Confessions of a Horrible Middle Manager

Most of the time, I think my bosses really appreciate me. I do what they ask. I get results. I make them look good to their bosses. Work gets done, and mistakes are a lot less frequent than they used to be. We are getting a lot of accolades from different sectors of my organization for those results.

A bit over a year ago, I took over a new job as a special education process manager, IEP chair, or whatever you want to call it. I oversee compliance with federal and state laws and regulations that relate to special education.

I make sure we meet deadlines to the best of our ability and stay in compliance, and also do everything in our capacity to do everything we can for the student. I used to be a special education teacher, and now I work with all of our special education teachers to make sure everything gets done and gets done on time. I make sure the arduous paperwork process is as seamless and efficient as possible.

Most people who have worked with me have loved me. But if people could see behind the scenes, they would see I am a terrible middle manager.

About two years ago, I interviewed for my current position at a different site and school. To the best I could gauge, the interview was going well. The boss asked me what I would do for an underperforming teacher or someone who was falling behind in their responsibilities.

“I would probably just do the work for them to take some of those responsibilities off their plate,” I said.

It was not an answer the boss liked. They asked, “how is that supposed to help the person build capacity?”

I said “I don’t know” and could tell that wasn’t the answer the boss was looking for. I didn’t end up getting the job.

At the start of this school year, we had a training where different types of weak leaders and teachers were highlighted. The trainer acknowledged that we all had different strengths and weaknesses, and in these shades of grey, no one was a black-and-white strong leader or weak leader.

One weak leader archetype that described me well was the enabler. An example is a parent who tries to get their kid to make their bed. The parent sees the kid tried, but the bed is still made horribly and not tucked in right.

“It’s okay, Johnny — thanks for trying!” the parent says.

Then, the parent proceeds to make the bed themselves because it’s not up to their standards of cleanliness and order. If the parent doesn’t want the kid to feel bad about themselves, they’ll do it in secret when the kid isn’t looking.

When the trainer described the enabler, my partner who is in the same role as me pointed at me across the room and laughed. I instantly raised my hand and acknowledged, “yeah, this is my problem.” When the presenter asked me to elaborate, I went into detail and said “if I see someone gave effort but the work still isn’t good enough, I’m not trying to hurt their feelings. I’ll just do it for them.”

I do a lot of work for the special education teachers I work with. I write reports of their educational assessments. Whenever they tell me they are stressed out with an observation, with different demands in the classroom, or something stressing them out in their personal lives, I take care of their responsibility.

That’s why most people who work with me love me — because I take work off their plates and make the work easier.

But that’s also what makes me a bad middle manager. What if they work at another school, and they don’t know how to do X, Y, or Z tasks because “Ryan always did it for me”? It would not only make that employee look bad, but it would make me look bad.

Not only that, but in every organization I left where I had some kind of leadership or management role, I left the person who replaced me or who is still there in a position of leadership in a significantly worse spot. I muddled the line of precedent and clearly defined roles and responsibilities by doing so much work for the employees.

And then the person who either is still there or takes my position is left with a substantial amount of pushback as the seeming bad guy. People will say, “well, Ryan always did this for me” as a perfectly understandable excuse for not doing something that was contractually always within their job responsibility. Because I went so far to be the good guy and the enabling manager, the existing or new manager would seem like an oppressive dictator, which wasn’t true and wasn’t fair to them.

One perfect example of when I was a special education teacher was when I taught a kid who couldn’t read. He would have a really hard time entering his password on the computer. He would enter it wrong several times get frustrated and give up. Naturally, I felt really bad for the kid, and I would just enter the password for him. I started doing this every time because I didn’t want to see him struggle and because there were bigger fish to fry than him putting in his password.

His teacher the next year told me she had to really drill down the skill of putting in his password on his computer. What was he going to do when he was at home and no one could help him? He told the teacher “Mr. Fan used to always do this for me.”

The biggest question others ask me and that I frankly ask myself in the world of middle management is whether what I do is sustainable.

Since I ostensibly run a very tight ship and get the best numbers, metrics, and results for my team, we are given a lot of autonomy and no one cares that I am an enabling middle manager. And it’s not like I am managing children anymore, but grown adults — some of whom are old enough to be my parents or even grandparents.

I will admit part of what motivates me is my own vanity and believing I am not only good at my job, but one of the best, most competent, and smartest people at what I do. I will admit that I also have very particular, nitpicky, and have incredibly high standards for my work.

