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    “Great graduation present!”

    Inspired to extend a helping hand to ambitious women working in corporate America, a veteran executive offers honest, practical, slightly irreverent advice about navigating companies that are run and populated predominately by men.


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    Learn to see yourself as others do and become magnetic, magnanimous, and memorable! Savvy advice, specific examples, and tactical exercises to develop your presence—in months, not years.

  • About the Author

    Jennifer K. Crittenden earned an MBA in finance and worked for over twenty years in the US and abroad, rising from financial analyst to chief financial officer. She is the author of five books, including the award-winning Discreet Guide for Executive Women. She offers professional development programs through her company The Discreet Guide.

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Do You Have the Right Boss, as an Individual?

Since my training programs include interpersonal skills, it’s no surprise that my clients and I often spend considerable time dissecting their relationship with their boss. What is surprising is how bad those relationships can be, sometimes really dysfunctional and toxic. And although it can take two to tango—that is, there are times when both parties have contributed to a nasty relationship—there are other times when the boss is so awful that I wonder who on earth thought this person was capable of being a manager.

There was the guy, for example, who, upon learning that his subordinate was going through my training program, said, “Why? So you can be that much better than me?” Really? Or the guy who told my over-worked client when she asked for additional staff, “This is how we test people here at [insert bad company name here]. If you’re not exhausted, you’re not working hard enough.” My client was black—did her boss fancy himself a slave owner? How about the CEO who used the organization’s funds for personal travel and then complained to the board that the COO had established weak travel policies? Who are these people, and more importantly, who let them be in charge of someone’s career?

The more I study organizational effectiveness, especially through the eyes of my clients, the more convinced I am that corporate America across the board demonstrates far too great a tolerance for poor managers. This is disappointing because over the last two decades, we have learned in detail how to manage people—how to motivate, mentor, support, and develop employees. We’ve got business schools, training programs, coaching programs, supervision certifications, innumerable leadership publications, endless articles on performance reviews—every aspect of management, from hiring to firing, has been analyzed and documented to death. It turns out not to be rocket science, and much of it is intuitive. Nevertheless, we are still allowing mediocre, limited, untrained, and sometimes just plain mean managers to damage, frustrate, and undermine our employees. Occasionally, I wonder if these people were this bad at the beginning of their career or if, like xxx in South Park, the hall monitor attitude developed when they got themselves a little “authorité.”

One recent survey showed that the majority of employees would knock $5000 a year off their salary if their boss would just be a little nicer. That hurts. That means these bad bosses are literally costing their companies money, besides contributing to poor morale and high turnover. Quantifying the cost of bad bosses would be a daunting task, but it’s not hard to imagine that it could run in the millions of dollars, even for medium-sized companies.

But what does that mean for you if you find yourself working with someone whom you don’t like? While these dire statistics may let you know you’re not alone, that can be cold comfort as you face work on Monday morning. For most people, the honest answer to the question, “Do you have the right boss?” is a resounding “No,” simply because most people don’t have very good bosses. Then the question becomes, “Is my boss tolerable? Or good enough for right now?” We don’t know the answer to this question until we have committed ourselves to attempting to improve the relationship. That takes work, and my hat is off to my clients who begin what will certainly be a difficult endeavor. Note that I am not asking if the person you report to is the logical choice from an organizational standpoint. That question is addressed in “Do You Have the Right Boss, Organizationally?”

The first step is to look on the bright side. Reporting to a messed-up individual is not without its benefits because it gives you the opportunity to learn to work with difficult people, which is a valuable skill. I often hear, as you probably have, someone say that they learned a lot from working with a terrible boss. Of course, that’s usually in retrospect, after the fact, when some of the pain has faded. Nevertheless, important techniques can be practiced and honed when you have to work with a challenging manager, such as learning when and how to confront, how to bring up sensitive topics, practicing disengagement, remembering the bigger picture, taking the high road, learning self-control, when to be silent and when to yell back…These are all skills we work on in my program.

Another useful consideration is to analyze whether you yourself are contributing to anineffectual relationship. In my first book, The Discreet Guide for Executive Women, I outlined some pitfalls to avoid, especially when the superior is male and the subordinate is female, such as when the male boss attempts to turn the subordinate into his wife, mother or secretary. It’s easy to fall into these roles because we have been socialized to respond that way to one another. They are however not appropriate for professional interactions.

Sometimes, my clients have fallen into other kinds of habitual behavior with their bosses. As in other close relationships—and if you are working together five days a week, it is a close relationship—they react to certain triggers they way they’ve always reacted, even if they recognize that it’s not productive. If one starts yelling, the other starts yelling. One starts complaining, and the other falls silent and sits unresponsive, getting depressed. One never gives a word of feedback; the other never asks for it. One holds a grudge for years; the other never attempts to clear the air. These are all ways in which we allow each other to get away with lazy behavior. It takes courage and hard work for my clients to break these habits and try to turn a poor reporting relationship into a more functional one.

If you’re still invested in trying to fix a relationship, it’s an indication that there’s hope, that there’s something worth salvaging. A guy who was in a troubled marriage once said to me that the hard part wasn’t figuring out how to save the marriage, it was deciding whether or not he wanted to save it. Those insightful words resonate in my ears when I’m working with a client on issues regarding his or her boss. At what point do you throw in the towel and say it’s time to move on?

Ideally, I would prefer that a decision to change jobs is based on position-related factors: a promotion, more money, new experiences, a geographic move, other issues. Until those stars line up, I would prefer that you continue building skills that improve your relationship with your boss. Partly, I don’t want to give a bad boss that much power—why should a jerk drive you to give up a good job or opportunity? And often, I’m hopeful that a client’s situation will change, the jerk might quit, the client could get promoted away from the jerk, or who knows, maybe we’ll get lucky and the jerk will get fired. And often, based on my experience so far, the client was right to stick it out—something did change. In the case of my examples above, the CEO eventually got fired, my client was transferred away from the slave driver, and the first client found a way to tolerate the paranoid, small-minded boss, and shine despite him, until her potential was recognized by upper management. They all say that they learned something from the experience of working for an inferior manager and are better equipped to handle the next one.

The best way to restate the “Do I have the right boss?” question is to ask instead, “Have I tried everything I can to make this relationship work?” It’s easier to try new ways of behaving when you have someone like me by your side, but I’m sure many of you can come up with new ideas and creative strategies to turn a relationship around. We can dream of being able to move on to a better boss, but with the statistics we have available, the next one is likely to be as bad as this one.

© 2016 Jennifer K. Crittenden

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