Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

Working With a Negative Boss

Dear Crucial Skills,

I need help with an ongoing issue. My manager is very negative and nothing ever seems to be good enough for him. He doesn’t think anyone can “exceed expectations” in a performance review and gives me a very mediocre review whereas past managers gave stellar reviews. I try to discuss this issue with him, but he is intimidating and loves to argue. I fear for my job. What do I do with this type of “leadership”?

Fighting Negativity

Dear Fighting,

I had an advanced placement English teacher in High School who was, I’m convinced, a frustrated University professor stuck in the only teaching job he could get. The first day of class he explained that he held “the highest standards of scholarship” and would only give an A grade for A work. He proudly announced that in the last three years none of his students had ever earned an A.

This was fine by me. I pulled in all B’s without doing much homework and was betting on a wrestling scholarship, but this did not sit well with some of the serious scholars who were trying to maintain their straight A run. They got their parents involved, who had several meetings with the teacher and the principal and eventually the school district officers. School officials ruled the teacher was using a ten step grading system instead of a twelve step—having for all practical purposes eliminated A’s and A-‘s. He was told to use the bell curve and told how many A’s to issue in each class of twenty students.

Performance review systems and rating and ranking systems are tough enough to understand and to administer. When you complicate the process with a boss who doesn’t follow protocol then it can be nearly impossible to receive fair evaluations.

Now, it could be that, like the school teacher, your boss doesn’t believe in high ratings and has impossible standards. But, there are also other possibilities. It could be your boss isn’t sure what would constitute a job well done, but will “know it when he sees it.” Another possibility is that the boss has a clear picture of what he wants, but has not seen you deliver it.

What these possibilities have in common is that you are left without clear expectations as to what you can do to earn a high rating.

I believe, at a minimum, all leaders owe those they lead a clear understanding of what is expected of them and how they will be evaluated. Without clear expectations and the ability to accomplish them, bosses are just playing a game called “Guess what I want?” This is manipulation and is both dysfunctional and hurtful. It’s certainly not leadership.

I would suggest your first efforts to improve your relationship with your boss should be to clarify expectations. It is reasonable to request that he explain what he wants you to do and how you will be evaluated.

Start by creating mutual purpose. Do this by sharing your aspirations. For example, you might say, “Mr. Vague, I want to talk with you about my performance in the coming quarter. My goal is to do an excellent job, achieve the desired results, and help you and the team succeed. I also want to earn an ‘exceeds expectations’ rating in my next performance review.”

This beginning statement clarifies your desires and assures him that your purposes and his are mutual—at least around the success of the team. This will also create safety and reduce defensiveness.

Next, ask for what you need to succeed. “In order to do this, I would like you to help me understand what exactly I need to do in order to make an excellent contribution and earn an ‘exceeds expectations’ rating.”

If your boss has in mind what he wants you to do, this approach will invite him to share it with you. If your boss doesn’t know exactly what he wants you to do in order to earn an ‘exceeds expectations’ rating, then your questions could help him think it through.

Ask questions which clarify and encourage specific detail. Such questions could include, “Is there something you’d like me to do more of? Is there something you’d like me to do less of? Is there something I’m not doing that I should start doing? Is there something I’m currently doing that I should stop doing?”

Ask questions that help to quantify your job. Ask about deadlines. Ask about results. Ask about components. For example, if the boss wants you to prepare a report, you might ask “Would you like my report to cover A, B, and C? Will it be helpful to send the report to you weekly? Would it help to have a paragraph that summarizes the data or would you prefer to have several pages of raw data? Would you like a section on analysis? Would you like a section on recommendations? Would you like a section on options?”

By asking clarifying questions you help draw out some of the details and specifics you need in order to know how your boss defines a job well done.

If your boss is not sure what he wants but believes he’ll recognize it when he sees it, then request more frequent accountability. For example, “Could we meet once a week and review my progress? That way, you can help me make course corrections so I meet your expectations.”

More frequent accountability will enable you to make quick course corrections and to check the boss’s satisfaction levels before it’s too late to recover.

