skip to Main Content

Send Your Boss Radical Candor

We often hear from fans of Radical Candor:

“Gosh, I wish my boss would read this!”


“How can I tell my boss about Radical Candor without implying I think she’s bad at it?”

We’ve said before that it can be risky to Challenge your boss Directly, even when you show you Care Personally. We’ve shared some tips on our podcast for giving feedback to your boss, but it’s definitely a tricky situation. Not everyone feels comfortable starting out this conversation, especially if the boss hasn’t been particularly open to feedback.

Buy Radical Candor for your boss

We’re here to help! We’ve set up a new site with our friends at BookPal to help you give the gift of Radical Candor. At, you can purchase a copy of Radical Candor, and we’ll take care of sending it directly to your boss. If you feel comfortable sending it openly, we’ll let them know it’s from you, but if not, we’ll send it anonymously!

What your boss will get

When you buy a copy of Radical Candor from, we’ll send:

  • A signed copy of Radical Candor: Be a Kickass Boss Without Losing Your Humanity
  • A letter from Kim Scott to your boss
  • A reading guide to help your boss and to provide ideas for rolling out Radical Candor to your whole team

Wait, doesn’t it seem counter-Radical Candor to send the book anonymously?

It’s a fair point that sending the book anonymously could seem passive aggressive — you’re not Challenging Directly. But you are showing that you care by doing something to try to help your boss. And if you’re familiar with the book, you’ll know about Kim’s Orange Box story: to get a culture of feedback started, it sometimes helps to start with anonymous feedback and build trust so that people feel comfortable sharing their thoughts openly.

Kim’s letter to your boss will acknowledge these points, that speaking truth to power is hard, and she’ll provide some advice for where to start with the book.

We’d love to know what you think of this program! Let us know in the comments below, or reach out at

Book Discussion Questions for Radical Candor

Discussing Radical Candor as a team can help solidify the ideas and get everyone thinking about how to start applying them to your day-to-day behaviors.

We’ve put together this list of questions to get you started with the discussions for each chapter, but we’d love to hear your ideas as well! Let us know what drives the conversation for you in the comments below.

Part 1: A New Management Philosophy


  1. Describe an experience when you didn’t give direct feedback, but you wish you did.
  2. Who are the best leaders you’ve worked for in your career? What made them so exceptional? What can you learn?
  3. Tell a story about the worst boss you ever had. What did they do that made them so bad? How can you avoid those mistakes?


Chapter 1: Build Radically Candid Relationships

  1. What does the book say are the key responsibilities of a boss?
  2. Many people mistakenly call Radical Candor the same as brutal honesty. What is the difference between Radical Candor and brutal honesty?
  3. What are some ways that you show you Care Personally at work?
  4. Do you think Challenging Directly is a strength or a weakness for you?


Chapter 2: Get, Give, and Encourage Guidance

  1. Describe an experience when you received feedback that you appreciated and that was delivered in a helpful and caring way.
  2. Describe an experience when you received feedback in a way that you didn’t learn from because you resented the way it was delivered to you.
  3. Have you ever been so nice that it ended up working against you?
  4. Have you ever felt there was no way to not be mean if you needed to get your desired outcome?


Chapter 3: Understand What Motivates Each Person on Your Team

  1. Have you ever underestimated an employee’s contributions because they weren’t gunning for a promotion? What happened? Did you regret it?
  2. Have you ever clipped the wings of an employee on a steep growth trajectory? What happened? Did you regret it?
  3. Are you more at risk of being an absentee manager or a micromanager? What kinds of situations push you towards one of these modes?
  4. Are you currently on a gradual or steep growth trajectory? Were you ever on the opposite one?


Chapter 4: Drive Results Collaboratively

  1. Have you ever tried to tell a team of people what to do? What were the results?
  2. Which step(s) of the Get Stuff Done (GSD) Wheel are easiest or most comfortable for you? What steps do you tend to skip? Where do you get stuck?
  3. What are some of the practices your team or organization has today that fall into the different steps of the GSD wheel?
  4. Are you a quiet listener or a loud listener?
  5. Do you want to foster a culture of debate on a team? If so, how will you do it? If not, why not?
  6. How do you help your team make decisions? Are you worried you grab too many decisions?


Part 2: Tools & Techniques

Chapter 5: Relationships

  1. What activities do you do to stay centered?
  2. Describe an experience when you weren’t able to bring your best self to work. What happened?
  3. How do you build trust with your direct reports/ staff? What strategies or activities have been most effective, and how can you tell?


Chapter 6: Guidance

  1. Have you solicited feedback from your direct reports/staff? If so, how have you done it, and has it been successful?
  2. Do you have a go-to question for soliciting feedback? What is it?
  3. What are some of the ways that you have rewarded criticism?
  4. Which of the book’s tips for giving guidance did you find most helpful?
  5. What’s something you could do tomorrow with someone on your team to offer Radical Candor?


Chapter 7: Team

  1. Do you or can you begin facilitating “Career Conversations” with your direct reports, as a way of caring personally and helping them map out their career trajectories?
  2. Do you know the balance of rock stars and superstars on your team? How do you think about growth for different people?
  3. Did any of the book’s suggestions for hiring and firing resonate as applicable to your team/company?


Chapter 8: Results

  1. How do you approach 1:1 meetings? How’s that different than the recommendations laid out in the book? Will you change your 1:1’s?
  2. How do you help nurture new ideas? Are there ideas from the book that you’ll adopt?
  3. Do you hold staff meetings? How do they compare to the approach in the book? Any recommendations that you’ll incorporate?
  4. Do you think the Big Debate or Big Decision meetings described in the book would help your team?
  5. What do you think about the number of meetings suggested in this chapter?
  6. How do you prevent meeting-creep from taking over the time your team should be spending executing?


We hope these questions are helpful in creating a meaningful discussion with your team! Of course, understanding the ideas is just the first step, and changing your habits and day-to-day actions is hard.

Let us know how it goes!

Back To Top