Most companies have a travel policy. Sort of. What usually exists is a document somebody threw together back when the company had twelve employees, and it hasn’t been touched since. That works fine until a client engagement or a product rollout requires someone to be on-site for weeks at a stretch. That’s when the gaps show up fast.
The booking and the calendar invite are the simple parts. What nobody budgets for is the messy operational space between a regular work trip and a permanent move. Extended assignments (the kind that last a month or more) sit in this weird gap where standard travel policies don’t quite apply but nobody’s drafted anything better. Companies that send employees on these longer stints, whether for client onboarding, project launches, or interim management roles, often find apartment rentals that are fully furnished in Toronto or similar arrangements make more sense than burning through nightly rates. But the accommodation piece is honestly the easy part. The harder stuff tends to sneak up.
Per Diem Math Stops Adding Up
Here’s one that catches finance teams off guard more than it should. The daily allowances that work fine for a four-day conference start looking pretty questionable at week three. The GSA’s per diem rate structure works well enough for its intended purpose, which is reimbursing federal employees on relatively short domestic trips. A lot of private companies model their own policies on those same numbers. The problem is those rates assume someone is passing through, not settling in for a month and a half.
Consider what happens in practice. Someone on a three-day trip is eating restaurant meals and maybe grabbing coffee between sessions, so $68 a day for food feels about right. Extend that to six or seven weeks, though, and behavior changes completely. People start cooking. They buy groceries. The whole spending pattern shifts, and the per diem either becomes a windfall (which feels weird) or companies switch to actuals and suddenly there’s a pile of receipts nobody wants to deal with.
Some companies handle this by creating a separate extended-stay policy with different reimbursement tiers after, say, 14 days. Others just wing it. The ones who wing it tend to regret it, not because of any single expense but because of the slow accumulation of inconsistent approvals and confused employees.
The Productivity Dip Nobody Talks About
There’s this assumption that once someone lands at their assignment, they just… get to work. But researchers at Harvard Business School found something interesting. A study looking at the connection between nonstop flights and innovation showed that face-to-face interaction across cultural or time-zone gaps genuinely drives results, but the logistics around that travel matter more than people realize.
The first week of an extended assignment is often a write-off, productivity-wise. Not because the person isn’t trying, but because settling in takes bandwidth. Finding a grocery store. Figuring out the transit system. Getting the Wi-Fi situation sorted in a way that actually supports video calls. It’s all small stuff, but it compounds.
What’s less intuitive is that the dip sometimes comes back near the end too. Around week five or six, there’s this restlessness. The novelty is long gone, the employee’s personal life is on hold, and motivation quietly erodes. Companies that build in a check-in at the midpoint (even an informal one) tend to see better outcomes than those that just assume everything’s fine until the return flight.
Compliance Details That Seem Minor Until They Aren’t
This one’s drier but arguably the most expensive if it goes wrong. Extended assignments can trigger tax obligations, employment law considerations, and reporting requirements that nobody on the project team is thinking about. If someone’s working in a different state or province for 30 or more days, there may be payroll tax implications. Some jurisdictions have thresholds as low as a single day.
It seems like it should be straightforward, but it rarely is. The rules vary wildly depending on location, the employee’s home base, and what exactly they’re doing while they’re there. One compliance manager at a mid-size firm reportedly described it as “the kind of thing that only becomes a priority after someone gets a letter from a tax authority.” Which, fair enough.
Companies that are scaling up and sending people on these longer assignments would do well to loop in legal or HR early. Not after the trip is booked. There’s a decent overview of the legal safeguards growing businesses overlook that covers some of the broader compliance blind spots, and extended travel is absolutely one of them.
Anyway. None of this is unsolvable. It’s just undersolved, mostly because extended work assignments fall into a category that doesn’t have a clean owner in most organizations. Travel manages the booking. HR manages the policy. Finance manages the money. And the employee in the middle is just trying to do the job they were sent to do.
It probably deserves more attention than it gets.
