From grimoire
Structured career development dialogue for managers to understand a direct report's long-term aspirations, identify growth gaps, and create a concrete development plan.
How this skill is triggered — by the user, by Claude, or both
Slash command
/grimoire:run-career-conversationThe summary Claude sees in its skill listing — used to decide when to auto-load this skill
Have a structured, future-focused dialogue with a direct report about their career aspirations, current gaps, and a concrete plan to grow — separate from performance evaluation and weekly check-ins.
Have a structured, future-focused dialogue with a direct report about their career aspirations, current gaps, and a concrete plan to grow — separate from performance evaluation and weekly check-ins.
Adopted by: Google mandates career development conversations as part of the manager effectiveness framework documented in re:Work; LinkedIn's internal "Employees' Best Interest" model requires managers to explicitly discuss external career opportunities with reports; Microsoft, Adobe, and Deloitte have replaced annual reviews with quarterly check-ins that include career development as a mandatory component; SHRM's Individual Development Plan (IDP) framework is the standard HR template across most enterprise HR systems Impact: Gallup's 2017 research (195k respondents) found that 87% of millennials and 69% of non-millennials rate career development as important to their job, yet only 37% strongly agree their manager helps them develop; LinkedIn's "Why Employees Stay" research (2019) found that employees who feel their manager takes an interest in their career goals are 2.6× more likely to stay; Beverly Kaye's research across 200+ organizations shows that the #1 reason high performers leave is not compensation — it is perceived lack of development opportunity Why best: Weekly one-on-ones focus on current work and immediate blockers; performance reviews evaluate past performance against current-role expectations; neither addresses where the employee wants to go and what they need to get there; without a dedicated career conversation, managers operate on assumptions about what employees want — often wrong assumptions — and employees feel invisible, which is the primary precursor to disengagement and departure
Sources: Google re:Work "Career Conversations" (rework.withgoogle.com); Gallup "State of the American Workplace" (2017); LinkedIn Talent Solutions "Why and How People Change Jobs" (2015); Kaye & Giulioni "Help Them Grow or Watch Them Go" (Berrett-Koehler, 2nd ed. 2019); SHRM "Individual Development Plans" knowledge center
Career conversations require 60–90 minutes and a different mindset than operational check-ins. Schedule them separately, at least quarterly. Announce the topic in advance:
"I'd like us to spend time next week not on current work but on your career —
where you want to go and how I can help you get there. I'll send some questions
to think about beforehand."
Pre-send 2–3 reflection prompts to give the employee time to think:
Open with the employee's aspirations, not with the team's skill gaps or the next available opportunity. The conversation should feel like it serves them.
Opening questions:
"What does a great career look like to you — not just the next role, but
the type of work, impact, or environment you're aiming for?"
"What are you most proud of in the last year? What did that tell you about
what matters to you at work?"
"If you could design your next three years, what would they look like?"
Listen without redirecting toward available opportunities. Your job in this phase is to understand what they actually want, not what you have to offer.
Once you understand their aspiration, explore the gap between where they are and where they want to go:
"Given where you want to go, what do you feel you're strongest at that will
take you there? What do you feel is most underdeveloped?"
"What experiences or skills do you think you need that you haven't had yet?"
"What feedback have you received that you think is most relevant to where
you want to go?"
Do not evaluate or correct their self-assessment in this phase. The goal is to understand how they see their own development, not to give your assessment (that is what performance reviews are for).
After hearing their view, share your perspective on their strengths and gaps as it relates to their stated goals. Frame this as additional data, not the authoritative verdict:
"Based on what I've observed, I think your strongest leverage for [stated goal]
is [specific strength]. The area I'd watch is [specific gap] — I've seen it come
up in [specific situation]. That's just my view — how does that land for you?"
If your observations differ significantly from theirs, name the gap explicitly:
"You mentioned [area X] as your biggest gap. I actually think you're stronger
there than you realize. What I see more limiting you toward [goal] is [area Y].
Can we explore that?"
Together, identify specific actions — not generic goals. Development actions should have an observable output:
| Type | Example (generic) | Example (concrete) |
|---|---|---|
| Stretch assignment | "lead something bigger" | "lead the Q3 customer migration project end-to-end" |
| Skill building | "improve communication" | "present at the all-hands in September and debrief afterward" |
| Exposure | "learn more about product" | "shadow the PM in 3 customer discovery calls by end of Q2" |
| External learning | "get better at data" | "complete the SQL for Analytics course by July and apply it to one project" |
Cap at 3 actions. More than 3 signals that the conversation was about identifying gaps, not committing to change.
Summarize the agreed development actions in a shared document — not a formal HR system form, just a simple written record:
Name: [report's name]
Date: [date of conversation]
Career aspiration: [their stated goal in their words]
Development actions:
1. [Action] — by [date] — support needed: [what manager will do]
2. [Action] — by [date] — support needed: [what manager will do]
Next career conversation: [date]
Share it with the employee immediately after the conversation. Both parties own the document. The employee owns executing the actions; the manager owns removing blockers and providing agreed support.
Career conversations are not complete until the development actions are embedded in the regular cadence. Check in on progress in monthly one-on-ones:
"How is [development action] going? Is there anything getting in the way?"
If an agreed action is not happening, explore why — the most common reasons are workload crowding it out (a capacity and priority conversation) or the action not being as relevant as it seemed (revisit the plan).
Run a full career conversation quarterly. In companies with strong development cultures (Google, Netflix), managers run them more frequently for early-career employees.
npx claudepluginhub jeffreytse/grimoire --plugin grimoireGenerates structured career goal plans with gap analysis, timelines, quarterly milestones, actions, and accountability for tech aspirations like senior engineer or tech lead.
Structure effective one-on-one meetings that build trust, surface concerns, and align on growth and development. Use when preparing regular 1:1s with direct reports or designing 1:1 practices for your team.
Facilitates a regular manager-to-direct-report one-on-one meeting to build trust, surface blockers, and develop the employee.