6 Ways To Manage A Difficult Boss

 6 Ways To Manage A Difficult Boss

Ways to manage a difficult boss

6 Ways To Manage A Difficult Boss

Have you ever had a supervisor who just finds faults with everything you do? Ever had your boss tell you that you are a serious unfit for the organization, for reasons best known to him/her? How do you deal with such a difficult boss?

Have you ever tried all you could to meet a supervisor’s expectations all to no avail? How do you deal such a demanding boss? Can I imagine that you have gone the extra mile, and out of your way to make them change their impression about you but still, they refuse to see your efforts but rather keep seeing the wrong stuff about you and your work?


I’m sure you’ve asked yourself the million dollar question ‘what does she really want from me?’ ‘how do i manage this difficult boss?’ but never got a clear answer!

But what do ‘difficult’ bosses really want? Why are they so hell-bent on making life miserable for their subordinates? You might have asked.


The new DDI research (December 2019) reveals that a whopping 57% of employees quit their jobs because of their bosses. This means that in most cases, people quit their managers and not the jobs. Very interesting!


Working with a difficult boss is in itself a difficult job, and you must succeed at it before you can achieve success on the real job.

The 6 strategies below is a good guide to help you manage a difficult boss if work with one and to have a win-win.


The first thing is to find out and be sure that you are really dealing with a difficult boss. Is your boss really a difficult manager? Is your boss difficult to everyone else or just you? Why is he/she being difficult? Do you really have a disrespectful boss? Is this the way he/she is or did something happen to trigger it?

Providing honest answers to these questions will go a long way in helping you properly x-ray the situation.

A few years ago, a lady visited my office and complained bitterly about how difficult her boss had been since she started work in the organization a month ago. After a short period of investigation, we found out that during the interview, the lady had boasted that no supervisor could boss her around, and that she would do her things her way and on her terms.  Unknown to her, the boss was amongst those on the interview panel. They employed her because of her skills for succession planning but had to put her to test to be sure she could really fit into the system.

That’s the reason for the difficulty she was experiencing with her boss. Immediately she realized and made changes, she began to enjoy a whole new working relationship with her boss. The tip she got helped her in handling the difficult boss.

But that is not the case for all. Some bosses are just there to frustrate one’s life.

Once you are sure of the situation at hand, you can move to the next step.


What does your boss want? What are his or her goals on the job and in his or her personal life? What motivates him or her? What kind of friends does he or she keep? What makes him or her happy? What kind of relationship does he or she keep with his or her own boss (if any)? What exactly made him/her a difficult boss?

Getting specific answers to most (if not all) of these questions, will go a long way to help you manage your difficult boss.

A lot of times, difficult bosses are very ambitious. They have high goals in the organization, so they tend to suspect and fight almost anyone to get to the top and be all they aspire to be.

You also need to have an idea of his or her circle of friends for comparison. This knowledge should help you strategize on the best ways to handle your relationship with him or her; giving what is for Caesar to Caesar, and what is for God to God.

Sometimes, you just need to buy him or her the preferred lunch as often as you can to keep him or her happy and keep the troubles away. I’m sure you wouldn’t mind that price. Sometimes, a little price can be required to manage your difficult boss.


Difficult bosses (like most difficult people) are very suspicious of others.

In their suspense, they are very quick to build fences and set defensive triggers like the military. I am sure you don’t want your boss to treat you like a terrorist. Lol.

No matter how difficult it gets, resist the temptation to work against his or her interests. Still protect his or her interests and speak well of him or her especially in the presence of their own boss as long as you are still interested in the job. It’s already bad enough, so don’t add to it by allowing him or her suspect that you are conniving with people against his or her interests. Working with this knowledge is one essential way to manage your difficult boss.

One of the major ways not to work against your boss is to do your job and do it excellently well. The reason is simple; your job is a part of your boss’ responsibilities. So if you are failing at it, it will affect her results. So try not to allow this affect your performance (although it’s not going to be so easy)!


