Upward Feedback: Give Your Boss Feedback Without Losing Your Nerve

Giving feedback to your boss can feel risky—but staying silent can cost even more. Here’s how to speak up with Radical Candor, build trust in the process, and make upward feedback a healthy part of your working relationship.

You notice something. A pattern. A problem. A behavior from your boss that’s creating confusion or tension—or just making your work harder. You want to speak up, but the words stay stuck.

Giving upward feedback is hard. There’s the fear of how it’ll land. The risk of making things worse. And the quiet calculation: Is it even worth it?

Yes, it is. And you don’t have to choose between silence and conflict. There’s a better way—one that works and keeps your integrity intact.

“Bosses are people too,” says Radical Candor author and co-founder Kim Scott. “They need to hear about the good stuff as well as the problems.”

As Kim writes in Radical Candor, Radical Candor is not a hierarchical thing. To be Radically Candid, you need to practice it “up,” “down,” and “sideways.” Even if your boss and peers have not bought into this method, you CAN create a Radically Candid microcosm for yourself and the people on your team. You are entitled to proceed with a little more caution with your boss and your peers."

So how do you actually say the hard thing to someone in charge? And how do you do it without turning the relationship into collateral damage?

Here’s how to approach upward feedback with clarity, care, and confidence.

Rethink the Power Dynamic

One of the biggest barriers to giving feedback to a boss is the hierarchy. It can feel like the conversation is rigged before it even starts.

“I’ve found myself unnecessarily fierce when giving feedback to my boss,” Kim admits. “Because I feel like I’m punching above my weight.”

That edge comes from fear. Soften it by shifting your perspective. Your boss is just a person with pressure, deadlines, and blind spots. When you drop the formality and focus on the relationship, feedback gets easier—and more effective.

Jason Rosoff, CEO of Radical Candor, puts it simply: “Treat your boss like a real person. That’s what a good working relationship is built on.”

Understand Before You Offer

If you’re frustrated, pause. Before you bring anything forward, ask yourself: Do I know what they’re dealing with?

“You probably have deeper knowledge in your area,” Kim says, “but your boss has broader context. If you don’t understand their point of view, you risk misreading the situation.”

This isn’t about excusing bad behavior. It’s about reducing confusion. Ask your boss questions. The more you understand their thinking, the more precise—and helpful—your feedback can be.

Start the conversation by asking your boss for their rationale for a particular 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 this decision because it’s affected my work.

Start with Feedback Hygiene

If the only time your boss hears from you is when something’s wrong, the dynamic suffers. Build trust over time by noticing what’s going well, not just what’s off.

“People often wait until things are really bad to say something,” Jason notes. “Then it’s the fifth piece of bad news your boss has gotten that day—and it lands hard.”

Instead, say more of the small stuff. Acknowledge effort. Express appreciation. Bring up small friction points early—before they stack up. If you’ve been quiet for too long, you might be carrying what Kim calls feedback debt. It builds quietly—and then hits all at once.

“Silence can turn molehills into mountains,” Kim warns. “And when you finally say something, it explodes.”

That silence-then-rage cycle creates tension that could’ve been avoided with a two-minute conversation days earlier.

Ask questions, 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?”

Use the CORE Model

When you’re ready to speak, it helps to have a clear framework. Radical Candor’s CORE model keeps things focused:

• Context: When and where did this happen?
• Observation: What did you see or hear?
• Result: What impact did it have?
• Expected Next Step: What would improve things?

Let’s say your boss frequently interrupts team members.

“In yesterday’s sync (Context), you cut off two people mid-thought (Observation). It seemed to shut down discussion (Result). Could we try a round-robin format next time? (Expected Next Step)”

Stick to facts. Avoid judgments. Keep it conversational.

Do It Now—Not Later

Timeliness matters. The longer you wait, the harder it is to recall exactly what happened—and the more emotional weight it carries.

“Don’t save it for your one-on-one,” Kim says. “Call your boss right after the meeting. It’s a two-minute call instead of a big ‘we need to talk’ conversation.”

Even better: say something the moment it happens, if appropriate. Catching things early creates more space for clarity and course correction.

That being said, unless your boss has explicitly welcomed feedback in front of others, do it privately.

• Ask first: “Is now a good time to talk about something I noticed?”
  
• Be clear: “I want to share something that could make our meetings more effective.”
  
• Stay open: “I’m curious how you see it.”
  

These simple openings set the tone and give your boss a chance to opt in.

Avoid Character Attacks

Don’t make it about who they are. Focus on what they did. That’s how you avoid what psychologists call the fundamental attribution error—assuming behavior is driven by personality flaws rather than context or intention.

Kim offers a reframe: “Don’t assume your boss is a terrible person. Just try to understand why they acted the way they did.”

Radical Candor Principal Coach & Podcast Host Amy Sandler suggests checking your own story before sharing it.

“Ask yourself: why is this bothering me? What’s the impact? What’s the feeling behind it?”

This short reflection often reveals what you really want to say—and how to say it In a way that moves things forward.

Remember, 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.

Prepare—Without Overthinking It

If it’s a high-stakes conversation, write down a few words to remind yourself what matters. Kim uses a Post-it with three or four bullet points in her pocket—not as a script, but as a nudge to speak up.

Others prepare emotionally. “A colleague told me he pictures the face of someone he loves before giving tough feedback,” Kim shares. “It helps him enter the conversation with an open heart.”

That kind of intention makes a real difference.  And if you're not sure where to begin? Start small.

“You don’t need to solve everything in one conversation,” Amy says. “But starting somewhere builds confidence—and trust.”

If you want to practice, you can ask our Radical Candor AI to role-play with you.

