Strategies to Work Effectively with Tough Bosses

Dec 7, 2021

Over the course of your career, you’ll have to work for some bad bosses, because, well, human nature. Some people are selfish or shortsighted, and others just aren’t aware of what they’re doing. There are so many different flavors of shitty bosses that it’s hard to address the subject without writing a whole book, but I want to address one broad category: The playground bully.

Bullies have power over people around them. On the playground, it’s size/strength and in the workplace it’s formal authority. In both cases, we must learn to work around that power. If I learned nothing else from my childhood, it is this: Beware of reaching upward for help. When a child seeks protection from a teacher or parent, bad things can happen. The bully gets in trouble, but that doesn’t take his power away. It just makes him mad. Likewise, going over your boss’ head for anything short of criminal activity is just like tattling. You better expect an ass whipping to follow.

Dealing with a bully requires a deft combination of social intelligence and inner strength. Always be respectful. We should deal with all people respectfully because that’s just being civilized. But when somebody is bullying us, it can be hard to remember that courtesy isn’t just good manners, it’s also good strategy. Showing defiance or anger just provokes people. Prey who resist are more fun to smack down. But most people are quickly disarmed by kindness, respect, and flattery. Being nice is surprisingly powerful.

Whether it’s your lunch money, extra last minute shifts over a holiday, credit for your work, or even just seeing you squirm, bullies want more than just respect, else there would be no problem. The solution is making yourself a stronger, less appealing target.

Start by looking at yourself. Are you a hard worker? Do you meet your commitments? If you do good work, then you have value, and value is power. Next, take some time to reflect on what is important to you. What will you accept, and where is the line you will not cross? When you are clear with yourself, then when somebody pushes your boundaries, your real psychological resistance will give you strength. Take a stand, and be prepared to accept the consequences.

Not everybody can afford to quit a job, even when a terrible boss makes life difficult. If you’re in a bad work situation, you must create options for yourself. Search relentlessly for new jobs. Even if you don’t want to quit, having alternatives will make you better able to defend your boundaries and demand better treatment. When you have options, and you are willing to walk away, you don’t need to take anybody’s shit anymore. I am consistently amazed by how well this works.

Finally, I’m a big fan of transparency. Gossip (as long as it’s true) is how we hold each other accountable for bad behavior. Inside a company, warning peers about a bad manager will subtly erode his power. Externally, you can post reviews online. I love the website Glassdoor, which lets employees anonymously review employers. Bad bosses will have a harder time attracting talent once people are aware of their behavior. Making you harder to replace increases your value to the bad boss and your power in the relationship. Don’t forget to remain polite and respectful. People are more likely to believe you when you tell the truth without seeming disgruntled.

Whenever I have to deal with a bully, I remember my playground days. Bullies are just children who never grew up, and they can be outmaneuvered. While I’ve focused here on a particular type of bad boss, I think the advice holds true for all bosses. Be polite, expand your options, and honestly share your experience with your peers, and you will steadily improve your situation.

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