Career Coach

---
name: career-coach
description: Clarify career direction, set goals, and build actionable development plans through structured coaching.
category: career
---

## Overview

Career coaching is not advice-giving — it's structured thinking with a partner.
This skill runs
coaching-style conversations: clarifying what the user actually wants (versus
what they think they
should want), diagnosing what's blocking them, and converting insight into a
concrete 30/60/90-day
plan. It asks more than it tells.

## When to use

- Feeling stuck, restless, or unsure about next career moves

- - Deciding between competing offers or paths (IC vs management, startup vs big
  tech)

- Planning skill development for a promotion or pivot

- Working through burnout, boredom, or a difficult manager

- Annual career reflection and goal-setting

## Core concepts

- - - **Values before tactics.** Decisions made on salary or prestige alone tend
  to unravel. Surface
  what actually matters: autonomy, mastery, impact, stability, recognition,
craft — then evaluate
  options against those, not against each other.
- - - **The energy audit.** Track for two weeks: which tasks energize, which
  drain. Career clarity
  often hides in the pattern of a normal fortnight, not in grand introspection.
- - - **Regret minimization.** For big decisions, ask: "at 80, which choice
  would I regret not
  trying?" It cuts through short-term fear reliably.
- - - **Reversible vs irreversible.** Most career moves are reversible (two-way
  doors). Treat them as
  experiments with a time box, not life sentences. Reserve agonizing for the
genuinely
  hard-to-reverse ones.
- - - **The 3-bucket plan.** Every development plan needs: learn (skills),
  demonstrate (visible
  proof), and connect (relationships/sponsors). People who only do bucket one
stall.
- - - **Coaching questions over answers.** "What would good look like in 12
  months?" "What's the
  smallest step that would tell you this is the right direction?" The user owns
the answer; the
  coach owns the question quality.

## Practical workflow

1. 1. 1. **Establish the real topic.** Ask what brought them here now, and
   what's at stake. Distinguish
   "I need a decision by Friday" from "I'm exploring."
2. 2. 2. **Clarify the desired outcome.** Push past vagueness: "a better job"
   becomes "a staff-level IC
   role at a mid-size SaaS with real technical ownership by Q2."
3. 3. 3. **Diagnose, don't prescribe.** Explore: What's working? What's
   draining? What have they
   already tried? What are they afraid is true? Listen for the gap between
stated goals and revealed
   preferences.
4. 4. 4. **Generate options.** Brainstorm 3-4 genuinely different paths (not
   variations of one).
   Include one "wild card" to break anchoring.
5. 5. 5. **Test with small experiments.** Convert each option into a 2-week
   test: informational
   interviews, a side project, shadowing, a course module. Decisions get easier
with data.
6. 6. 6. **Build the 30/60/90 plan.** Concrete actions with dates: 30 days
   (quick wins + experiments),
   60 days (deeper bets), 90 days (decision point or milestone). Each item has
an owner (them) and a
   success signal.
7. 7. 7. **Schedule the check-in.** Coaching without follow-up is conversation.
   Set a review point and
   define what "on track" looks like.

## Common pitfalls

- - - **Solving before understanding.** Jumping to "you should do X" in the
  first five minutes. The
  first job is diagnosis.
- - - **Confusing venting with coaching.** Letting the session become a
  complaint loop with no forward
  motion. Acknowledge, then pivot: "given that's true, what's one thing in your
control?"
- - - **Advice that ignores constraints.** Recommending a pay-cut pivot to
  someone with a mortgage and
  no runway. Always surface financial, family, and visa constraints early.
- - - **Infinite exploration.** Some people research forever to avoid deciding.
  Time-box exploration
  and force small experiments.
- - - **Measuring the wrong thing.** Tracking applications sent instead of
  conversations had, or
  courses completed instead of skills demonstrated. Define outcome metrics, not
activity metrics.
- - - **Neglecting the sponsor problem.** Individual effort stalls without
  advocates. Every plan
  should include building relationships with people who influence the user's
trajectory.