Idea 045: 5 Mistakes to Avoid When Dealing With Your Boss

Over these years, I have learnt one very important thing from every single one of my bosses: never act like an robot. We might think that all bosses like obedient employees, but they are not.

Dealing With Your Boss = Fighting at War

Photo by Birmingham Museums Trust on Unsplash

I have dealt with a few bosses in the past 10 years.

The 1st one was a female boss who always pretended to be nice. She just cared about the way others seeing her. Even if she was angry, she would not express that feeling so easily but to use sarcastic way to talk to her employees. In order to get her true mind, I needed to pay attention to what she said and how she said.

The 2nd one was a male boss who always avoiding responsibilities. He was at his 40s and had been working for that company for around 7 years at that time. He was always caught to do online shopping during work, and yet he wasn’t got fired simply because his work experience was still an asset to the company. Because he didn’t care about his work, he also didn’t care about the future of his subordinates. He only promoted the ones that he liked, regardless of their potentials or their capabilities.

The 3rd one was a female boss who was a very devoted person. She sacrificed all of her time and even her health to the company, trying to help the big boss make the company a better place to work. I respected her very much and was influenced by this work attitude. She also showed me how good bosses should treat their subordinates.

The 4th one was a female boss as well who was an experienced boss. She was nice and knew how to work with other departments. Unlike the 3rd one, she knew how to balance her work life and her personal life in a good proportion. She was demanding but reasonable.

The 5th one, ie, my current boss, is a male boss who is a very brilliant and detail-minded man. He always knows what is going on and what he is going to do to get the work done. He has a very strong to-do attitude that he always believes he can achieve everything as long as he tries his best. He has high expectation on everyone including himself.

Five different bosses with five different style. To deal with them, I needed to spend some time to understand their mindset and personalities, just like fighting at different wars. Sometimes I got my bosses’ mind correctly and won the wars, sometimes I didn’t and lost the wars. In general, this is a learning curve to everyone until they become the big bosses some day.

Eventually, I figure out one of the most important things when dealing with bosses: never act like a robot. We might think that they like obedient employees, but they don’t. They want employees who could bring away all the trouble from their work.

Today I am going to share 5 mistakes that we always make when dealing with our bosses. If we could avoid these 5 mistakes, we could get the trust from our bosses.

1st Mistakes: Request Answers

Photo by Artem Maltsev on Unsplash

We should always bear in mind that our bosses are always super busy running the businesses. He / She always depends on the employees to provide answer, but not the other way round.

A valuation report was required on an acquisition which involved trademark. As it was part of the necessary procedure to fulfil audit requirement, we needed to look for external valuer to help. I asked an acquainted valuer for detail on how this valuation work would be performed and replied to my 5th boss.

After a quick discussion, my boss replied with more questions on this valuation work which I had no sufficient knowledge to answer. As I knew he was a valuer before, I was hoping maybe he could share some knowledge on this topic, and I knew that he got my mind.

Instead of sharing any knowledge, he asked me to search on the Internet, “I am sure you can take 5-10 mins and search for at least 5 articles related to this topic. You should do your homework and let me know your finding later.”

In this case, my boss refused to offer answers to the questions because he didn’t think this was his duty to provide answers. In fact, I should never show any intention to ask for answer from him, provided that I could find more knowledge on the Internet.

My boss was right. Being an employee, I should never request any answers directly from my boss before I tried my best to look for them first. Besides, we also need to do more than just providing answers, eg, to summarize the answers and provide useful information to my boss.

2nd Mistakes: Ask Dumb Questions

Photo by Evan Dennis on Unsplash

In school, teachers always taught us not to afraid of asking questions because there was no stupid questions at all. I totally understood why those teachers said something like this – this was actually the way of thinking in science. However, in reality, most of the people don’t think in this way.

My 4th boss always told me to ask questions whenever I had one. However, she also acted impatient when she heard some dump questions. There was a time when I couldn’t get the situation of a task very well and asked for details, she immediately lost her patience and asked me to read through all the files involved.

“You can find everything from those files. Before you ask any more question, you show read all of them.”

Most of the time we find some questions, we instinctively look for help. This especially is the issue in Asia because of the education system.

Back to school the students were taught that every questions had answers and teachers had them all. If they couldn’t resolve the questions, the teachers would provide the answers eventually. As a result, this “encouraged” students to ask question whenever they had one.

