How to Survive the Difficult Boss

by / ⠀Startup Advice / March 14, 2022

angry-boss-2Let’s face it.  We don’t like being told what to do.  As GenY’ers, we want the freedom of choosing our own path, often down to the very last detail, which is why entering the real world can sometimes be a bit rockier than, well, the baby boomers’ entrance.  However, whether you work for a large corporation or are self-employed, to be successful you shouldn’t only tolerate, but excel when it comes to working with others, and choosing to not associate with someone who you despise simply isn’t an option.  Assess and understand a difficult work relationship, implement some new actions, and before you know it you’ll find yourself going from hiding behind the water cooler, to suggesting a drink after work.

1. Understand the Problem

Find a pattern.  Is your boss being difficult especially on Monday mornings?  Just because you’re the employee and subordinate, don’t underestimate the power you have to empower your boss by proactively contacting them before they contact you.

Ask yourself: Are they being difficult to just me?  Or everyone?  If you feel as though you are meeting their expectations, make an appointment saying you’d like to talk and get some feedback so you can see where you can improve your performance.  Get to know what their expectations really are.  Give them a free checkpoint to evaluate you.  They’ll most likely see you as mature enough to take ownership and you’ve immediately shown that you are trying to understand them.  We usually expect the boss to tell us when something is wrong, but they don’t always do this, so this is your chance.  Also, don’t bring anything up at the very start of the week or near big deadlines.

2. Don’t Take it Personally

Perhaps upper level management is constantly on your boss’s case and they are then taking it out on you.  Maybe there are personal issues they are experiencing at home.  By staying professional, you automatically eliminate any unnecessary emotions.  Remember, it is not their goal to make you miserable.  Be objective.  Discuss the situation with someone outside the company who is in a higher level position and ask for their honest sincere opinion.

3. Assume You’re the Problem

For a moment, step back and tell yourself that you are the problem.  This can benefit you in several ways.  First, you now become the one in control and the situation isn’t just a cause-and-effect.  Second, you allow yourself the ability to change the difficult work relationship.  For example, when appropriate, reach out to your boss to seek what they’re expectations are for an upcoming project before you even begin.

4. Keep the Line of Communication Open

If your boss overreacts, stay calm and professional.  Just like the customer’s always right, so is the boss.  Often we think we must have consensus on everything and our ideas must be heard, but remember the office is not a democracy.  We can only expect a good boss to give us an opportunity to provide input.  At the end of the day, it’s their decision and we must respect it.

If you’re waking up every morning absolutely miserable, then it’s time to make a change.   When talking about your past, always focus on the positive aspects of your experiences; you don’t want your past to be perceived as a negative attitude.  See if there are openings within your organization that you can apply for or maybe you can afford to be on the job market for a few months as you look for a new job or launch your dream start-up.

Uptin Saiidi is the author of the Life-After-College blog, Eruptin.com. He graduated from the George Washington University in May 2008 and currently works as an analyst at a media company in New York City.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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