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Podcast Episode 5: Career Conversations

As a manager, your job is to help your people grow. But have you ever asked yourself, “Grow into what?” This week, Russ and Kim talk about a technique for getting to know the people on your team, understanding the things that motivate them, learning about their dreams, and helping them make tangible progress towards those dreams.

Listen to this week’s episode:

In this Episode

In previous episodes of the Radical Candor podcast, Kim and Russ have talked a lot about feedback. This week, they dive into another way to build relationships with people on your team: Career Conversations.

Russ developed this process when he was at Google when he noticed that a lot of people felt frustrated that they weren’t getting where they wanted to be in their careers. They felt stuck, like they weren’t making any progress.

Russ came to realize that these people needed a sense of their endgame and an intentional process for putting together a short term plan, so he came up with this Career Conversations approach.

Kim and Russ share stories about people they’ve worked with, and even their own experiences with career dreams and conversations. Kim acknowledges:

It’s hard to say your dreams out loud, especially to your boss.

But as a boss, part of your responsibility is to encourage people to dream, and to help them take a step in the direction of their dreams.

You need to give people license to dream.

Russ and Kim finish off the episode with tips for getting started with Career Conversations.

This Week’s Candor Checklist

Tip 1: Have a Life Story conversation

Tip 2: Have a Visions conversation

Tip 3: Create a Career Action Plan

Learn more about these tips by listening to the episode!

Related Links

Get a little more detail on the Career Conversations process with the following links:

Candor T-shirt Winner!

This week’s Candor t-shirt winner is barbskinner1! Barb, you’ll be getting one of these shirts that Russ wears pretty much every day, as you can see in this photo of Russ and Kim.

Listeners, you could be our next winner! Just leave us a review on iTunes to enter. We’re randomly selecting listeners from iTunes reviews and announcing them on the show each week. Tune in each week to hear if you’ve won a Candor t-shirt.


We’ll be back next week with a new episode!

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Tell us what you think, and share your stories with us!


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This Post Has 8 Comments
  1. I think if my boss asked me tell them my life story from kindergarten on, I’d feel obligated to do so but I’d be super uncomfortable. I’d probably make something up that sounded ordinary and reasonable, bc my past is neither of those and asking about it when there’s an unbalanced power dynamic is weird and invasive.

    1. Hi Candace –

      First, thank you for this input. This is a reasonable point, though the main reason that I added this particular conversation to the process was because through experimentation, I’d learned two crucial things: Most people – and by most, I mean 99% – have a great experience with this. One person I worked with at Twitter, not knowing I’d developed the process, came out of the conversation with his manager so psyched and said, “WOW! I have never had a career conversation more focused on ME!” There are a lot of benefits to this conversation for manager and direct alike, and in my experience both tend to think it’s positive.

      That, however, doesn’t matter for someone like you who would find such a conversation invasive. I teach a workshop on this, which is much longer and more detailed than a :25 podcast, and one of the points that I make is about honoring boundaries. I will more or less put the managers on high alert that some – few – but some will be uncomfortable with one aspect of this or another and that it’s crucial to listen someone dropping a boundary and then honor it aggressively.

      I was having this conversation with someone in my organization years ago, and he revealed to me that he was transgender. For me, not a big deal, but for him, as he noted, this was the first time he’d ever disclosed this fact to someone at work. He was comfortable, relaxed, and it just sort of came out. This became a focus for him in the conversation. I assured him, of course, that the conversation was confidential (notice I’m not naming a person, a company, or even a time frame, and I might even have intentionally mixed up the gender here) and that we needn’t dwell on that at all, which we didn’t.

      Luckily, he and I had a good relationship and we got back into a groove, and simply I took his lead on whether his gender transition was further discussed or not (turns out he wanted to talk a little bit more, so it was ok).

      I use this, though, as a real life story to make your exact point – there are aspects of people’s lives that they do not want to share with their bosses and you, as a boss, need to make it clear that they are fully empowered to drop the boundary curtain – simply by not mentioning things they don’t want to mention – and if a boundary is dropped, I tell managers that they must honor the boundary to the fullest.

      Approaching thousands of iterations, have not had a person fully punt on having this conversation, but if they say “don’t want to do this,” that needs to be ok, too.

      I hope this helps clarify.

      1. Thanks for your reply. Since you couldn’t squeeze the importance of recognizing and respecting boundaries in this 25 mins, that might be could a good topic for another podcast episode. I know any number of people who don’t feel like their boss knows the difference between a boundary and an invitation.

  2. I love the idea of having a career conversation but I’m the employee. Typically some of the basics are covered during the interview process, but I actually got my current job based off previous work experience and didn’t do a formal interview with my current boss. So I feel like having a career conversation would be very beneficial, but how do I approach the subject as the employee not the manager? I’ve been loving the podcast and am super excited to read the book! Thanks so much!

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