[OPEN]
I was hoping you’d reach out so we had the chance to more formally exchange words.
[FRAGMENT]
Of course, you know that there are different types of “instruction” and you’re not going to (and shouldn’t) see the same thing in every classroom.
[OPEN]
My goal with this email is to respond to your message, provide context on my classes, offer some words of advice for a new leader entering our school, and learn more about your goals.
[FRAGMENT]
If you want to know about what we do here, I’m happy to have a conversation and would have loved to have that conversation in the moment today instead of being dismissed.
[FRAGMENT]
[REDACTED].
[FRAGMENT]
Beyond these relatively contrived metrics, though, [REDACTED].
[FRAGMENT]
If you want to see all of the planning and instruction around this material, just ask. It’s all neatly catalogued in my google drive and we can discuss more if you wish.
[FRAGMENT]
The previous administration once put forward messaging pushing for “purpose over power” in our interactions and culture. While this wasn’t always adhered to, that messaging was incredibly meaningful for me to see. I, and many others, would love it if that sentiment persisted, but today was, unfortunately, one of the clearest demonstrations of purposeless power I’ve seen in a long time.
[FRAGMENT]
Leadership is something generated through the actions one takes, rather than simply the title one holds. In the same way that teachers place a lot of careful effort building student buy-in, school leaders should act similarly and place humanistic purpose over titular power.
[FRAGMENT]
Here’s a word of advice for a new leader coming into a space like [REDACTED], where people have been effectively teaching and administering for an atypically long time: try to do more listening than dictating right from the start. Perhaps you’ll learn something about the best way to lead. It is incredibly hubristic to assume you know what is going on in a room when you walk into it, with no context about [REDACTED].
[FRAGMENT]
Today was not a great first impression and unfortunately that sentiment seems to be felt across our school.
[FRAGMENT]
One thing about me is that I’m not going to shy away from bringing up these issues to anyone, so I’m happy to both be a vocal mouthpiece, as well as receive any kind of criticism in return.
[FRAGMENT]
I returned to teaching after receiving my master’s in education policy and working within education-focused strategy consulting. It is an intentional choice to be here building out a radically democratic class with these students. This requires a specific kind of critical pedagogical focus that I often don’t see prioritized within typical [REDACTED] dictates.
[CLOSE]
I look forward to your response.
[OPEN]
As we wrap up this school year and look towards the future, it’s important to revisit these issues and set clear intentionality for concrete improvements.
[OPEN]
In light of recent student reporting indicating widespread [REDACTED] caused by [REDACTED], and a clear belief among students that these policies are inadequate, I’d like to formally reopen a conversation I’ve attempted to raise multiple times this year. My hope is that next year, this will no longer be the unresolved issue it has been.
[FRAGMENT]
Beyond the now-documented [REDACTED], I want to reiterate that our current practices are in direct violation of [REDACTED]. Most notably, we are out of compliance with [REDACTED]. I have flagged these [REDACTED] consistently throughout the year, but they’ve yet to be substantively addressed or factored into policy decisions. This exposes the institution to unnecessary legal risk, in addition to potential [REDACTED] consequences.
[CLOSE]
If there are students who need more targeted behavioral support to make good choices, that is where interventions should lie. Blanketed restrictions and collective punishment end up creating systemic issues and more harm in the process.
[CLOSE]
I’m happy to work collaboratively on solutions (I have several ideas that could work, if you want to discuss further). I’m happy to offer specific examples of challenges as I’ve done throughout the year. I’m happy to escalate this further and loop in someone from [REDACTED] if that would be helpful.
[CLOSE]
There are many paths forward, but what cannot continue is the categorical dismissal of the policy challenges we’ve seen this year. If nothing changes, please be advised that I will continue to exercise my discretion in disregarding existing policy.
[CLOSE]
Thanks for taking this seriously.
[FRAGMENT]
I want to name that today was listed as a [REDACTED] for weeks, and many students arrived confused about why they were expected to [REDACTED]. I understand this changed earlier in the week, but the communication, timeline, and its rationale were unclear to both students and many staff. I’m noting this not as a complaint, but because moments like this erode student trust and teacher clarity. If policy shifts or [REDACTED] changes are going to occur, can we ensure both the logic and logistics are clearly & proactively communicated?
