How to Evaluate Your Potential Boss

Welcome to the very first installment of ‘Ask a Career Counselor,’ a new feature that gives you access to career advice from some the most respected and experienced college career counselors on the planet.

Today we’re joined by a really great group of people: Mary Schilling (from my alma mater, The College of William and Mary), Russ Coughenour (University of Tennessee), Christian Garcia (University of Miami), Nicole Van Den Heuvel (Rice University), and Burt Nadler (University of Rochester). They all volunteered their time, so be sure to thank them in the comments.

We asked each counselor the following question:

Few things in life can take a bigger toll on your personal happiness than having a bad boss. What is one effective way to evaluate a potential boss during the job interview process?

Their answers are below. We hope that you find their unique perspectives helpful, actionable, and inspiring as you navigate your way through the job search process.

Mary Schilling

Executive Director of Career Development, College of William & Mary

Let’s assume that you’ve done as much research as possible on your potential boss. That means checking her/him out on LinkedIn, Google, and the employer’s site. Those sources will at least provide you with background information as well as professional context.

Take advantage of informal times during your interview day by casually asking employees – your potential co-workers – whom you meet: “What’s it like to work here?” “Can you tell me about the culture of the organization?” “How are performance appraisals handled?” “Describe the leadership of the department/unit/organization.” From responses to these questions and others you may be able to assess whether or not there’s a sense of shared values and mission, a spirit of teamwork, a community of support. Watch for body language, attitude, and even word choice. Do you hear the words “teamwork” and “our team” or do you pick up the sense that the co-workers work “for” the boss in a more hierarchical way.

Ask your potential boss questions like: “Could you tell me about your management (or supervisory) style?” “How would you describe the culture of your work group?” “How much turnover is there on your team?” “How would my performance be evaluated?” “How do you manage your staff through change?” “How often will I meet with you?” If you are curious, ask to see an organizational chart, so you can see where you fit in and ask for a description of the dynamic of the organization. Answers to this type of question may provide contextual if not direct information which might help you to assess whether there’s a good fit with the potential boss.

You’ll have to assess whether you are getting real, honest, accurate perceptions. You can’t really know what it’s like to work for or with someone until you are actually transitioned into the position. But you will, at the very least, have done “due diligence” before accepting the position. That’s the sign of a true professional!

Director, Career Services, University of Tennessee, Knoxville

There are several scenarios where you could be interviewed by your potential boss. The first would be at the place of business where you both would work. I would pay very close attention to how others interact with the boss. Do they call him/her by their first name? Or are there yes sirs or yes ma’am’s? Does he/she have personal assistants? How is the workplace decorated? How is the boss’s office decorated? Are their personal items that would allow insight into the boss’s lifestyle? Or is it relatively austere with little indication of personal interests. Is the office spotless with little to no clutter or is it messier with multiple projects seemingly going on? Close observation of language, vocabulary and dress might also offer some possible inferences that an interviewee could draw from.

When in a more public setting I would look for how the potential boss interacts with wait staff or others that he/she comes into contact with. Do they seem warm friendly and accepting or are they cold, demanding and picky. You can still pay close attention to language, vocabulary and dress even when in “neutral” locations but you don’t have the ability to examine the boss’s personal work space.

In either situation, asking the boss carefully crafted questions when appropriate is probably the most important. A couple examples might include: Can you give me an example of the type of work you would expect me to be doing after six months on the job? (You know what you can do now, the boss’s answer will give you insight on how much growth you will be expected to achieve in a relatively short period, which is somewhat equivalent to how demanding the boss may be).

Another example might be: What are your hires from 2-3 years ago doing for the organization now? (see how many are still under the direct supervision of this particular boss….this might provide insight in to how many people stay working for this particular manager).

Christian Garcia

Executive Director, Toppel Career Center, University of Miami

An effective way to evaluate a potential boss during the job interview process is to ask specific questions about his or her supervision and leadership style.

Some questions to consider include: How do you communicate your expectations to your staff members? How do you hold your staff accountable? How involved are you in your staff members’ day-to-day work? What kinds of professional development and/or coaching opportunities do you provide?

It is also important to be very observant during your interview and take note of how he or she interacts with his staff and other colleagues. Does there seem to be open communication? Do employees look engaged?

Also, if other staff members are involved in the interview process, take that opportunity to ask them about the boss’s supervisory style. Remember, if employees love their boss, they will happily share that with you. If they are not, their silence will speak volumes.

Director, Center for Career Development, Rice University

First impressions. They count during the interview and that process runs both ways – for the interviewee and the interviewer. Start with the body language and how the interview is being conducted. What is his/her tone of voice in asking the questions – friendly, aggressive, impatient, engaged? Look for those non verbal cues – the level of interest in their questions and in your answers and their eye contact.

Probe about work style and job expectations: Ideally a good interviewer will allow for and elicit questions from the interviewee. This can be very insightful in determining the expectations of a future boss. The trick is asking those questions in the right way so as not to come across as taking control of the interview or putting the boss on the offensive. How your potential boss handles deadlines and missed deadlines, team motivation and communication, delegation, what their key priorities are, can indicate the work style of a boss. You can’t ask those questions as if you are interviewing your future boss so you have to be subtle, humble, and keep it conversational. An example question might be: “How do you assign projects and keep track of the progress?” The answer might give clues as to how effectively this person delegates and provides feedback and whether they operate in a last minute mode which can lead to stressful work environments.

Burt Nadler

Director, Career and Internship Center, University of Rochester

The most effective way to do so is to remember that “post offer analysis” takes place, as per the phrase, after the offer. The interview is when you present yourself as qualified for a position and earn the offer.

Of course, you can ask questions regarding the context within which you will perform your duties and those you will be reporting to and collaborating with; and you should have lots of questions. But, you must still be “diplomatic” and “sensitive” to the fact that you are the candidate during the “selection phase.”

I am not in favor of you thinking you are “interviewing the interviewer,” until after the offer. Once the offer is extended, create “real questions” you need answers to. Ask for a “return visit” when you can speak more honestly and inquisitively with all involved. Do some appropriate in person and email interactions; while remaining upbeat, enthusiastic and professional; as well as politically savvy.

A well conceived post offer analysis strategy will enhance your potential for immediate and long term success and happiness. Please do remember that overall job search strategies of recent grads will differ from those who are “more experienced” candidates. The nature of your pre- and post-offer queries and actions will vary depending upon your age and stage, and the nature of the field, function and firm.

Thanks so much to all of our participants. If you have a question that you’d like us to ask in the future, let us know on our contact page.

Updated: 09/02/2017
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Adil Khan
Adil Khan is freelance writer and a Computer Engineer by profession. He started writing articles for CareerThoughts.com in 2016. He writes a opinion column for a local newspaper. He is yet to join Twitter!

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