PTO: 3 mistakes your manager won’t forgive
Requesting time off shouldn’t feel like rocket science – but our employee Dave somehow managed to test every wrong way to do it in just one year. He’s the living embodiment of time-off request mistakes that no manager wants to deal with. Some are hilarious, some are chaotic, and some will make you wonder: “Who even thought this was a good idea?”
Disclaimer: Dave is a fictional character – but his story was inspired by true events, based on anecdotes from coworkers, friends, acquaintances, and family.
Method #1: The Stealth Announcement
Dave had a plan: a weekend getaway to the coast. All he needed was one day off – Friday. Instead of filing a proper request, he decided to “slip it into conversation” under the radar.
So one Monday, three weeks before his trip, he casually bumped into his manager and started talking about… plaster types. Seriously. Vapor permeability, mineral compounds, and other topics that made his manager mentally check out by sentence two. Somewhere in that monologue, Dave threw in a little gem:
“...and then we’re heading to the cottage, so I’m off on Friday.”
The only thing the manager retained was “plaster.”
Friday came. Dave disappeared. No one knew where he was, and two coworkers were seriously considering calling missing persons.
Method #2: “Everyone Knows When I Take Time Off”
Last year, Dave was off from August 1st to 14th. This year? Same thing. “It’s the only time my wife’s company has collective leave.” Fair enough. Except… no one knew he was off again this year.
Dave thought casually mentioning it during lunch or hallway chats was enough. After all, doesn’t everyone keep mental notes of small talk between two weather updates?
Unfortunately, tradition isn’t a formal request – and verbal vacation notices just don’t cut it.
Method #3: A Slack Message at 10:48 PM
For an added layer of awkwardness, Dave opted for the classic “late-night Slack message”. At 10:48 PM, he sent a short, context-free message:
“Just so you know, I’m off from Wednesday.”
His manager was online (unfortunately), and visibly unimpressed. At one point, he briefly considered quitting – himself, not Dave. The next morning at 9:00 AM, Dave had to submit a spreadsheet with last month’s working hours.
Karma? Definitely.
How to Handle the Daves in Your Company
Let’s face it: no one wants to be that manager who tracks PTO manually. And no one enjoys working in a team where vacations live in Slack DMs, vague memories, or hallway gossip.
That’s why there’s Kloki – a time-off management tool that offers:
✅ Clear, simple requests for vacation, sick leave, remote work, and more
✅ A calendar that’s visible to everyone (and based on facts, not vibes)
✅ Accurate, accessible records – no spreadsheets, screenshots, or guesswork
Forget “I told you” or “You should’ve known.”
With Kloki, everything is submitted, visible, approved – and forgotten only when it’s supposed to be.
Curious about cost? Check out Kloki’s pricing plans – there’s even a free option for small teams
Because you don’t have to put up with the Daves.
You can bring in structure. Without sounding like a robot overlord.
Just smart. With Kloki.