Fearless Feedback: How New Managers Can Ask for Feedback Without Fear

There’s a simple behavior that makes a good leader a great leader.

It's being brave enough to ask a question that scares most leaders:  

"What am I doing wrong?"

Here's the data: Leadership researchers Jack Zenger and Joseph Folkman analyzed 51,896 executives and found that the top 10% of leaders who ask for feedback on a regular basis were rated in the 86th percentile for leadership performance. Meanwhile, those who don't ask for feedback landed in the bottom 15%.

That's a leadership chasm.

Early in my leadership journey I was in that same chasm. I had the naive assumption that feedback would just... happen naturally. I thought people would feel comfortable walking up to me and saying, "Hey Damon, here's what you're doing wrong."  

Spoiler: they don't. And why would they? I was the guy signing their paychecks, after all.

But here's what I've learned after helping upskill over two million people: The difference between leaders who thrive and those who struggle often comes down to actively seeking feedback even when— especially when— it’s a little uncomfortable.  

I’ve broken down five simple strategies that you can begin today to put yourself in a feedback loop that raises your game and improves the quality of your relationships.  

And if you're a new or emerging leader reading this, thinking "there's no way I'm confident enough to ask people what I'm doing wrong," trust me—I get it.  

But that's exactly why you need to start now. Because the leaders who figure this out early are the ones who end up in that 86th percentile.

I want you there.  

Let’s go.  

Strategy 1: Invite Feedback with Vulnerability

Swallow your pride. It isn’t helping you grow.  

When I was writing my book The Learn-It-All Leader, I realized I was creating in a vacuum. Here I was, writing a leadership book while making the classic leadership mistake of assuming I knew what my audience needed without actually asking them.

So I reached out to two people who fit my ideal reader profile. One was a guy named Nick, and I'll never forget the conversation. Instead of presenting my work like it was already polished, I led with vulnerability.

I said, "Hey Nick, I need your help with something. I'm writing this chapter on how to be a better coach, and honestly, I'm not sure it's either clear or going in a direction that people will actually find useful."

Notice what I didn't say. I didn't ask, "What do you think of my brilliant chapter?" I didn't fish for compliments. I admitted uncertainty right upfront. I left the field open to invite honesty.

This made Nick feel safe to give me real feedback. He came back and said, "You know what, Damon, I can totally understand the why in here, but the how to become a great coach is unclear. You really need to address that."

That feedback was gold. It completely changed how I approached that chapter. It made the book better.  

Here's what I learned: When you lead with humility and openness, people feel psychologically safe to give you the truth. But when you present your work (or yourself) as already perfect, you're essentially asking people to tear down what you've built. Nobody wants to do that.

For new leaders, this might feel counterintuitive. Shouldn't you project confidence? Absolutely. But there's a difference between confident leadership and pretending you have all the answers. The most confident thing you can do is admit what you don't know and ask for help improving it.

Strategy 2: Connect. Then Ask for One Specific Thing

I learned this strategy about nine months ago in the most unexpected way. I was wrapping up a podcast interview with a leadership expert and the moment we finished recording, he immediately asked me what he could’ve done better.

He said, "I'm just like you. I’m always looking to get better. What is one thing you'd recommend I do differently when it comes to being interviewed on a podcast?"

Let me break down the genius of what he just did.  

First, he connected with me by establishing common ground: "I'm just like you, I'm always looking to get better." That created an instant bond between us.  

Second—and this is crucial—he didn't make it a binary question.

He didn't ask, "Is there anything I could do differently?" Because that makes it way too easy for me to say, "No, everything was great!" Instead, he asked, "What is ONE thing..." That phrasing assumes there's something to improve and forces me to think of a simple and specific answer.

And you know what? I had one. His question made me stop and actually consider his performance instead of just giving a polite brush-off.

Connect first, then ask for something specific.  

I’ll give you an example. After your next team meeting, pull an employee aside and say, "Like you, I want our team meetings to be more effective. What is one thing I could change about how I run them?"  

It's a simple way to elicit genuine connection and collaborate with others on your growth opportunities. And when they watch you take their advice, you’ll have not only grown, you’ll have strengthened your relationship with that person.

Strategy 3: Meet Them Where They're Comfortable

Picture this: You call one of your team members into your office, they sit down across from your big desk, and you say, "So, give me some feedback on my leadership style."

Can you feel how awkward that is? You've just created the most uncomfortable power dynamic possible. They're in your territory, sitting in the subordinate chair, being asked to critique the person who signs their paycheck. Of course they're going to tell you everything is fine.

Instead: go to their space. Walk over to their desk for a casual conversation. Better yet, ask if they want to grab coffee, your treat. The goal is to find a place and time where they feel comfortable and relaxed.

Environment shapes behavior. When people feel physically comfortable, they're more likely to be mentally and emotionally open. In their own space or in a neutral setting, the power dynamic shifts. You're no longer the intimidating boss demanding feedback; you're a colleague genuinely interested in improving.

For remote leaders, this principle still applies. Instead of a formal video call from your home office, maybe suggest a walking meeting where you're both on your phones, or a casual coffee chat where the cameras are off. The key is removing the formal, hierarchical feeling that makes honest feedback feel risky.

