Patrick Coppedge
over 6 months ago


Working With A Difficult Boss

Even the best office relationships hit a rut, but if it’s your relationship with your boss that’s suffering, work can be especially challenging. Maybe you’ve lost their trust, or you haven’t been seeing eye to eye lately, or maybe you’ve never really gotten along. Whatever the reason, how can you build a connection that’s more than just average? What steps can you take to improve your interactions? And are there times when you have to accept that the relationship may never get better?

Experts say that having a positive, productive and healthy relationship with your boss is critical to your professional success. Being on great terms with your manager helps you stay aligned with the priorities of the organization, understand its constraints, and get access to the resources you need to get things done. Work is not a popularity contest, but the reality is, your boss’s opinion of you matters. It matters for functional reasons because of the control or influence your boss has over rewards like special assignments, your visibility, and compensation, not to mention - your advancement in the company. But it also matters for psychological reasons. We are wired to please authority figures. When your boss doesn’t like you, it’s painful. Here are some strategies for interacting with your manager to get what you need, support your boss’s success, and excel at your job.

Diagnose The Problem (If there is one)

If you have an inkling that your boss isn’t keen on you, the first question you need to ask, is whether you’re sure the problem is you. Maybe your boss is cold, distant, or a more contained individual who doesn’t convey much positive affect. Try to figure out whether there is specific annoyance directed at you. If your boss interacts with you differently from your colleagues, then yes, it probably is something about you. In this case, you need to ask yourself: Am I working on the issues that my boss wants me to be working on, in the way they want me to be working on them? Have I been disregarding their feedback? Have I done something to lose their trust?

Take Responsibility

If you have done something to undermine your boss or lose their trust, it’s up to you to take responsibility. You need to be the one to own it. Acknowledge that you’re at fault and apologize. The good news is that even strained professional relationships can be repaired. The key is to assure your boss that you want to work on things and ask for help in getting back on track. Be patient, it will take time to win back his good opinion. Most bosses appreciate employees who work hard, mean well, ask for help, and follow through. The worst employee is a gifted individual who doesn’t give their best.

Align On Goals

After identifying the problem, you now need to work on a solution. If you’re unsure of what your boss expects, it’s time to clarify. We want our bosses to be proactive, but the onus is on you to establish a two-way conversation that aligns their priorities with your own. It’s a partnership. The trouble comes when you think their expectations are unreasonable. Sometimes there’s a sense that bosses are not fighting the right battles, so we dislike them. Instead of dwelling on that, you should try to see things from their perspective. Think about the world in which your boss is living, where these priorities make sense. And then signal to your boss that you’re getting with the program.

Focus On The Positive

Aligning yourself with your boss’s agenda might require an attitude adjustment on your part. Chances are you’re not hiding your negative emotions. Your boss knows you don’t like him. Maybe not the extent of your disdain, but he knows it. The more you obsess over your boss’s irritating habits and tendencies, the more the relationship will suffer. Deliberately changing your mindset by trying to find the positive. Focus on the strengths your boss has, not her weaknesses. In addition, do your best to reduce the intensity of your annoyance or antagonism. Here, again, it’s helpful to empathize. Try to step into the shoes of your boss and see the world from his point of view. Understand her priorities and the demands she faces. It’s important to remember that your boss is human too.


Another way to build rapport with your boss is to connect with them on a human level. Try talking to your manager about topics beyond work. Find a subject that would create a bond. Try to figure out what your boss cares about. Is it a sports team? Stamp collecting? A particular music group? You don’t need to feign interest if you genuinely have none, but learning about who your boss is as a person and finding genuine overlaps in interests will give you a deeper understanding into what makes them tick. Ask her to coffee or invite her to lunch, so you can get to know each other on a personal level. That said, if a personal relationship isn’t easy, don’t force it. It’s okay if you don’t have chemistry.

Seek Your Boss’s Counsel

Asking for advice is a good way to improve a person’s opinion of you. It shows you respect their judgment and their intellect. It also increases their investment in you. But asking your boss for advice or help is a delicate matter. You don’t want your boss to think you’re delegating back up or putting the problem back on them. Make sure the boss knows you’re paying attention to the pressures he’s under. Phrase your request as asking their guidance to help you think things through. Show that you’re still willing to do the work. Say, ‘This is how I’m thinking about things. These are the trade-offs I’m considering.’ Bear in mind that once you ask for advice, you have to follow through on it.

Make Your Boss Look Good

The best way to have a strong relationship with your boss is to do your job and do it well, but that may not be enough. Go further by anticipating your boss’s needs and pitching solutions to problems. This will make their life easier. While sucking up is not advised, it’s always smart to make your boss look good. Compliment your boss in front of colleagues. Demonstrate loyalty to your boss’s vision. Don’t be a sycophant and don’t be dishonest. If you’re singing your boss’s praises or rushing to her defense during watercooler chat, you have to mean it.

Consider Moving On…Or Not

Working for a boss you don’t like is demotivating and de-energizing. People describe it as a crucible experience. When your relationship with your boss seems beyond repair and you’ve done everything in your power to make it better, consider looking for a new job, or at least a new manager. If you can’t trust your boss, it may be time to get yourself out from under that person. Though it doesn’t necessarily mean you have to leave the company. Alternatively, you could develop a slightly thicker skin and think, This too shall pass. After all, bosses come and go, and it’s good training to work with a difficult personality. You will find out how to operate at your peak despite a sub-optimal relationship with your boss. You will develop resilience.

Principles To Remember


Empathize with your boss in order to get a clearer understanding of their priorities and the pressures they’re under.

Build a personal relationship with your boss by engaging them in conversation topics beyond work.

Ask your boss for their guidance and counsel; this shows you respect their judgment and intellect.


Assume your boss’s attitude toward you is personal.

Figure out the extent to which your boss behaves differently with you than with other people.

Harp on your boss’s annoying habits. Focus on his positive traits.

Give up and look for a new job too soon. Working for a difficult personality helps you build resilience.

Ashley Wilson

Thank you for sharing this Patrick Coppedge ! Now I happen to love my current boss, but in the past, I have had some REAL doozies haha. Some I tried to speak to and make sense of how cruel they were and others I just couldn't handle and left that job. It's always a better feeling to solve an issue, but in the end, it comes down to the two of you and if one person isn't willing to work on things then it might be best to part ways. Great insight and ideas for strategizing how to address a difficult situation at work! Happy Monday Patrick you're starting us off strong! ; )

Mary McLain

A Boss verses - A Leader

A Boss lacks experience - feeds off of EGO & Promotes & Supports Like Individuals of same I.e., Culture, Ethnicity - mindset, etc.

A Boss sets the Culture of the Organization - so “No Matter “ what you do or say if you DO NOT fit that Culture - You are the odd man out. Nothing you say or do will EVER be right. They will support each other no matter what to FORCE you out.

Recognize the signs & Get Out! Before they - Destroy you & your Career. IF you can !

A Leader Leads & Accepts Responsibility.

A Boss Leads with EGO & Takes No Responsibility.

Less Experienced Leaders go with the Ones in Power - to be liked

Experienced Leaders Lead by Example - ensures Policy & Procedures are in place - lays boundaries & Enforces Regulations.

Values & Supports Good Employees - etc.

Not afraid to put things in writing - Policy

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Jason Olson

True cuz at my last job my boss spent to much time being the company puppet for the higher ups and he also flirts with all the girls for the attention and not get anything done. Employees come to work everyday to a dump it sucked

Bashir Youssouf

A need work jic honda Jefferson oh

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