12 Ways Bad Bosses Lose You Money

Updated: Feb 26


The Bad Boss would be a cliché were they not so widespread and destructive. At their mildest, they may simply be ignorant of the damage they cause. At their worst, they may be, let's face it, psychopathic, malevolent narcissists, who blithely leap from organization to organization, carefully covering their tracks, leaving destroyed organizations and lives in their wake.


As an executive leader, it is critical that you learn to detect and root out bad bosses. Preferably, you should develop the skills to screen them out right from the interview stage, but that is a topic for another time. Here, I want to focus on a dozen ways they pad their pockets while being a cancer on your organizational bottom line. If you see any of these symptoms, you may have a bad boss in your ranks as a root cause.

  1. They drive away good people through bullying and intimidation. Consider how much money it costs to find, recruit and onboard high quality talent. Nobody hits the ground running, at 100% performance levels, on the first day. Once they reach their stride, your people are, by far, your greatest strategic advantage. The old chestnut of "our people are our greatest asset" is, sadly, only lip service within far too many organizations, who look only at the latest sales figures. Bad bosses encourage this skewed priority, and use it, often openly, to dehumanize the workplace. Know this. The people you need, to succeed as a business, have options as to where they work. They also tend to be loyal, which bad bosses abuse, but, ultimately, will walk away. And tell everyone they know. And yes, there are companies that have been blacklisted by the talent you need, on career websites.

  2. They create toxic work environments through workplace harassment. Workplace harassment is against the law in Canada, the United States, and within the European Union, among others. But, on the ground, in the real world, it is rampant. From overt sexual and physical harassment, to passive aggressive suggestion, withholding of promotions and resources, or simply being ignored, bad bosses ultimately create such toxicity within your culture that you lose all the passion, discretionary effort, and sheer people power you need to maintain and grow your business.

  3. They lie to you. All the time. At a minimum, they selectively feed you information about what is really going on, always having some way to spin the facts and distract your attention onto something else. At the worst, they make things up as they go along, telling you what they need you to believe, supported by opinions presented as facts, with fabricated numbers and invented quotes from others that they know you won't actually check out. Bad bosses are often sly storytellers who ease your fears and reduce your need to actually follow up on your own.

  4. They play favourites, imposing unreasonable deadlines on others to create professional failure in those they do not like. Bad bosses demand personal loyalty to them, not only as the most important quality in their people, but the only one that matters. Talent doesn't matter. Facts don't matter. Skill sets don't matter. The company doesn't matter. You don't matter. Those who provide them with unfailing, toady obedience are rewarded, for now. Any infraction, real or perceived, will put anyone on the enemies list, at any level of your organization. Bad bosses are populist dictators.

  5. They take the glory for the accomplishments of others, while always having a way to blame someone if their own ideas fail. Much has been written about this. One way to identify a bad boss is how often they use the word "I", rather than "we", when discussing achievement. Conversely, bad bosses will always have a "they", "her" or "him" to blame for failures. In fact, the double whammy of a bad boss with evil intelligence will deliberately design all situations and scenarios to create these outcomes, in advance.

  6. They interfere with the relationship building done by their people with key clients, who then leave you when that person is gone. When your highly motivated, diligent hunter and farmer sales and technical support people have built a successful relationship with a client, the bad boss will horn in on it and take it over, often with the message that this "key account" merits executive level service. Conversely, when they sense a client relationship is failing, they will foist it upon one of their people, masked as a "great client that I am gifting to you." Of course, if the relationship is unfixable, the bad boss has someone to blame. Do this enough, and your company loses both the talent that built the relationship, and the client. If everything discussed so far is already happening, your good person may simply quit for your competition, or become your new competitor, as soon as the writing is on the wall. And the client follows them. Your real product is your people. They go, your business goes, too.

  7. They interfere with idea generation, insisting on always having their own way, often turning a good idea into a bad one. Shrewd people working for bad bosses learn very early on that the best way to get a good idea through is to make the bad boss believe it was their idea. Even then, once in the hands of the bad boss, they will muck it up, simply because, while they have none of the hard fought, hard won expertise of their people, they unshakably believe in their own innate superiority at everything. In very short order, people will keep their best ideas to themselves, smile and nod at the increasing ego-speak, and put their resumes on the street.

  8. They don’t care about anything but their own gains, anyone but themselves, and everyone who works for them sees it every day. Bad bosses almost universally suffer from the delusion that nobody knows what they are really up to. But the simple fact is that they are fooling no one who actually works for them. Conveniently for them, they really don't care about that, because as long as they are fooling upper management and the clients, that's all that matters.

  9. They cozy up to power, both internal and among your clients, convincing them what a wonderful person they are, while trampling everyone over whom they have power. This one is insidious. When you work for a bad boss, you will often hear, in meetings, a very different version of events than what actually happened. Sometimes you will hear it from a client; sometimes, from a senior executive at a quarterly status meeting. From the bad boss, their people will hear about all the social events they were not invited to, personal and professional favours, and accolades bestowed on the bad boss by people of influence and power, with zero credit to the team. This creates understandable anger and bitterness throughout that team. That, in turn, can sink your business. Go watch the movie "9 to 5" for a great summary of this point.

  10. They distrust facts, and suppress those who disagree with their world view and opinions, creating a culture and practice that is detached from reality. Over time, bad bosses create an organizational culture that is quite detached from client, product, and business realities. If high enough in the organization, they carve out an organizational world view that is increasingly inflexible to change. When the real world moves on, either incrementally or through the emergence of a technological or societal disruptive innovation, your entire organization may simply be unable to withstand the shock wave of the adaptive cycle. Think about the top companies in any market sector 30 years ago. How many of them are still at the top of their game? How many are still around?

  11. They short circuit your succession planning by reducing the workforce to toadies. Succession planning is, or should be, a Top 5 strategic priority in any business. On my very first day in my first management role, my boss told me my number 1 job was to identify and train my replacement. I was more than a bit taken aback. But then he explained to me that the company didn't want me to be stuck in my current role forever, any more than I did. If I failed to develop the next generation, the company would not be able to promote me. I took this to heart. Bad bosses destroy succession planning through everything I've described so far. They create a sad reality of their own indispensability. Then they leave you, anyway, stuck with zero options but to hire from outside.

  12. Bad bosses make a lot of money, your money, while providing little or no measurable value that can be traced back to just them. They keep making more money by doing all of the above, meeting or achieving short term, short focus goals like revenue, and concealing the long term, and often, irreversible damage they are causing to your company. When it looks to them that you might be close to realizing this, they jump ship to your competition, using a heavily leveraged and false resume, extolling their accomplishments and leadership skills, for a whole lot more money, leaving carnage in their wake. They may even have convinced you that the person you need to put in their place is someone just like them, who is now in their debt for “helping them with their career”. The only silver lining is that you are finally rid of them.

At the end of the day, as an executive leader, you have to ask yourself, "can we afford bad bosses?" If it is simply a matter of training, coaching and mentoring, that's one thing. If it's more than that, you need a strategic plan. We can help you either way.


Copyright 2020 Jason Questor. All rights reserved.

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