[FRAGMENT]
At the start of the year, we were tasked with discussing shared professional values. “Accountability” came up, yet the intentions behind this word have been unheard by this administration. Instead of honoring its context, it was quickly weaponized as a way of ensuring compliance from staff for administrative dictates. However, our interpretation of “accountability” was towards administration itself.
[FRAGMENT]
Emails I have sent have been critiqued for “unprofessionalism” or “uncollegiality,” when in fact it’s not unprofessional at all. It isn’t unprofessional to point out systemic issues. If anything, it is one of the more professional things one can do because it hits at the core demands of our PROFESSION. Not once have the underlying issues been addressed. Not once has it felt like there has been even an ounce of accountability or ownership from this administration. I have little to no faith in the leadership of this school, as a result.
[FRAGMENT]
Thanks for finally shifting the schedule to accommodate urgent setup demands for [REDACTED]. In the spirit of this broader conversation around [REDACTED], I’ll be following up after [REDACTED] with a more detailed overview of what could be improved in future cycles from a systems and planning standpoint. The goal is to ensure smoother coordination and prevent the kind of last-minute shifts and confusion we experienced this time around.
[OPEN]
The BCC format of your email (which limits collaborative dialogue), paired with its oddly misdirected focus on a non-issue, does little to acknowledge the very real frustrations teachers have faced over the past two weeks. As a result, the message was not received well.
[CLOSE]
Let’s have a strong [REDACTED]. Afterward, let’s all talk.
[FRAGMENT]
We need some clarity and quick decision making around [REDACTED]. Let’s promptly enact [REDACTED]’s proposed proctoring switches so that we can have a clear plan in place for these rapidly approaching [REDACTED] that meets and solves all urgent demands. The appropriate comments remain in the sheet to promptly apply. Alternative plans are also welcome, but we don’t have time for inaction. My [REDACTED] setup demands were communicated on [REDACTED]. [REDACTED]'s proctor switch plan was communicated on [REDACTED]. It is now [REDACTED] and [REDACTED] is three school days away. This kind of inactive silence is deafening.
[CLOSE]
We have stressed improving on the "little things" all year...but this is quite a big thing that remains frustratingly unaddressed. If you have any questions, please let me know.
[FRAGMENT]
Still, a lot can go wrong if not planned for appropriately and quickly addressed on the day of [REDACTED]. Limiting this potential chaos will ensure the calmest, cleanest, and most focused environment possible for [REDACTED]. If we value “data” and want [REDACTED] then this is where that happens. If the day is a mess, then [REDACTED] will be a mess, and it will be more difficult to [REDACTED].
[FRAGMENT]
Here’s what I’ll be doing during [REDACTED] while [REDACTED and [REDACTED]:
* Solving [REDACTED[ (including [REDACTED], if needed)
* Ensuring that [REDACTED], and [REDACTED] as needed.
* Answering any final questions or concerns about [REDACTED]
* Potentially hopping on the phone with [REDACTED] while we [REDACTED]. This has happened before on [REDACTED], so is now something I will always plan around. It happened twice already this year with [REDACTED].
* [REDACTED].
* Double checking that [REDACTED] (this wasn’t done last year)
[FRAGMENT]
Unfortunately, every year that [REDACTED], something has gone unfortunately wrong with [REDACTED]. This has been the result of administrative mishaps on the backend that [REDACTED] don’t have access to ([REDACTED]). Based on this history, you’ll hopefully understand that I’m not too trustworthy of our current capacity for administering [REDACTED] and I would like to be available to ensure that [REDACTED] is as smooth as possible.
[FRAGMENT]
Since I’ve joined the school, this is the first time that we have [REDACTED], let alone one that requires a lot of technical intricacies and moving parts. It’s also the first time I’ve seen us [REDACTED]. So why would we want to add further complications?
[FRAGMENT]
I have put in the planning to ensure that the setup process is as smooth as possible, regardless of what issues might arise. So why are we committed to discarding this preparation and leaving the day up to chance? Why do we want to take risks with all these variables?
