Giving Feedback to Engineering Leadership (Without Getting Labeled a Whiner)

Let’s be honest—giving feedback to your VP, CTO, or director can feel like walking a tightrope. You’re paid to have a point of view. You’re expected to flag concerns. But the moment your tone feels off or your message lacks clarity, it can backfire. No one wants to work with the person who sounds like a constant critic. At the same time, being silent helps no one—especially not the company.

So how do you do it right?

First, remember your role

If you’re in a lead, manager, or even director-level role, your job is not just to execute—it’s to observe and report. You’re the eyes on the ground. You see things execs don’t. That’s incredibly valuable. You’re not there to rubber stamp every decision. You’re there to say, “This makes sense,” or “Here’s where I think we might be off.”

The key is how you say it.

Lead with the problem—then bring a solution

One of my all-time favorite quotes is from John Taffer on Bar Rescue:

You can flag problems all day long—but if you’re not offering a path forward, you’re just dropping weight on someone else’s plate.

Say this instead:

“Here’s something I’ve noticed. I think it’s hurting our velocity and maybe morale. I have a couple ideas for how to address it—do you have 15 minutes to talk it through?”

Short, respectful, solution-oriented. Now you’re having a real conversation.

Skip the Slack novella. Book the damn meeting.

There’s a time and place for async feedback. This ain’t it.

Big topics—especially feedback for senior leadership—deserve real-time nuance. Body language. Tone. Back-and-forth. Trying to cram all that into a message thread just increases the chances of miscommunication.

Instead, throw 15 minutes on the calendar. Frame it like this:

“I wanted to share some feedback on [X]. I’ve got a few thoughts that might help, and I’d love your take.”

You’re not calling them out. You’re showing up as a partner.

Don’t be a yes-man. Don’t be a contrarian either.

The best team members are the ones who can say, “I disagree, and here’s why,” without making it weird. That means knowing when to push—and when to trust the person above you has broader context.

But staying silent out of fear? That helps no one. If something doesn’t sit right, you owe it to your team—and your company—to speak up. Just do it like a pro.

You’re not there to win the argument. You’re there to help get to the best decision.

The takeaway

If you want to be trusted by senior leadership, don’t come with problems. Come with insight. Come with perspective. Come with a mindset that says:

“I want to help this team win, and here’s something I’ve noticed that might help.”

You’re not complaining. You’re contributing.

And that’s how you give feedback to the top.