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How to Practice Radical Candor With Your Boss 3 | 9

How to Practice Radical Candor With Your Boss 3 | 9

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On this episode of the Radical Candor podcast Kim, Jason and Amy discuss clearing the cruft and the art of upward feedback. It's true that it can be really daunting, and a little risky, to practice Radical Candor with your boss, but giving feedback to your boss is 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:

 Episode at a Glance: Practicing Radical Candor With Your Boss

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:

Practicing Radical Candor 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.

 

Practicing Radical Candor with Your Boss

Radical Candor Podcast Checklist: Practicing Radical Candor With Your Boss

  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.

 

 

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.

 

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Key Questions Covered

How do I start a feedback conversation with my boss without it feeling confrontational?

Start with questions, not assertions. Instead of leading with "you're wrong," open with something like, "I'd love to understand the rationale behind XYZ decision, because it's affected my work in this way." This invites dialogue rather than setting up a fight. Asking questions first also gives you context you might not have had, and it shows your boss you're approaching the conversation with curiosity and good intent — not an accusation.

What mindset should I adopt before giving upward feedback?

Assume good intent. Most bosses don't make decisions specifically to make your life harder — they're usually acting on information and priorities you may not be aware of. Going in with the assumption that your boss was doing what they thought was right puts you in a calmer, more productive headspace. Pair that with genuine humility (acknowledging you might not have the full picture) and you'll be far more likely to have a constructive conversation.

Should I ask my boss for permission before giving them feedback?

Yes — and the Radical Candor framework strongly recommends it. Try something like, "Would it be helpful if I shared what I thought about X?" Most people will say yes, especially if they feel their perspective has already been heard. Asking permission lowers the defensive barrier and signals that you're offering a perspective, not launching an attack. If your boss says no, respect that and don't proceed.

What is the CORE model and how does it help when giving feedback to a boss?

CORE stands for Context, Observation, Result, nExt stEps. It's a structure that keeps your feedback clear, concise, and action-oriented. Instead of vague complaints, you describe the specific context in which something happened, what you observed, what result it produced, and what you'd suggest as a next step. Using CORE is especially helpful when giving upward feedback because it keeps the conversation grounded in facts rather than emotion or assumption.

How do I manage the risk of giving my boss candid feedback?

Start small. Test the waters by raising a minor issue first and observing how your boss responds. Have the conversation at the highest-bandwidth channel that's comfortable for both of you — ideally in person. Ask before diving in: "Is it OK if we talk about this?" If the answer is no, don't push. Building trust gradually through small, well-handled feedback moments makes it safer to tackle bigger issues over time.

Why does giving feedback to your boss matter for your working relationship?

When you can share honest feedback upward, you build a stronger, more authentic working relationship. Your boss gets information they may not be getting elsewhere, and you feel more ownership over your work environment. Radical Candor's premise is that candor flows in all directions — not just top-down. Employees who practice upward feedback tend to enjoy their work more and collaborate more effectively with their managers.

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