Book excerpt: How to turn a bad boss into a good one

It’s another excerpt from my book, Brazen Careerist: The New Rules for Success. This is tip #33 : There Are No Bad Bosses, Only Whiny Employees.

Want to deal with a bad boss? First, stop complaining. Unless your boss breaks the law, you don’t have a bad boss, you have a boss you are managing poorly. Pick on your boss all you want, but if you were taking responsibility for your career, you wouldn’t let your boss’s problems bring you down.

Everyone has something to offer. Find that in your boss and focus on learning everything you can. Or leave. The good news is that in most cases, you don’t have to leave. You just need to manage your relationship with your boss with more empathy, more distance, and more strategy.

My favorite example of a managing a bad boss is one I had at a software company who refused to learn how to use a computer. I conducted most communication with him via phone, and I often played the role of secretary even though I was a vice president. He once said to me, “You’re such a fast typist!” And I thought, “You’re such a complete idiot!”

But in truth, he was not. He was a top negotiator of government contracts. I stepped back and recognized that he was overwhelmed with the prospect of changing the way he had been working for twenty years, and I was in a position to help him. I found that the more dependent he was on me for email, the more I was able to insert myself into high-level deals that he would not otherwise have let me in on. I helped him avoid having to change, and he taught me how to be a dealmaker.

It’s always important to weigh the benefits. A good boss would have learned to type and never would have thought of delegating his typing to a vice president. But I didn’t have a good boss. I had a typical boss – one with poor execution of good intentions. He had knowledge and skills to offer me as long as I could manage our relationship productively. I never expected him to manage the relationship for us, because I wanted to make sure I was getting what I needed out of it.

I could have spent my time complaining. There was a lot to complain about. Instead I always approached him with empathy and knew when to put my two cents in and when to shut up.

Aside from cutting a deal, he didn’t have a lot of management skills, and this gap left more room for me to shine. My solid interpersonal skills helped fill in what he was missing and helped me to get what I wanted: A (reluctant and difficult but ultimately) very useful mentor.

So take another look at the boss you call bad. Think about what motivates him: What is he scared about that you can make easier? What is he lacking that you can compensate for? What does he wish you would do that you don’t? Once you start managing this relationship more skillfully, you will be able to get more from your boss in terms of coaching and support: You’ll be able to tip the scales from the bad boss side to the learning opportunity side.

In fact, you should always hope for a little incompetence on your boss’s part. The hole in his list of talents provides a place for you to shine. The point, after all, and no one shines when they’re complaining.

Posted in Managing up, No image
26 comments on “Book excerpt: How to turn a bad boss into a good one
  1. Anna says:

    Let me just please say , congratulations ! I just spent the whoooooole night , literally ; reading your ENTIRE blog . I am fascinated , awed , feel tantalized and titillated with all these great nuggets of information . With some I agree , with some I do not . But I appreciate your candor , accessible language , hands on tips (the psychology!) , and the UN political correctness ! (Thank Sweet Holy Smokes !) . Amazing , amazing . Now that I have that out of the way –

    I waited , I patiently read . I read post after post after post . Undaunted a gleely googled (and yahooed and MSNed , even ASKED JEEVES) . I grew desperate , I pawed through page after page of "stuff" , and looked ; to no avail . I am a 21 year old college age student and a proud Polish-American . I have been (unconsciously  ) following your advise to a T. I said screw the high end U.N.I.V.E.R.I.S.T.Y. and the diploma; except with that piece of paper they forget to add the thousands of dollars of debt, the uncertainty of the entry level job in your "field" and all the glory . But hey , its Princetion y'know ? I went through a good state school for two years. And then –

    I said screw that also ! I threw caution to the wind and decided to be a glob trotter . A member of the cosmopolitan society so to speak . I applied to the 5 year masters in psychology program at Warsaw University. Everyone shook their head . Poland , with the communists roaming and vodka running in the streets everyone told me forgetaboutit . Well , Poland is flourishing and the old , totally un-American way to education is bringing my whole education to not a national networking but a GLOBAL networking level . I meet people from all over Europe, the Americas, Asia, Africa in conferences (and students here actually attend!) I gave up two years , scrapped my life in USA , quit my job (but not before saving, saving, saving!) Got a grant, and flew over , and never regretted it !

