With Martin G. Moore

Episode #284

Giving Your Boss Feedback: How honest should you be?

I spend a lot of time and energy helping leaders to build their capability in giving feedback to their people: how to engage them in difficult conversations; how to review their performance; how to know when it’s time to say goodbye to someone who isn’t performing.

Let’s face it, if you want to be even mildly competent as a leader, this is a core skill. It has a technical element (of course) but, even more important are the psychological and emotional elements.

In this episode, I flip the script to look at how to give feedback to the people above you. How can you give feedback to your boss, in a way that is respectful and direct? But more importantly, in a way that gives you a high chance of success — that is, your boss actually listens to you!

 I cover how to tell if your boss is receptive to feedback and, if so, how you earn the right to provide it. I explore the role of the trusted advisor. And I give you a practical, seven-step process for delivering feedback to your boss.


Get yours delivered straight to your inbox by filling out the form below 👇

Please enable JavaScript in your browser to complete this form.


Episode #284 Giving Your Boss Feedback: How honest should you be?


In last week’s episode, I flipped the script on the topic of trust. Instead of focusing on the question that’s most commonly asked: “How do you win the trust of your people?”, I came at it from the opposite direction and asked, “As a leader, how much trust should you give to your people?

In this episode, I want to continue the theme of flipping the script. I spend a lot of time and energy helping leaders to build their capability in giving feedback to their people: how to engage them in difficult conversations; how to review their performance; how to know when it’s time to say goodbye to someone who isn’t performing.

Let’s face it, if you want to be even mildly competent as a leader, this is a core skill. It has a technical element for sure, but even more important are the psychological and emotional elements.

So, I want to take a look at how to give feedback to the people above you. How can you give feedback to your boss in a way that is respectful and direct but, more importantly, in a way that gives you a high chance of success? That is, your boss actually listens to you.

I begin by helping you to work out whether your boss is likely to be receptive to feedback. I then explore how you can earn the right to deliver personal feedback upwards. I provide some practical pointers for actually delivering the feedback, and I finish with a few words on becoming a trusted advisor.


There are many different types of bosses, as I’m sure you’ve already discovered. As you gain more experience, you learn to identify both the positive characteristics and the red flags in any manager much more easily.

It’s worth bearing in mind that most bosses are at least trying to operate in good faith, and the relationship you develop with your boss will be unique, regardless of the type of relationships that other people have with the same boss. So, it’s worth giving them the benefit of the doubt and trying to build the most productive relationship that you possibly can.

Good faith aside, every manager has the benefit of legitimate power. This is the formal power that comes with the position you hold. You have it with your people, and your boss has it with you. This gives the leader who holds the hierarchical power the upper hand in any conversation.

Feedback, regardless of which direction it’s going in, is affected by this power dynamic, and the power differential is important to understand. So important, that one of my foundational podcast episodes explored this topic (Ep.5: Using Power Wisely).

Just as you choose how to exercise your positional power, your boss does exactly the same thing. If you look at the way your boss behaves through the lens of this power dynamic, you can learn a lot about him. This is going to inform, at least to some degree, how likely he is to receive feedback willingly. For example:

  • Is your boss curious and open to new information?

  • Is he happy to be seen to be wrong about something?

  • Does he seek guidance and input to his decisions?

  • Does he bring out other people’s contributions in group forums?

  • Does he work at the appropriate level and leave his people to get on with the jobs that they’re paid to do?

  • How does he react when you bring in bad news?

  • How does he react when you push back on non-valuating work or resource constraints?

  • How does he respond to “yes men” who just spend their time sucking up to him and telling him how smart he is?

  • Does he define loyalty as blind obedience to his wishes or courageous challenge that increases value and reduces risk?

  • Does he share the information that he has access to?

If you consider these behaviors, you should have enough information to answer the first critical question. Does my boss genuinely want feedback, or does he just want words of affirmation and unquestioning compliance? If you have an insecure boss who clearly just wants you to do what you’re told without challenge or question, well, you can probably forget about the notion of giving him feedback, right there!


Let’s think about what it takes to earn the right to give your boss feedback. I like to separate feedback into two broad categories: personal and impersonal.

Impersonal feedback is about the work itself: the decisions that are made; problems that are encountered; opportunities to improve performance; ways to improve strategic alignment; managing resource constraints, and so on.

Personal feedback is very different, because it’s about the individual: their own behaviors, the things that they do to either improve or degrade performance; their leadership blind spots; the mistakes they make.

