Coach Someone Through a Career Transition
Team & Leadership · 4–6 sessions · Intermediate
The job
Help an individual redesign their career by applying business model thinking to their professional life.
What the sponsor gets
Each canvas and map from this playbook — Empathy Map, Persona Canvas, Lean Canvas, Assumption Map, Prioritisation Matrix — exports as a PDF, or as PowerPoint on Pro, straight from the session, and the whole run exports as one PowerPoint for the sponsor. Nothing is redrawn.
The method
Map where they are now
Create an Empathy Map for the coachee's current situation. What are they thinking and feeling about their career? What are they saying to others vs what they're keeping inside? What's driving the desire for change?
Tip: The stated reason for wanting a change ("I want more money") is rarely the real one — listen for what's underneath.
Build a professional identity canvas
Create a Persona canvas, but for the coachee themselves. Define their strengths, values, non-negotiables, and what energises them. This becomes their decision-making compass for evaluating options.
Tip: Pay attention to what they talk about with energy vs obligation — energy signals are more reliable than rational preference.
Apply business model thinking
Create a Lean Canvas treating the coachee as a "business of one." Who are their customers (employers, clients)? What's their value proposition? What channels reach opportunities? What's their unfair advantage?
Tip: The "Unfair Advantage" box is always the most revealing — it forces people to articulate what makes them specifically valuable.
Test career assumptions
Map the assumptions behind each career option. "I'd need to retrain," "That industry doesn't pay well," "I'm too senior/junior for that." Plot by importance and certainty, then design ways to test the critical ones.
Tip: Most career-limiting assumptions are untested beliefs from 5+ years ago — even one informational interview can shatter them.
Design career experiments
For the top 2–3 options, design low-risk experiments: informational interviews, shadowing days, freelance projects, volunteering. Each should give a genuine feel for the work, not just confirm existing assumptions.
Tip: A conversation with someone doing the target role is worth more than 10 hours of internet research — make introductions.
Evaluate and commit
After experiments, plot the options on a Prioritisation Matrix considering fit (energy + values), feasibility (skills + finances), and timeline. Choose one primary path and one fallback.
Tip: The goal isn't to find the perfect option — it's to find one worth committing to. Commitment beats optimisation.
The canvases and maps
- Empathy Map
- The goal first, then what the person sees, says, does, hears, thinks and feels, so the room separates what it has observed from what it is guessing.
- Persona Canvas
- Goals, frustrations, behaviours, motivations and needs side by side, so the person you are designing for is specific enough to disagree about.
- Lean Canvas
- Nine boxes from problem and customer segments through to costs and revenue, so a whole business idea fits on one page and its weakest box shows.
- Assumption Map
- Assumptions plotted by importance and certainty, so the leaps of faith that need testing first stand apart from the safe bets.
- Prioritisation Matrix
- Impact against effort in four quadrants — quick wins, major projects, fill-ins and avoid — so the team trades off instead of calling everything a priority.
What it doesn't do
It doesn't run the room for you or decide for the client. The steps, canvases and duration are a starting point you adapt; the judgement stays yours.