One More Thing: Feedback Goes Both Ways

Your boss may not show it, but many are desperate for feedback. As Jason notes, a lot of leaders live in “feedback deserts.” They’re not hearing what they need to improve—and they know it.

That said, your job isn’t to fix them. Your job is to care personally and challenge directly. For example, imagine you work in a marketing team, and your boss often schedules meetings at the last minute, which disrupts your workflow and makes it difficult for you to meet deadlines. You want to address this issue without coming across as disrespectful or overly critical.

Approach your boss with a mindset of mutual respect and a genuine intention to improve the situation for both of you. You might say:

"I've been thinking about how we can make our team even more effective. I really appreciate how you lead our projects and value your insights. I wanted to share something that could help us work even better together. I've noticed that when meetings are scheduled last minute, it can be tough for me to manage my tasks efficiently. Would it be possible to have a bit more notice for meetings? I believe it could help us all stay on track and meet our deadlines more consistently."

If they respond well, great. If they don’t, you still showed up with integrity.

“The goal is to help your boss succeed without shrinking yourself in the process,” Kim says. “That’s the kind of relationship where everyone wins.”

Finally, we'd be remiss if we didn't advise you 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. If you find yourself unable to communicate with your boss and are looking for a new job, here's how to ensure you end up with a radically candid boss in your next role.

Why It's Crucial to Your Success

From the book:

The ability to be Radically Candid with your boss is crucial to your success. One of the most difficult things about being a middle manager— and, since most CEOs report to a Board of Directors, pretty much all managers are middle managers—is that you often wind up responsible for executing decisions that you disagree with. This can feel like a Catch-22. If you tell your team you do agree with the decisions, you feel like a liar—or at the very least, inauthentic. If you tell your team that you don’t agree with the decisions, you look weak, insubordinate, or both.

Radical Candor is the way out of this dilemma. If you are able to tell your boss that you disagree with a decision, then at least you can have conversations that will allow you to better understand the rationale behind it.

And once you understand the rationale more deeply, you can explain it to your team— even if you don’t agree with it. When they ask, “Why are we doing this, it makes no sense to us, didn’t you argue?” you can reply, “I understand your perspective. Yes, I did have an opportunity to argue. Here’s what I said. And here is what I learned about why we are doing what we are doing.” 

If they insist on knowing whether you agree, you can tell them in all honesty that your boss listened to your point of view, that you were given an opportunity to challenge the decisions, and that now it’s time to commit to a diff er ent course of action than the one you were arguing for. 

Andy Grove had a mantra at Intel that we borrowed to describe leadership at Apple: Listen, Challenge, Commit. A strong leader has the humility to listen, the confidence to challenge, and the wisdom to know when to quit arguing and to get on board.

Your Upward Feedback Starter Kit

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. Ready to give it a try? Here’s a simple checklist to keep you grounded:

✔ Seek first to understand

Before offering feedback, ask about your boss’s perspective. They may be working from information you haven’t seen. Questions like “What’s your thinking behind X?” or “Can you walk me through the decision on Y?” help build shared context and reduce assumptions.

💡 This helps you avoid falling into the trap of blaming intention when what’s missing might just be visibility.

✔ Ask for permission

Check in before giving feedback. A simple “Would now be a good time for a quick thought on today’s meeting?” gives your boss a chance to be present and receptive. It also shows respect for their time and space.

💬 Try: “Is it okay if I share something I’ve been thinking about?” or “Would feedback on this be helpful right now?”

✔ Use CORE to structure your message

The CORE model keeps your feedback grounded:

• Context – When and where did the situation happen?
• Observation – What did you notice?
• Result – What was the impact?
• Expected Next Step – What would improve things going forward?

🎯 Use this to stay specific, not vague. Feedback isn’t helpful if it’s just “You’re always micromanaging.” Instead: “In Monday’s project meeting (Context), you reviewed the deck slide-by-slide (Observation), which seemed to slow momentum (Result). Could we try sharing comments ahead of time next round? (Expected Next Step)”

✔ Focus on behavior, not personality

Avoid labels like “controlling” or “unapproachable.” Stick to what happened and how it affected you or the team. This helps prevent defensiveness and keeps the conversation productive.

🚫 Not helpful: “You’re really disorganized.”
✅ More helpful: “I noticed there were last-minute changes to the deck this morning, and it created some confusion with the client.”

✔ Do it in private

Unless your boss has explicitly invited public feedback, share criticism one-on-one. Private conversations allow for more open dialogue and reduce the risk of embarrassment or escalation.

🤝 Think of it as a personal check-in, not a performance review.

✔ Offer praise too

Make feedback a two-way street. Highlight what’s working, not just what isn’t. This builds trust and shows that your intent is to support—not tear down.

🙌 “I appreciate how clearly you set expectations in that kickoff meeting. That kind of clarity really helps me stay on track.”

✔ Be timely

The best feedback happens close to the moment. When something feels off, don’t let it sit. If emotions are too high, take a breath—but don’t wait a week. Waiting too long dilutes the impact and makes it harder to remember details.

⏱ “Right after the meeting” is better than “sometime next month.”

✔ Practice

Rehearse what you want to say with a trusted friend, mentor, or colleague. Practicing out loud helps you clarify your message, reduce nervousness, and prepare for possible responses.

📝 You can even jot down 2–3 key points on a sticky note to keep yourself grounded during the conversation.

✔ Stay human

Above all, remember: you’re not giving feedback to a job title. You’re talking to a person. Lead with curiosity. Speak from a place of care, not contempt. And don’t expect perfection—on either side.

💬 “I’m sharing this because I care about doing great work together.”

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If you understand the importance of receiving feedback in the workplace, then you need 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 to up your helpful feedback EQ.

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