[FRAGMENT]
I would much rather not have to worry about [REDACTED] and just [REDACTED]. I would much rather not have to consistently worry about the backend administrative processes for ensuring [REDACTED] are set up properly (even this year, we almost didn’t [REDACTED]). It is far easier to simply [REDACTED] than to have to [REDACTED], especially when there are so many administrative bottlenecks. I have no problem [REDACTED], and would happily do so if not for clear, time-sensitive obligations.
[FRAGMENT]
This issue is not something that we want still up in the air a few weeks from [REDACTED]. The longer we wait on this, the longer the [REDACTED] exam is also in logistical limbo and the less time that [REDACTED] (or another proctor) will have to lock down the [REDACTED].
[CLOSE]
There is no “network,” no “big other,” no higher power to blame for this and act like your hands are tied. This is on you all as a school-level administration. Make the shift.
[CLOSE]
Please advise and amend accordingly.
[CLOSE]
The egos of adults are currently putting the success of our students at risk.
[FRAGMENT]
It is difficult to understand why when I bring up my urgent time demands I’m met with these kinds of responses.
[FRAGMENT]
The hubris here is astounding.
[CLOSE]
Why would we intentionally create all of these risks? For what reasons do we have to act this way? Why would we want to purposefully avoid planning around known challenges? This is absolutely foolish and not the type of thing that we want still up in the air this close to the deadline. Please stop.
[OPEN]
I wasn’t going to respond to that email, but you did ask for my thoughts and I now feel that this whole exchange warrants clearer documentation to prevent similar communication and planning issues in the future.
[FRAGMENT]
I want to address the “unprofessional” callout in my last message. Expressing concerns about planning and organizational challenges, especially ones we have been aware of for months, is not inherently unprofessional. There was no new information in that email that wasn’t made clear back in [REDACTED]. I made a deliberate choice to be direct and matter-of-fact because the moment is urgent and the stakes are high for students. That tone reflects the reality of the situation, not a lack of professionalism. When I think about professionalism, I think about the core demands of our profession: advocating for students and holding systems accountable to do the same. This is the spirit I bring to any extended email or impassioned communication, especially when there are urgent time demands. I hope we can all align on this approach moving forward.
[FRAGMENT]
If we are here to discuss solutions-oriented planning and proactive communication, let’s please do that. Let’s first all acknowledge that I’m writing this while we don’t have a definitive [REDACTED] plan in place...and it’s almost [REDACTED]. A revitalized focus on prioritizing proactive planning is more important now than ever.
[FRAGMENT]
For my specific current situation, I would love to set a clear documentation of what happened at the start of the year and how that set this year up on a terrible note for me. That poor planning is now coming to a head and this simply cannot exist in future years.
[FRAGMENT]
Knowing that [REDACTED], I raised concerns early about whether [REDACTED]. I assumed there would be [REDACTED] or an administrative plan to accommodate [REDACTED]. This [REDACTED] was my primary concern over the summer.
[FRAGMENT]
When I returned at the start of the year, I was told [REDACTED]. That turned out not to be the case. The [REDACTED], and this discrepancy only surfaced after I flagged it.
[FRAGMENT]
One potential solution was to [REDACTED]. I began planning for this months in advance, [REDACTED]. None of this was formally my responsibility, but I knew there would be no movement otherwise.
[FRAGMENT]
This was done 2 weeks before [REDACTED]: theoretically plenty of time to execute and maneuver the course into the schedule, or continually iterate to find the best solution. The potential solution was there and it could have worked out in some form, but due to the critically late timeline of [REDACTED], it didn't. Reasoning provided for why this solution didn’t work was cursory and easily addressable, representative of poor time management in the [REDACTED] process, rather than solution infeasibility.
[CLOSE]
There are email records for all of this, if it helps to refer back. I can forward as needed.
[CLOSE]
So what message does this whole timeline send me as a teacher at this school? Unfortunately, it tells me that proactive, solution-oriented planning and communication mean very little. It tells me I am on my own and have to scrape together an effective class, despite being set up for failure. Thus far, I've managed to somewhat do that, yet at an unfortunately less effective level than in previous years. At the end of the day, I'm here to [REDACTED]. I am happy to be here and contribute towards our mission in this regard. I chose to return to teaching (and at [REDACTED], specifically) for this reason. However, this takes a lot of individualized student attention that gets impossibly strained when there isn't effective administrative planning on the backend. As teachers, we do our best to plan around challenges and set our students up for success. I expect the same level of planning from this administration (each of whom is an expert teacher in their own right) for their "students": the staff. Focus on that and instead of trying to instill some false authority over me.
