Moving Up the Care Personally Axis (Radical Candor)

Share the love

I just finished up with Radical Candor, a book on leadership by former Google and Facebook executive Kim Scott. Scott lays out two axes that exist within leadership—care personally and challenge directly. Together, they create the radical candor framework.

A visual depiction of the radical candor framework
This post on First Round Review offers a great breakdown if you just want to learn more about the framework. Image from Radical Candor.

Care personally is just that—demonstrating to your teammates that you give a damn about their well-being and success.

Challenge directly is all about helping them improve, giving them feedback, and pushing them to excel.

I want to talk about moving up on the Care personally axis and moving towards Radical Candor pulling both from the book and personal experience.

Moving Up the Caring Personally Axis

More often than I’d like to admit, I fall into the “Ruinous Empathy” category, which is arguably one of the worst categories to be in second only to “Manipulative Insincerity.” The truth though is I do care about the members on my team and their success.

Demonstrating that you care about your employees starts on day one with your first one-on-one. It’s important to get to know your teammates on an individual level for reasons that will become clear later.

In my mind, caring personally breaks down into three main bullet points:

  • Do I understand what drives and motivates this person?
  • Do I understand what type of work this person naturally excels at?
  • Have I invested in learning about this person on an individual level?

What drives and motivates you?

This is an often overlooked piece to the Care personally axis. Understanding their drive and motivations more clearly will help you to understand how you can push this person in the future (the Challenge directly axis).

Learning about their drive and motivation doesn’t have to be some formal conversation. It can be super casual. I recently did a “Values Clarification” exercise that was immensely helpful across a team I lead at Automattic. I sent over a list of values to each member of my team and asked them to rank the top five to ten values they thought were most important. The list included things like leadership, creativity, help others, friendship, etc.

Once each team member had completed the exercise, we talked about it together (one-on-one). I shared my list with them, and they shared their list with me. For each value, we discussed why this value was important and how they see it manifesting in their work. For example, I listed “Challenge” as one of my values. In practice, this means that I like being tasked with difficult things to work on (more difficult = better). I also prefer to find my own way versus being micro-managed (I’d venture most feel that way). A good follow-up question when someone lists a value: “Talk to me about a time at work when that value really shone through.”

A values clarification exercise isn’t the only way to do this, but it’s one way (that I’ll write more about later). The goal is to get at what motivates each person on your team so you can use that information to push them forward.

What type of work does this person naturally excel at?

Invariably, there will be areas of work where members of your team naturally excel. There are dozens of exercises you can do with members of your team to suss this out.

One exercise involves making a list of all tasks involved with their work. Then, separate out that list into four quadrants. The horizontal axis would run from “I don’t look forward to this” to “I love doing this”. The vertical axis would run from “I have to work hard at this” to “I have a natural talent for this”. We’re left with four quadrants:

  • Love doing; Natural talent.
  • Love doing; Have to work hard.
  • Have to do; Natural talent.
  • Have to do; Have to work hard.

The eventual goal would be to move most of the tasks to the “Love doing; Natural talent” quadrant, which can be tricky (businesses have needs too!).

A simpler way of sussing out the answer to this question though is to pay attention in one-on-ones.

  • What types of tasks does this person have no trouble completing from week to week that others struggle with?
  • Which areas of the business do they work on during their free time?
  • What topics do they choose to bring to our weekly discussions? Are these topics all clustered around a similar type of work?

Have I invested in learning about this person on an individual level?

This includes learning about their career ambitions and also their personal life (if they want to share). For learning about their career ambitions, I loved the three-part conversation that Scott lays out in Radical Candor (the process was actually borrowed from her co-founder at Candor, Inc, Russ).

Conversation one: life story
“Starting with kindergarten, tell me about your life.” Then, he advised each manager to focus on changes that people had made and to understand the change…you’re just trying to get to know people a little better and understand what they care about.

The second conversation: dreams
Bosses usually ask about “long-term goals” or “career aspirations” or “five-year plans,” but each of these phrases, when used by a boss, tends to elicit a certain type of answer: a “professional,” and not entirely human, answer…Russ recommends that you begin these conversations with, “What do you want the pinnacle of your career to look like?” Russ suggests encouraging people to come up with three to five different dreams for the future. This allows employees to include the dream they think you want to hear as well as those that are far closer to their hearts.

Conversation three: eighteen-month plan
Here’s what to do: make a list of how the person’s role can change to help them learn the skills needed to achieve each dream; whom they can learn from; and classes they would take or books they could read. Then, next to each item, note who does what by when—and make sure you have some action items.

I haven’t followed this process exactly, but I’ve touched on each of these points in a roundabout way. If you don’t want to break this out into three different conversations, you can just ask some general questions:

  • What do you want the pinnacle of your career to look like? (I stole this from the book)
  • Are there other areas of the business you’re interested in?
  • What would you work on if you have unlimited time/flexibility?
  • What skills would you most like to learn in the next six months?

For learning about their personal lives, I dedicate 10 minutes of each 30-minute one-on-one  to personal chatter, learning about their weekend, asking about any fun plans, and sharing what I’m up to. I’ll learn about birthdays, big celebrations, and memorable events in their lives (selling a house, for example).

Pulling Everything Together—Moving Towards Radical Candor

After addressing all three of those questions, we now have a more complete picture of who this person is, where they want to go, and how we can potentially help them.

  • We understand what drives and motivates them. Whenever we need to present feedback or push them towards a new project, we can do so in a way that naturally aligns with their personal motivations.
  • We understand the type of work they naturally excel at and enjoy. We can connect them with opportunities that hit both of those key points and maximize their talents. This leads to team members demonstrating their expertise and feeling successful.
  • We know a bit more about their personal ambitions and life outside of work. We can celebrate achievements with them and be cognizant of when we might need to step in and help out. (I highly recommend reading the section titled “Growth Management” on p. 47 in Radical Candor as it addresses this piece directly.)

In practice, moving up the “Care personally” axis looks like going from this:

Megan, I need you to take on project __. Can you do that?

To this:

Megan, an opportunity has just popped up to lead project __. I think you would be a terrific fit. You’re great at doing __, and this would give you the opportunity we’ve been looking for to learn more about __. Let’s talk more about the opportunity and how I could help shuffle your existing work to make room for the project.

The second variation is better on many levels. You’re directly connecting it to an area of expertise. You’re explaining what they could learn and how that ties into their career ambitions. Finally, you’re offering to help shuffle existing work responsibilities so they don’t get overloaded.


I almost titled this post “Giving a Damn About Your Team Members” because that’s what this boils down to. Demonstrating a personal interest in helping every team member succeed. If you’re leading a team, that’s your main responsibility. Do that, and all the right business metrics will follow.

Share the love
Strategies on solving problems and wowing customers every Sunday 👉
Strategies for solving problems and wowing customers 👇