You just spent months recruiting a fantastic new employee. They’re brilliant, motivated, and a perfect fit for the culture. After a few weeks of training, they head out on their first business trip.

Then, their first expense report lands on your desk. It’s a mess.

It’s over budget, they booked their hotel on a random website, and they’re missing half the receipts. Now, instead of focusing on the great work they were hired to do, they’re stuck in a frustrating back-and-forth with finance. You have to have an awkward conversation about the rules, and your new star employee feels embarrassed, confused, and unsupported.

This isn't their fault. It's a failure of your onboarding.

We spend weeks training new hires on our products, systems, and culture, but we often throw them into the complexities of business travel with zero guidance. It’s time to fix that. Here is a simple checklist to make travel policy training a seamless part of your onboarding process.

The High Cost of a "Trial-by-Fire" Approach

When new employees are forced to learn the travel rules through trial and error, it creates real problems.

• •
  It Creates a Terrible First Impression: A new hire's first interactions with their manager and the finance team about money shouldn't be negative and stressful. It sets the wrong tone for their entire employment experience.
• •
  It Wastes Everyone's Time: The employee, their manager, and the finance team all lose valuable time correcting mistakes that were completely preventable.
• •
  It Establishes Bad Habits: It signals that the company's processes are confusing and that policies aren't communicated clearly, which can lead to a career of compliance issues.

The 4-Step Checklist for Travel Policy Onboarding

Integrate these simple steps into your existing new hire plan to set every employee up for success.

1. Provide the "One-Page Cheat Sheet" on Day One.

No one wants to read a 30-page legal document in their first week. Instead, include a simple, visually appealing "Travel Quick Guide" in their digital welcome kit. This one-pager should cover the absolute essentials:

• •
  How to get a trip approved.
• •
  Where to book travel (the official tool).
• •
  The most common budget limits (e.g., hotel caps, meal allowances).
• •
  Who to contact for help.

2. Hold a 20-Minute "Travel Philosophy" Session in Week One.

Schedule a brief, informal meeting to walk them through the travel program. The goal isn't to read the policy aloud; it's to explain the "why" behind it.

Frame the conversation: "Our goal is to ensure you are safe, comfortable, and productive on the road, while being smart with company money. Here’s the tool we use to make that easy."

Do a live demo: Spend 10 minutes showing them the actual booking platform so they know exactly what to expect.

3. Assign a "First Trip Buddy."

The first time is the most critical. There’s a huge difference between seeing a demo and booking a real trip under pressure.

The action: For a new hire's very first business trip, have their manager or an assigned "travel buddy" do a quick 10-minute screen-share with them as they book. This hands-on guidance builds confidence and catches any confusion in the moment.

4. Let the System Be Their Ongoing Guide.

The best training is a system that makes it hard to make a mistake. Make sure the new hire is set up correctly in a modern travel management platform that has your policy rules built-in.

How it works: The system's automatic guardrails, like flagging an out-of-policy hotel or filtering out business-class flights, will provide constant, gentle reinforcement of the rules long after onboarding is over.

Onboarding is your first and best opportunity to show a new employee how your company works. By making travel policy a clear and supportive part of that process, you can eliminate a major source of new-hire friction and start building a foundation of trust and compliance from day one.