How to work effectively with a difficult boss


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    Key Books

    Power Freaks: Dealing With Them in the Workplace or Anyplace

    How to Manage Your Boss: Developing the Perfect Working Relationship

    Bully in Sight: How to Predict, Resist, Challenge and Combat Workplace Bullies

    Five Questions to Always Ask on an Interview

    Posted: 5/1/2006 8:13:03 AM

    These five questions go beyond the obvious ones, such as the title of the job, the job description, to whom it would be reporting, and other such basic questions. In fact, it's unlikely you'll even need to ask those questions, as they're usually outlined for you.

    With some preparation and thought, you should be able to easily come up with 15 - 20 first-interview questions to ask. But these five - in some form - should always be asked. Not only will they help you to ascertain if the job for which you are interviewing meets the criterion of your perfect job, but the answers, when put together, will give you a fairly accurate picture of what's really going on behind the interview.


    A title alone tells you nothing. The job description won't reveal much either, except whether or not you're capable of doing what's required functionally on a daily basis. For the same reason that you put your accomplishments on your resume - and not just the job description - here, too, you want to get a sense of the individuality of this job in this company.

    Was everything left running smoothly? Is it pretty much picking up and continuing daily functions as normal? Or is there damage control that needs to be done? If so, is there a time line for the repair, and is it an achievable one considering your capabilities? Is it realistic regardless of who holds the position?

    If you don't have any information, this will begin to clue you in about both the supervisor and the previous employee. If you have been provided with some detail already, then the answer should track with what you've already learned.


    Generally, in answering the first part, the interviewer will answer the second part as well. But if they don't, then ask it. And if that person was there an oddly short time, you also want to know how long the person before that was there.

    See where I'm going with this? If the job is in disarray, and the last two people were there a short period of time and were fired, you don't need to ask any of the other questions here. Exit gracefully and then run! Because before long, you, too, will be terminated for not achieving whatever it is they want done - regardless of if the stated time frame sounded realistic or not.


    Is he a micro manager? Is he an information hound that needs to be kept informed of everything? Does he leave people alone to do what he hired them for and simply keep on top of what's going on? Does he help you if you have trouble? Do any mentoring? Or is he a berating, derogatory, jerk?

    Obviously he's not going to come right out and tell you he's a micro manager! Instead he might say, "I like to keep a very close watch on what's going on in my department," or "I visit with each member of my department on a daily basis to make sure they're staying on track," or something similar.

    You'll find that the person will be fairly straightforward in sharing their management style with you. What you want to pay attention to is how they word it.


    Workaholics? Ones who are self-motivated and manage themselves well? People who work well in teams or committees? Employees who keep their supervisor informed of "where they are with things" on a daily basis?

    This tells you something about the pervasive culture in the company or department. Generally speaking, companies - or departments - tend to be made up of similar types of people that are in harmony with the company culture and philosophy.

    An entrepreneurial person won't function well in a committee environment. While sales personalities can vary greatly, the top achievers are goal driven and motivated to achieve, rather than complacent. People who are accustomed to thinking for themselves will find themselves chafing in a company that has a more dictatorial style, while those who perform better when they're told what to do will find themselves adrift in a company that requires its employees to think for themselves.


    The answer to this question will give you an indication as to the feeling or health of the department or company. The way in which he answers the question will also give you additional insight into your potential boss, his management style, and what type of people excel in the department or company.

    These are informational questions, not challenges. Be genuinely interested in the answer, because you're gaining valuable information that has to do with your future. When you leave the interview and process it within yourself, you'll be matching what you learned with what you are looking for.

    Pay attention to the interviewer's body language and facial expressions. Is he relaxed? Does he fill in some of the spaces? Does he speak TO you - or AT you? Does he answer the question briefly and then quickly fire off another one? These, too, are valuable cues, and after the interview, you'll need to piece them together with the verbal information you received.

    Your perfect job might land in your lap by grace and good fortune. But more likely, you'll need to look for it. It's there - but to recognize it, you'll need to know what it doesn't look like, as well as what it does.

    About the author:

    Judi Perkins has been a search consultant for 25 years in both the contingency and retained market, with a short stint in the temporary and local permanent placement markets. She has owned her own firm and successfully assisted numerous repeat clients in hiring all levels of management. Learn thousands of powerful concepts to find your perfect job at

    Email Link  |  iFaveIt

    Comments: [add a comment]

    User: anonymous
    Date: 3/22/2007 6:56:00 AM

    Thank you! This is a fabulous article. I have had two bad employment situations in a row. Having these questions would have clued me in much earlier as to the "real deal" at both workplaces. Given the overall poor working conditions so many of us encounter in a post 9-11, globalization world, I don't necessarily believe that I will find a job where I'm treated with respect. However, having these questions will at least give me an indication from the get-go about how to succeed on the job. My current position was presented to me as a "team atmosphere" and a safe enclave from the rest of the agency. I did not know that the person saying these things had made so many enemies that she depended on her staff for emotional support that was not reciprocated. She had a "divide and conquer" style among her own employees and then left when things got too hot. Unfortunately, I am now left with a direct supervisor who didn't want me to work for her in the first place, so I've been frozen out with no real power to do anything about it. I'm trying to get out, and know it will happen eventually, but the emotional, physical and psychological toll has been very difficult, to say the least.

    User: anonymous
    Date: 11/26/2007 3:03:00 PM

    I have had a similar experience: 2 bad bosses in a row! I should have asked each of these questions at my last job! I had some bad feelings during my interviews who wants to turn down a well paying job based upon subjective emotion. These questions will ensure I avoid a negative people and can find a positive, family friendly, employment experience

    User: anonymous
    Date: 8/16/2008 11:20:00 AM

    I am totally saving this article for reference for all future job interviews. Wish I'd been more savvy for the job I am at now. My boss subtly hinted during my job interview what a demanding mess she would be but I didn't pick up on it. My therapist that I see now (because of this boss) said I shouldn't have taken this job based on my original job interview. Live and learn ! But I can't say I wouldn't make the same mistake again. The hint of what a witch of a boss I wound up with was too subtle. And besides, I was trying to get out of an equally miserable former workplace. That makes any other place seem better !

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