Managing A Difficult Boss, and How to Learn From One

Throughout a career in corporate America, and individual may have 30+ bosses.  They come in all shapes and sizes, interests, pet peeves, dispositions, and intensities.  Assuming you are a generally amiable person with adequate people skills, a minimal ability to read non-verbal queues, and a smidgen of adaptability, you will find most of your bosses to be bearable, if not down right agreeable.  After all, most people are good on the inside…right?

Out of those 30 or so bosses, there is a chance that you will be reporting to someone that just absolutely rubs you the wrong way.  You don’t see eye-to-eye on anything from policies to politics to pantaloons.  Your ultimate antithesis.  Vader to your Skywalker, Luther to your Superman, or Kribke to your Sheldon Cooper.  You’re screwed right?  Nah, there’s good to be taken from this situation.

(The following assumes that your new boss is not down right evil.  A bad person.  Or an ax murderer.  If you find this to be the case, report them to HR or quit.)

First things first.  Identify why you don’t like your new boss.  Look very carefully.  It is likely that he/she is better at some part of the job than you.  For example:

Carter has been a notoriously slow closer of big sales deals.  He ultimately gets the job done, but his efficiencies compared to some of the top sales people is lacking.  The new boss, on the other hand, closes deals fast.  He never gives the customer a chance to say no, and it seems as though he will say almost anything to get a deal done.  In the end, his productivity is best in class.

Carter has to face facts.  It’s not that the new boss is a bad person.  He’s not doing anything unethical or even misleading the client.  He’s just doing what an aggressive salesperson does…..close deals without emotion.  Carter takes a much more modest approach because an aggressive approach doesn’t fit his skill set or personality.  Carter needs to do one of two things:  1) Learn from it an appreciate the unique styles of other individuals or 2) Be bitter about it for the rest of his tenure under the new boss.  I choose #1.

Secondly, you have to understand where your boss is coming from.  What are the expectations from the bosses boss?  What goals are laid out for him?  What past positions has he held in the past that helped form his current style and opinions?  We are often products of our last position, bosses, experiences, and influences.  Try to understand his perspective and view the workplace through a different color lens.

After you have figured out where the new guy is coming from, you may better appreciate his perspective and approach.  If you choose to be critical and analyze every little decision this person makes, I urge you to make sure you are holding yourself to the same standard.  Take a good look in the mirror and convince yourself that you have the highest level of integrity and have never made a mistake.  Good luck.  Everyone makes mistakes.  Everyone lets their guard down for a moment or two.  Don’t make a final judgement based on a single act or decision.  We’re all human.

Lastly, learn from this person!  Whether you like it or not, this person is your boss and likely excels in an area or two that you do not.  Put your pride on the shelf and objectively analyze the results based on the goals of the position.  A good manager is always seeking feedback on their weaknesses and working to improve upon them.  Reach out to your boss directly and ask for feedback.  Brace yourself for his candor and take the comments to heart.  Validate the comments by asking the same of your peers, HR representatives, or friends.  You may be surprised to hear a consensus.  Accept the fact that you have areas you can improve on, and build a plan to do so.

When you find yourself in a position where you just can’t get along with your boss, remember to take the emotion out of it and try to objectively determine why.  Remember that when your weakness is someone else’s strength, it can become aggravating and cloud your judgment.  Open up your mind and work to improve the relationship.

Or……you can just go on be miserable and ultimately quit or get run out of your position.  It’s up to you.  Expand your influence.

Love it?  Hate it?  I wanna hear about it!  Comment below or email me direct at


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