How to give critical feedback to your boss

Where dragons dwell

First, let's clear up a common misunderstanding. It is fashionable for the current crop of leaders (including executive ones) to say that they are open to feedback. It is mostly false. From my experience, the more senior the person, the less they will be open to feedback. That is the harsh truth. 

In the book Leadership on the Line, the authors discuss two types of issues leaders face. Technical issues and Adaptive issues. Technical issues have known solutions. E.g., If you see a spike in production incidents, you can fix it by allocating more people toward stabilizing production. Adaptive issues require changing people's hearts and minds. E.g., if most leaders in your organization are assholes, fixing that will require an overhaul of the company's belief systems, which will require people's hearts and minds to change.

Feedback also comes in two flavors. Technical feedback and Adaptive feedback. If you want your manager to reduce the number of meetings, she will make it happen. It is Technical feedback with a known solution. However, if you want her to change her attitude, it is almost impossible because it requires changing her heart and mind, which is an Adaptive change and near impossible to do for most people.

The people most walled off to adaptive feedback are people with C titles. It makes sense, though. Companies hire C-level leaders in specific roles because they have a specific skill set and a specific way of operating. If they are infinitely pliable and malleable through feedback, they will most likely not be able to accomplish what they were hired to do. A cost-cutting CEO is expected to cut costs ruthlessly and not suddenly become empathetic to the organization's feelings because of feedback she got from her organization. I also believe (maybe to a lesser extent) that as one grows older, they become set in their ways. Why change the very thing that bought you success in your career? Jeff Bezos is not going to become kind now suddenly, is he?

If giving feedback is filled with so much peril, why even bother? Because it is good for your soul. I know it sounds cheesy, but it is true. If something is weighing heavy on your mind, you must do something to eliminate that baggage. The common trap people fall into is by airing their grievances to a peer or a friend. They complain about their bosses to their friends. That won't lighten your load. In fact, it will make it even heavier. The longer you go without acting on it, the more frustrated you will become, and one day you will realize that you have become ineffective in your job. Earlier in my career, when I used to withhold feedback, it started to affect my personal life as well. I used to get annoyed at my family for no reason. Withholding feedback is like holding your breath. You can only go so long without exhaling. 

So before you decide to give any feedback to your bosses, figure out if the feedback you are about to give is Technical or Adaptive. Here are some examples of adaptive and technical feedback.

Critical feedback should be given in person or via live video calls. Do not put it in an email or on Slack or any form of instant messaging. Emails, slack messages, and DMs can't properly convey the tone and emotion behind your feedback. The person receiving the feedback should be able to understand the emotion you are feeling clearly. You need to be able to look into the eyes of the person receiving your feedback and convey your sincerity.

When giving critical feedback, don't aim for anger, sadness, or grief in your tone; instead, aim for genuineness.  

If you are giving technical feedback, then the path is clear. Meet your boss in person or on a live zoom call and give the feedback to them. If you already have a solution, suggest it to them when you talk to them. There is no guarantee that they will accept your solution, but bringing a problem and a solution is always good form. If you are about to give Adaptive feedback, you must strategize first.

Often, adaptive feedback is the harshest type of feedback a person can receive. It will strike a blow at the very foundations of how a person's professional, moral, and ethical compass works. I have yet to meet someone who wasn't shaken in some way after receiving Adaptive feedback. Before deciding to give adaptive feedback, you will have to understand how open the other person is to receiving adaptive feedback and also how they will react. The best way to do that is to give them smaller pieces of adaptive feedback and see how they receive it and what they do about it.

The trick is to use your adverbs intelligently. Take these two sentences.

"That was harsh."

"That was a little harsh."

When used correctly, adverbs of degree will dramatically lessen the impact of adaptive feedback and allow the receiver to process it without getting overwhelmed by the typical bitterness caused by unfiltered, critical, adaptive feedback. As you give lower-temperature feedback to the other person, watch for their reactions to determine how they will react to stronger feedback in the future. 

If her reaction to this watered-down micro feedback is unintentional unawareness, she will most likely receive adaptive feedback without blowing up. However, if her reaction is defensiveness, delusions of discipline (i.e., they believe it's their job to be harsh), feigned unawareness, or straight-up rudeness, you can expect her reaction to stronger adaptive feedback to be poor. To get a complete picture of how your boss will react to stronger feedback, you will have to analyze her reactions to multiple pieces of micro feedback. 

