run-career-conversation

Run Career Conversation

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.

Why This Is Best Practice

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

Steps

1. Schedule separately from one-on-ones

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:

• What kind of work energizes you most right now?
• Where do you want to be in 2–3 years — inside or outside this company?
• What skill or experience do you feel is most limiting your growth?

2. Start with their vision, not your needs

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.

3. Map their current state against that vision

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).

4. Share your observations — as input, not verdict

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?"

5. Identify 1–3 concrete development actions

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.

6. Write it down and share ownership

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.

7. Follow up in one-on-ones

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.

Rules

• Career conversations are not performance reviews — do not evaluate past performance or raise compensation in the same session; mixing the two causes employees to focus on evaluation rather than exploration
• The employee sets the career goal — managers can offer market context and growth feedback, but cannot dictate what an employee should want
• Write it down — verbal commitments are forgotten; a short shared document creates accountability for both parties
• Development actions belong in the employee's current role — exotic stretch assignments that require role changes are valid aspirations but not substitutes for near-term development in the current job
• If the employee's aspirations require leaving — engage with that honestly; suppressing it does not retain them, it just accelerates their departure without giving you a chance to influence it

Common Mistakes

• Conflating career conversations with performance reviews: evaluation creates defensiveness; exploration requires safety; combining them produces neither well.
• Waiting for the employee to initiate: most employees wait for the manager to signal that career development is a legitimate use of work time; if the manager doesn't initiate, the conversation doesn't happen.
• Development actions that are aspirational but not actionable: "become a better communicator" is not a development action; "present the Q3 results at the leadership review and debrief with me the next day" is.
• Forgetting to follow up: a career conversation with no follow-up in one-on-ones signals that it was a box-checking exercise; employees disengage faster after a career conversation that goes nowhere than if no conversation had happened at all.
• Assuming you know what they want: managers regularly assume their best engineers want to become engineering managers, or that their ambitious reports want to stay in the company; ask explicitly.

When NOT to Use

• In the first 30–60 days of employment — employees need to establish a baseline understanding of their role and environment before they can meaningfully reflect on career direction; focus on onboarding first.
• As a response to a resignation — a career conversation initiated in response to an announced departure is perceived as reactive retention, not genuine development interest; it rarely succeeds and damages trust.
• When the manager has already decided the employee's next move — if the conversation is actually a communication of a pre-made decision, call it that; a career conversation requires genuine exploration, not a scripted reveal.