    I think, how many MA students of psychology will finish in X state school then work in X public school as a guidance counselor with X mortgage in the great American City of X that embraces college students with an X education . Why not expand my horizons ? Yes I chose to do the long haul , but a little known fact is that my credits, grades transfer and my diploma is recognized (I even qualify for FAFSA aid).

    In this new world of GEN X & Y you frequently talk about , expanding not only in themselves , being happy , and not going to grad school – abroad also an answer ? I am going to London for 5 months in a year ; and I plan to write my masters thesis in Sweden under a great professor I clicked with when he came as a visiting professor ? I am going to be staying in Uzbekistan with a dear friend I met here ; then I flying over to Bulgaria for a psychology seminar .

    What a great resume ? That's why I was so disappointed (to strong of a word , my apologizes , but I did mention I stayed up all nigh reading ) with the lack of interest, mayhap? In studying abroad , its cheaper in most instances, a ton of fun, amazing to meet people that say are from this and this country and speak like a zillion languages, the bar of excellence is higher – so why not ?

    I know America is the greatest country in the world, but USA has to stop being so arrogant, other places in this world are also beautiful and just waiting to be discovered and reaped for the NEW generation of glob trotters .

    Thank you,

    Anna

    * * * * *

    Hi, Anna.
    Thank you for your email! I love your enthusiasm — very fun to read.

    The first chapter of my book is about how important it is to travel. But you make me realize that I do not write enough about it on my blog. I will write more. Thank you for the suggestion.

    Penelope

  2. Recruiting Animal says:

    “I didn't have a good boss. I had a typical boss -one with poor execution of good intentions”

    But Gen Y is going to be different though, right?

    * * * * *

    I’m not totally sure what you mean here, but I think the problem of good intentions with poor execution is timeless. In all aspects of life, not just work. Execution is very hard.

    –Penelope

  3. Erin says:

    Great post. I’ve fallen victim to “a boss [I am] managing poorly” and it brings me down every single day. But complain no more.

    To poorly adapt a great quote: “Ask not what your boss can do to bring down your day; ask what you can do to make yourself look better.”

    What a good post for a Monday morning.

    * * * * *

    Love that adaptation. Thanks, Erin.
    -P

  4. Danielle says:

    I totally agree with the managing up philosophy. I worked in a warehouse for 4 years, not really part of my career path, but one of the most dynamic learning experiences as far as office politics. I had a boss who’s motto was, “Always look out for number one.” So I made sure that I always looked out for his best interests and made him look good. Granted, sometimes I wanted to ring his neck — as did some of the other guys that I worked with. But I knew that his priority was to make the numbers come out right – no matter what it took. I would never run things the way that he did, but I most certainly learned a lot from him.

    That being said, this is completely off topic: Do you have a comprehensive list of all the books you reccomend in Brazen Careerist?

  5. AlmostGotIt says:

    Great advice. The sooner we learn how to live (and work) with dysfunctional people, the better. I would add a couple of caveats, however:

    1. Be sure you ARE weighing the benefits and getting what YOU need out of it. The career world gives you no points for being a martyr/masochist.

    2. If you do need to leave because of a bad boss (and statistically, our years at a given job get shorter all the time) be impeccable with your timing. It’s best to get the next job in place BEFORE you leave, but it’s also best to leave BEFORE things get so bad with your boss that you start acting out… or are permanently damaged!

  6. Stephanie says:

    Penelope,

    I love reading your blog and I agree with you on this post to a certain extent. Most bosses aren’t as bad as some employees think they are. In fact, I would say that there are times when employees think the boss is the problem, when in reality, the boss may be trying to implement good changes while employees are trying to hold onto the status quo because they fear change.

