The Art of talking back the right way - Upward Feedback That Works

You can disagree with your boss respectfully!

Giving feedback to your boss is one of the hardest conversations you'll ever have at work.

Not because you don't know what to say, but because you're wondering what it might cost you. Will you be seen as disrespectful? Difficult? Uncooperative? So, many of us stay quiet, even when we know speaking up could help the team make better decisions.

In this episode, we unpack the delicate art of giving upward feedback. We explore why timing matters, how to raise difficult conversations without making them personal, and simple ways to frame your feedback around impact, outcomes, and solutions instead of blame.

But the conversation doesn't stop there.

We also turn the mirror on ourselves: How well do we receive feedback when it's our turn? Through a personal story about receiving tough presentation critiques, we discuss why the ability to accept feedback with humility is just as important as the courage to give it.

Whether you're an individual contributor, a manager, or an aspiring leader, this episode is a reminder that healthy feedback isn't about criticism; it's about building trust, improving decisions, and helping everyone do their best work.

Transcript

Why Upward Feedback Feels Risky

SPEAKER_00 0:00

Upward feedback, the art of talking back the right way. Did I just hear silence in the room? Alright, let's talk about something that makes a lot of people sweat. Giving feedback to your boss. Yes, yes, I said it. Upward feedback. That moment where you have to tell the person who signs your appraiser that they are wrong or that they could do better. So what do you usually do? Do you sugarcoat it? Do you see nothing and just suffer everything in silence? Or do you just risk sounding like a know it all? You know, those guys. Look, we've all had awkward feedback moments, and trust me, I've had my own fair share. And I will share that story someday. But let's break this down. Giving feedback downward, that's easy. Telling an executive or an intern or someone that reports to you, hey, you should probably check your creatives, should probably read your copies twice or double check your email. That's easy. But telling your boss, hey, your leadership style isn't working, that's your career roulette right there. That fear is real. What if you take it personally? What if they label you as difficult? Or what if your next promotion mysteriously just poop-poop-poop-poop.

Why Silence Keeps Bad Decisions Alive

SPEAKER_00 1:23

But here's the thing the best of leaders actually want feedback. Problem? Most of us are too scared to give it. If you don't speak up, bad decisions will keep happening. The cycle repeats itself. Everyone suffers, project suffers, everyone is frustrated. There's also a right and wrong way to give of all feedback.

Timing And Tone That Land Well

SPEAKER_00 1:46

Don't just tell your boss they are wrong in the middle of a high-stake meeting or a presentation or a stand-up meeting. The best feedback happens when the person is receptive and not defensive. I once saw a junior exec tell a CMO one time like that, middle, middle, middle of his presentation, and he said, I think your strategy is outdated. The silence in the room that day. Another thing is, it's not what you also say, it's how you say it. I mean, instead of saying you never listen to the team, I think the team would really appreciate more space to contribute ideas or to be creative. Instead of telling your boss that your decision is wrong, why don't you try, can we explore a different angle? Here is how I think it would work.

Can You Take Feedback Too

SPEAKER_00 2:27

Let's flip the script. Let's be real. Are you as good as taking feedback as you are as giving it? Because again, it's also easy to be on the side of giving it. No one likes hearing, hey, you could do better. But if you shut down every time someone critiques you, how would you grow? A real story. A time in my career, about eight to nine years ago, my boss told me, your presentations are solid for you talk too much. Give clients more space to engage. Did I like hearing that? Nope. Did I improve on because of it? Absolutely. So, upward feedback isn't about challenge and authority, it's about making

A Real Story And The Takeaway

SPEAKER_00 3:01

things better. And if you do it right, you won't just earn respect. You will build the kind of career where people want to hear what you have to say. Save it, share it with someone who needs to hear it, and catch you on the next one on Market Table.