These are some strategies for creating a greater understanding and clarity for both you and your boss.

It might also be helpful to include feedback, evaluations, and ratings from key stakeholders who receive the output of your work. In this way you escape the my opinion vs. your opinion argument and can present the boss with ongoing data showing that others are pleased with your work. This will demonstrate the high quality of your work.

The final step should be an effort to get your boss’s commitment to the plan and might sound like this: “If I accomplish the things we’ve discussed by the end of the quarter, would I then receive an ‘exceeds expectations’ rating?” If his answer is wishy-washy, then you need more dialogue to define and clarify expectations. If the answer is “Yes,” then you are set. Do your very best work, make your very best effort, and check with your boss regularly to see if any mid-course corrections are needed.

In the worst case, such as dealing with a boss who refuses to be satisfied or begrudges his direct reports for their successes (perhaps he was weaned on dill pickles and can’t help himself), and after trying some of these strategies without success, it may be time to escalate the evaluation of your performance up the chain of command, or involve Human Resources. Know that this would be a last-ditch effort and would severely damage your relationship with your boss. Sometimes, however, this is the only way to fairly document your good work and receive a fair performance evaluation.

Short of using this nuclear option, if you make it safe for your boss to have a performance conversation with you and help him to clarify and express his thinking, you should be able to reach agreement about what constitutes good performance and good ratings.

I wish you the best in creating clear expectations with your boss. Don’t be reluctant, you are after all, merely helping him perform the minimum requirement of a good leader.


Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

17 thoughts on “Working With a Negative Boss”

  1. Elizabeth

    I don’t mean to side with this particular boss necessarily, as he may in fact be unfair. But I have kind of a gripe with evaluation systems and their language, and your reply here points it out. The questioner is trying to earn an “exceeds expectations” rating. Yet in explaining how s/he might get his/her boss to specify what he wants, you refer to *meeting* his expectations. I don’t think that’s accidental. Many evaluation systems today set up a disconnect between the actual language that’s used and the way the rating is interpreted in the real world. I am often bothered by customer satisfaction rating systems used by companies where the employees make it clear to me, as a customer, that anything less than “the most wonderful customer service experience I’ve ever had in my whole life” (or whatever the option is actually called) is considered a failure. It’s the Lake Wobegon problem: 100% of the students cannot be above average, and to use “excellent” or “exceptional” as synonyms for “good” means that nothing can ever again be truly exceptional.

    Okay, that’s the end of my rant. It might or might not be relevant to this employee. Sorry.

  2. Melissa

    Since when is “meeting expectations” a bad thing. I think employees have unrealistic expections that they deserve a stellar evaluation for doing what is expected of them. An occasional “exceeds” may be warrented but if that is always the rating what is there to reach for and it just moves the bar higher. Somehow we need to help employees feel validated for doing their job without needing excellent ratings.

    1. Michael W

      Melissa, you sound like an HR person, or simply a disconnected supervisor. I’m in a situation where my supervisor isn’t even ON SITE, but he’ll be the one doing my evaluation. He works in two different areas, on opposite sides of the city, and when he’s at our site, he spends 99% of his time in his office. He receives bonuses for the output of his workers, but, like you, doesn’t feel that anyone deserves anything above an “average” work review. How do you feel about people who give reviews about employees that they rarely are present to observe? Is it, in your opinion, okay to just take a ‘lucky guess’, and expect the people earning your bonuses to be okay with that?

  3. Charlie

    Hi Ron,

    I have employed this strategy for quite some time and have to say that it does work. The biggest thing is that you manager actually gets that you have a mutually agreed upon contract. I do these things and you agree to respond with this ranking or promotion for that matter. Expecting that the manager will figure it out and do the right thing has let to disappointment too often. On the reverse side, when I was the manager, I make the handshake agreement with my subordinates. You do these things that I layed out and I will reward you with the rank that you are looking for. In some cases where the tasks were fairly straight forward I alerted them to the fact that the ranking went by relative performance and gave them the metrics that would be followed. Nothing is 100%, but this system has a great track record.

