The part of being a jounin-sensei that no one talks about is having to handle genin paperwork.
If Hiruzen had known that having genin would increase his piles of personal hell, then he would have jumped out the window before anyone could assign him any. Because while the Academy supposedly teaches genin how to write and file proper mission reports, scraping a passing grade is incredibly easy, and it's as genin teams that these lessons first get put into real practice.
Writing a mission report in class about how your weekend went is very different to writing an actual mission report about how your latest C-rank went, and it's the jounin-sensei's job to teach that difference.
It's their job to make sure that the report is written to acceptable standards and not filled with petty, genin-level drama (as opposed to jounin-level and ANBU-level drama, which is always interesting). The desk-shinobi do not want to read about how your teammate kept putting slugs in your tent and other useless facts, such as how this started a prank-war that you totally won or how snakes are obviously superior to slugs in literally every way imaginable.
Good god, goddamn preteens are the worst.
It's not actually that genin mission reports are considered very important and regularly consulted – the jounin-sensei's report, being to acceptable standards, is the one that gets read over by the important people when necessary. It's just that the desk-shinobi consider proper paperwork exceedingly important and wield a truly fearsome amount of power. They don't want to have to deal with the genins' future terrible paperwork and the jounin-sensei don't want to experience the seven levels of administrative hell that the desk-shinobi can unleash on uncooperative jounin-sensei.
It's a silent understanding between Konoha-nin: teach those little fuckers to write legibly and clearly or drop down dead for the preservation of your sanity.
Which brings Hiruzen to his team of uncooperative fuckers... Team Seven.
Even though his children have left the rank of genin behind them and are becoming truly excellent and unparalleled shinobi in their own rights, they're still causing him hell. Because the desk-shinobi still hold him responsible for them and not a single one of his students could just be goddamn normal and just do their fucking paperwork properly and just stop causing him headaches.
He regrets not jumping out that window and running far, far away.
The biggest of his headaches by far is Tsunade.
She's an incredible kunoichi who will only become greater – and who expected anything otherwise from the Senju princess, anyway? Hiruzen may or may not have heard the rumor that the hospital's medic-nin have a shrine to her hidden in a janitor closet somewhere – which many injured and hospital-imprisoned ANBU dare themselves to find out of boredom – but that's completely besides the point.
The point is that Senju Tsunade won't do her shinobi paperwork worth a damn.
A fierce personality, she burns with Konoha's famous Will of Fire – a will that is determined to never complete her mission reports and to set all her paperwork aflame. Hiruzen doubts that he will ever get the girl to stop proclaiming it to be an enemy in itself, and to stop killing it with fire and then handing the ashes in three weeks late.
And the thing isn't that she can't do paperwork – put her in a hospital and she becomes a demon for proper paperwork and impeccable filing – it's just that apparently mission paperwork is boring, soooo boring, sensei, I can't do it, I'll diiiie.
Hiruzen just doesn't know what to make of it all. He doesn't know if she's just trying to push his limits or play a prank or what, but whatever the case, Tsunade clearly has no room whatsoever to tease her teammates for being overdramatic over the littlest things. None at all.
The performance of betrayal she enacted in the team's early beginnings after her male teammates banded together and refused to write her mission reports for her... Good god, what a show. The tears, oh, the tears.
So far, Hiruzen has received poorly-written reports (of an illegibility worthy of only a medic-nin) on restaurant napkins, an old towel, a broken bar-stool (who the hell is letting the girl into bars ), several take-out menus, old Academy tests and handouts, old sealing scrolls, old explosive tags, and various rags that seemed to be ripped pieces of clothing ranging from a serving apron to socks.
It's a prank, he's sure of it, but he doesn't know how to make her stop.
He'd gone hunting for advice, since he doesn't understand young girls, but his teammates had only raised their eyebrows in the way that meant they were laughing at Hiruzen and coolly informed him that they couldn't do Hiruzen's jounin-sensei duties for him. Her parents had just shrugged and told him that she'd probably stop eventually, once she no longer got a kick out of it. And the desk-shinobi still somehow all love her because they remember her (with much cooing) as a toddler running around the Hokage's Tower.
For awhile, Hiruzen had been convinced it was a Senju conspiracy.
(He's still a little convinced. Just a bit.)
The next of his headaches is Orochimaru, who does admittedly actually do his paperwork and is a genuine genius and a brilliant shinobi. It's just that Orochimaru is... moody. Through him, Hiruzen has been thoroughly educated in the concept of the tempestuous genius and, correspondingly, been educated in the various effects that this can have on Orochimaru's paperwork.
There's the “cold shoulder” mood, where he only writes the very bare minimum required for an acceptable mission report to show he's severely unhappy with absolutely everyone.
There's the “bored scientist” mood, where the report focuses almost entirely on a particularly interesting new jutsu or bloodline and various hypotheses. The Research Department has committed ruthless violence to get their hands on some of these. Absolutely brilliant and mildly horrifying stuff, apparently.
And then there's the “I don't deserve this” mood, where he laments his genius being forced onto such an idiotic mission or with such bothersome teammates or the sheer injustice of his life.
