How to Overcome the Challenges of a Bad Boss

If a difficult supervisor is making your work life miserable, it’s time to learn how to ‘manage up.’

How to Overcome the Challenges of a Bad Boss

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If you dread going to work every day because your boss is — in a word — bad, maybe this will provide a little solace: You’re not alone, not by a long shot.

For anecdotal proof, Google the phrase “my boss is killing me,” then make yourself some coffee and start perusing the millions of results. Or consider a recent survey conducted by, a global employment website, which found that 32 percent of employees rated their bosses as “horrible.” Moreover, 50 percent of the 2,555 respondents gave their immediate supervisor a ranking of one or two on a scale from one to five, with one being “horrible” and five being “excellent.” In stark contrast, only 15 percent described their manager as “excellent.”

Jim Clifton, CEO of noted analytics firm Gallup, conservatively estimates that there are millions of bad managers wreaking havoc on the American workplace. He bases that determination on Gallup’s periodic State of the American Workplace polls that consistently find a majority of American workers aren’t engaged at work, which Clifton views as a direct indictment of managers’ collective deficiencies.

But while misery may love company, it doesn’t do much to make your day-to-day work life any better. Dana Brownlee, a corporate-training consult and founder of Professionalism Matters, suggests taking another more proactive route: Manage up. 

“From what I hear anecdotally (at training sessions and seminars), you’re lucky to have one or two amazing, phenomenal bosses in your career,” Brownlee says. “They’re like unicorns. In my training sessions, I get a lot more questions about dealing with bad managers.

“Typically, employees think about doing their jobs. But unless you’re at the top of the food chain, you need to manage: Find a way to achieve the best results in spite of a difficult manager. Making life easier for a manager — taking things off their plate and anticipating their needs — all falls under the umbrella of managing up. People who fly up the promotional ladder tend to be good at this.”

To provide more specific solutions for boss-challenged employees, Brownlee has some strategies for managing up with three common kinds of bad managers. 



The first one earns the moniker the Tornado — a force of nature who likes to think he or she empowers staffers but instead runs roughshod over people during meetings, stifling new and innovative thinking.

Brownlee’s solution centers on talking with the manager before a big meeting. The purpose is to solicit the manager’s advice about how to obtain more candid feedback from a team. Like so many things in life, it’s all about context. If you go in and try to tell your boss what he or she needs to do, the reception may be lukewarm at best. Instead, be more strategic about your approach.

“You can point out how hierarchy makes a difference and that people tend to defer to what the boss thinks,” Brownlee says. “Tell your boss that you’re struggling with how to challenge the team to come up with new and interesting ideas.”

This softer, more preventive approach makes the boss still feel a sense of control over the matter. Equally as important, it preserves your relationship, too. 

“It also gives the manager the opportunity to be the coach — the expert or problem-solver,” Brownlee says.


Wishful Thinkers

Then there’s the Wishful Thinker who wants you to boil the ocean — by end of day tomorrow, please.

Dealing with this brand of manager requires doing some due diligence about the mission impossible with which you’ve been tasked. That means collecting data showing that the project the boss unrealistically believes is a slam dunk will actually take a lot more time, resources and money than imagined, Brownlee says. 

“The Wishful Thinker might not suffer from a personality defect,” Brownlee says. “It may be more of a case where the further up the food chain you go, the more removed you get from the day-to-day work, which distorts assumptions about things.”

It helps if you can gather objective data from a representative cross section of employees.

“Getting together with all the subject matter experts helps to quantify the risks of the project and makes your information more credible,” she says.


Clueless Chameleons

Then there’s the Clueless Chameleon — the supervisor whose best skill seems to be giving vague or confusing directions, or whose priorities shift more often than a NASCAR driver at the Daytona 500. This requires you to proactively probe with specific questions that help ferret out details omitted during the initial assignment. 

“The danger here is that just because managers aren’t clear about what they want doesn’t mean they won’t hold your feet to the fire in the end when their expectations aren’t met,” Brownlee says. “If you’re not getting clarity, you have to pull it out of them.”

Perhaps that requires making a mock-up of a report or spreadsheet or an outline of a project and asking for feedback, just to be sure you’re headed in the right direction.

“I also tell people to ask the three magic questions: What is your manager’s understanding of the task (be sure to repeat it back to them for verification), what will the final deliverable look like, and what are the first three steps you’re going to take?” Brownlee says. “These steps are helpful because your vision of what constitutes a business plan, for example, might be different from your manager’s vision of one.”

In other instances, this kind of manager may even be unsure of exactly what he or she wants, due to lack of experience or skills. If that’s the case, working the manager through a process of elimination to find out exactly what they’re looking for can be helpful.


Be Authentic

In the end, it’s how you express things that counts. Managing up requires employees to walk that thin line between Eddie Haskell-esque brown-nosing and flattery, and overtly telling someone stationed at a higher pay grade how to do their job. Yes, it may feel awkward at first as you step out of a certain comfort zone and try to be more proactive about the process.

“It’s not about sticking your nose into things you shouldn’t be,” Brownlee says. “I’m not talking about going in and trying to do your manager’s job. But when you’re put in a situation where you know there’s a problem and you’re not getting a lot of support, you still want to be successful. In fact, the more successful you are, the better it is for your manager.

“So you have to find the right approach, and there’s no one-size-fits-all solution. You have to do what feels the most authentic — customize your approach to fit the person with whom you’re dealing, and do some relationship-building along the way.”

During the process, you’ll learn new skills that will serve you well throughout your career. As Brownlee observes, it doesn’t take any extraordinary amount of skill to be successful when you have an amazing manager.

“But it requires another level of sophistication to be successful when you’re saddled with one of these types of bosses,” she says. “And the skill sets you develop will serve you wherever you go. I call it organizational savvy. It’s an element that’s hard to define, but it makes a huge difference in how successful you can be in an organization.”



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