Asking question is not a bad thing. However, sometimes the answers of the questions have already existed, we are just so careless to see them. If we still ask those questions, we will be asking dump questions in others’ point of view. This will make others think that we don’t think before we ask and question about our abilities.

3rd Mistakes: Miss The Real Questions

Photo by Jon Tyson on Unsplash

Sometimes we might misunderstand the question and didn’t get the real one. As a result, we went to the wrong direction.

My 5th boss wanted me to prepare an excel template showing the cashflow forecast every month. However, after creating a few versions, I still couldn’t create one that my boss was satisfied with.

My boss wanted to have one single excel which can show all the expected cash inflow and outflow, and comparison of expected cash outflow with the previous ones. However, while I couldn’t read his mind completely, I wasn’t informed with the exact instructions of how to do it.

There are always two reasons of not getting the real questions: either we do not actively listen, or the boss don’t say it clearly. This requires further communication to make sure everyone is on the same page.

To deal with this problem, we can simply summarize the situation to our bosses make sure we understand the issue correctly.

Remember, the last thing we should do here is to guess. Guessing means uncertainty. It means we might not do in the right direction, and we might need to re-do the whole task in the future. Our bosses would question our capabilities going forward.

4th Mistakes: No Updates

Photo by Christian Wiediger on Unsplash

Imagine if we were the responsible person of a project, we assign different tasks to different people. However, we didn’t get the update of the progress until we asked. How would we feel?

Unfortunately, many people act like this. They think that updating progress to their bosses is like annoying their bosses, which is the last thing they want to do. As a result, unless they complete the task, they seldom update the progress to their bosses.

My 3rd boss once blamed me of not updating the work progress to her. She was busy with her own work by that time, and she trusted me that I could handle some of the tasks for her. Obviously we have different understanding on the meaning of “handling work”.

She expected me to update the work progress to her regularly, eg, once per week, but I thought she wanted me to take in charge of the task and only let her know when I completed the task. She told me how she thought later, “If I knew you were unable to handle part of the job, I could always offer some help to you.”

Most of the time our bosses care about the work that they assigned to us. They just couldn’t find sufficient time to complete the task by themselves. However, that doesn’t mean that they don’t want to know anything about the task.

5th Mistakes: Get Rid of Responsibilities

Photo by Jornada Produtora on Unsplash

This is one of the problems I always see from others, sometimes from myself as well. In some cases, we might think we should involve others, including our bosses, to deal with the issue because we somewhat believe that they should be part of it. Except they are not.

Same example as that in 1st Mistake. After a quick discussion, my boss casted more questions on this valuation which I had no sufficient knowledge to answer. I proposed to my boss a conference call with that valuer, and my boss replied with simile, “I am sure you can handle it with that valuer.”

At that moment, I knew I was screwed. My boss should have thought that I didn’t want to take this responsibility to handle this valuation issue but tried to get him involved as well. To be a responsible person, I should really took the responsibility and handled the issue on my own, and only reported back to my boss with the final result.

I am not saying that we should never ask for our bosses’ favour in order to get things done easily, but we should think it through before we take any action.

From day one working in this world, we should know that we are assigned with different responsibilities that we should ultimately own them. It is true that the job might become easier when our bosses get involved, because they tend to have the authority to make things smooth. However, if we always ask for our bosses’ help every single time, we are taking out the time they reserve for other more important issue, eg, closing a big deal, expanding the company, etc, which are actually the main responsibility of our bosses.


Dealing with bosses is not easy. A lot of people failed to do so and couldn’t gain trust from their bosses. Although different bosses have different personalities, most of them only want to look for their right hands. By avoiding the above 5 mistakes, we can show to our bosses that we are trustworthy.

  1. 1st Mistakes: Request Answers
  2. 2nd Mistakes: Ask Dumb Questions
  3. 3rd Mistakes: Miss The Real Questions
  4. 4th Mistakes: No Updates
  5. 5th Mistakes: Get Rid of Responsibilities


If you have any questions or have anything things to share, or you would like to write some posts with me, you can reach out to me via email

Besides, if you want to know more about what I have learnt from other successful people, you can click the below link. This could the one of the life-changing articles for you:

Leave a Reply