Let’s face it, impersonal feedback is much easier to give. For a start, it can be given either in a one-on-one or a group setting. It’s not as threatening as personal feedback, even though your boss might still feel a strong sense of ownership, and take it as a slight on their capability and competence.

The acceptability of impersonal feedback is dictated by your team culture as much as anything else. What are the accepted protocols for challenging something in the work environment? It’s really just about challenging strategies, tactics, decisions, and opinions in order to optimize performance.

But personal feedback is much trickier. It should only ever be given one-on-one, and it really requires a strong relationship and mutual respect to make it work. Let’s assume you have a boss who’s at least somewhat receptive to personal feedback. In order to provide that feedback, you first need to earn the right.


During my own executive career, I’d like to think that I was open to feedback from anyone at any time, and on that list of questions we just ran through (above), I’d also like to think that my people would’ve answered positively on most, if not all of them. But there were occasions when this absolutely wasn’t the case… when I wasn’t receptive to feedback.

Although many years have passed since, I can still feel my shoulders tense up when I think of one executive who, at the time, was within a hair of being fired, who proceeded to offer me feedback about a supposed breach of values in a leadership meeting I had run.

For a start, it was all about virtue signaling, which p!sses me off immediately, anyway. But more than that, the feedback was coming from someone who was a terrible leader, who wasn’t performing in their role, and who didn’t even have the intellectual horsepower to know why.

Even if the feedback was accurate and helpful, that executive completely lacked credibility in my eyes, and hadn’t earned the right to give me personal feedback. I had no respect for this person’s competence, and even less for their intent. Did this make me a bad boss? I don’t think so. I think it just made me human, and it reaffirmed in my head that my judgment was pretty sound.


So, let’s turn this around. What does your boss think of you? Before you consider giving your boss personal feedback, you have to make sure that you have three preconditions in place:

  1. Your own performance has to be strong. That is to say, you need to have demonstrated competent and consistent delivery of high-value outcomes in complex environments.

  2. You have to have already established a foundation of trust with your impersonal feedback, in both group and one-on-one forums. You should be able to get a pretty good feel for this based on the way other people, including your boss, react to your observations in meetings.

  3. You have to know what you are talking about. You have to have thought it through carefully. The surest way to kill your credibility is to go in with half-baked opinions and unstructured thought bubbles.

If you manage to get over those hurdles, you’re going to be in pretty good shape. So, stick with me. We’ll keep going.


Let’s break personal feedback down even further into two subcategories: solicited feedback and unsolicited feedback. Solicited feedback is feedback that you are actually asked to provide. Just be careful here: your boss will often ask for feedback, when what they really want is reassurance and praise. So just consider this before you tee off.

Often, solicited feedback comes in the form of a 360° survey. This is a formal assessment survey of a leader’s behavior and operating style over a broad set of criteria, which is filled out by many different people. The results are then aggregated to highlight the averages and trends of how a leader’s behavior is perceived by those around them.

These types of surveys are commonplace in larger organizations. However, the mandate to conduct 360° feedback often comes as a result of someone higher up deciding that everyone’s going to do it. So, often, it just becomes part of the organization’s HR policy. It’s thrust upon every leader in the company, and they have no choice but to comply.

Clearly a process like this is going to turn up a bunch of unwilling conscripts to the process, and this is the context that informs my advice to you: if you are asked to provide formal 360° feedback for your boss, be honest, but don’t be cavalier.

To be more specific, answer all the multiple-choice questions as honestly and accurately as you possibly can. But whenever you’re asked to provide free-form comments, just bear in mind that your boss will have access to these. So, just be a little cautious about making negative comments that can be clearly attributed to you. If you do have this type of feedback to give, you’re much better off trying to give it as personal feedback in a one-on-one setting.


Let’s focus on unsolicited feedback. Assuming you are in a position to give your boss feedback — that is to say, you have trust and credibility with them — and you believe that they might be receptive to feedback, there are some important techniques to master.

I’m going to outline a seven-point checklist, which I’ve produced as a free PDF resource for you to download.

  1. Pick your time. Of course, this feedback will always be given in a one-on-one setting. So, make sure that you aren’t catching your boss off-guard. Make sure you have ample time booked to get into a deeper discussion, if that’s where the conversation goes. And, above all, read the play. If your boss seems particularly stressed, distracted, or disinterested, abort the discussion before it begins and keep your powder dry for another day.

