Something to doGetting ahead
Talk about their career, not their performance
A longer conversation to understand where someone wants their career to go, kept apart from how they're doing
Why it’s worth your time
People say different things when they know they aren't being evaluated. Fold career talk into a review and most people will tell you what sounds promotable; hold it on its own and you're more likely to hear what they actually want. That's what lets you match people to the work and chances that will keep them growing.
How to have a career conversation with an employee
You’ll come away with a clearer picture of where they want to go, and one thing you'll help with this year.
We’ll send you a calendar invite.
- Book it on its own.
Forty-five minutes, separate from any review or project check-in, with what it's for in the invite. If review season is close, wait until it has passed.
To: your reportI'd like to set aside some time just to talk about you and your career: where you've been, where you'd like to go, and what you want to learn. It isn't about performance, and it isn't connected to any review.
There's nothing to prepare, and we can split it into two shorter chats if you'd prefer.
Swap the highlighted parts for your thing. Works on Slack, in email, or said out loud. - Start with their story.
Ask how they got here, and listen for the choices rather than the job titles: why they moved, what they loved, what they walked away from. That tells you more about what they value than any direct question.
You“I'd love to hear how you got here. Start wherever you like, and tell me about the choices along the way.” - Ask what they hope for.
Not their next title. What they'd love their work to look like in a few years. Some people have a clear picture; many don't, and that's fine.
You“If the next few years went really well for you, what would your work look like?”Tip: If they don't know, ask what they'd want more of and less of in the job they have now. It's an easier place to start.
- Ask what they want to learn next.
Bring it down to the next year or so: one or two things they'd like to get better at, and what kind of practice would help.
You“What would you like to be better at a year from now?” - Say what you'll do, and write it down.
Name one thing you'll look out for, and be honest about what isn't likely here. Send a short note afterward with what you heard, so they can correct it.
Tip: If what they want can't happen here, saying so is still a kindness. Helping them plan for it anyway is part of the job.
Good moments for this: once a year with each persona month or two after someone joinswhen their role changes
We’ll send you a calendar invite.
Keep going with Truest
Small actions add up. Truest helps you find the next thing worth doing, make the space to do it, and keep a record of your progress. It’s a private place to work on your career, and it’s yours, not your employer’s.
- It actually happensWe’ll put it on your calendar and remind you before it starts.
- A living page in your VaultKeep it as one page you add to, next to your reviews and your files.
- It’s yours to keepEach thing you do is saved to your private record, there when your next review or job search comes around.
Anything else we can help you with this week?
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
It makes this a conversation between two people rather than an interview. A detour or two from your own path, told honestly, makes it easier for them to be honest about theirs.
What might make this harder
Say plainly that nothing from this goes into any rating, and keep that promise. Trust tends to arrive in the second conversation, not the first.
Questions people ask
What is a career conversation with an employee?
A conversation about where someone wants their career to go, held apart from performance reviews. It usually covers their story so far, their hopes, and what they want to learn next.
What questions should I ask in a career conversation?
Start with how they got here and the choices along the way, then what they'd love their work to look like in a few years, then one or two things they want to get better at next.
Should career development be part of a performance review?
It can come up there, but it works better on its own. People tend to answer more honestly when they know they aren't being rated.
What if my employee's goals don't fit my team?
Say so honestly and help anyway. People often stay longer, and work better, for a manager who takes their whole career seriously.
Why this works, and where it comes from
Ask someone during their review where they see themselves in a few years, and you'll usually get an answer that sounds promotable. It isn't dishonest. It's what anyone says with a rating on the table. What they actually want stays unsaid, and a year later they may leave for something you'd happily have helped them find.
Kim Scott, in Radical Candor, describes a set of career conversations she credits to a former colleague: start with the person's life story, move to their dreams, then turn those into a plan for what they want to learn in the next stretch. Her version runs across separate conversations. This one folds them into a single longer one, with the option to split it, because what matters most is that it happens, and that it happens apart from performance.
The story is where the value hides: why someone left a job, what they loved about an old team, which choice they'd make again. What people have chosen often says more than what they say they want. Listen for the pattern. Someone who keeps moving toward people problems may not want the technical track you had in mind for them.
It isn't the right conversation for someone who is struggling in their role right now, or in the week a review lands. Whatever you intend, they'll hear it as a verdict. Settle the performance question plainly, and let the career conversation wait until it's no longer in its shadow.
Other simple things to consider
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Written by Truest, based on Radical Candor (Kim Scott). Last updated October 29, 2026. We sell a career membership; where that’s relevant above, we say so.