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Why Giving Feedback Feels Hard

Let’s talk about something that makes even seasoned leaders squirm: Giving constructive feedback.

It sounds like it should be simple, right? Be clear. Be kind. Focus on behavior, not personality.

But real life isn’t that neat.

In the coaching room, feedback conversations come up constantly. Often as a point of tension, confusion, or avoidance. And not because leaders don’t care. It’s because feedback is personal, even when we try to make it professional.

It brings up emotion. It stirs up power dynamics. It triggers our fear of being misunderstood, disliked, or making things worse.

That’s what I worked on recently with a group of rising VPs inside a global media company. Smart, accomplished, thoughtful leaders…and nearly every one of them admitted: “Giving tough feedback stresses me out.”

They weren’t weak. They were human. So, we started there.

Here are the three most common traps I see leaders fall into and how you can shift into clarity, connection, and confidence instead.

1. You try to regulate their emotions…and ignore your own.

The Trap: You think: “I don’t want to hurt their feelings.” So you soften the message. Delay it. Avoid it. Or, skip it entirely.

But beneath that hesitation is often your own discomfort.

What’s really happening? Your brain is trying to avoid social pain. It perceives feedback as conflict, and conflict as danger. Your nervous system goes into protection mode. So, you sidestep.

The Shift: Before you even open your mouth, check in with yourself. Ask: “What am I afraid of in this conversation?” Naming your fear is the first step in regulating your response.

And when you are calm and grounded, you don’t project that anxiety onto the other person. You are able to lead the conversation, not avoid it.

Try This: Before giving feedback, take 2 minutes to slow your breathing and center your body. Then set your intention. That emotional regulation? That’s leadership.

2. You overthink every word and end up saying nothing at all.

The Trap: You obsess over phrasing. Rehearse lines in your head. Maybe even script out the conversation. But when the moment comes? You freeze. Or, ramble. Or, say it halfway.

Why This Happens: When your brain senses emotional risk, it kicks into perfection mode, believing that the “right” words will protect you from being misunderstood or rejected.

The Shift: Instead of chasing the perfect sentence, anchor in your intention. Ask: “What is the one thing I want them to understand or shift after this conversation?”

That becomes your north star. From there, you don’t need perfect language. You need honest, clear, steady communication.

Try This: Before giving feedback, write a single sentence that captures your main point. Then let the rest of the conversation be human and responsive.

3. You fall into mindreading.

The Trap: You assume how they will react. You imagine they will get defensive, shut down, or not care. And you carry that prediction into the conversation…bracing, tiptoeing, or avoiding altogether.

What’s Actually Happening: Your brain is creating a future-based threat to avoid potential discomfort. That triggers preemptive protection and often prevents the conversation from even happening.

The Shift: Get curious instead of certain. Feedback isn’t a monologue. It’s a dialogue.

Try This: Say, “Can I share something I’ve noticed? I would love to hear your take on it.” You’re not accusing. You’re inviting. And that changes everything.

The Bigger Shift: From Overthinking to Powerful Leadership

When leaders learn to manage their internal world, before they speak a word out loud, feedback becomes something else entirely.

✅ You move from tension to clarity

✅ From people-pleasing to leadership

✅ From silence to impact

You already know how to lead. You just don’t need to carry so much fear with you when you provide honest and necessary feedback.

Your Next Step: Want to Know How to Make Giving Feedback Easier?

If feedback, or anything about how you’re showing up as a leader, feels harder than it should, it’s time for a reset.

Book a free 30-minute strategy session with me. We will look at what’s driving the overthinking, hesitation, or second-guessing and map out immediate, personalized strategies to shift it.

No pressure. Just clarity, insight, and next steps designed just for you.

👉 Book your free 30-minute strategy session here.

Phyllis Reagin is the go-to coach for high-achieving leaders ready to ditch self-doubt and own their brilliance. As the founder of At the Coach’s Table and a former entertainment exec herself, she knows what it takes to lead in high-pressure industries and she helps her clients do it with confidence, clarity, and purpose.

Armed with neuroscience, sharp strategy, and a signature Hello Inner Genius framework, Phyllis helps leaders unlock their true strengths so they can lead with impact and feel lit up doing it. Her superpower? Helping bold professionals push past their limits, silence their inner critic, and become the leaders others want to follow.