Change the location, change the dynamic.  

When people feel like they can speak freely without worrying about office politics or formal consequences they are more likely to give you something profound and honest.  

Strategy 4: Make It Safe Through Systems

The first three strategies all require one-on-one conversations, which can feel intimidating for both new leaders and their team members. That's where systems come in—they create a safe space for feedback without the pressure of face-to-face vulnerability.

At LearnIt, I set up what we call the "Help Damon" Google Doc. It's completely anonymous, and I share it with the entire team. The document has specific prompt questions that help people think through their feedback:

• What am I doing that's getting in your way?

• Where am I being unclear in my communication?

• What should I be doing to better support you?

• Is there anything else I should know?

These questions are designed to elicit actionable feedback. Instead of asking "How am I doing?" (which gets you nothing), I'm asking for specific areas where I might be creating friction or missing opportunities to help.

But I also make this visible. At our all-hands meetings, I'll share one or two pieces of feedback I received and, more importantly, what I've done about it. I might say, "Someone pointed out that I tend to jump into solution mode too quickly in our team meetings instead of letting people finish their thoughts. So I've been practicing waiting three seconds before responding."

This creates a feedback loop that encourages better feedback. When people see that their input actually leads to change, they're much more likely to keep contributing. It transforms feedback from a one-time event into an ongoing conversation about continuous improvement.

Strategy 5: Leverage AI as a Feedback Machine

This is my favorite strategy because AI is available 24/7, never gets tired of your questions, and will give you brutally honest feedback without worrying about your feelings or their job security.

Here's how I use it practically:

For meeting performance: Most of my sales calls and team meetings are recorded with transcription. After important conversations, I take the transcript and drop it into ChatGPT with this prompt:

• "Please act as an executive leadership coach with 20 years of experience. Analyze this meeting transcript and give me specific feedback on my performance. What did I do well, and what could I do differently?"

The feedback is often surprisingly insightful. AI will catch things like when I interrupted people, when I missed opportunities to ask follow-up questions, or when my responses were too long-winded.

For strategic decisions: Recently, I was revising our sales team's compensation plan. I fed the existing plan into ChatGPT and asked it to act as an HR consultant with extensive experience building comp plans. I asked specific questions about potential gaps, fairness issues, and motivation factors. The AI gave me detailed, actionable feedback that I incorporated into the final plan. When I presented it to our CRO, he said it was one of the most thoughtful comp plans he'd seen.

For communication: After every podcast interview I do, I run the transcript through AI and ask for feedback on my interviewing skills. What questions did I miss? Where did I talk too much? How could I have drawn out better insights from my guest?

The beauty of AI feedback is that it's completely judgment-free. You can ask the same question fifty different ways, experiment with different approaches, and get honest input without any social or political consequences. It's like having a personal coach who never gets frustrated with you for asking the same thing twice.

For new leaders who might feel intimidated asking for feedback from humans, AI is perfect practice. It helps you get comfortable with the process of seeking input and acting on it, building your feedback muscles in a low-stakes environment.

Making It Stick: Two Critical Rules

If you want these strategies to work long-term and if you want people to keep giving you honest feedback, there are two non-negotiable rules you need to follow.

Rule 1: Don't get defensive. I know, I know—easier said than done. When someone tells you that your communication style is confusing or that you interrupted them three times in the last meeting, your first instinct is to explain why they're wrong or why the circumstances were different. Breathe. Resist that instinct.

Instead, treat feedback like data, not judgment. It's information about how your actions are being perceived and experienced by others. You don't have to agree with it. You don't even have to act on all of it. Getting defensive and arguing will guarantee that person never gives you honest feedback again.

Rule 2: Thank them and follow up. When someone takes the risk of giving you real feedback, acknowledge it. A simple "Thank you for taking the time to share that with me" goes a long way.  

And if you do implement their suggestion, circle back and let them know. "Remember when you mentioned that I tend to dominate team meetings? I've been working on asking more questions and pausing for input. How do you think it's going?"

This follow-up is magic. It shows people that their feedback matters and leads to real change. Once people see that their input has impact, they'll be much more willing to continue being honest with you.

Your Challenge

Alright, here's my challenge for you.  

I want you to think about one specific area where you want to improve as a leader. Maybe it's running better meetings, communicating more clearly, or being more supportive of your team's development.

Now pick one or two of these above strategies that you could implement this week.  

Maybe it's setting up an anonymous feedback doc, or maybe it's reaching out to someone with vulnerability about a project you're working on. Whatever feels most doable for you right now.

And then—this is the important part—actually do it. Don't just think about it. Don't add it to your someday/maybe list. Take action before the end of next week.

Because here's what I've learned: The leaders who consistently seek feedback aren't necessarily the smartest or most talented people in the room. They're just the ones brave enough to ask the questions that everyone else is too scared to ask. And that bravery, more than any other single factor, is what separates good leaders from extraordinary ones.

The 86th percentile is waiting for you. It’s where you belong.  

All you have to do is ask the right question.