    However, there are some instances of really bad bosses. Bosses who can’t be “managed up”. Bosses who could be described as toxic. I’ve run across a few of these and no amount of management will work. The best option is for the employee to leave the situation. Toxic bosses will act in a way that is hurtful to the employee or the employee’s career — often through manipulation, deceit, or through some other abusive behavior. These bosses aren’t necesarily incompetent — although, toxicity combined with incompentence is a horrible combination.

    How does one differentiate between the “incompetent good bosses” and the “toxic bosses”? Think about how they make you feel. If you simply feel frustrated with your boss or their behavior, then they are probably an incompetent good boss and can most likely be managed as you describe in this post. If their behavior makes you feel depressed, burned out, incompetent, abused, or fearful, then they are probably toxic and you need to get the heck out of that situtation.

    Just my two cents on the issue. Keep up the excellent writing!

  7. Cara says:

    Stephanie makes an important distinction that bears repeating: you can manage an incompetent boss, but you canNOT manage a toxic one. The key is knowing the difference. I’ve dealt with my share of toxic bosses and colleagues, ones who used personal attacks to undermine someone else’s credibility and reputation, passive-aggressive bosses, screamers, throwers, out-and-out chauvinist pigs who say, out loud, that the women they work with are all f— ups, ones who make sexist or racist jokes or nickname a male colleague “Homo” because he’s not a “man’s man” (yes, even in the 21st century), ones who don’t care that a boss is having an affair with a subordinate even though it affects work distribution. You cannot manage these types of people and situations. The only solution is to leave.

    * * * * *

    Cara,
    Yes, all these examples are very bad. But I’m afraid that in the list of awful things a boss could do, most are doing one or two. And I’m not sure it’s reason to quit. I have a boss who had an affair with one of my direct reports and asked me to give her better work while the affair was going on and get rid of her when the affair stopped. Insanity, right? (No, I did not fire her.) I kept working with him and I learned an incredible amount about running a company from him. In the end, we parted ways because I couldn’t take how he was treating people. But when it comes time to ask yourself if it’s time to quit, I don’t think the answer is so black and white. It’s complicated, and trying to manage your boss in a way that you can learn from him or her is part of that complicated process.

    Penelope

  8. Veena says:

    Also, to be successful in managing the so called ‘bad’ boss, the challenge lies in gathering loads of patience, employing all the oft spoken about skills like stress management and interpersonal skills to work while maintaining sanity, and then seeing the results.

  9. A Stressed Employee says:

    Penelope,

    I have read your articles on handling bad bosses, difficult co-workers, etc. I’ve also read other articles on other blogs about dealing with difficult bosses and co-workers. But I am stumped on my situation.

    What are your comments on my situation? Any advice?

    My boss poorly treats anyone lower than him in rank, while he sucks up to anyone higher than him in rank. He treats some peers with respect and to other peers he is two-faced.

    I guess overall he is two-faced. To most people (peers and higher-ups) he is nice and friendly to their faces, but talks down about them behind their backs. He uses me as a sounding board; I hear what he has to say about everyone. I am his only full-time direct report; he has two part-time college interns.

    I disgust the bad-name spreading by him of others; he thinks he is better than everyone. Although, most of the talk is about his peers or higher-ups, so I don’t feel the cost/benefit ratio of speaking up is worth it. He is very aggressive, confrontational, and vengeful. If I upset him, he watches a very careful eye over everything I do for the next few days and puts my work down or criticizes marginal behavior wherever possible–seriously; he becomes paranoid and untrustworthy of me in those situations; it’s weird and stressful; I am a trustworthy guy in all my relationships with people.