  4. Rebecca


    This is excellent advice on approaching a boss to clarify expectations. My experience tells me, however, that there are a small minority of people who walk around believing that they are “exceptional.” They are intent on proving their “exceptionability” by doing things THEY want to do THEIR way and declaring anything the BOSS requests as “stupid” with a capital “S”. These type of employees want nothing more to impress others by doing the things that would impress themselves.

    I’m curious to know what the “argument” actually entails. Let’s face it: at the end of the day you are responsible for meeting your boss’ expectations, not your own. If you believe the boss is that far out in left field, then you really need to give up negotiating and find another job.

  5. Michael

    Hello Ron,

    I had such a boss, which was the perfect micro manager. And, unless you were on her list of favorites, nothing was ever good enough. The yearly performance evaluation was a long list of negative remarks, I’ve never heard a good or encouraging word from her. Her behavior was borderline to bullying, but was considered “management style”. On my every attempt to be proactive and try to find out what I should do to please her, I was told that she does not have time to waste with me. I personally think that there is nothing that can change this type of managers. In my case, she moved to another group, problem solved – I am now again the wonderful employee that I always have been.

  6. Dan Weber

    Asking the boss about what ‘exceeds expectations’ means to him shows the employee will never exceed expectations. I believe a preferred approach would be for the employee to develop a performance plan that he believes is worthy of the desired rating. Then meet with the boss to explain and adjust the plan so it describes the performance level in mutually agreeable terms. Most (i.e. average) employees compare themselves to others; top performers compare themselves to benchmarks and goals that they know will challenge and push them to be the very best they can be.

  7. Terry

    Hi Ron – I absolutely agree with your comments, as well as others’ who have written, but I also feel the pain of Michael via his comments. What do you do if your boss is the head of HR and behaves this way? I am a very mature individual with good communication skills, but talking to your VP about bad behavior is not easy. Many of her direct reports feel the same way, yet none of them will give her this much needed feedback, because they are fearful of her response/reaction. It’s not good to be the only giver of feedback about bad behavior, and even though I have worked very hard to prepare my conversations with “mutual purpose”, my perception is that she does not like it when this happens. As an experienced HR leader, I know these are challenging conversations for both the sender and receiver, but I feel very discouraged with the results, and at this point, I’m beginning to feel like it’s not worth it . . .

    I guess I am really just venting, like Elizabeth!

  8. Harry

    I have such a boss, who is the perfect micro manager. And, unless you are on her list of favorites, nothing is ever good enough. Her behavior is borderline to bullying. I just document and make sure my performance matches mission. The total organization is like this. I am looking to get out and tell everyone to go to he double toothpicks. I am finding patience is the best watchword. When she goes over the deep end I have caught her breaking policy and I hate it but I use my strong backbone and push back. She goes away. Now that we have reorganized not sure what will happen. My guess is she will eventually implode and we will all be better for it. I usually do not wish ill on people but.

  9. Anne

    Hi Ron: I like your suggestions and, in fact, used something similar recently to see what my supervisor is specifically looking for and trying to match my growth skills. This is something an employee always should strive for: self-improvement! I, too, have been confused by poorly-worded evaluations and vindictive and baseless personal attacks landing in a review in a job in the last decade. This was done by a 29 year old manager after I worked there for four years! I was confused and hurt. I have decided, as I get close to my sixth decade, to continue taking relevent classes and improve myself for me. Few read performance evaluations and as long as I know I am checking in, staying on track, being a team-player and, yes, having fun while doing intense work is the best reward for me. There will always be a certain percentage of grumpy Peter Principle folks who take it out on others via this one-two power-punch. Thanks for another “keeper”.

  10. Steve Kaye

    Your advice is excellent assuming both sides understand mature dialogue. What does someone do when the boss uses anger and insults when asked to specify standards (or talk about an vital issue)? Then the employee is stuck in a dilemma. Going to HR for help can make the situation worse. Changing jobs can be expensive. And staying keeps the employee in an unrewarding job.

