Radical Candor Podcast

Podcast Season 3, Episode 10: How to Practice Radical Candor With Your Boss

On this episode of the Radical Candor podcast Kim, Jason and Amy discuss clearing the cruft and the art of upward feedback. We get a lot of questions about how folks can practice Radical Candor with their bosses as many people are reluctant to give feedback to their managers. It’s true that it can be really daunting, and a little risky, to practice Radical Candor with your boss, but it’s such an important skill. If you can share feedback with your boss, you’ll have a much stronger working relationship, enjoy your work more, and be able to do better work together. So, how do you do it? 

Listen to the episode:

Radical Candor Podcast Episode at a Glance

People have a lot of preconceived notions about bosses, which makes them intimidating to approach. It’s important to remember that most (unfortunately, not all) people don’t intentionally make decisions to make life more difficult.

When giving feedback to your boss, assume they were doing what they thought was the right thing. Starting with that kind of mindset puts you in a better position to deliver feedback to your boss.

Here are some other helpful things to keep in mind when going into a feedback conversation with your boss:

Don’t assume that you’re right.

  • Be humble.
  • Start the conversation by asking your boss for their rationale for XYZ decision. This can start opening up the conversation.
  • Instead of starting from a position of, I’m right, you’re wrong, start from a position of, I would really love to understand what the rationale was for XYZ decision because it’s affected my work.

Start with questions, not assertions.

  • Don’t set it up as a fight.
  • By asking questions, you could get some context that you didn’t have. It could potentially help you understand a broader situation.
  • Try to have a little empathy for your boss; it’s common that a boss will have greater context than you do. Just try to put yourself in their shoes. Go into the conversation understanding their perspective before issuing your opinion.

Assume good intent going into the conversation.

  • Most people don’t intentionally make decisions to make life more difficult. Assume they were doing what they thought was the right thing.
  • Starting with that kind of mindset puts you into a better position to deliver feedback to your boss.

Don’t let it build up.

  • Ask questions and listen to understand and ask for permission to give another perspective.
  • Almost always the person will say yes. It’s the rare person who’s not open to another perspective. Especially if that person feels heard and that their rationale and reasons have been fully talked through, and you’re asking reasonably, “Can I offer a different perspective.”
  • Have the conversation in person or at the highest bandwidth that’s comfortable for both of you.

You also have to manage your risk.

  • When it comes to being radically candid with your boss, you have every right to be careful, and asking these questions will help you be careful.
  • Start with the little things and ask, “Is it OK if we talk about this.” If they say no, don’t proceed.
  • Don’t kiss up.


get feedback

Radical Candor Podcast Checklist

  1. Approach Radical Candor with your boss the same way you do with your team — ask for guidance before you give it. Remember, you want to understand the other person’s perspective before you start dishing praise/criticism.
  2. Ask permission to give guidance, “Would it be helpful if I told you what I thought of x?” If your boss says yes, start with something small and see how they react. 
  3. Start with questions, not assertions, and assume good intent going into the conversation. Starting with this kind of mindset puts you in a better position to deliver feedback to your boss.
  4. Use the CORE model to deliver your feedback. Remember, CORE stands for Context, Observation, Result, nExt stEps and it will help you keep your feedback, clear concise and action-oriented.
  5. Finally, as always Radical Candor takes practice. Prepare what you want to say and rehearse it before having the conversation with your boss. Read more about being Radically Candid with your boss in chapter 6 of Radical Candor.


Radical Candor Podcast Listeners Get 10% Off The Feedback Loop


Improvising Radical Candor, a partnership between Radical Candor and Second City Works, introduces The Feedback Loop (think Groundhog Day meets The Office), a 5-episode workplace comedy series starring David Alan Grier that brings to life Radical Candor’s simple framework for navigating candid conversations.

You’ll get an hour of hilarious content about a team whose feedback fails are costing them business; improv-inspired exercises to teach everyone the skills they need to work better together, and after-episode action plans you can put into practice immediately.

We’re offering Radical Candor podcast listeners 10% off the self-paced e-course. Follow this link and enter the promo code FEEDBACK at checkout.

The Radical Candor Podcast theme music was composed by Cliff Goldmacher. Order his book: The Reason For The Rhymes: Mastering the Seven Essential Skills of Innovation by Learning to Write Songs.


Sign up for our Radical Candor email newsletter >>