Giving Your Boss Feedback—Like a Boss

What’s on your mind? It’s not just a rhetorical question. Your boss actually wants to know.

Regular feedback for and from employees is ingrained in company culture, and it’s no longer in the traditional top-down format. Feedback is a two-way street, and employees telling their managers what they think of their performance has had a powerful impact at companies across the world.

Of course, just because it’s encouraged doesn’t mean that the process is any less scary. In fact, giving your boss feedback probably isn’t your favorite meeting of the year. Not only do you need to determine what to say and how to say it, but you might also be losing sleep wondering just how fragile your supervisor’s ego is and if you’re risking your career by being honest about their performance—or lack thereof. 

To put the cherry on top of this potentially not-so-appetizing sundae, given how so many employees are either fully or partially remote, you may not even have the benefit of having this meeting in person where you can read body language and pick on other cues that get lost over Zoom. 

Take a deep breath because the truth is the benefit of an honest dialogue with your boss is the foundation of better communication and collaboration. It builds a culture of trust within a team, establishes a positive mindset, and boosts morale as everyone shares the goal of helping each other succeed.

If done respectfully, upward feedback can improve your working relationship and help your manager grow as a leader. Good managers will always appreciate that you want to help them develop, which will, in turn, make your working relationship better for both of you.

But don’t bust out the party flags just yet—you still have to get through the meeting! You want to offer actionable feedback, say it well, and walk out of that meeting with your manager’s feelings (and your job) intact.

Here are a few pointers to help you talk to corporate like a boss.

Prepare your thoughts

Upward feedback is not the time to test your improv skills or discover how articulate you are at speaking “off the cuff” or “from the heart.”

Before scheduling your feedback meeting, find some quiet time to think over and write down exactly what you want to say. When you plan out the overall structure of your feedback and particular phrases you want to say, you will ensure you include everything relevant and navigate sensitive topics politely.

Read your notes out loud to test how your feedback sounds. The tone and phrasing of this meeting, especially how you start it, can be the difference between a productive, beneficial conversation and a, well, awful one.

Reading your points a few times will also help you familiarize yourself with your thoughts so that during the meeting you come across as natural and not like you’ve memorized a script. 

While prepping for your meeting, it’s important that you’re in a relaxed and calm frame of mind—the last thing you want is to inadvertently plan out an aggressive rant.

And in the (perhaps paranoid?) interest of not leaving behind a paper trail of your unfiltered thoughts, remember to keep your notes somewhere other than the company-issued Google Drive!

Stay specific and impersonal

It can be tempting to use a meeting where you’re finally being heard as an opportunity to unload all your grievances, like how lacking the remote benefits are, and how you really feel you’re due for a raise, and what is with everyone being late to the weekly stand-up anyway? Two words: Stop yourself.

Remember, this meeting is not a free pass to unload on your boss. Rather, it is an opportunity for you to share reflections on how you can both work better together.

A feedback meeting should be very specifically about your boss. Focusing exclusively on your intended feedback about their performance as a manager increases the chance that the meeting is perceived as beneficial and growth-oriented.

Try to avoid mentioning multiple unrelated issues, as it can come across as scattered and disrespectful. Instead, focus on the most immediate issues and possible solutions that need to be discussed.

Most importantly, be practical and not emotional. It’s easy to deliver a laden statement like, “I don’t feel valued by you,” but that’s not really useful to your manager. Now they have your feelings to deal with and may be unsure on exactly how to respond to this type of statement. Generalized statements can also come across as accusatory, especially if you have no details to back up your claims.

Instead, use specific, concrete examples. When your manager receives feedback with a high degree of specificity, it’s harder to dismiss and easier to tackle. For example, if you say something like, “In the last three team meetings, I made suggestions but didn’t receive any acknowledgement from you. I felt my suggestions were brushed away without consideration. That made me feel a little uncertain if I was on the right track or not. Can you suggest how each team member’s ideas can be heard within the meeting?” In this example, you’ve expressed your feelings but also tied those feelings to a specific incident and a particular ask.

Ask questions

Which brings us to a key framing mechanism to keep in mind. Remember the good ol’ compliment sandwich? It’s a form of feedback where you say something complimentary, then insert the meat of your criticism, and then end with something complimentary again, so the hard stuff is literally “sandwiched” between soft, squishy, bread-like gentleness. Yeah, that’s old news and everyone can see right through it.

The new tactic to try when giving anyone (but especially your boss) feedback is to ask probing questions. This frames the discussion respectfully and creates a collaborative dynamic.

Asking questions is also more indirect. So, instead of directly calling out any mistakes, your questioning suggests there might be other ways of going about things while leaving your manager’s authority and dignity intact. Using questions to frame your feedback also shows your curiosity and eagerness to learn.

Asking questions taps into your manager’s motivation to be solution-oriented and moves the focus of the discussion to the bigger picture: the overall success of the team and company.

End strong

Don’t let the meeting end awkwardly or on a sour note. That’s a recipe for simmering resentment which could spill over to future projects.

No matter how many sticking points were addressed, make sure the meeting closes on a positive, upbeat tone. Communicate that you felt heard and reiterate optimism that working together is going well for you.

Once it’s time for the goodbyes, your manager should feel respected by you and convinced that they can count on you to keep delivering under them.

And be sure to thank your manager—because who doesn’t like to feel appreciated for their time? And if the meeting was over Zoom, thank them doubly, because Zoom fatigue is real and everyone deserves a medal for more meetings. 

Most importantly, don’t forget to do that frozen-smile-and-wave thing as you hit “End Meeting.” 😃 👋 

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