The How, When and Why of Giving Feedback to Your Boss

Ultimately, feedback is intended to help someone be better at doing their job which means that giving feedback to your boss should be easy, right? Think again….

How to give feedback to your boss


You want your boss to give you feedback because you want to get better at your job. In the. long run, this benefits you because in order to get better at your job, you need to improve your skills and connections—which will improve your career options.


Your boss wants to give you feedback because they want you to get better at your job. Your boss should want you to succeed as an individual, but at the same time they also recognize that each employee’s efforts contribute to the team or department outcomes—which shape the overall organization's success.


With all of that in mind, it only makes sense to add one more cause-and-effect scenario to the mix: your boss needs feedback to help them get better at their job—which partly entails helping you succeed. So if you want to be better, your boss needs to be in a position to help you with that. And you can help your boss get there. See where I am going with this? Yup—you need to get comfortable at giving feedback to your boss, too.


Tread Carefully


First and foremost: it’s very important to remember that your boss is not your peer but, well, your boss. Even if your desire to give your boss feedback arises from the best of intentions, this conversation still takes place within a boss-employee relationship. That means if your boss isn’t open to receiving feedback from you, you can’t make them accept it.


This situation isn’t a 100% reversal of the boss-to-employee feedback stream. In those cases, the boss is trying to help the employee improve generally, in ways that are typically not specific to the boss-employee relationship.


Here, though, your goal of giving feedback to your boss that is specifically relevant to the boss-employee relationship. 


Specifically, you want to tell your boss when their actions have a negative impact on your ability to do your job—and you want to give them suggestions for how not to do that any more. 


As you consider whether to approach your boss about giving them feedback, you need to weigh two critical factors:


  • Your boss’s personality
  • Your relationship with your boss


It’s healthy to have conversations about feedback, and everyone should embrace the opportunities to receive and give feedback. But not everyone takes feedback well all the time, and sometimes egos are bruised. When that happens, some people can get defensive and react badly—and if one of those people is in a position of authority over you, they might take it out on you. 


The last thing you want is for your boss to be gunning for you because you had an unwelcome conversation with them and told them something they didn’t want to hear. Sure, they should act like a professional under these circumstances. But don’t assume you will always get that reaction.


You need to walk a fine line here. Yes, employees shouldn’t be afraid to give feedback to their bosses—but at the same time, they shouldn’t feel entitled to give it. Your boss gets to decide if they want to hear what you have to say. If you ever find yourself about to step on the wrong side of that line, stop. Take a moment to regain your balance and then think hard about whether you really want (or need) to continue on this path.


Setting the Stage


If you’re thinking about giving feedback to your boss, you can’t just walk into their office and announce that you have a few thoughts you’d like to share with them. First, you need to think carefully about this entire process and be sure that this is something you really want to do. Then you need to figure out how to do it well. 


For me, if my boss is completely driving me nuts and it’s affecting the quality of my work, then it’s time to have a conversation. I think of it like a light switch – once it flips, I HAVE to give feedback to preserve my sanity (and not walk out the door and never come back!).


Examine your intent

Why do you want to give feedback to your boss? Are you truly motivated by a desire to improve your work situation (and theirs, too)? Or are you subconsciously using feedback as a disguise for criticism and venting? If the latter is even a remote possibility, stop immediately. Going down that path won’t help you at all and could even stir up more problems for you.


Is giving feedback to your boss worth it?

The reason for you to give feedback to your boss is because you want to address an issue that involves the two of you. It’s important to understand, though, that no work environment is perfect. No matter where you go, there will always be something that’s not quite right. And sometimes, that “something” will involve your boss.


So you need to ask yourself (and answer honestly) if the current issue you’re facing is something that will destroy your enthusiasm (and perhaps lead to you leaving the organization)? Or is it something you can live with? Because here is the cold hard truth: no matter how “professional” everyone claims or aspires to be in situations of disagreement or conflict in the workplace, personal feelings can and do enter the equation. 


The right place and time

Both the request for a feedback conversation and that conversation itself should take place in a professional context. It should go without saying that nonwork sites don’t fit this description, even if you encounter your boss there during work hours. The office breakroom, with other people coming and going, doesn’t count either. What you need is a place that’s appropriate for having a confidential discussion about sensitive topics—ideally, a closed office or meeting room.


Pay attention to your boss’s schedule and their mood to determine when the time is right to approach them. If they just got out of a stressful board meeting, for example, that is not a good time to talk to them about giving them feedback. If they’re not a morning person, try to catch them after they’ve had some coffee (but before the post-lunch lull sets in). 


The Content of Your Feedback


The day of your conversation with your boss has arrived. You’re sitting face to face, and it’s time to give them your feedback about their performance—and odds are good you’re feeling somewhat anxious about the whole thing. Take a deep breath. You can do this. 


Be prepared. 

How to give feedback to your boss

Do your homework. Don’t even think about winging this. Plan out your arguments, research your supporting data, and then write everything down and bring your notes to your meeting. This effort and attention to detail demonstrate to your boss that you’ve thought about all of this carefully and that you’re here not to talk about a one-off event or misinterpreted situation that can be overlooked (after all, everyone makes occasional mistakes, right?) but to discuss repeated incidents and patterns that are harmful to you both in the long run. 


Be sincere. 

The goal of this conversation is to improve your relationship with your boss so that you can do your job better. Why wouldn’t you want to be honest here? If you aren’t open about your concerns, then you’re just wasting everyone’s time. (Besides, if you try to manipulate your boss, they will know—and then you’ll have more problems.)


Be specific.

Few things are as irritating as generalizations. When you lack specific details to support your claims, it’s easier for people to dismiss what you’re saying. “This happened on these three occasions: X, Y, Z” is much more powerful than “this happened a lot.” Clearly documented and detailed examples are hard to ignore. 


Show the impact

For the feedback to be effective, you need to be sure your boss understands the negative effect their behavior is having. As you frame your feedback around a particular issue, be sure it addresses this key question: How does this issue affect your ability to do your job?

How to give feedback to your boss


Obviously, you don’t want to make this all about you and your personal concerns. You can lightly connect the dots between your work and the needs of the team/department/company, but don’t belabor the point. Too much “explaining” on your part might give your boss the impression that you think they don’t see the connections or can’t figure this out. And if you’re trying to improve your relationship with your boss, the last thing you want is for them to think you don’t respect them. 


Also, be sure you are speaking only for yourself. This should be about just you and your boss, so don’t try to include other people. If you find yourself using phrases such as “lots of people here think . . .” or “I’ve heard others say . . .” or anything else that brings someone other than you and your boss into the conversation, stop right there. Not only does this water down your own argument, but it puts you dangerously close to gossip territory (if not standing right in it). Just stick to your firsthand experience and what you yourself know. 


When Not to Give Feedback


As I’ve mentioned many times, feedback is a Very Good Thing. Under the right circumstances, it can do wonders for people’s day-to-day work product, professional relationships, personal growth, and long-term career opportunities. But it can’t be truly effective unless both the giver and the receiver are willing and eager participants in the conversation. 


Sometimes, one of those parties is so closed to the idea of making any changes at all that giving them feedback is a totally futile endeavor. If you think your boss is the kind of person who will never change, there is still a way you can change the situation: you can recalibrate your attitude and your expectations about it. 


I once worked for a boss who had quite the reputation as a yeller and screamer. He got away with this in part because he was kind of like Oprah in that everything he touched turned to gold. I realized early on that the downsides of working for him were easily outweighed by the benefits: he was really, really good at what he did, and I was able to learn a ton from him during my time as his employee. (Plus, I recognized that he yelled at everyone, so I didn’t take it personally.) I knew with every fiber of my being that there was no way he would ever change his behavior—and that he would react very badly to any feedback about it. So even though I wasn’t a fan of the screaming, I adjusted my outlook: I imagined all of his comments bouncing off an invisible shield around me. 


If you’re in a similar situation, you might find that the best solution is not to confront your problematic boss but to keep your head down and take shelter behind your own invisible shield. However, if there’s no upside at all to your situation (remember, mine was the opportunity to learn a lot from someone who was a leader in that field), you need to get out right away and move on from that soul-killing job. Sometimes a work situation is so irretrievably broken that the only solution is to leave it completely.


Final Thoughts


In the end, because of the power dynamics involved, you must do a cost-benefit analysis to determine whether giving your boss feedback is a good idea for you. Ideally, this conversation should benefit you both. But in reality, that isn’t always the case. You may end up changing nothing—or you may end making things worse for yourself. But if you decide that the conditions are right for a feedback conversation with your boss, I think you’ll be amazed to see just how much of a positive impact it can have for you! 


Remember, too, that feedback is designed to help people grow. Sometimes that’s accomplished by pointing out room for improvement. But it’s also important to highlight what people are doing right: positive reinforcement is valuable, too. So in addition to letting your boss know what you’d like them to change in order to help you do your job better, be sure to tell them what you appreciate about them too. 


If you have any tips or personal success stories about giving feedback to a boss, please share them in the comments below!

1 thought on “The How, When and Why of Giving Feedback to Your Boss”

  1. There’s very little upside to balance out the risk of providing a boss with feedback. Val, what are some mitigations for this?
    1) What can a boss do to create experiences of trust; experiences that will encourage feedback?
    2) What do reports need to know about repairing harm when they error in their learning of how to give feedback to their boss?

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