Hiring The Right Boss

  • Author
    Lori Ressor
  • Categories

In the book Beginning Your Journey, Schneider and Bailey (2009) wrote a chapter about supervision, including the suggestion that supervision is a two-way street. Like any relationship, we all have different styles, expectations, wants, and needs. We also know that some student affairs staff members excel in their supervision skills while others should not be in this role. Most graduate students and new professionals feel tremendous pressure to find their first professional job and may spend all of their time selling their skills and abilities to potential future employers. This article encourages job seekers to do some self-reflection and preparation to ensure their first job is a good match for both the future employer and prospective employee.

Defining a Good Boss

So what makes a “good boss”? A number of articles, books, and resources are available to help us learn how to be a good boss as well as how to evaluate whether one is effective or not. Robert Sutton, author of Good Boss, Bad Boss and The No Asshole Rule, asked this question: “Would your employees - if given the choice - ever want to work for you again?” (Sutton, 2012). While most of us as supervisors probably know we would not get a positive response from every employee we have supervised, we hope the majority would say "yes".

Most positive traits of effective supervisors are obvious, and Douglas (2013) cited a few worth repeating: 1) sets clear expectations, 2) gives feedback, 3) recognizes efforts, 4) is inclusive, and 5) is open and truthful. Good communication skills, integrity, and being an effective listener are also components. Leaders or supervisors often lack self-awareness, a key attribute for success (Carry, 2014; Goldsmith, 2007; Sutton, 2012). Leaders must be open to feedback and have a desire to improve. Goldsmith (2007) highlighted common work habits that successful leaders need to break in order to be even more successful.

Job seekers should try to read about what makes an effective supervisor and see what resonates with their personal style and needs. Speaking of needs, are you aware of what your needs are as an employee? If you have not taken a personality or leadership test, like the Myers-Briggs Type Inventory or StrengthsQuest, now would be a good time to do so. Knowing your strengths, preferences, and challenges will help you articulate the type of employee you are as well as help you determine the type of supervisor best suited for supporting and challenging you to grow and learn.

We developed questions to which a mid-level professional (John Bulcock, Assistant Director for Greek Life & Off-Campus Housing at Minnesota State University, Mankato) and new professional (Rachel Burchfield, Program Counselor for the School of Health Professions at the University of Alabama at Birmingham) would respond in order to provide real perspectives from student affairs professionals in the field. We also provided some reflection questions for you - as the reader - to ponder as you prepare to “hire the right boss.”

It is important for new professionals to reflect on characteristics that they are looking for in a supervisor. How should graduate students and new professionals do this? What should they think about?

John: I think it is important to acknowledge that, when searching for a first job or a job early in one’s career, there can be so much pressure to finally land a job—period—that even stopping to think about the relationship with a potential supervisor is not something new professionals or graduate students may find time to do or find important. I will be honest and own the fact that early on [thinking about the potential supervisory relationship] was not something I focused on. Even though we covered it in the capstone class for my master’s program, and even though I had been out working for 4 years before going back to graduate school, I didn’t think too much about the potential relationship. I wanted to make sure that I landed something and had somewhere to go when graduation came around. As a matter of fact, I knew during the interview process for my first post-graduate school job that the person who would be my initial supervisor was in an interim role. There would be a national search commencing shortly after I was hired to fill the other position, and the person who was in it at the time may or may not continue.

While the relationship wasn’t a primary focus for me, I did ask the standard questions: “What are you looking for in a team member? What is your leadership/management style like?” I think that any potential employer anticipates these questions, has a stock answer they’re prepared to give, and is keenly aware of what not to say. I’ve never been told, “I’m looking for someone to put in 60 hours a week, and I’m expecting perfection” or, “I’m an overbearing micromanager, and I have a hard time trusting my team members to actually do what they’re supposed to be doing.” I would always receive fairly similar responses that indicated a desire to make sure the team “collaborated” and to allow for autonomy in the office. In many cases, you can probably come close to paraphrasing the answers to these questions before asking them.

While visiting about this article with some colleagues, we reminisced about the interview experience, and one thing that was common among all of us is that during interviews, we were asked to “give specific examples of times when _____.” I believe since candidates are asked to do that, it would be appropriate for them to also ask similar questions of potential supervisors based on the type of experience that the candidate may find important. It could be very telling to ask something like, “Can you give me an example of a time when an employee of yours proposed a different approach to an issue than you may have had in mind? How did you react, and how did the situation work out?” Another good question might be, “Can you give me an example of a time when you went to bat for or advocated on behalf of a member of your team?” If you ask for a specific example, it can help you see a real-life application of the other’s philosophy.