[CLOSE]
With all this in mind, hopefully you'll see where I'm coming from in my frustrations with the way this year has been delivered. This has created an overall reticence towards communicating with this administration, and I don’t like that email has now become the dominant mode of getting these ideas out. It feels more focused on “documentation” than actual “dialogue,” but that’s a structural critique that deserves separate attention. With all of the issues I’ve raised here, perhaps there were external factors that I'm not aware of that complicated these issues. If there are higher-up issues from [REDACTED] that created these challenges, please let me know so I can know where & whom to appropriately direct my frustrations.
[FRAGMENT]
In contrast, I found components of your response quite unprofessional: less focused on collaboration and more on reasserting authority. That is really not where my focus is (particularly this week) and, as a result, the message was not well-received.
[FRAGMENT]
I’m curious where the unprofessionalism occurred in that email. It was direct and matter-of-fact. It was probably from me calling out how this current problem is a direct result of admin’s poor planning? That was well documented and discussed back in [REDACTED]. I can pull up the email chains if you’d like.
[FRAGMENT]
Informed by what happened in [REDACTED], it is beyond frustrating to hear any kind of plea towards solutions-based planning. You had 3 weeks to enact the clearly planned and outlined solution to prevent this and didn’t. Even as I write this, we still don’t have a definitive plan for [REDACTED]. This is not strong, proactive, solution-oriented planning.
[FRAGMENT]
You may never know the full impact of your planning failures because too often teachers pick up the slack for you.
[FRAGMENT]
Examine your own messaging and consider what was critical for effective collaboration and solutions, and what was condescendingly seeking to establish a sense of authority (quite an unprofessional approach).
[OPEN]
Sure, happy to discuss all of this as much as needed to prevent similar issues in the future. I didn't go to [REDACTED] today, for all the reasons I brought up. If you want to "write me up," that's fine by me. Keep my tab open.
[FRAGMENT]
I really can’t do [REDACTED] this week. I don’t want this to flood that group chat, but here’s the deal, quite bluntly: [REDACTED] (frankly, as a direct result of documented admin mismanagement), and there are now [REDACTED].
[CLOSE]
As admin, please support here. My obligations are elsewhere.
[OPEN]
Yes, thanks for meeting. I thought it was a productive conversation. To maintain transparency for all those now cc’d in this new email, here are some more of those meeting specifics & information to keep in mind for future decision-making. As you all decide on potential changes, it is important to note the legal and health liabilities our policies can create.
[FRAGMENT]
After doing this, I was told that I shouldn’t have trusted these students and should enforce the rules regardless of circumstance. However, it turns out these students were right and I am glad that I was able to safely & communicatively accommodate an immediate need. I appreciate the way you looked into this issue and have now ensured that it won’t be [REDACTED]. It has not been an issue since. Still, an attitude of universal & immediate distrust towards students will be incredibly detrimental in the long run. I urge us to keep this in mind for future student interactions and in shaping future policy.
[FRAGMENT]
I also want to highlight other potential solutions we discussed. Similar to adjusting [REDACTED], prioritizing quick & straightforward solutions can do a lot of immediate good. You mentioned in our meeting being available to [REDACTED] during [REDACTED]. If you, or another member of the leadership team, can consistently assist here, that would be excellent and would largely solve the problem.
[FRAGMENT]
To aid in the leadership team’s decision making, it’s important to note the [REDACTED]. We’re all doing our best here to maintain school safety, but these guidelines exist for a reason, and it’s important for us all to not open up potential legal risks.
[FRAGMENT]
I’m really trying to be honest & upfront in this communication. I am not trying to violate rules; rather, I want us to have the best rules possible. I am trying to remain fully transparent and continually communicate in good faith.
