First Time Student Staff Supervisor: What I Wish I Had Been Told

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This series will explore what I wish I had known about advising and supervising students, staff and volunteers. The third in the series will be about being a first time supervisor of student staff.

Earlier this summer, I asked my readers to help me choose topics to explore. The most popular choices will be part of a new series of posts. The first in the series will be about being a first-time advisor and supervisor. I’ll explore this topic and look at the following roles I held: advising students, professional staff, and part-time employees. I’ll also look at times when I had to supervise volunteers.

In my career, I have learned that I need to ask people for help. I have worked in solo positions, so I have had to figure out what I don’t know quickly but still need to deliver. Most of the positions I have held I was the first person to do so. So I know and understand the pressure to start something I had no blueprint to do, or operational book to train me. And yet, two decades later I am still here. There is much I wish I had been told to get me started quicker, and I hope what I share will help you jumpstart the beginning of your own career.

Wanted: Phenomenal Students, No Experienced Required

I had the incredible pleasure of working with incredible students at all of my institutions. I’ve covered this topic before but will share more about other lessons learned. I’ll focus on one student at each of the colleges that taught me something I believe is worth sharing. Each let me know that what I thought was the right decision was always to my benefit instead of theirs.

What I learned: Be Willing to Let Your Best Students Go

When I worked in a multicultural affairs office, I was responsible for coordinating our annual leadership retreat. I hired a student coordinator who had loved her experience the prior year and was on-board with the work for the current year. But I knew that something was amiss when the new semester began and her attention was waning.

I learned that she wanted to quit because she needed a better paying part-time job. But she didn’t want to let the department down, too. So there was my dilemma. Do I keep her on board for the rest of her contract or do I let her pursue her own passions and needs? It seems like a simple decision now, but as a young advisor, all I could think was how much more work this would put on me. How overwhelmed I felt nearly all the time. What would this mean for the program we were planning together.

Cartoon illustration of two people talking. One has a word bubble with ellipses (...) and the other has a word bubble with an exclamation point (!).  Image for first time supervisors blog
Learning a favorite student wants to leave a position early is always a surprise. But how we react shows how we care about the choices as an adult.

Ultimately I learned from this situation that I needed to pay more attention to my students’ lives outside of our lives and help them learn to speak up. I had to learn that blind allegiance to our work was always to my benefit and not to theirs. We stayed in touch after she left the role and now two decades later I can see that it was the right choice to let her go. She grew into a phenomenal student leader and student affairs professional in her own right. And each student I said it was ok to leave a role has gone on to do amazing things, too. I am proud of all of them.

What I Wish I Had Learned: Don’t Keep Students on Staff Who Make You Cry

Some of the phenomenal students I worked with weren’t easy to supervise. One comes to mind very easily, because he made me cry twice. He was great at the work he did, but he had an ownership of the work he thought was higher than mine. And for some reason, he thought he could call me out for not doing the work ‘on-time’ for him.

Mind you, I had a masters degree and was the Associate Director for the department.

Looking back, and learning about his patterns of bullying behavior, his behavior was rooted in misogyny. I just happened to be one of his targets. At the time, I didn’t feel I had the power to confront his behavior and just cried in my director’s office.


A cartoon of faceless men, with the one standing pointing aggressively at the one sitting, looking startled.   Image for first time supervisors blog
Bullying can take place in any environment, including the workplace. And even from students to staff.

I’ve since learned that workplace bullying doesn’t require that it follow titles. This student, while very competent, just knew how to bully his way through his leadership experience. In hindsight, I should have let him go after the first incident and reported his behavior to the Dean of Students. And I know now that I need to interrupt the behavior in my supervisory role and make sure that other staff feel safe to do their work.

What I Wish I Had Learned: Don’t Keep Students on Staff Who Fake Cry for Attention

I am also reminded of an RA I worked with who learned quickly to be moved to tears when we had to have tough conversations. I began to sense the pattern after two different sanction meetings for failing to turn in paperwork in on-time and she would immediately cry on cue. In the third meeting, I knew I had to address this behavior.

When we started the meeting, she began the tearing-up process, and I told her “if you need to cry, you can do this outside and come back in when you’re done.” I closed my folder and looked her in the eye. She immediately stopped the crying, looked at me with a different look in her eyes and replied, “no, that’s ok, let’s get this over with.” It was at that moment that I realized she had been playing on my empathy to get less harsh sanctions. From that point on, her demeanor changed from sympathy-seeking to passably-agreeable to avoid being terminated.

I don’t want to make it sound like I was being insensitive to her emotions. But was also a student studying acting professionally and cuing up emotions at the drop of a hat was well within her skill-set. She was actually very good! But she wasn’t very good at accepting the critical feedback to improve her work.

I have more stories about her (and others from this staff team), but I will save them for another post.

What I Wish I Had Learned: Take a Chance On the Introvert

One of my most memorable students was a chance hire. When I worked at a small college, managing the campus center, I placed the TV set and gaming systems in front of my office door. Each Friday, the gaming club would set-up camp and play video games for hours and hours. They reminded me of the engineering students I had worked with previously. I knew I needed at least one of them on the Orientation staff I was helping to hire.

I approached all of them, encouraged all of them to apply and ask me for details if they wanted. One of the men, Daniel, asked me about the orientation position and if I thought he had a chance. He was painfully shy. One of the most quiet voiced, unassuming people I had ever met. Never looked me in the eye. But he was intentional. He disclosed that his shyness was something he wanted to work on and he knew that with practice he could do the job.

I had worked with students like Daniel before, but had never thought of them as orientation leader types. Most of the other hired staff was as extroverted as you could be, and he took up as little space as possible. But his earnestness was something I couldn’t ignore. So I hired him as an alternate, and within two weeks he had a permanent position.

…And boy did he shine!

He was right, all he needed was some practice. We worked on his public speaking, using cue cards to help organize his thoughts when in small groups. He found the best ice breakers for his personality. And during his sessions, he could troubleshoot issues without freaking out, preferring to be in the background.

A cartoon of smiling men, with one with a first place ribbon on his chest.  Image for first time supervisors blog
We play a role and can make bold choices to hire students based on their potential, which allows them to shine!

We hired him as a new event planner, and his skills just kept building. His ability to listen to others allowed him to create the highest-attended programs on campus, even more than the Program Board events. He moved to a supervisory role and helped manage Orientation programs, and he was unshakeable.

He told me before the College closed that no one had ever had faith in him to do something because he was so shy before. I told him that everything great was already inside of him. And he taught me that sometimes we need to take a chance, listen to the intentions of the students asking for a chance, and give them one.

Want to Explore This Topic Further?

I will explore tips for first-time supervisors, next time about supervising professional staff. You can read my related content about advising students and supervising students, or read through any of my current posts about supervision. Feel free to ask questions in the comments below!

In addition, I have worked with entry-level and mid-level career professionals for nearly ten years, helping them reconsider their strengths and ways to learn new skills. Let me know if there is anything I can do to support you as you develop this new skill.

Schedule an introductory meeting so we can discuss a plan that works best for you.

About Post Author

Joseph Rios, EdD

I am Joseph Rios and I believe that leadership is an expression of our values
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