In order to really find out what you want to know about your potential supervisor, you need to think about what is important to you. Think about what you want, but also think about what you don’t want. If you only think about one of these categories, you’re likely to leave out some key things. Write these thoughts down, and try to come up with questions that will indicate whether or not the fit is right. If the right questions aren’t obvious, bounce your ideas off of someone else.

Rachel: Even before I began to figure out what my plans would be after I graduated with my master’s in May 2011, I started to think about my priorities and values. What part of the country did I want to live in? What type of institution did I want to work for? In what field specifically did I want to start my career in student affairs? One question that wasn’t at the forefront of my mind, but should have been, was what type of person do I want to work for?

The truth of the matter is that one’s first supervisor as a new professional can either be an extraordinary asset or an extraordinary hindrance in the trajectory of our path in student affairs. I have known the right supervisor to cause an employee to become even more passionate about student affairs, and I have also seen the wrong supervisor cause an employee to leave the profession of student affairs altogether. Looking back, I would have thought of a supervisor who I really grew from, and I would have written down five adjectives that described that person. While I was interviewing, I would have been intentional about asking my potential future supervisor if those characteristics described him or her, and I would have asked my potential future colleagues if that supervisor demonstrated the characteristics that matter to me. These five adjectives will be different for everyone and the potential future supervisor might not hit all five. That doesn’t mean you shouldn’t take the job, but it is a good start for deciding about accepting a job or not with a clearer handle on who you will be working for. It matters.

Reflection Questions for the Reader:

What five adjectives would you use to describe your ideal first supervisor?
How would you describe the best supervisor you have had so far? The worst? Identify the attributes that made them so effective or not as effective in working with you.

It is important for a work environment to be open and supportive, which is often created by the leader or supervisor. How does a candidate assess if that is the case with their potential employer?  What recommendations would you have for candidates?

John: One of the most important characteristics, I think, of a supervisor, is that they are open to feedback and questions, and that they are supportive of the personal needs and professional development needs of their employees. It’s important for job seekers to ask about professional development opportunities when interviewing for a job. Many times, there will be opportunities internal to the university community. Other times, an employer might let you know what is available in terms of financial support for conference attendance, professional association memberships, and more. In addition to formal educational opportunities, a supervisor should be willing to expose you to other jobs, duties, or opportunities that will help you enhance your skill set. Whether this involves committee service, new initiatives, or cross-departmental collaboration, this experience can be invaluable. During the interview, ask about opportunities like this.

In many cases, a candidate will have an opportunity to have a conversation with potential colleagues while they’re on campus for an interview. I think that it is perfectly acceptable for a candidate to ask their potential colleagues about the environment. I have done it, and it has led to some great conversations. One question that has led to good information is “what makes you look forward to coming into work every day?” or “why would I want to work in this office?” I also like to ask about what others would change about the work environment if given the opportunity. This can help you determine where others see room for improvement.

Rachel: I think two great questions to ask a potential future supervisor are: “where are the last three people who worked for you at now in their career?” and “do you still keep in touch with them?” If I have a positive relationship with a supervisor, I am going to keep in touch with them, whether that means having breakfast with them at our annual conference or sending them a holiday card. I am also going to call on them for advice if I need to. On the other hand, if that supervisor was terrible, I am probably not going to keep in touch with them after I am out of the job that bound me to them. A good answer to the aforementioned questions would be that the former employees have grown professionally—whether in a bigger role at the same university or somewhere else - and that they do keep in touch, because the relationship was meaningful enough for there to be some amount of contact there.

Of course, while interviewing, it is also imperative to have honest discussions with potential future colleagues whose supervisor is also your potential future supervisor. One can usually gauge by the passion in the potential future colleague’s voice whether there is true camaraderie there or not, and watching the interactions between your potential future supervisor and his or her employees can tell the whole tale.

Reflection Questions for the Reader:

What are your expectations of a positive work environment? What role do you expect your supervisor to assume in creating that work environment? What expectations do you have of your colleagues? What role do you typically play in a team environment?
Do you expect to be “friends” with your coworkers and supervisor? Is that a reasonable expectation? Why or why not?

We know that it is important to have cross-cultural communication and support in a supervisory relationship. How do candidates assess the cultural competence of their supervisor and whether the supervisor creates an open environment that engages dialogue about diversity and social justice topics?

John: Assessing the cultural competence of a potential supervisor can be an intimidating task. The topic of diversity is often times a sensitive one that many want to avoid unless they know someone well. Being a member of many privileged groups, I have not experienced an uncomfortable situation as it pertains to being a member of an underrepresented or oppressed class. At a previous institution, I worked with a Black woman who commented that she would often interview without ever encountering another person of color during the entire interview process. She commented that she would regularly ask how to go about connecting with another person of color working at the institution and in the division, if possible. She described this as “acknowledging the elephant in the room,” and said that bringing up the topic of diversity herself helped put others at ease.

