Career Transition Planner

A 41-year-old litigation partner at a mid-size law firm has been saying she wants to move in-house for three years. The goal is credible — she has the skills, a relevant network, and a clear preference for the operational work of corporate counsel over the business development grind of partnership. She has never written a transition plan. Every coaching session produces good analysis and no action. The Career Transition Planning worksheet forces her to translate 'I want to go in-house someday' into a current-state skills inventory, a target role profile, a 12-month phased plan, and a risk assessment. The planning artifact is the diagnostic: what she puts on paper and what she omits both tell you something.

Frame this as converting a wish into a project. 'You've been clear for a while about the direction. What you don't have yet is a project plan — current state, target state, timeline, risks. This planner builds all four. It won't decide anything for you, but it will make the gap between now and the target visible in a way that a conversation can't.' The resistance this scenario invites is timeline avoidance — she may complete the current-state and target sections well but leave the 12-month timeline vague. Name it: 'The milestone section is where this planner does most of its work. I want you to resist writing it as a general intention — give me months and specific actions.'

Watch for her risk assessment to be the shortest section — or written in abstract terms ('losing income,' 'uncertainty') without naming the actual numbers or thresholds that would make the risk real. The safety net section is especially diagnostic: does she have six months of savings, a financial partner, a returnable situation if the move doesn't work? If the risk section is vague, that vagueness is doing protective work. Also watch for the target role profile to describe in-house counsel at any company in any industry — if she hasn't narrowed by sector, size, or deal type, the profile will need another round before it can drive outreach.

Start with the 12-month plan. 'Walk me through the milestones you wrote — month by month.' Then pick the first one: 'What specifically needs to happen in month one? Not what you'd like to happen — what are you committing to do?' If the milestone is 'start networking,' push for specificity: how many conversations, with whom, initiated how? Then turn to the risk assessment: 'You named [her stated risk]. What's the number below which you wouldn't take the move?' The number test is whether the risk is named or felt.

A 36-year-old staff software engineer at a fintech company has decided she wants to move into product management. She has made the decision with clarity and confidence. What she hasn't mapped is the gap between her current skills and what the target role actually requires — the gap that would make hiring managers skeptical. She came to coaching with a destination and no route. The Career Transition Planning worksheet will produce both a skills inventory (what she has) and a gap analysis (what she's missing relative to the target profile), which is where the actual work of transition begins.

Frame this as building the map, not the destination. 'You know where you want to go. The planner builds the map between here and there — what you're starting with, what the target role actually requires, where the gap is, and what a realistic 12-month path looks like.' The gap analysis section is the one to emphasize: 'I want you to look at five real PM job descriptions before you fill out the target profile. Use those to define what the role actually asks for — not what you imagine it to be.' That instruction prevents the target from being shaped by her existing strengths, which is the most common trap in this type of transition planning.

Watch for her skills inventory to include soft skills heavily and technical/domain skills lightly — the reverse of what hiring managers for PM roles at tech companies typically weight. If she lists 'communication,' 'problem-solving,' and 'leadership' without listing product analytics, roadmap management, or user research, she has filled the inventory with what's safe to claim rather than what the role requires. Also watch for the risk section to underweight the career cost of a lateral move: stepping from staff engineer to associate PM often means a title regression and compensation reduction, and if she hasn't named that explicitly, the plan is incomplete.

Start with the gap analysis. 'You completed the target profile and your current inventory. Where are the biggest gaps?' Let her identify them first. Then: 'If you were a PM hiring manager looking at your background, what would your concern be?' That external perspective question often surfaces what she already knows but hasn't said. Then move to the timeline: 'The plan has milestones for closing the gap. Which one is the highest leverage — the one where, if you did it in the next 90 days, it would change how you look on paper?' One concrete accelerant is more useful than a full 12-month plan.

A 44-year-old VP of marketing at a consumer goods company has been offered a voluntary separation package following a restructuring. She wants to use it as a launch point to pivot into independent brand consulting. She has a general concept, two informal conversations with potential clients, and two teenage children in households with a dual income they are both depending on. She came to coaching because her plan lives in her head and she needs it on paper before her window closes. The Career Transition Planning worksheet is the structure that converts the concept into something her family can also read.

Frame this as making the plan legible — to herself and to others. 'You have a clear direction and a real window. What you need now is a plan that's specific enough to pressure-test. This planner builds the current-state picture, the target, the 12-month path, and the risk and safety net section. That last section is the one I want you to take most seriously — because this plan isn't just yours.' The financial runway and support network section of the risk assessment is where the coaching work will concentrate. If she hasn't run the budget numbers separately (Budget Tracker), that may need to precede or accompany this planner.

Watch for the safety net section to be underdeveloped relative to the ambition in the rest of the plan. If she lists 'severance package' and 'two client conversations' as her full safety net, the plan has optimism where it needs specificity. Specifically: what is the minimum monthly revenue needed to sustain the household, and by what month does she need to hit it? Those numbers should be in the plan. Also watch for the risk assessment to describe risks at the category level ('income uncertainty,' 'client instability') without naming the threshold at which she would return to full-time employment — the plan is incomplete without a re-entry trigger.

Start with the safety net. 'You wrote your safety net section. Walk me through it.' Then: 'At what month in this plan do you need to be generating X in revenue to stay the course? And what's the month where, if you're not there, you activate a different plan?' Those two dates are the spine of a real plan, not an aspirational one. Then go to the first milestone: 'Month one. What specifically are you doing in month one — not hoping to do, committing to do?' The gap between what she wrote and what she can commit to out loud is where the plan needs revision.