[FRAGMENT]
I would love some guidance here concerning my main issue with these policies: [REDACTED], it will naturally be difficult to deny [REDACTED]. I highly value [REDACTED] (as I know you do as well) and these moments feel like [REDACTED]. I also value the importance of school-wide norms that can help ensure student safety, but when I see these blindspots in their delivery, my unilateral buy-in for these norms is drawn into question. We rightly emphasized the [REDACTED] for rule enforcement during [REDACTED], which feels particularly relevant for these moments, yet this approach has been startlingly absent from our policy enforcement this year. So please help me to morally settle my internal conflict here: what do I do and say to these students when these issues arise so [REDACTED]? On a school-level, fully codifying and communicating what to do in these discretionary moments will do a lot to help with overall staff and student buy-in.
[FRAGMENT]
[REDACTED].
[FRAGMENT]
It is important to maintain effective "habits" and ensure safety across the school. No one can deny this. But at what point are we leaning more towards controlling kids' bodies and [REDACTED] for the sake of universalized rules? The consistently high number of emails we receive about [REDACTED] suggests that it is a critical issue that should be remedied. Can we please start a more open dialogue around the solutions that make sense and can achieve school safety goals, while still honoring [REDACTED]?
[OPEN]
I have sent other emails about this, but there has been some confusion, so let me be incredibly clear here. If anything remains unclear, I am happy to discuss further. There are significant safety concerns related to the recent enforcement of [REDACTED] policies at this school. I understand that the enforcement of these rules comes from a goal of keeping the school safe and cutting down on potential incidents. These are legitimate concerns, but in the rigorous enforcement of our policies, there are other safety concerns that are disregarded and, if anything, made worse.
[OPEN]
I imagine that this is just a templated email sent out to every teacher who isn’t finished with [REDACTED], but here are some things to keep in mind.
[FRAGMENT]
This takes a very long time to do well and will not necessarily align with arbitrary school timelines. If these timelines are more of the priority, then there should have been some kind of deliberate action towards the efforts I attempted before the year started to [REDACTED]. Otherwise, please leave me off these template emails. That said, I plan to be done by Wednesday.
[CLOSE]
The kids, against all odds, are performing quite well.
[FRAGMENT]
This has been one of the worst starts to a school year I have ever witnessed. We are [REDACTED], but little to nothing was done to substantively prepare for this inevitability. When [REDACTED], it is impossible to be set up for success. As teachers, we put in meticulous planning to set students up for success. The same should apply at the school-level leaders planning for teacher success. Yet, there is an almost willful negligence on behalf of the administration to put in the necessary backend work that will ensure the success of this school and shepherd us through difficult times. This focus on "tiny habits" is impossibly inconsistent when the BIG significant administrative demands of an effective school are carelessly neglected. How can we focus on these small changes (and it's a focus almost solely offloaded down onto teachers) when there are such large & glaring gaps? This inconsistency does not create cultural buy-in nor team cohesion.
[FRAGMENT]
When new, ill-prepared initiatives like [REDACTED] are enacted, there is no teacher input, no "trial" period, just a poorly planned mandate that immediately faces challenges and teacher admonishment for not blindly "buying in." While this is just one quotidian example, it's representative of the same punitive approach that is expected to be passed along to students.
[FRAGMENT]
The term "culture" continues to become glued to this idea of punitive box checks that fail to set students up for success beyond that of becoming mindless automatons (the same kind of robotic compliance demanded of the teachers).
[FRAGMENT]
I will not be [REDACTED]. I did not attend it last time, not only due to more urgent demands, but due to an overall disagreement with its administration and requirements. On the whole, I believe that our emphasis on [REDACTED] this year has been misplaced.
[FRAGMENT]
While this does not directly apply to me, on principle I will not [REDACTED]. It was carelessly set up and, from what I have gathered, carelessly administered. Continue to admonish me for this all you want. I stand by my decisions here.
[FRAGMENT]
Additionally, this year I am fully and completely prioritizing my limited time on that which is most directly impacting my students. Before the start of the year, I made it very clear to administration that [REDACTED]. NOTHING was done to prevent this, despite fully planning an incredibly actionable solution.
[FRAGMENT]
The rollout to the start of this year was one of the least organized I have ever witnessed. It is clear to me that, on an administrative level, there is, was, and will not be anything done for [REDACTED]. At the start of the year, I have embraced this very clear reality and, therefore, to ensure both my sanity AND the success of our students, I am trusting in my best judgment on the most pressing uses of my time. This mostly revolves around [REDACTED]. Everything else is quite simply NOT my priority right now.
