7 Signs Your Boss Is Old School – And How To Deal With It


The Old Boys’ Club

Time marches on, but some managers don’t march with it. There are a ton of personalities that end up working in management, but the old-school boss is one of the more difficult to deal with. You’ve probably seen the old-school character at some point in your working life: He expects employees to drop whatever they’re doing if he needs something, doesn’t think telecommuting is a real thing, and can’t understand why someone wouldn’t want to come in on Saturday. His calendar says 2015, but his attitude toward female employees says 1950… and he may or may not keep bourbon in his office. This personality varies across industries, but managers of this flavor remain sprinkled across modern organizations to differing degrees.

How can you tell if your boss is one of these old-school thinkers?


1. Your boss won’t allow telecommuting.

Modern managers realize the benefits of allowing employees to work from home, even if it’s only once a week. Reduced stress, better life balance, and cutting commuting costs are all good for both employees and business. The old-school boss thinks that presence in the office is equal to effort, and these telecommuters are at home slacking off in their PJs in front of the TV. If you’re trying to negotiate telecommuting with an old-school boss, be sure to present data and records of accomplishments working from home. It’s hard to argue with numbers!


2. Work/life balance is a foreign concept.

Back in the day when most households lived on a single income, a wife at home meant domestic responsibilities were taken care of. A company man in the office wouldn’t need to go pick up his kids from school! Fast forward to 2015 and the modern two-income household, both partners need some flexibility to handle life outside of work. A sick kid or an exploding water heater can’t take care of themselves, but the old-school boss doesn’t always recognize the importance of balancing work and everyday life. Appeal to your boss’ emotional side, and try to draw parallels between your needs and previous situations when your boss needed help or time off. It doesn’t always work, but it can be worth a shot.


3. Leaving at 5pm sharp is frowned upon.

Do you feel pressured to stay more than 8 hours per day in the office? An old-school boss will often see leaving on time as a sign that you are not committed to your job. Same goes for lunch, as these bosses are often disgruntled to see employees take leisurely lunch hours outside the confines of the cubes. To appease your boss, make it a point to arrive early (say 8:30am), and send out emails or otherwise be noticed before the working hours commence.



4. His body language communicates superiority, and not in a good way.

Body language often conveys more information than anyone’s words. Does your boss physically dominate you by standing over you at your desk? The old-school boss will subconsciously try seem bigger than you, much like outdoor experts tell campers to create the illusion of being large to an approaching animal. He might not even be aware of it, but this is a good sign your manager is trying to rule with fear rather than lead by example.

Does the word “condescending” come to mind? Old-school managers will often disregard your opinion or ideas with body language, turning away from you as you speak or otherwise communicating a lack of interest. Respond with your own body language, by asserting a dominant stance and looking your boss in the eye. Don’t shrink back physically when your boss is speaking with you, be sure to assert yourself as an equal.


5. You’re expected to drop what you’re doing if called upon, even for superfluous personal requests.

Have you ever been absorbed in a task, and your boss calls for something unimportant? How would he react if you said you were busy? The old-school manager doesn’t care if you’re busy, because in his mind whatever you’re doing is less important than what he needs NOW. Whether it’s a lunch recommendation for clients, an empty water cooler, or an actual emergency on an important project, the old-school boss expects you to be available for his needs at all times. Try to find a balance between being responsive and being abused; occasionally say no, or that you will attend to it in a moment, and justify why with a detailed explanation of the project you’re working on.

6. Despite your accrued vacation days, your boss won’t let you take time off.

You have two weeks of vacation time to use, but your requests for time off have been denied because “there’s too much to do”. Effective managers can easily redistribute workloads to accommodate employee vacation time, but the old-school boss likes to remind you of who’s in charge. Millions of unused vacation days go to waste each year in the United States, and it’s not always because employees don’t desire a week’s vacation. Old-school bosses take advantage of any way to feel superior to you, the employee, and denying requests for time off is the most obvious way they do it. Legally, a boss can’t deny you the vacation time you’re entitled to, so if this continues to happen you may need to contact HR. Otherwise, try to choose a season like Christmas-New Year’s when most industries have slowed down. It’s less likely that your boss will deny a vacation request if half the office is out anyway.


7. Your input is not taken seriously; or if it is, your boss takes credit for your ideas.

How many times have you been in a meeting, and your boss regurgitates your idea from two days ago that he said was “probably not going to work”? Have you suggested a workflow modification that would make a process more efficient, but have been told “that’s not how we do it”? Old-school bosses don’t like to change, especially if the change wasn’t their idea (or they can’t take credit for it).


My boss is old-school… now what?

Some people have the social skills to discreetly navigate an old-schooler’s personality quirks to get what they want. Others find they are constantly butting heads, and feel stunted by their bossy boss. Only you know what will make you happy, but recognizing a management style will help immensely when you’re confronted with challenges or new lifestyle adjustments (like having a baby).

What are some things your old-school boss did that drove (or continues to drive!) you crazy? Share your story in the comments.

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