  2. Speaking of keeping your powder dry, pick your battles. You need to be selective about the areas in which you choose to give your boss feedback, especially at first. Don’t pick on low-value or marginal things. Make sure you only address the really big-ticket items, which you’re confident will make a meaningful difference to you and the team. As time goes on, of course, you’ll earn the right to become more expansive with your feedback.

  3. Before you launch into feedback, ask permission first. Never launch into unsolicited feedback without checking. I like to use the sentence, “Look, I know this is completely unsolicited, but I’ve got a few observations that you might find useful. Would you be okay if I shared them with you?“. There are very few bosses who will say “no” to this question, but you still have to read the play. Their mouth might say “yes”, but do you really think they want to hear it? The good news is, even if they don’t, they at least know intellectually that they’ve given you permission to proceed, which is an important safeguard for you to have.

  4. Be constructive — don’t complain, and be genuine. The surest way to get your boss to put their defenses up is to tell them what they’re doing wrong. Always couch your feedback as an opportunity to improve performance, or to optimize, or to get better outcomes. You can begin your sentences with phrases like, “I think there’s a real opportunity for us to do X, especially if you can manage to do Y.” This has a much better chance of success than phrases like, “If you can fix this problem you have, it’ll be better for everyone.

  5. Be respectful and be honest. Once you’ve crossed the threshold, don’t waste the opportunity. Think about exactly what you need to say and how you need to say it. Recognize your boss’s prerogative to do whatever the hell he wants. So, make sure your tone is assertive but it pays appropriate deference to your boss’s authority.

  6. Be specific, so that your boss knows exactly what you mean. You have to do your homework beforehand. You should have multiple examples to illustrate any points you’re going to make. And, if you’re claiming there’s a path to better outcomes, well, you’d better be able to articulate exactly what those improved outcomes would look like.

  7. Let your boss arrive at their own answers. Ask for his opinion and guidance, rather than telling him where he’s going wrong. If at all possible, position the feedback as a question. It’s going to feel a lot less confronting, and it will enable your boss to arrive at the solution himself. It feels less like you are telling him what to do. So, for example, you could say something like, “I’ve observed X, and I’m hoping you can think of some ways to improve the outcomes.”

If you follow these seven rules of thumb, you’re likely to have a great experience in any feedback conversation. And at the same time, further your standing as a trusted advisor to your boss.


Speaking of which, I just want to finish with a couple of words on trusted advisors. The vantage point where you can have the most impact is from the role of the trusted advisor. If you become a trusted advisor to your boss, he will solicit your feedback. So, it’s pretty easy to have the types of conversations that make a real difference.

Your objective with any boss should be to earn enough respect and credibility that they use you as a trusted advisor. If you want more detail on this, have a listen to Ep.183: Mentors, Coaches, and Trusted Advisors. As a trusted advisor, you see how your boss performs and behaves in the heat of battle, day-to-day. This can be a great source of value, because you help your boss to reflect on the things that he can’t necessarily see for himself.

There are a host of benefits to you becoming a trusted advisor. For a start, it’s a signal that your boss sees you as ‘first amongst equals’, which puts you in a great position for winning that next promotion. You can’t become a trusted advisor unless your boss believes that you have the capacity, experience, and vision to think through the sorts of challenges and problems that he deals with at his level.

It usually means that you’ve established yourself as a high performer. Your boss probably sees you as someone who is fair and balanced, and largely untainted by self-interest or politics. And, of course, he’ll consider you to be intellectually astute, with a pretty reasonable level of emotional intelligence to boot.

Your boss is unlikely to ever tell you formally that he sees you as a trusted advisor, but you’ll be able to tell by the frequency of interactions, and the type of questions he asks when you’re together. If you do manage to become a trusted advisor, then giving your boss feedback becomes effortless.


Giving feedback to your boss can reap incredible value if you can position it (and yourself) in the right way. But you need to understand the rules of engagement and work to build the type of relationship that enables you to have that influence. A boss who doesn’t take feedback and advice from those around them can be downright dangerous. If you follow the feedback principles I’ve outlined in this episode, you’ll learn pretty quickly what you can and can’t achieve under their leadership… and that can often save you a whole lot of pain and frustration.



  • Explore other podcast episodes – Here

  • Take our FREE 5 Day Leadership Challenge – Start Now

  • Check out our 8-week online leadership program, Leadership Beyond the TheoryLearn More


Here’s how you can make a difference:

  • Subscribe to the No Bullsh!t Leadership podcast

  • Leave us a review on Apple Podcasts

  • Repost this episode to your social media

  • Share your favourite episodes with your leadership network

  • Tag us in your next post and use the hashtag #nobsleadership