Promoted From Teaching to Leading? Do This…

Out Of the Box July 19 / Special / July 21, 2019

 – Terra Graves –

I feel guilty asking my team to do things. Is that crazy? I know a huge part of this is because I am now supervising people whom I have been coworkers with for many years. I know the workload because it used to be mine. I also know that my work habits were not typical of most of the group. I loved the work, and I didn’t stop working in the evenings or on the weekends. Now that I am the boss, I have to be more aware of the expectations I place on my team. My biggest struggle right now is that I feel like I should help them carry the workload.

Additionally, I am a doer. I thrive on tasks that allow me to be creative. However, there are new “boss” things I have to do that put demands on my time and mental energy. It’s not that my people can’t handle it; they can with flying colors. I look at my supervisor, who held this position before me. He didn’t do a lot of the things I am doing with regards to being closely intertwined with the nitty-gritty of the work that we were doing. Should I step back more? Or, do I just have a different leadership style? Is there a certain level of distance I need to establish now that I am the boss? This is the myth that I believe is holding me back as an administrator.  

During my journey through this first year as an administrator, I’ve been reading a lot about leadership. I will share some thoughts on a few resources that I found helpful below.  

In 13 Things Bad Bosses Do That Great Managers Never Would, I found a couple of things that have definitely been a challenge for me, and I know that I will continue to work on them.  

  • Playing favorites: As mentioned before, I am now supervising former colleagues. I strive to keep things fair and equal. I hope that I am doing that, but I’m not sure if that is how things are perceived.  
  • Invading employees personal time: Before I became the boss, I didn’t hesitate to contact a few of my colleagues in the evenings or on weekends regarding work-related stuff. Now, I have to be very careful about this. I even had to explicitly state I do not expect people to respond to emails, etc. when they are off work, and if I do need them to respond, their time will be compensated. I think this helps. There are still a couple of people who work around the clock like me, but I have to continue communicating that this is not the expectation.  

Emma Brudner writes about 10 Hard Truths About Management No One Tells You on Some things that really resonated with me:

  • GSD (Get Sh*t Done) turns into GTD (Get Thinking/Talking Done): This is EXACTLY what I mentioned above! I have been getting sh*t done for so long that I’m not sure how to transition. Brudner discusses that it may feel like you are not doing anything, but that it’s more the stuff you are doing is not typically stuff you can “check off” on a to-do list. It’s ongoing thinking, planning, meeting with others, etc. Not having completed products will be a challenge for this overachiever. 
  • Your relationships change: Yes. Yes, they do. These past seven months have been hard because of this very thing. As much as I would like for it not to happen, the friendships I have developed in the department have to change. This is seconded by a quote shared by Amy Gallo in How to Manage Your Former Peers for Harvard Business Review, “If you’re not feeling a little bit lonely and left out, that can be a sign that you’re not distancing yourself enough.”

On my search to validate if feeling guilty as a manager was a “normal” feeling, I found a few articles that said that “guilty people make good managers” (Harvard Business Review) and “feeling guilty may make you a better boss” (BBC World Service) and that “guilt makes workers more trustworthy” (Daily Mail UK). I believe all of these articles refer to the same studies done by the University of Chicago and Stanford University’s School of Business. Basically, employees with more “guilt-proneness” tend to feel a greater sense of responsibility for the completion of tasks, ethical actions, and stronger work ethic. They are high-performers and tend to feel positively toward their organization. For me, the guilt I feel is a little different. It’s more about trying to take care of my team so that they do not feel too overloaded. I don’t want them to feel like now that I am the boss I will push all my work onto them. It’s called “delegating,” Terra. That’s one challenge here. What should be delegated? The other challenge here is that each person on my team has strengths and talents in certain areas. Sometimes, I need the same person to take on more because it suits their strengths. Is that fair and equitable? 

Lighthouse’s blog on Leadership and Management Advice shares some ideas for What to Do When You Start Managing Former Peers.  

  • Use your previous role to your advantage: This is absolutely where I am at right now. I am losing two people from my department and hiring four more for this coming school year. For my remaining team members, I know their strengths and talents, so I can assign programs to them in which they will be joyfully productive. This process is a huge benefit of working with everyone for as long as I have. Communication is not a challenge because I know how and when to approach each person depending on what the issues are.  

Finally, Dan Finnigan’s Show ‘Em Who’s Boss: 4 Tips for Successfully Managing Your Peers After a Promotion gave me two things to work on.

  • Be clear about your expectations for performance: Something I discovered in the last couple of months is that I need to be more direct in what “done” looks like and when the deadline is. A couple of situations occurred that made this clear. Just because something is in my head a certain way does not mean that other people share that vision. I spoke to my team about helping me to remember to set deadlines for them so that we are all on the same page. This action is a big goal for me this coming school year. 
  • Tell the team what to expect from you: Reflecting on this past seven months, I am not sure that I have made this clear to my team. Maybe once I can clarify this, I can lessen the guilt I feel?

Going forward, I believe I can let go of the myth that is holding me back. I spoke with my supervisor today, actually, to get some clarity. Basically, he said, “It’s a HUGE gray area.” Meaning, being in middle management, I have to manage, but I also have to do. I need to step in and share the workload if it is necessary. This concept made me feel better. I think I am going about this the right way. I (mostly) trust my instincts, but getting validation from him helps.  

This article is the seventh in a series. If you haven’t read the others, feel free to check them out below! 


Terra Graves
Terra Graves
Terra has been an educator for over twenty years. She is the Project Coordinator/Administrator for the 21st Century Learning Department in Washoe County School District, NV. Prior to this position, she taught elementary and middle school, supported novice teachers as a full-time mentor, served as an Ed Tech Specialist, and a Program Specialist in the 21st Century Learning Department. Terra is Flipped Learning 3.0 Level-II Certified and a founding member of the FLGI International Faculty.

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