When you have become a director or VP at a tech company, you have probably realized a few things.
- Your boss stopped coaching you. They’re too busy, too overwhelmed, or frankly, not capable.
- Managing your boss is a requirement for your sanity.
- The traditional feedback frameworks don’t work for giving your boss feedback, and mistakes can kill your career.
This guide will give you a framework for understanding how (and when) to give feedback to your boss.
It should be noted that there is more to managing up than giving your boss feedback; this is just one critical aspect. In my coaching practice, we explore the full range of these challenges.
Why Giving Feedback Up Is Different (And Dangerous)
If you have reached the level of Director or VP, you have probably become pretty good at giving your team feedback. (If not, check out this article.) But giving feedback to your boss is a lot harder. With your team, there is a structural reason for them to listen to you. While they may choose to ignore any feedback you give, get defensive, or even discount your perspective, you ultimately have power over things that matter to them, such as raises, bonuses, performance ratings, and choice project assignments. As such, they are interested in meeting your expectations and adapting to them. Which means that even when you give feedback poorly, they still want to understand it and get it right for their own interests.
With your boss, that is no longer true. Yes, your boss likely needs you, but most people have also realized at this point in their career that everyone is expendable, and having your work respected by your boss is a material criterion for your continued employment. Your boss’s focus is on meeting their boss’s expectations, not yours. And so while your boss may say they value supporting their employees the best that they can, your feedback is going to be lower on the priority list than that of their manager, and when their feedback contradicts yours? Well, you know who will be ignored.
And there is another risk: your leader is just like everyone else, and at times, we can all take feedback poorly. When the person receiving the feedback is someone you report to, the risks associated with this are different than when it is someone who reports to you.
I recall working for a Product VP who consistently stated that they wanted feedback and were open to it. And, sometimes, they were. For example, when I expressed that my team felt they were receiving numerous last-minute, urgent requests for reports or process changes that never seemed as important as the urgency would suggest, my boss took this feedback well.
However, two days later, when a new urgent request came in, I gave new feedback. I even used the SBI framework.
Here’s what I said, “We just had a conversation with the team last week about how they are getting stressed out by these last-minute deadlines. And now you have received a new request with a last-minute deadline, which you have passed on to the team. The team feels like their concerns weren’t heard and that we are doing the very thing we said we would try not to do.”
It did not go well. In fact, it landed poorly, very poorly, and damaged that relationship.
Why?
For one, I was wrong about how open the manager was to feedback. I thought I could share all feedback directly, and they would take it positively. The reality was that while the manager said they didn’t want to have blind spots, they also didn’t want them called out.
It was easy for them to hear the feedback in the abstract, but not so easy to be called out on it specifically. At that instant, a contradiction arose: my boss genuinely desired to support the team as they requested, yet also needed to prove themselves to their boss. They could no longer pretend they were doing both. And that wasn’t feedback they were prepared to face.
There was another context as well; this was their first time leading at this level, and I had done that before. That meant any feedback I gave could be seen as a critique, using my greater experience, which could put anyone on the defensive. And, if I am honest, there was part of that feedback that was probably about me reminding my boss that I was more qualified than he was.
I learned a great deal from that experience, and this framework has served other leaders and me well since then. I will work through what I would have done differently with this framework.
The three key questions to ask when planning to give your boss feedback are:
1: What do I really want and why?
Understand what your desire to give feedback is really about. Sometimes it is about protecting your team from unfair or harsh criticism, and sometimes it is about your own ego. Knowing what is at stake for you and why that matters is the first step in planning the feedback.
2: Is it worth acting on this?
Based on what is at stake, consider the potential consequences and how they may impact you or the team. This can include material constraints, ideological positions, and your obligations and commitments. Given those, is it worth acting?
3a: How do I act given structural realities?
If it is worth acting, what is the most effective approach, direct or indirect? Understanding your boss’s constraints and position is crucial to knowing how to approach them effectively.
3b: If I choose not to act, what am I accepting?
If you choose not to give feedback, you are allowing some behavior to continue. Can you be honest about the choice? “I am choosing the ability to pay my mortgage over the psychological safety of my team.”
After this question, you may need to go back to question 2.
Let’s go into each of these in more detail.
Question 1: What Do I Really Want and Why?
We may initially say that we want our boss to change. Ok, but why do we want them to change? Do we want to see our needs as valued and important? Is it so that we can be right? Or to make our leader conform to our idea of leadership?
Sometimes, when we feel we have been treated unfairly or disrespectfully, we may want to share how we feel to get it off our chest or to ensure our boss knows how we feel. But why do we want that? So we know they respect us?
For this, it is important to be aware of the structural position you occupy. You are a middle manager, dealing with the contradictions between a team you want to support and a leadership that wants more from it. Your boss, unless you are reporting to the CEO, is likely in the same position, and even CEOs have the board to worry about.
Because of your structural position, you are seeing the situation through a particular frame. And you can’t see it without a frame, what you can do is be aware of the frame you are looking through. (Even this awareness of the frame is from within a frame, but that is a topic for another time.)
This awareness won’t resolve the contradiction. You’ll still be caught between your team and leadership. But it might help you see when your ‘support’ for the team is actually about managing them more effectively for the organization, or when your critique of your boss is actually about your own ego.
It’s also worth examining why you are in the position you are in. Are you trying to be “the manager who gets it”? The fantasy that you can make the system work better? The satisfaction of being needed by both your team and your boss? These investments aren’t wrong, but they do shape what you can see and what you’re willing to do.
Once you see these multiple motivations, you can ask: “If I give this feedback, which desire will it actually satisfy?” Often, we tell ourselves we’re acting for reason A, but we’re actually acting for reason B. And the feedback will land differently as a result.