But why put in all this effort? Because a poor reaction to adaptive feedback from your manager can put your relationship with him on notice and jeopardize your career in that company. 

Giving adaptive feedback to a new manager is like learning to run for the first time. The first time you decide to run, you probably won't make it more than thirty yards before bending over and trying to catch your breath. But if you do it repeatedly and regularly keep increasing the distance you cover, you will begin to master it. A mile becomes two, and two miles becomes five, and soon you will be upgrading your plain trainers for tempo shoes.

Every time I get a new manager, I make it a point to understand what makes them tick. As part of my profile-building exercise, I consistently give them adaptive micro feedback and see how they react to it. Sometimes I don't even present my thoughts as feedback for them but just as observations. E.g., if I just saw them knocking somebody in a meeting, I might say something like, "That meeting was rough," and see how they react to it. As part of my profile-building exercise, I also watch them carry themselves in both low-pressure and high-pressure situations. One can learn much about a person by observing their body language. Leaning back versus leaning forward conveys much information about how the person feels about you. 

In most cases, softer, consistent, adaptive feedback will help you build a fairly robust relationship with your manager. In about six months, you should feel comfortable giving stronger adaptive feedback. As I mentioned, there is no guarantee that your boss will act on that feedback immediately, but you should do it anyway for your sanity. However, I have seen some leaders adjust their professional compasses ever so lightly IF they have received the same feedback from multiple employees and peers. 

What about situations when you know that your manager will react poorly to your feedback? Should you bother giving your manager harsher feedback when they didn't react appropriately to softer feedback in the past? The answer is yes; you should still unload that feedback but be ready to walk away from that job. There have been situations in my career when I was proven wrong, and my manager reacted pretty positively to harsh adaptive feedback, but as a rule, when I decide to give harsh upward feedback, I also mentally prepare myself to walk away from that job if my boss decides to make my life miserable. The bottom line is if your manager consistently reacts negatively to feedback and, or deflects and ignores your feedback, it is time to move on. 

Personal Anecdote 

A long time ago, or maybe not that long ago, I got a boss who was a bonafide enigma. His credentials were impressive, but it didn't show in the way he interacted with his organization of more than four hundred people. He didn't talk much, and when he did open his mouth in meetings, it was almost always a piece of blunt criticism. He rarely thanked anybody in public. He was inactive on common Slack channels and never engaged with any popular watercooler threads. Nobody knew anything about his personal life because he never shared it with anyone. Nobody in the company knew what made him tick. What made him angry, or what made him laugh, or what he cared about. As I said, a bonafide enigma. And then there was his facial expression.

He didn't have one. Actually, he did have one, but no one could infer anything from it. He showed no emotion on his face. No raised brows, no frowns, no smiles, no nothing. No one could tell what he was thinking or how he was feeling. His face looked like it was carved in stone. Nothing moved. His expression on his face was not dissimilar to the one worn by the farmer in the famous American Gothic painting. If I had to pick one word to describe his resting facial expression, it would be puritanical. As a lifelong learner and user of facial expressions, this frustrated me immensely. And not just me, everyone in the company was utterly baffled by the demeanor of this new enigmatic leader.

A few months after he was hired, he started to make meaningful changes to the way the business was run, which in turn started impacting employee workflows. Because he was emotionally unavailable, employees were reluctant to give him any direct feedback. The one or two times people tried to give him feedback, they were met with mostly indifference. As a result, most employees resigned themselves to begrudgingly carry out his bidding, including myself. He was our boss, after all. Until one day, I decided to change that.

The disaster that precipitated my change in attitude was the departure of a key team member. One of my teams was working on a project deemed critical by our mysterious overlord. As a result, the team worked nights and weekends to get this project over the finish line just to make the boss happy. I was trying my best to keep their spirits up, but the obvious lack of validation from the uber boss was not lost on the team. 

