"Employees might think, 'This is great and wonderful to take as much time as we want. But the question is, how much can I take now?'"
Online dating site eHarmony have just announced their Australian staff can now enjoy unlimited annual leave, and managing director Nicole McInnes told news.com.au the policy was met with more questions than smiles at first.
"It sounds like you could take a year off, but you can't," she says.
"Even my most junior staff were like, 'We know we have to get our work done' so it was nice to see the responsibility kick in almost immediately."
The fact is, if you push the boundaries, you'll likely limit your chances of a promotion, and if you're never around there's a good chance you'll reduce your capacity for networking with your superiors and positioning yourself for a coveted role.
At any rate, McInnes says eHarmony management will still retain approval over leave requests and people won't be able to take eight-week chunks off.
"We are a small team and it would be too hard to cover it," she says.
"I'm thinking that instead of taking one week in the middle of the year, I'll do two, and will take ad hoc leave without worrying about running out."
McInnes says another bonus is that you don't have the angst of asking for the odd day off to move house, go to the dentist or look after your kids on school holidays - plus doing so won't mean cutting a later holiday short.
"There is a shift towards understanding that productivity and contentment in the workplace is linked," she says.
From all the things we are seeing and companies we talk to, it seems to indicate that employees are not taking any more or less [vacation days].
"All the psychological textbooks say that if you want people to behave in a certain way then you have to treat them like they are already there - so if you want trust from somebody, you have to trust them."
Melburnian Elsa James is working for a New York ad agency who also offer unlimited leave and says that it doesn't mean holidays every second week - in fact, staff rarely take more than four weeks in a year.
"In New York, people will take a week at a time - the culture isn't really to take long holidays or lots of holidays," James told news.com.au.
James says that you have to be thoughtful and reasonable if you're planning to go away, so she usually takes a Christmas break, two weeks midyear to come back to Melbourne and a couple of long weekends throughout the year.
"I don't think unlimited leave necessarily means 'take a huge amount more leave'," she says. "I haven't seen anyone abuse the unlimited leave here, but I wonder if that's connected to the culture. Like any good relationship, when you're onto a good thing, you do everything in your power to not abuse that respect and trust."
From a legal perspective, the additional leave may not have the same protections as annual leave, meaning an employer may be able to dismiss employees for taking additional leave.
Andrew Jewell, principal lawyer at McDonald Murholme, told news.com.au that staff ought to ask their employer to clearly articulate their unlimited annual leave policy.
"From an employee's perspective it would appear that the policy is all positive, however the downside may be that employees are reluctant to take additional leave when offered," he points out.
"From a legal perspective, the additional leave may not have the same protections as annual leave, meaning an employer may be able to dismiss employees for taking additional leave."
Jewell says that the quickest way to eliminate an unlimited leave policy would be if employees abused the system, so the onus is on staff to use it wisely so they can keep cashing in on a bit more downtime.
"Organisations have realised that if they keep employees really happy and content then they are actually going to give more back to the company - it's a give and take situation," McInnes adds.
"For me [this policy] is about freedom. It doesn't mean you can take two or three months off at a go because that puts your colleagues under too much pressure. I think it means an extra two-week holiday a year."
And we doubt anyone who's used to four weeks annual leave would complain about that!