In my case, my primary conscious motivation was to support my team; I wanted to ensure I was doing my part to stop the behavior they were struggling with. However, if I dig deeper, I also wanted to show that I was doing what they asked better than he was. And that, I was more qualified for his role than he was. And if I’m completely honest, there may have been a part of me that wanted my team to see me take on my boss, to be the hero who protects them, which served my need to be valued by them. Although the desire to support the team drove the decision, other reasons likely influenced the approach. Understanding that in advance would have helped.
Question 2: Is It Worth the Risk?
Now that you understand your own motivation, you are in a better position to assess whether it is worth it. By knowing what you are trying to achieve, you can look at what is really at stake.
Start with material reality: Do you have other allies in leadership within the organization that can support you if you need to move roles? How much reputational capital do you have, and how much of it are you willing to spend on this? Can you afford to lose this job? How is the job market? Do you have dependents? Healthcare needs? Debt? How long could you survive unemployment? These aren’t abstract questions. They determine what risks you can actually take.
Once you know what you can materially afford to risk, get honest about what you’re choosing: If you decide not to act, what are you choosing to accept? What is the risk to your well-being and the well-being of others if you don’t act? Who suffers the most and in what ways? Be specific. The point isn’t to guilt yourself, it’s to be clear-eyed about the trade-off you’re making: your material security in exchange for this situation continuing.
One mentor told me that you should never quit a job; you should always be fired. That is a perfect encapsulation of this position. If you are willing to quit over it and have the means and job options to make that possible, then it may be worth it. In tech roles, the worst-case scenario is usually being let go with severance, which is far better than walking out the door with nothing but your ego. If it’s already bad enough that you’d quit and can afford to take your chances, you have nothing additional to lose by pushing.
But you need to be realistic. Is this a hill you want to die on? Can you sustain a loss here materially?
With our example, I would have felt comfortable with the risks. I was in a good position, and the impact on the team was severe enough that I would have proceeded anyway. And even with how it worked out, I am glad I gave the feedback, because the result was that I went around my boss to talk to the person who actually initiated the directive, who clarified that the deadline was arbitrary and that it was fine to extend it. I also had an internal network strong enough to survive the loss of that relationship with the boss and to move to another team. That said, I could have provided the feedback more effectively.
Question 3a: How Do I Give This Feedback Effectively?
Part of crafting effective feedback to your boss is recognizing the structural position they hold. It is more likely than not that the reason they are doing the things that you see as issues is related to forces that make those very things successful: the demands of their boss, the constraints of their own position, and their own overwhelm.
Rather than seeing your boss as a hero within their own mind, see them as a symptom of a larger system. Think about what their boss wants to see, what other pressures they’re managing. Analyze your boss’s structural position: their constraints, their blind spots, what the system demands of them, what they literally cannot see from where they sit – not to accommodate them, but to understand how power operates through them. Not to make excuses for them, but to create an explanation where what they are doing is the work of a rational actor.
Find where that behavior is contradicting something else that they say they value. These could be values they’ve explicitly stated to you in recent conversations (the strongest because they’re specific and recent). But you can also reference organizational values (especially useful if your boss presents themselves as aligned with company culture) or values they’ve demonstrated through past actions. The key is that the value must be one they’ve publicly committed to. You’re not guessing at their internal beliefs; you’re using their own stated or demonstrated positions.
Show them what it will cost not to act, so they can see the broader picture and make a decision. You also must decide how hard you want to push.
From there, you can craft your feedback in this format.
- Name the structural reality: “I understand you’re under pressure to [X]”
- Surface the contradiction: “You said [stated value], but this action contradicts that”
- Show the cost: “Here’s what each choice costs…”
- Force the choice: “What’s the actual priority here?”
Notice what this does: By referencing what they said they valued, you make it impossible for them to ignore the contradiction without explicitly choosing which commitment to break.
In our example, I should have given the feedback in a way that was contradiction-aware,
I understand that you’re under pressure to meet this deadline, and I know you want to support the team here, as you shared last week. So we have a contradiction: this urgent deadline goes directly against what we agreed was important. What’s the actual priority here? If the deadline is more important, I need to know that so I can be straight with the team about what’s happening. If supporting the team is the priority, what do you need from me to push back on this?”
What is presented here is the lightest version of the feedback, likely to make the fewest waves. There are times when the last line needs to draw a much clearer boundary. And instead of asking how they can manage it, be clear about what you can accept or support.
In my example, it could be, “Regardless of the costs, I need to back the team here. Is this something you can support me on, or should I talk to the person who sent the directive to you?”
Question 3b: If you have chosen not to act, what are you supporting by your non-action?
You won’t always decide to give feedback, and that is ok. The question you then have to answer is: what is your silence doing, what is it supporting and enabling?
What will need to change for you to take action?
The answer may be that if it recurs and worsens, you will need to revisit it and provide feedback. It may be if you see evidence of deeper harm than you suspected. But whatever it is, be clear what you are choosing to accept, who may be hurt, and at what point your position will change. The point isn’t to avoid making this choice altogether; it’s to make it consciously, without alibis.
Conclusion
With my next VP, I used this approach. I was able to give them feedback about how they were managing competing priorities, and they actually thanked me for naming the bind they were in. We didn’t resolve the contradiction, but we could at least be honest about which commitment we were breaking.
If working through this framework consistently reveals contradictions you can’t resolve, or if you’re questioning your position itself rather than just specific feedback situations, that’s when working with a coach becomes valuable. These structural questions require deeper exploration than a framework can provide.
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