    But one day he bad mouthed one of my peers behind his back. This was the last straw; it was time for me to stand up for someone. Let’s call my peer, Joe. Joe is a direct report of my boss; Joe is a college intern. Joe wrote about 25 pages of documentation, per my boss’s request, for a new software application I made. Joe emailed the documentation to me and my/his boss. My boss kindly emailed back to all saying that he made a revision to the doc. Then my boss came over to my cube said emphatically, “Did you see Joe’s documentation? It SUCKED!”

    I was very upset. I defended Joe, saying that it didn’t suck, and that it actually was good work. My boss got upset and defended himself. Then I replied by saying that he shouldn’t talk about other employees like that, especially direct reports. At that point, I got too worked up and quit talking; I let him finish his words, and that was that. Mind you, at least other two employees heard this all from nearby cubes.

    It goes on. He forwards me email exchanges between him and peers or subordinates in which he is “winning” an argument/issue. He tells me how inept people are at work and why.

    He seems to be threatened by me and others. For instance, I recommended an improvement to a software design of his; then he recommended a different improvement on his own design and called my improvement suggestion “irrelevant.” I retorted with: well, responses like that don’t motivate me to give feedback to your ideas in the future; then he replied to me with a much more mature answer. I also notice his competitive win-lose conversational style in those email exchanges he forwards me with other employees.

    He seems to be very fear motivated and talks highly of his boss who is, according to him, a “ball-buster.”

    So, I sought help from friends and family. My objective was to learn how to deal with the issue; should I stay or go? If I stay, how do I deal with him? My friends and family either said stay or go, but no one had good advice on how to manage him.

    Next, I went to a counselor. She was not helpful. She didn’t really have much to say. She just pointed out the obvious, like he is physically unhealthy and possibly mentally unstable. It was my first time going to a counselor, so I didn’t know what to expect.

    Then, I escalated to HR. The HR lady did a great job of analyzing the issue based on my story. I asked her afterward, what I/we should do. She said she was meeting with someone else later that day with a similar issue. Hold tight.

    Cue Jane. Jane is very similar to me in age, rank, job description. She works for a different boss than me, but she works on some projects that my boss and I do. My boss thinks she is very inept and talks down to her and gives her the run-around as far as project cooperation. After months of this building up and getting worse, she finally stands up for herself. She talks back and demands respect. My boss, surprised and offended, zones out and walks away. Jane’s had enough of my boss.

    Jane escalates the situation to HR. She meets with the HR lady a few hours after I meet with HR. They talked for a good hour.

    The next day the HR lady says that more than two people have addressed concerns with my boss recently. She said it’s more of a subtle issue. She said she will have a talk with him. I can tell by my boss’s demeanor that she hasn’t talked to him yet; it’s been over a week.

    So, I tried to explain the situation as best I could without writing a book; I could write more and fill in more of the story. So, any comments or advice are welcome. Thanks.

    * * * * *

    Get a new job. It’s a great job market out there. Unemployment for college grads is less than 2%. Take all the energy  you’re exerting to take down your boss, and put it toward getting a new job.

    Penelope

  10. A Stressed Employee says:

    One more thing, regarding the story about Joe’s 25 page documentation: My boss only changed the introduction page. He replaced a crude diagram with a more sophisticated one, and replaced the laymen’s terms introduction with technical speak and buzzwords. I didn’t realize this until I brought the issue up to HR. He only changed one page, the introduction, yet he said that the whole documentation sucked. I would have reacted even stronger had I realized that on the day of the event.

    Thanks for taking the time to read this. I appreciate your feedback.

  11. ronnie says:

    this advice can turn someone’s career life around. the wisdom you have in this specific article really has some propulsion within itself. these are tips for career success, and the most practical i have seen. …thanks!

  12. Recruiting Animal says:

    “The sooner we learn how to live (and work) with dysfunctional people, the better”

    This just reminded me that Albert Ellis has a book from 1957 called How To Live With A Neurotic (which was the common Freudian lingo back then). I read it years ago and don’t remember much but I like his writing in general.