The project's lead engineer was the most burnt out. The lead engineer was a very empathetic leader who was very much in sync with his team's emotions and cared tremendously about their work-life balance. So when the team started working nights and weekends to hit the deadline, he decided to work even harder to give the rest of his team rest over the weekends. After a couple of months of burning the midnight oil, his wife stepped in and reminded him that if he kept working at this pace, he was going to have a heart attack. After a couple of days of deliberations about the project, the company, and his leaders, he decided to quit and put in his notice. I got on a call with him and tried to convince him to stay, but it was clear from the beginning that he had made up his mind. He was also not the mudslinging type, so he tried to keep his true reasons for leaving private, but when I kept pressing, he finally gave me the real reason. He said, "Mahesh, you are a terrific leader. You are not the reason I am leaving. I am leaving because your boss is extremely un-inspirational. I can't follow someone who has the personality of a fish".

I was speechless. I was stunned. But not surprised. At this point, the new leader had been in the company for a few years, so most of the organization knew about his personality or lack thereof. So I wasn't surprised that this lead engineer has caught on to the new leader's American Gothic persona. What was stunning to me is that an engineer who is three levels removed from this new leader and has probably interacted with him once in all of his time at the company is leaving a stable company with excellent compensation and leaving a team that he really loved just because the boss's boss was lacking in the personality department. In the end, I just told the engineer he was making the right decision.

Life is too short to be spent following poor leaders.

Until then, I had never given any adaptive feedback to any of my bosses. I had never told any past boss that they were not inspirational enough. This time around, I decided to change that. I wasn't sure if my current boss would change and suddenly start engaging with his teams more, but I was sure that delivering that feedback would unlatch the iron maiden that had started to clamp down on my conscience since the day my new boss got hired.

I reached out to a handful of peers and mentors about how to give adaptive feedback, but I didn't get anything useful besides almost everyone wishing me good luck. Gulp. So I wrote down a few tenets for myself before getting on the call with my boss

• I will be kind

• I won't expect any change to happen

• I won't mince words or soften the message

• I will be ready to part ways with the company if needed

The last one was pretty important because it acted as the ultimate release valve for me. What's the worst that can happen? They might fire me, and that was OK by me. So I decided to drop the feedback on him in our next 1:1. The exact words I wanted him to hear were, "Bob left because he thinks you are not inspirational, and others might leave if you don't change that perception of yours." 

He was a few minutes late, and by the time he joined the call, I was a nervous wreck. My palms were a sweaty mess. My heartbeat was so loud that I could hear it in my head. After joining the call, he fixed his 'perpetually disappointed dad' stare at me and said, 'OK, what do you want to talk about?'. At that moment, I almost lost my nerve and decided not to share my thoughts. Almost. But then I thought about the iron maiden of shame and guilt tightening around my conscience, and I decided to go through with it.  

I started off by saying, "Hey, as you know, Bob is leaving, and when I tried to save him, he told me that he is leaving because he doesn't find you inspirational." My boss leaned forward and said, "hmmm, OK". But his demeanor slightly changed. His eyes took on a look of curiosity. He wanted to know more! That was my cue to speak more, so I took it and ran with it. 

I gave him my point of view on how leaders should engage with their teams. How and when to be empathetic. How to act in crisis moments without eroding trust. How using fear to motivate teams will not work, and so on and so forth. I ended my impromptu leadership sermon with a warning. If he couldn't figure out how to craft and share an inspirational vision, more good people will. Throughout my spiel, his impassive demeanor didn't change much. He didn't ask any questions, interrupt me, or defend his actions. When our time ran out, he just hung up after saying a quick goodbye.

I felt relieved. My conscience had successfully broken out of the iron maiden of guilt. I was slightly fearful for my future in the company, but the overwhelming sense of deliverance smothered every other emotion that tried to rise to the surface. 

So what happened to the taciturn leader? Not much. However, a few weeks after our conversation, I did get a Slack message from him thanking me for an all-nighter I had pulled the day before to put out a crisis. That was the very first time I had received any Slack message from him, which wasn't a question or a complaint. A small win. I will take it.

A quick recap of takeaways from this chapter

• Feedback comes in two flavors, technical and adaptive

• Before giving feedback, decide what type of feedback it is

• Openness to feedback diminishes with seniority

• Adaptive feedback is hard to give, but not giving it will make you feel worse