If you have spent any part of your career in HR, you already know this feeling: an employee walks into your office, or sends a hesitant email, and says they need to take some time off. Maybe it is a health crisis. Maybe it is a new baby. Maybe they are completely exhausted and do not know what else to do. You want to help them. That is why you are in this work. But behind that simple conversation sits a minefield of regulatory obligations, documentation deadlines, eligibility calculations, state laws, return-to-work protocols, and accommodation assessments. And you have 47 other open cases.