In the book Radical Candor, there’s a section that goes over how to talk to your team about their career aspirations. Typically it happens in 3 parts. You can do these in your 1:1 meetings or schedule separate time for these 3 conversations.

Part 1: Tell me your life story

In part 1, you won’t do much talking, but you should take a lot of notes. Ask them to tell you their life story up until now. Don’t provide too much direction with your instructions, the main goal is to get them talking about themselves. Along the way you might pick up on certain things that they value or that seem really important to them. Make sure you get especially good notes on:

• What’s important to them?
• What do they value?
• Why did they make certain major decisions in their life?
• What did they learn along the way?

I’ve gone pretty in depth into my answer in my post about Why I Became A Manager.

Part 2: At the peak of your career, what does that look like?

In conversation 2, you’re going to ask them to think about their future. We try to get 3 visions for the future.

In my career conversation I had a really hard time thinking of a third ideal future. My top 2 were being the director of curation at my current company, or working for some sort of think tank. Over time, I’ve added some more goals to my ideal future. I want to be an advisor for startups, have published a book on management, and generally be seen as an expert in my field.

Part 3: How can we make changes to your current role to put you on track for that future?

In part 3, I get them to consider what sort of skills they need to have to get them to that ideal future. We build out lists of skills for each of the 3 ideal end states, and then we think about activities through work, or professional development on their own time that they can start on to put them on the right track. Some skills have prerequisites and need to be built on top of other skills, some skills just take a long time to build up. Whatever the case, we try to build a rough timeline of skill development that would keep people on track to achieve their dreams.

Wrapping up

Remember, that people are not machines. They grow and change all the time. So just because you’ve gone through this process once, don’t think you’re done. Every now and then, bring up your notes from the career conversations. Are these still the dreams? Has anything changed? How are you progressing on the path? Are there any changes we need to make?

By keeping these conversations fresh, you can continue to encourage everyone on your team to grow.