The Three Career Conversations
Past, dreams, and action plan — three 45-minute conversations to show you care and grow people
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 3
- Confidence
- 85%
A structured way for managers to have meaningful career conversations with direct reports, split into three separate 45-minute conversations: their past/life story, their long-term dreams, and a concrete career action plan. It shows care personally and lets you work backward from where someone wants to go.
Origin
Kim Scott's practice, developed in parallel with Russ Laraway (her Google colleague and co-founder), whose book 'When They Win, You Win' devotes ~100 pages to career conversations.
Core principles
- 01Understanding what motivates someone at work requires understanding their past and their dreams
- 02Work backward from the person's aspirations to the skills they need now
- 03Very few people know what they want to do when they grow up, so ask for multiple pictures of the future
How to run it
- 1
The past / life story conversation
Spend ~45 minutes on the person's past — whatever they're comfortable sharing — to understand what motivates them at work.
- 2
The dreams conversation
Spend ~45 minutes on their future dreams, not just the next couple of years. Ask: 'imagine at the height of your career you have everything you want — what does it look like?' Ask for three or four different pictures.
Pro tip Multiple pictures matter because few people have a single clear answer.
- 3
The career action plan conversation
Sit down and build a plan: given what motivates them and where they want to go, what skills should they develop? Who can you introduce them to? What educational opportunities exist? Can you tweak their job so they gain those skills?
Pro tip Even a step toward the dream counts — the goal is movement in the direction of their aspirations.
In the wild
Lenny describes his version: ask what someone wants to achieve and where they want to go, make sure they know you understand it, then work backward — here's what you need to get right and here's the recent thing that's off-track.
→ Career feedback becomes about serving the person's own goals rather than the manager's agenda.
Common mistakes
Only asking about the next couple of years
Limiting the dreams conversation to near-term goals misses what actually motivates the person over the arc of their career.
Is it for you?
Best for
Managers who want a concrete cadence for investing in direct reports' growth and demonstrating care
Not ideal for
Relationships too shallow or short-term for the person to share their life story candidly
From the transcript
“I would have like three separate 45 minute conversations so one about their past one about their future their dreams for the future”
“imagine at the height of your career you have everything you want what does it look like and give me three or four different pictures…”
“the third conversation is to sort of sit down with your director report and come up with a career action plan”
“did you read the book uh when they win win by Russ lway”
From the episode
Radical Candor: From theory to practice with author Kim Scott