When others do not meet those standards, I am not patient enough, most of the time, to give very extensive feedback and nitpick and criticize everything the person is doing wrong. I have done that on certain occasions and realized I could come off as a lot more critical and as a stickler than I ever imagined, and make that person feel completely incompetent and really bad about themselves. I’ve always taken that kind of super abrasive feedback somewhat personally when it is directed toward me, and it pained me to realize I had the capacity to be that monster and make other people feel that way, too.

The problem with this critical and perfectionist nature is that I’m also a super non-confrontational person who is also a people pleaser. So it’s a bad combination of not wanting to offend the other person and wanting the work to meet a certain standard of quality.

There’s always a bad part of me that feels a sense of pride and vanity when I hear an organization I did a lot of work for, then left, is completely struggling after I left. People who didn’t appreciate me at the time realize there’s a huge void in the volume and behind-the-scenes work I did to keep operations running smoothly, and the organization is scrambling to find someone or multiple people who could replace my work and productivity. Part of me feels guilty I wasn’t a good enough leader to help them succeed when I left. But there’s also a subconscious part of me that likes to feel needed and important, and that’s something I’m working on because it’s not healthy for myself or others.

Instead, the easier thing to do while abiding by my values of being nice, sympathetic, and kind is to say “I’ll take care of that for you,” take care of it, and move on with my day. I will admit that it’s much easier for me to just do the work for somewho who is struggling in terms of the paperwork so they can focus on other aspects of the job. It’s also easier for me to just do it at a much higher quality and higher speed than the person I think is not doing the work right than wait for someone else to do something right. If I see the employee gave an honest and genuine effort, that’s enough for me. I don’t need to nitpick and critique any further because I know how particular I can be about something as important and imperative as a child with a disability’s individualized educational plan (IEP).

The monster in me is the part that can be super nitpicky and critical. And when it is something I cannot do but that needs to get done, I can be known as the person who “does not play” about making sure things get done. The biggest example is progress reports. Teachers have to submit a progress report for their student with an IEP for every IEP meeting. As much as I would like to help, I cannot write the progress report for the kid because I don’t teach them.

I have a system where I give a reminder of the progress report the weekend before it is due. If it is a day late, I give a gentle written nudge. If it is two days late, I get a bit crazy and can be tough about making sure it is done.

There are other responsibilities that I cannot take care of that my high-achieving, ambitious nature doesn’t tolerate not getting done.

So I am aware that I have this enabling weakness when it comes to work. The results are there, and no one is complaining that not only are the results good and the operations functioning well, and everyone else’s life is easier but mine. I admit I can have huge trust and control issues when it comes to relying on someone else to do something that reflects on my aptitude and competence. If a work product is not up to my standards of quality, then I will take control because I’m not trying to have it reflect poorly on me.

There are several valid critiques of this enabling style of leadership. I can tell you that it’s just what we have to do in the field of education. Being a teacher is notoriously stressful, and education is notoriously an understaffed field. Someone being willing to take work off your plate and make your life easier is incredibly helpful when you’re so stressed you can barely think or function.

Because there are so many other classroom-based stressors, I’ve seen these very same people I take on a lion’s share of work for take many days off due to mental health and stress, or even have to see the doctor because of work-related stress. It’s not easy, and anyone willing to support you helps.

And while people do think my willingness to just do work for them is support, the truth is it’s not sustainable in the long term for all parties. Say there are significantly more students, or the person does move to another school. Say I leave my workplace and do something else, and everyone is left scrambling again.

This is what makes me a bad middle manager, even if it seems like I’m helping to run a well-oiled machine.

In reality, work is messy and life is messy, and you do whatever you can to make it through the day and get things done. I’ve had plenty of people who have heard about the way I navigate my work and joke “can you be my manager?”

And because it’s working in getting results, accolades, and wins without taking a significant toll on my ability to balance other responsibilities, I have no reason to stop my managing methods any time soon.

For me, it will take some sort of big interfering event to change my ways. It’ll probably take becoming a parent, being struck with some sort of chronic illness, or having some sort of personal tragedy to manage the way most people manage or the way I’m supposed to.

I know it isn’t the best for myself or other people in a very stressful and overworked profession. But I know, to some degree, I can’t help myself and this is just who I am.

I hope one day, for myself and others, I can change.

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This post was previously published on MEDIUM.COM.

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