Request to meet him or her (one on one) about your job. The request could be made via a phone call, verbally or through a text message to his or her phone.  Ensure to get her a response on the specific day and time for the meeting.

At the meeting, appear nice and professional. Start by thanking him/her for giving you his/her time; out of his/her busy schedule.

Speak courteously and straight to the point about the work and nothing personal. The idea is that you want to know how to better work with him/her so you can have better results. Let him/her know you care, you are working towards better results by doing things differently and that you will value getting responses in ways you best understand. Let him/her know she can trust you as your commitment is not in doubt.

Using the above guide is not a guarantee that things will change, it’s however important and shows that you are not just desirous of a change; you are actually doing something worthwhile to make it happen.

A lot of difficult bosses have actually changed their ways through this kind of encounter. We have cases of those who then take the opportunity to pour out their hearts to their subordinates and tell them the reason they behave the way they do. In many cases, it’s the loneliness they feel inside that triggers it while for others, it’s the terrible situation at home or the way they were brought up.

Don’t give up if things still don’t change or even get worse after this meeting.


Having someone mentor you in situations they have been through provides lots of advantages. Get a reliable mentor.

Always talk things through with your mentor so he or she can provide you with help as you journey on. A good mentor will not only advise you on the ways to get along with a bad boss but will also lead you through how to build and survive the many challenges in your journey to a fulfilling career.


This is one last thing you must do if other points didn’t produce the desired results, and you are sure that you are not the problem.

Continuous interaction with a bad boss affects not just your work life, but other areas of your life.

You can close for the day and leave the office but the treatments meted out to you and words spoken to you will not leave your head and life just that quick. The worst is after a while; these ugly experiences begin to form part of your life. After all, it’s said that whatever you could do consistently within 30days becomes a habit.

There are 3 ways you can fire your bad boss as shown below:

  • Report to The HR or The Relevant Authority

Find the energy and courage to approach the HR department to report your ordeal. Request that he or she should be invited and interviewed. Here, you are not directly reporting him or her but the situation, since it’s affecting your work.

The HR department will take it from there. In a situation where the HR system is not so effective and your rights are not so guaranteed, speak to the person/office you think can do something about it without creating unnecessary drama.

  • Request A Transfer

Write to the relevant authority for a transfer to another unit or department.

At this point, a transfer will be helpful to get you going on your job and in the organization. Many employees have lived miserable lives because they simply couldn’t muster the courage to insist on what they want even though it is available and staring them in the face.

The request for transfer should not be hinged on the fact that you have a difficult boss but on the fact that you need something more challenging and fulfilling in the organization and that your current responsibility does not offer such. The case of your difficult boss is second on the list. This way, you are not seen as a whining plague that other bosses within the organization may want to avoid.

  • Leave The Organization

Yes, you read right, leave the organization. Resign!

It’s better to leave the organization than to lose your personality and sanity. As long as you are alive and conscious, there are loads of other opportunities for you to explore.

4 Things That happens When You Stay Too Long With a Difficult Boss

  1. You lose your self esteem
  2. It leads to a gradual death in your career
  3. You lose your personality
  4. You become a worse boss yourself


If you are a boss, check yourself to be sure you are not a difficult one. There is no reward anywhere for being a bad person.

One simple question to check yourself with is this ‘. . . Will the people I lead still relate with me the way they do if I was not the boss?’. Being the boss is an opportunity, use it well!

If you are experiencing a difficult boss, take it easy with yourself, it is only for some time, it is not the end of the world. Carefully consider and practice the steps listed above and choose a better life.


Cheers!! See you on the winning side!

About the author

Richard Uwamari – Richardizm is a certified management consultant and leads the team at hrm2day.com. He is also the consulting partner at Richystar Consulting limited, a management consulting firm based in Lagos Nigeria.

Having been in the HR industry for over a decade now, he’s contributed his expertise in servicing several local and international organizations. Asides his great knowledge in other areas of the management consulting field, Richard remains one of the best names to mention when it comes to employee engagement.



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