How to Choose a Boss

How to Choose a Boss

by Jon Lederer

Choosing a Boss is very similar to choosing a significant other. Actually, if you truly think about it, you will probably spend more time making decisions to please your Boss than any other person in your life. If not, you are most likely looking for another job or you will be shortly. However, in my opinion, if you follow these basic rules, your chances of making a good decision dramatically improve. These rules are as follows:


On the interview, come in with a series of questions. It is essential to recognize that you are interviewing your prospective Boss as much as he/she is interviewing you.


Never choose a job without meeting your Boss and their Boss, too. It is not only important to get along with your Boss, but to understand the dynamic between the person you report to and their Boss (ask to speak to them separately — this way, your new Boss is not on their best behavior). This also enables you to see if there are discrepancies in what the position entails.


Go through typical day-to-day scenarios. How do you react in XYZ situation? If they respond similarly to you, certainly let the individual know that you would react in the same way (this illustrates that you are both on the same page). If he/she does not react in a way you like, reevaluate your position. You can love a job, but if you can’t interact with your Boss positively, the job is not worth it.


Watch the way in which your Boss responds to your questions. Body language is as important as verbal communication. Remember, your prospective Boss may love your resume; however, in six months, if you don’t get along, his/her memory gets extremely short.


Can you manage their expectations? The job may be fantastic, but your new Boss may not truly understand what it will take to be successful. Your approach, in solving issues, may be very different from the way your new Boss may solve the same dilemma. Politically, you can still get into trouble even if you resolve the issue.


Do your personalities clash? Be honest with yourself and say, “Can I spend the rest of my life with this person?” If your answer is no, then you better run.

Like all relationships, interacting with a Boss takes hard work, understanding, dedication and communication to make it work successfully. Only you can decide who is right for you; however, with all good decisions, knowing what you are looking for always makes the decision that much easier. Have questions or comments about Jon’s article? You can email him at
  Copyright 2003 Dale Kurow. Reprinted by permission of Dale Kurow, a career and executive coach who helps individuals find success and personal enrichment at their vocations and who works with corporations to maximize the potential of valuable employees. For more insight about her services and to take free career quiz, visit her web site, or email: This article is reprinted with compliments of Jonathan Lederer, VP of Sales of Popkin Software.