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How Bosses Unknowingly Sabotage Their Employees

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There are truly horrible bosses out there; tyrants who undercut their employees at every turn, whether from insecurity, a sadistic streak, or any number of personality flaws. But mercifully, while those cases receive a great deal of attention in the press, they’re not the norm.

A far more common problem is bosses who, notwithstanding good intentions, unknowingly sabotage their employees. This can take many forms, but one of the most commons types of sabotage is unrealistic expectations around deadlines.

Many (if not most) leaders started out as frontline employees. They excelled in their individual contributor roles and, by virtue of performing their work faster and better than their peers, were rewarded with management jobs. It’s critical to understand this dynamic because lots of managers use the lofty standards they achieved as frontline workers to secretly judge their current employees. 

Imagine a manager who, when they were a frontline employee, completed reports in one day. Now, as a manager, they’ve been directed to give employees three days to complete the same reports. Whether consciously or not, a decent number of managers will think that three days is a bit ridiculous because they used to get it done in one-third the time.

They surely understand that not everyone has the ambition or ability to complete the reports in one day, but it’s difficult to turn off the judgment when they have proof that one day is an eminently doable deadline.

How does this become sabotage? When the boss sees employees failing to meet their standards, that boss is less likely to give employees the same career opportunities, mentoring and promotions that they received as an individual contributor. This is an unconscious form of sabotage, to be sure, but it’s harmful to employees’ development nonetheless.

This occurs more with some leaders than others. More than one million leaders have taken the test, What’s Your Leadership Style?, and the Pragmatist is more likely to fall into this trap than any other style of leader.

This type of leader has incredibly high standards and unashamedly expects everyone to meet those standards. This leader is competitive, ambitious and they prioritize hitting their goals over people’s feelings. As you might expect from that description, many famous leaders, including Jeff Bezos, Elon Musk and the late Steve Jobs, exemplify that style.

Employees who thrive on tough challenges and those with high levels of ambition are likely to respond incredibly well to this type of leader. And rather than viewing unrealistic expectations as a form of sabotage, they’re often going to perceive those expectations as a challenge to further their growth. But for those employees looking for a more relaxed workplace, those intense and unspoken expectations will often feel like sabotage.

Fortunately, there’s a quick trick to put a stop to this sabotage, whether it’s happening as a result of the boss’ conscious or unconscious thoughts.  The next time you get an assignment, simply ask your boss, “How long do you think this project should really take?”

By asking this question, you’re revealing the unspoken standards by which you’re being judged. If the boss originally told you that the deadline was three days and they respond to your question with “three days,” you’re likely fine. But if they tell you, “Even though I originally said three days, truthfully, I would probably have gotten it done in one day,” then you know what you’re up against.

You may not be able to meet that one-day standard, but at least you now know how you’re being evaluated. And if you can meet that standard, then you’ve just been given the key to absolutely wowing your boss.

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