career-coach

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.