  13. Kathy Senescall says:

    Well, it is an interesting article, although I have had some bad bosses in the past, so I don't agree with the author on that point.

    However, making the point of controlling what you can and not dwelling on what you cannot is probably a valid one.

    Sometimes you need to start from scratch.

  14. Alan says:

    Very nice post. I think it’s an old lesson which we already know that before we judge someone, we must try considering first. Even with that, we still manage to forget about it probably because of the feeling we have which we prioritize..

  15. Andrey says:

    Penelope,

    The article proves advantages of communication and search for solution of issues over complaining about them. We should treat our work with passion and empathy, being thoughtful and intelligent while communicating and taking decisions.

    Though, many peolple would disagree with you that there are ‘no Bad Bosses’. We can see this from the story of A Stressed Employee, where even you advised ‘quit the game’. But there are also instances, when the bad gay is fired as an ‘irrelevant manager’!
    What will you say?

    Anyway, your instance is very enlightening. Thanks, Penelope

  16. Dunkirk Dave says:

    But what if your boss really IS an idiot? What if she is petty and/ or backstabbing and you can’t trust her? Then how do you ‘manage up’?

    I’ve worked for three companies before my current one and I know the difference between a great manager and a poor one.

    * * * * *

    The essence of managing up isn’t trusting your boss but understanding your boss. If you boss is not that bright, or not that nice, as long as you understand where he or she is coming from, managing shouldn’t be that hard. The hard part is if you refuse to take the time and energy to figure out what makes your boss tick.
    Penelope

  17. Fran says:

    I agree. We should learn how to consider. It could be bad at first but if we give it time, I think there will be some changes. Thanks for the advice.

  18. Anna says:

    While working with a toxic person (a**hole, compulsive liar, cokehead),I found hardly any advice from career writers and advisers about truly toxic bosses and coworkers, besides quitting. (I did quit a month after he became the department manager, promoted by one of his coke buddies. If a company is tolerating/denying drug cliques forming, its another sign to leave as soon as you can.)
    A lawyer advised me to start a daily journal when I start a new job and record the good and bad. Also to track my own work so it can’t be questioned in a dispute. Psychos, sociopaths, compulsive liars, and addicts drag bystanders into their dramas when they get called on their behavior.

  19. sarah says:

    Interestingly, I have a boss who – it seems – may indeed have been breaking the law. I feel all vindicated for all my whining now ;)

  20. A Stressed Employee says:

    Penelope,

    Thank you for your advice to get a new job. I put my resume online June 30, and by July 5 I got a new job with a 17% raise! Wow. Unemployment for recent grads IS low.

  21. Brooklynite says:

    Great piece– I’m a big fan of your book and blog. Do you have any advice for managing up in a situation where your boss is “afraid” (in his or her own words), to advocate for you when necessary? I work in a very large organization where, in order to get office equipment/amenities/ (all of which I need to fufill my job duties,) you need your supervisor to “nudge” higher-ups– which my boss claims to be too scared to do.

  22. Sherlock says:

    I really enjoyed the ‘How to turn a bad boss into a good one’ and i loved the example you gave about the software company manager. However, i disagree that it’s possible to turn every boss into a good one – I currently work for a guy who doesn’t show any appreciation for the work we do. He’s very quick to come down hard when he considers something hasn’t been done properly but will never offer any positive feedback when things are done well. Now this has made for a very poor working environment and non-existent employee moral.
    I fail to see any positive in this situation – the man is not for turning

  23. Aviva Gabriel says:

    I guess my comment was deleted?

  24. Pinka says:

    It’s impossible to change people. I’m lucky, because my boss is ok, but former boss was awful, and nobody can change him.

  25. samuel says:

    agree

  26. Carol Schilling says:

    I think this is “Blame the victim” mentality-bosses who refuse to look at themselves honestly. If a relationship is tilted in one direction that much, than it isn’t a relationship, it’s servitude. Shame on you!

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