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 clarity and care, 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.”

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.

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 ensure end up with a radically candid boss in your next role.

Your Upward Feedback Starter Kit

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

• Seek first to understand. Ask for your boss’s perspective before offering your own.
• Ask for permission. “Is now a good time?” or “Would it be helpful if I shared something I’ve noticed?”
• Use CORE. Context. Observation. Result. Expected Next Steps.
• Focus on behavior, not personality. Be specific and nonjudgmental.
• Do it in private. Unless invited, avoid public criticism.
• Offer praise too. Don’t make feedback a one-way street.
• Be timely. Address things quickly—before they fester.
• Practice. Rehearse if needed. Prepare to listen.
• Stay human. Speak from care, not just critique.

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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.