The PTO request that taught me something about scaling challenges
Workplace Jiujitsu #12: When good intentions meet growing company constraints
I thought I was just asking for time off. It turns out I was seeing the reality of small company growing pains.
Here's what happened: I proactively requested additional PTO for a health matter. The response? "We can't approve extra days, but you can take as many unpaid days as you need. We try to be flexible."
Good intentions? Absolutely.
But it highlighted something interesting: The gap between wanting to help and having systems to help consistently.
At smaller companies: → HR is often one person wearing multiple hats → Policies get made case-by-case instead of systematically → What works for 10 employees breaks at 50
This wasn't about bad culture. It was about growing faster than processes.
The insight for job seekers: Ask about the company stage, not just company values.
"How do you handle exceptions to standard policies?" "What happens when situations don't fit your current processes?" "How are you scaling your people operations?"
Bottom line: Sometimes "we're figuring it out" is the honest answer. The question is whether you want to grow with a company or join one with established systems.
Both paths have tradeoffs. Neither is wrong.
What stage of company growth fits your career needs right now?