  11. MissPriss

    Well it is funny. I can completely empathize with what the employee is dealing with. Sometime you just live throught a poor boss to come out the otherside in one piece as long as at the end of the day you know that you did a good job just let the manager give you and average review. I understand the frustration of always striving for greatness and told that you are just average or that you “meet expectation” but just take it for what it is. If a new manager comes in, they will look at the past reviews and if you are correct he gave most lower than previous reviews it will come out. Just be sure you are holding yourself to the highest standards as possible and if he tell you that you are doing something wrong ask him for guidance to do it right. STAY POSITIVE & let the negative go.

  12. Bruce Wilkinson

    I think it is worth exploring whether or not the position really warrants effort that exceeds expectations. Sometimes what the position is worth is someone who simply does it exactly as expected–no more and no less–and handing out an exceeds and the accompanying pay raise, even if merited, is not a good value proposition for the employer. There may also be the issue of grading on the curve relative to other employees–which may or may not be up for negotiation. I am not taking sides in this particular case but some employees are not happy unless they get external validation of the opinion they would like to have of their value to the company. There is nothing really wrong with not exceeding expectations. Meeting expectations is what an employee is paid to do. If a person exceeds job expectations continually, they are probably in a position that is beneath their capabilities and should be looking for advancement–with or without their manager’s recognition. I would advise this employee to ask the manager if they really want an employee in that position who exceeds expectations or are they actually more satisfied with someone who merely meets them. The answer should be informative. If the answer is that the manager is satisfied with meets and the employee is thinking exceeds, then your assumption of common purpose is almost certainly inaccurate.

  13. Grizzly Bear Mom

    I lead perforamnce for a large government agency. OUr perforamnce management system demands high standards from its employees merely for them to “meet expectations.” It is not logical that the same person would continue to be excellent or outstanding regardless of work assigned. Those appraisals are earned anew each year. Additionally according to the Federal Office of Personnel Managment 3% of employees are problem employees, but not one in 3,000 fails their perforamnce plan. The system is skewed artificially high with more excellent appraisals than meets expectations one. (And no we don’t have great or particularly adequate leadership) Appraisals should look more like a bell curve. However this supervisor sounds like a jerk. I worked for one who would tell me to write briefings but wouldn’t specify on what, and would the one page emails of why we shouldn’t do it that way. I recommend that this person study his organizations perforamnce plan to see how each level of perforamnce is described, and ensure he can demonstrate that he has achieved that standard. It sounds like this person needs to call in a mediator. It sounds like the superivsor doesn’t think anyone is as good as the supervisor is, and won’t advocate for you of all in the division to get the high appriasals if it came to that.

  14. Nancy

    The problem could be easily solved by allowing the employee to give reverse feedback to the manager. Unfortunately, that never happens in Dilbert run offices. That is why American business is so broken. Read up on CNNs recent article about the prevelance of psychopaths and sociopaths in upper management and realize for the most part this is not an “employee” problem.

  15. Adrian

    I have this manager as well. I’ve worked for her for 10 years and I think she has given me an Exceeds rating maybe once, even though I do about 30% more work than anyone else in the group. I am in a different state and have a great team leader, so she actually only speaks to me about 3-4 times a year and each time I come away so defeated and discouraged that it takes me about a week to get back on track. I think she just has very poor people skills and totally unrealistic expectations of what an Exceeds rating is. Last year, I disputed the rating and left a detailed comment of what I had accomplished and what awards I had received during the year. She had not documented a single thing I had done wrong, or could have done differently, so I think anyone looking at the review would realize that she had rated me inaccurately. I know I should have a conversation with her, but it is like dealing with a human bulldozer and I just don’t know if I’m up to that. We’ve been promised a new manager for over a year now and I keep hoping it will happen before review time, so I can get an unbiased review.

  16. JB Weld

    @Melissa you sound like a typical wage slavedriver.

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox