than five gaps total):

1. WebSearch for current, well-regarded resources — include the current year in the query.
2. Pick 2-3 (prefer hands-on labs, official docs for tooling, books for domain). Name + URL + one-line why.
3. Write a study direction tailored to the candidate's background — what to skip, where to start.
4. Estimate time to working proficiency (be realistic, err high).

Group by theme (Cloud & Infra, MLOps, Domain, Soft skills, Certs), then add a Suggested study order with dependencies first, critical before high, quick wins early, domain knowledge alongside projects.

Rules

1. Never fabricate a resource. Only cite real WebSearch results — no invented courses, URLs, or authors.
2. Search with the current year so results stay fresh.
3. Be generous with profile matching — avoid false-positive gaps.
4. Show the heatmap before the plan.
5. Offer to save the plan as an artifact (or a note) the candidate can revisit and track progress against; next time, diff against it to show gaps closed + new gaps.