How Do You Deal With A Difficult Boss? (Workplace Conflict Series 2/3)

Regina Zafonte
6 min readJan 19, 2021

Steve Jobs has had a complicated legacy. While few would doubt his visionary abilities, many would call into question his leadership style and weak interpersonal skills. He has been described as deceitful and cruel, even by his friends. It is known that he cheated his co-founder out of a big bonus and lied about it. While Walter Isaacson was conducting research when writing the biography of Jobs, Apple Engineer Johnny Ives told Isaacson that when Jobs got frustrated, his way to achieve catharsis was to hurt someone. According to Ives, Jobs felt he had the liberty and license to do it.

Like Jobs, there are hundreds of other leaders who treat their employees poorly. Research shows that leaders who demean their workers have rationalized their aggression because, at times, they can get short-term results so they feel vindicated in their unsavory behavior to achieve their goals. This problem is compounded when the long-term damage they are causing to others is invisible to them. Bad bosses may also see the situation in black and white terms, thinking — “I have to use this behavior or I will not get these outcomes.” But there is a big difference between being demanding (having high expectations for others) and demeaning (devaluing other people, even treating them disrespectfully and making them feel worthless). This tradeoff does not need to exist because it is possible to show respect and set a high bar. Kim Scott’s Radical Candor uses this exact leadership approach — caring for somebody personally and challenging them professionally.

The impact of toxic bosses can be quite detrimental. Here are some company consequences:

1. Negatively affects performance and reduces worker productivity. The presence of a bad boss can cause team members to make mistakes and doubt themselves. In one experiment with a medical team in Israel, a doctor berated his team and said he was not impressed with their medical care and that they would not last in the department for more than a week. In the ensuing days, the percentage of an accurate diagnosis by the team went down by 20% and the procedures they did were 15% less effective. When we work with somebody who has abused us mentally, our cognitive abilities decline. Essentially, working with an angry boss makes us dumber. In another experiment, students were instructed to walk into a testing room, but instead accidentally walked into the professor’s office. Immediately, the professor berated the students and said, “Are you not smart enough to see the do-not-disturb sign?” They then took a math test and solved a quarter fewer anagrams correctly compared to the students who were not just lambasted.

2. Less likely to help others. In that same experiment, people who were just scolded by the professor opted not to help others when they had the opportunity to do so. In another experiment, as students were leaving the school building after enduring some harsh words, they saw a few classmates drop a bunch of books and choose to keep walking instead of helping to pick them up. The best teams are collaborative ones so if people are holding back with their assistance, teams cannot reach peak performance.

3. Creates silence and shutdown. Toxic bosses create an environment where people stay quiet because they want to avoid rocking the boat. They are trying to stay under the radar because they do not want to be a target for any abuse. This significantly hurts teams and organizations because there is no feeling of psychological safety for people to contribute their ideas, especially when half-formed. Having that environment where you can comfortably share and be supported is a necessary component to reach collective intelligence and do great work.

Responses to Avoid

When you are feeling abused and wanting immediate reconciliation, it can be tempting to opt for less helpful responses that may feel good in the short-term but carry severe negative long-term consequences. Here are some to avoid:

1. Do nothing and endure. This decision can eat you up inside and cause resentment. The discontent cannot only manifest at the workplace but also at home and create an unhappy disposition with the people you care for the most. When we continuously repress our feelings, it comes out in other ways, often when we least expect it or cannot afford for it to leak out.

2. Fight back at the moment. It is not the best idea if you have not collected your thoughts, yet choose to unleash them spontaneously for the sake of justice. After all, you believe that this person simply cannot go around rebuking people the way they do, and you are going to be the person to change their behavior. The problem with this savior mentality is that it is immediately going to put the person on the defensive and they have been playing the angry-and-public-ridicule game for much longer than you have so picking a fight on their turf may be gratifying at the moment, but most likely does not lead to a productive resolution.

Responses to Consider

Here are some helpful steps you can take to confront your boss thoughtfully and productively so you can decide your next move:

1. Focus on personal impact. See if you can find a respectful way of letting them know the impact they are having on you. People sometimes do not see how upsetting, demeaning, and unprofessional their actions are to you, your team, or the organization. Other people’s intentions only exist in their hearts and minds so we cannot assume that we know them. We feel hurt so we think that they intended to hurt us, but when we can disentangle intent from impact and apply curiosity, we can get more information on how best to respond and understand why this is occurring. The best-case scenario is that they understand just how much you have been affected and take steps to change their behavior.

2. Change teams. If you believe in your company’s purpose and vision but are having a hard time with the manager, see if you can change teams so you are no longer reporting to your boss. If enough people are requesting a transfer, it will become obvious where the source of the problem exists.

3. Change jobs. If you conclude that the other person had intentions to hurt you or does not plan on changing, and this is typical of what goes on in different parts of the organization, you may want to consider leaving your job. What is all this heartache and pain costing you? Find that leader in a people-first company who will not only treat you with dignity but will inspire you and bring out your very best.

The big question that people always ask about Steve Jobs is — did he have to be so mean? Walter Isaacson would argue that he succeeded in spite of his cruelty, not because of it. The kindness routes are always the better paths to travel down because you will get better results and create stronger relationships along the way.

Quote of the day: “Having a bad boss isn’t your fault. Staying with one is.” -Nora Denzel

Q: How have you handled a difficult boss? Comment and share with us, we would love to hear your opinions.

As a leadership development and executive coach, I work with people to have courageous conversations, contact me to explore this topic further.

[The next blog in this series 3/3 will focus on what organizations can do to prevent difficult people from tanking the culture]

How do you handle a difficult boss?

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