[FRAGMENT]
At the end of the day, I am putting nothing short of a herculean effort towards [REDACTED], and I’m happy to do it. It would have been easiest, [REDACTED], to not actually [REDACTED], but it’s clear that this is what best [REDACTED]. I’m here to do meaningful work. If I wasn’t invested in this, I’d have remained in strategy consulting, making twice the money for a quarter the effort.
[FRAGMENT]
I am not concerned with how this administration views this and how it doesn’t make me a “team player” and how it doesn’t “culturally” fit into [REDACTED]’s mission. If this is where we are prioritizing our time & effort, then I would challenge us to reexamine what our culture really is. For me, it’s students building confidence in their own voices, tightening their project management skills, and achieving demonstrable levels of college-ready writing.
[FRAGMENT]
If this school has no interest in helping me achieve these goals without an inhuman amount of work, then I have little interest in ill-defined and ill-planned meetings. Every teacher is [REDACTED] and it’s terrible. Don’t make the situation worse. Focus on how to best weather these difficult times.
[CLOSE]
This is something that has come up before and it’s something I will continually bring up. Thanks.
[FRAGMENT]
This is really quite unacceptable and that solution does nothing to address the core issue. The “solution” you have offered is the standard approach and nothing being done to solve the issue.
[FRAGMENT]
It is unmanageable to [REDACTED]. It is unmanageable to [REDACTED]. It is unmanageable to [REDACTED]. This approach will burn me out, burn the kids out, and not result in the kinds of successes we saw last year that I had hoped we could effectively build on this year.
[CLOSE]
This response is strongly worded by design. I want it known that this approach is setting me up for failure and, more importantly, setting the students up for failure. The [REDACTED] issue was a challenge that I had mentioned last year after [REDACTED]. This is something I brought up 3 weeks ago at the start of [REDACTED]. This is something that I put planning into to see how it can potentially work out: [REDACTED]. It is beyond frustrating that this kind of blanketed decision was made so close to the year. It is not something that leaves me inspired and energized to start the school year. Let us please talk through solutions that can address the core issue here: class sizes. I am open to anything.
Messages I Never Sent
Has anyone ever been truly convinced by an email? Probably not, yet institutions and relationships too often devolve into email’s digital void screams. As Upton Sinclair wrote after losing the 1934 California gubernatorial election, “It is difficult to get a man to understand something, when his salary depends on his not understanding it.” The will to change one's mind often comes with challenge of acknowledging the illegitimacy of the systems that provide you with power, security, or both.
My final year at my past job was one of deep frustration, and my attempts to improve the situation were unsuccessful. Part of these efforts included strongly worded emails, some sent, but most remaining as drafts in my computer’s notepad app. The creation of these drafts (and ultimate emails) became an interesting practice in interrogating institutional dynamics and rhetorical expression. My emails were easy to dismiss as unprofessional diatribes, yet documentation remained the one thing feckless bureaucrats feared. So, it was only through these emails that even a modicum of progress would occur (though, often it was just lip-service toward progress). Direct conversations, with their lack of documentation, almost guarantee issues disappear. So what happens when a culture rewards aggressive communication that only makes everyone feel worse? We get a lengthy log of overly impassioned writing to turn into art.
These messages exist because something had to be said, even though saying it would never land. Some of my best, most fluid, and most alive writing happened here. It was fast, unblocked, and poured freely through my fingers within a moment. And it’s in that moment where that language generally stayed, until it now appears again within this project. These words would never have the artistic impact where they were sent; they would be read as a tone problem, a threat, or a general nuisance to disregard. The "frustrated work email" medium exists without an audience, so instead these drafts get frankensteined together here, reshuffled and released back into the void, one random generation at a time.
Clicking “Generate” will deliver a random collection of fragments from real email drafts that I composed on a notepad app. I redacted overly-specific, identifying, or sensitive information from these drafts to only leave the raw sentiments. The fragments don’t necessarily cohere cleanly and repetition replaces conclusion. This mirrors the experience itself with no closure, no resolution, no “lessons learned,” and no meaningful dialogue that can lead to real action.