Getting along with Difficult Employers

Remember Sam Malone from “Cheers,” Donald Trump from “The Apprentice,” Jack Shepard from “Lost,” Simon Cowell from “American Idol,” Michael Scott from “The Office” and of course Ebenezer Scrooge? What all these TV characters have in common is that they are bosses. They do differ in some ways. Malone is considered a fun and amicable boss and Shephard is seen as smart and caring, notes Rosemary Haefner, Vice President of Human Resources at But the others named are judgmental, nasty and conflictive. If you were to compare your boss to these TV characters, who would he/she be?

With the unemployment rate forecast at 9.6% in June (according to the Financial Forecast Center, LLC), anxieties, pressures, depression and negativity can build up and affect everyone in the workplace. Employers and employees are being asked to do more with fewer resources, often resulting in conflict.

Even in good times, conflicts between employee and employer are inevitable, says Ramon Greenwood, head career coach at If you are a get-things-done employee, sooner or later you will come into conflict with your boss or supervisor as you move ahead on your career path. The same sort of assertiveness and confidence that can lead you to career success has helped your boss earn his/her position. But sometimes conflicts cross the line and can prove hazardous to your health or your career, if not handled with common sense.

Have you encountered any of these sticky situations at work?

Your boss:

  • frequently loses his/her temper, maybe even to the point of abusiveness
  • makes outrageous demands, like expecting you to work all weekend
  • continually asks you to pick up his/her dry cleaning or do other chores
  • grumbles when you need to use vacation time
  • takes credit for your work
  • never provides positive feedback
  • favors certain employees and grants them special privileges.

Saying “no” or speaking up to the boss is very difficult for some employees. They fear it will ruin their relationship, appear disrespectful, or even cost them their job. So they avoid outright conflict, while simmering with resentment or anger. But with the right strategies, it’s possible to be candid and respectful at the same time.

  • Let your boss know you care about his/her interests.If you have a problem with your boss assigning extra work, say “no” diplomatically: “I’m afraid the additional assignments may be affecting the quality of my work.”
  • Focus on what you can do. If your boss makes an unreasonable demand, instead of saying “no,” offer, “Would you like me to cover your phone calls while you are out of the office instead?”
  • <When your boss criticizes you, don’t react out of emotion or become confrontational. Use the criticism as an opening for a discussion of interests, goals and solutions to problems, and ask for advice. A boss who criticizes your work probably has an idea of how it should be done and improved.
  • Avoid derogatory labels. It’s impossible to change someone’s personality; especially a difficult one. Don’t label your boss a jerk; just accept that this is your boss and try to find a constructive way to work with this person.
  • Examine your own performance and ask if you are doing everything right, before you blame or attack your boss.
  • Look for allies. If others share your concern about an abusive boss, their support gives you additional persuasion power. An interdepartmental alliance may work to bring about positive change.
  • Have a Plan B. If these strategies do not result in successful negotiation with your boss and if your job has become extremely stressful, have an “out” ready. Plan B would probably mean having an actual job offer with another employer in hand. An alternative plan empowers you with the ability to walk away, should the situation not change.

You don’t have to make your boss your friend, or even like this person. You do need to carry out instructions dutifully as a subordinate, just as you would expect your boss to be professional and fulfill his/her responsibilities as a supervisor. The best strategy is to remain professional and get the job done.