There's also the “I was testing some new drug or building up my immunity to some poison” mood, which is either admirably coherent if a wild ride to read – Orochimaru's report of an A-rank infiltration mission written while high on happy drugs is still, hands-down, the most hilarious piece of literature that Hiruzen has ever read – or pages and pages of words that are completely incomprehensible if not illegible if not in another language or complex code known only to Orochimaru.
And who could forget the special “dark and/or psychotic undertones” mood? Where one got a chilling feeling the more of the disturbing report they read and Hiruzen got worried notices from the Psychology Department suggesting that Orochimaru get therapy right now.
One would think that the Psych Department would have given up after the first time Hiruzen tried that and Orochimaru, in one of his more pleasant and cordial moods, had ended up accurately psychoanalyzing the therapist to tears instead, but it was sort of sweet that they were still optimistic about a different outcome. Orochimaru doesn't exactly work along the lines of anything resembling "normal", anyway. If normal doesn't frustrate or confuse him, it bores him.
A brief list of Orochimaru's other common moods included: “Jiraiya did something stupid again and I hate his stupid face so much” anger, “Tsunade shouldn't be the boss of me why do I keep listening to her commands she's shorter than me” defiance, and “something unrelated occurred that has ruined everything like my hot water going out last night” passive-aggressive irateness.
The worst part of the chaotic mood-swings was that Orochimaru never failed to invent more.
And then there was the last of Hiruzen's headaches... Jiraiya.
Hiruzen originally thought that Jiraiya, being... well... Jiraiya, would end up doing like Tsunade: handing in extremely late reports that were written in jam on a paper plate in illegible nonsense. But Hiruzen turned out to be more wrong than he ever could have imagined.
Jiraiya's handwriting, unlike his teammates' scrawls, is flawless.
It's so neat. It's so beautifully written that every page looks professionally printed rather than something that could be accomplished by a human hand. It's nearly enough to make Hiruzen cry sometimes. And it makes sense in hindsight, what with Jiraiya's passion for sealing and more secret passion for literature, but it was unexpected at first for Hiruzen to see it and the sheer pride that Jiraiya took in his writing abilities.
And the sheer joy, because Jiraiya doesn't turn in mission reports so much as he turns in daring tales of shinobi adventures and complex short stories of the dangerous world of a shinobi. The boy is a natural storyteller with incredible observation, crafting together the necessary details with his own analyses to create compelling mystery action-adventures and angst-filled tasks of hardship and sacrifice.
Hiruzen tried to tell him to stop it, because it seemed like fiction at first, but the thing is that Jiraiya's never actually wrong. Every detail in his mission reports is exactly as he observed them, nothing more and nothing less, without embellishment or added fiction. They're non-fiction... in a fictional style.
Apparently he saves his fiction writing for his personal projects. Otherwise, he'd said jokingly to his sensei, his mission reports would be rated for inappropriate content and a lot of it. Insert suggestive eyebrow waggle. (Oh god, Hiruzen had a sneaking suspicion then about that new author writing short stories for a certain adult magazine that he definitely doesn't have a subscription to.)
Jiraiya apparently enjoys the challenge in creating a captivating story solely out of reality.
Hiruzen then tried to tell him to stop the complicated analyses of enemy-nin, their operations, their motivations, their backstory, and so on. But Jiraiya is always perfectly clear in his reports that his hypotheses are just that. And the damn thing is that the boy is right more often than not.
Jiraiya once accurately guessed a Suna missing-nin's backstory down to the hidden child with the secret mistress from Kiri, and Hiruzen had to bang his head against a wall for five minutes to get over that, which Tsunade had not been happy about. (It's either that or smoke himself up like a chimney, and apparently that's bad for him too.)
Hiruzen tried to reason that Jiraiya was putting way too much time, effort, and unnecessary detail in, and that such reports really weren't proper shinobi behavior, but it sounded weak even to him. It's probably far better the boy create masterpieces of non-fiction fiction than find some other hobby.
Besides, if Hiruzen ever succeeded, he'd probably get gutted for making Jiraiya stop.
Hiruzen has seen adult desk-shinobi tackle each other to be the one who gets to read Jiraiya's latest mission report first – biting, there was definitely biting involved, and some hair-pulling. He's seen adult kunoichi who will kill men with their hairpins weep over some of them. He's seen hardened members of the T&I Department gush over their favorite parts of some others. (What is it with T&I and romantic comedies, anyway? That's just... disturbing.)
Hiruzen also may or may not have once pulled an all-nighter to read one of Jiraiya's mission report mysteries once. It was really good and he still can't get over the unexpected twist at the end, even though he went on that mission.
If only Hiruzen could stop having desk-shinobi come up to him and report that Jiraiya's paperwork had once again exceeded acceptable lengths, and then ask in the next breath if Hiruzen thought Jiraiya might ever write a sequel. You know, to mission such-and-such, because it really deserved a sequel. They wanted to find out what happened to the village healer woman and if she ever reunited with her lost kunoichi lover again, and what the village's fate would be with the implied threat of bandits rising in the near future.
Hiruzen usually had to stop and blink at that. Because a sequel? To a mission report?
(He remembered that mission. That was a good one. He'd really like a sequel.)
In the end, no matter his efforts, Hiruzen is pretty sure that he will never get a normal piece of paperwork out of any of them. But then again, Team Seven wouldn't be Team Seven if they were anything near normal.