I think that observation can be essential when trying to assess the cultural competence of others during an interview. How do people of color or members of other groups interact with the person who may be the supervisor and with others in the office, for that matter? If gathering information by observation isn’t sufficient, I think that enough people in higher education acknowledge the importance of social justice that it is acceptable to ask about it directly. If you are a social justice advocate, acknowledge it, and ask what the department or the supervisor, in general, does to promote social justice in the college or university community.

Rachel: While interviewing, I think it is so important for interviewees to ask questions. No amount of questions is too much! If a potential future supervisor gets annoyed by the amount of questions you are asking, that is a red flag as to how he or she might react to you asking thoughtful questions while you are learning the ropes of your new job. As an interviewee it is so easy to get caught up in answering the interviewer’s questions “correctly” that we forget that we are also interviewing the institution and all who work there.

I would ask my potential future supervisor how he or she creates an open environment, and I would hold their feet to the fire and ask them to share examples of how they do so. An ideal interview is a conversation, not an interrogation (on either side). Let’s talk about diversity and social justice topics. I want to hear what my potential future supervisor has to say, and I want to see that he or she is as engaged as I am in the topic.

Reflection Questions for the Reader:

What are your values related to multiculturalism and social justice? What are your expectations of a supervisor to help you learn and grow in this area?
How important is it to have a supervisor who shares your cultural background or who might come from a background different from yours?

Do you have any other advice or suggestions to help new professionals hire the right boss?

John: I am a huge advocate of the use of humor when appropriate. I think that humor, when tastefully infused into the interview, can be very helpful. It can help you become more comfortable and it can help those on both sides of the interview more fully see a personal side of each other. How one responds to humor can be telling. Usually, a candidate will be able to tell how humor might be received fairly early on in the interview process. If it appears as though expressing the sense of humor would be well-received, give it a chance. From experience, I can tell you that the best bosses enjoy a good laugh, even if it’s sometimes at their own expense!

Rachel: It is so hard to do in the interview process, but try to force yourself to be a little bit selfish. Realize that this first job and your first supervisor are really important, and it really can determine your long term future in student affairs. I love the Maya Angelou quote: “when someone shows you who they really are, believe them – the first time.” Don’t get so caught up in impressing interviewers that you overlook and gloss over major red flags. If there is a problem brewing while you are interviewing, chances are the problem will still be festering when you arrive for your first day of work. Forty-plus hours a week is a good chunk of your life. Just like in other facets of your life, make sure your time is spent with people who grow you and make you better.


We know it is challenging to be vulnerable in an interview setting and ask what may be perceived as difficult or sensitive questions. While we know all interviews have a level of artificiality, shouldn’t we strive to have more open and real conversations with our future colleagues and especially our future supervisor? If we cannot take a risk at this stage of the process, what will become safer once we are in the position? We realize what we are suggesting may seem too idealistic; however, in writing this article, we agreed that it is important to challenge the status quo and to encourage interviewers and interviewees to have more real and honest conversations about expectations, work culture, and style. It is the beginning of an important work relationship. Shouldn’t honesty and authenticity be a part of the foundation?


Carry, A. (2014). Taking the next step: Executive transitions in student affairs. Leadership Exchange, 11(1), 16–19.

Douglas, M. J. (2013). What makes a great boss? Retrieved from http://hiring.monster.com/hr/hr-best-practices/workforce-management/hr-management-skills/what-makes-great-boss.aspx

Goldsmith, M. (2007). What got you here won’t get you there. New York, NY: Hyperion.

Schneider, R. S., & Bailey, K. W. (2009). In M. J. & L. M. Reesor (Eds.), Beginning your journey: A guide for new professionals in student affairs (3rd ed., pp. 61–88). Washington, DC: National Association of Student Personnel Administrators.

Sutton, R. I. (2012). Good boss, bad boss. New York, NY: Business Plus.

Lori Ressor is the Vice President for Student Affairs at the University of North Dakota. In the Vice President role, Lori advocates for all students and seeks to create a positive learning environment for all students especially outside the classroom. John Bulcock is the Assistant Director for Greek Life & Off-Campus Housing at Minnesota State University, Mankato. John has the privilege of advising 7 fraternities and 4 sororities, two governing councils, and two honorary organizations whose members include nearly 350 of MSU's most involved and energetic student leaders. Additionally, he serves as the university's liaison to the surrounding neighborhood associations and to property managers throughout the Mankato community. Rachel Burchfield is a Program Counselor for the School of Health Professions at the University of Alabama at Birmingham.

comments powered by Disqus