For all its upsides, bleisure isn’t without pitfalls. The most obvious is blurred lines between work and play. When an employee tacks on personal days to a business trip, who pays for what? Flights may cost more if return dates shift, hotels may creep above policy limits, and meal expenses can get messy when family joins. Without clear guidelines, finance teams are left untangling half-work, half-holiday receipts.

There’s also the question of duty of care. Companies are responsible for employee safety on business travel, but does that responsibility extend if the trip runs into personal time? If someone falls ill or faces an emergency during the “leisure” part of their stay, it can get complicated fast. Grey areas around insurance cover, liability, and emergency response expose companies to risk if not thought through in advance.

Productivity is another pressure point. Most employees treat bleisure responsibly, but there’s always the concern that “I’ll work from the hotel in the morning” turns into lost hours or missed meetings. For managers, setting expectations up front is crucial to avoid misunderstandings that can sour both the trip and the team dynamic.

Finally, there’s the optics. Colleagues who aren’t travelling might see bleisure as a perk handed to a select few, especially if communication isn’t transparent. Left unchecked, that perception can cause resentment and chip away at team morale.

None of these risks mean companies should shut the door on bleisure. They simply mean policies need to keep pace with reality. Clear rules on what’s covered, where the company’s duty of care begins and ends, and how expenses should be logged remove the guesswork. That way, employees can enjoy the benefits of bleisure without exposing the business to unnecessary headaches.