I just got back from a work trip and am here to give you all the advice I can think of on all the questions you might have including what to wear, how to act, how much to drink, booking flights, spending time with your coworkers, and so much more! 

If you’ve never been on a work trip, have one upcoming, or may have one soon in the future, this is for you.

The Ultimate Work Trip Guide: 7 Essential Tips for Your First Company Offsite

Going on your first work trip can feel overwhelming. Whether it's a company-wide offsite, client visit, or team retreat, these trips require a different mindset than your typical 9-to-5 routine. After completing a recent company offsite in Austin, Texas, here's everything you need to know to navigate your next work trip successfully.

Understanding the Purpose of Work Trips

Work trips serve various purposes:

• Company offsites: Bringing remote or distributed teams together

• Client visits: Face-to-face relationship building

• Training sessions: Skill development away from the office

• Team retreats: Strategy planning and team bonding

Remember, regardless of the specific purpose, you're being paid to be present and engaged the entire time.

1. Master the Booking and Travel Process

Flight and Hotel Arrangements

• Most companies book accommodations for you, typically in economy class

• You'll likely get your own hotel room (companies can't legally require roommates)

• If you prefer a specific seat, ask first—don't upgrade without permission

Key Questions to Ask Before You Go:

• What's my daily spending limit or stipend?

• How do reimbursements work?

• What transportation is covered (Uber, parking, etc.)?

• Are seat upgrades allowed?

Pro tip: Don't assume anything is covered. Always ask before spending, or you might end up paying out of pocket.

2. Prepare for an Intensive Schedule

Work trips are typically scheduled from morning to night. Unlike your regular workday where evenings are yours, work trips often include:

• All-day meetings and sessions

• Group lunches and dinners

• Evening activities or networking

• Hotel bar conversations

Reality check: These days are NOT your days. You'll be "on" the entire time, which can be mentally exhausting.

3. How to Behave Like a Pro

The No-Phone Rule

Many successful work trips implement a no-phone policy during sessions. Put your phone in your pocket and stay fully present during:

• Presentations and meetings

• Group discussions and brainstorms

• Team meals and activities

Drinking Guidelines

• Remember you're still in a work environment

• Know your limits and stick to them

• Consider having one alcohol-free evening to stay sharp

• Don't let free drinks lead to poor decisions

4. Dress Code Strategy

The golden rule: What you wear to work is what you should wear on the work trip.

Smart Packing Tips:

• Pack multiple outfit options

• Ask a trusted coworker what they're planning to wear

• Prepare for both formal meetings and casual activities

• Don't be afraid to ask the trip organizer for dress code guidance

5. Network and Build Relationships

Work trips offer unique opportunities to:

• Get to know remote coworkers personally

• Have deeper conversations than typical Zoom calls

• Build relationships across different departments

• Learn about colleagues' lives outside work

Action steps:

• Sit next to someone you haven't talked to much

• Ask about family, hobbies, and interests

• Suggest grabbing a drink at the hotel bar

• Be genuinely interested in getting to know people

6. Improve Your Professional Presence

Speak Slower and More Intentionally

• Fast talking can make you sound nervous or unsure

• Speaking slowly conveys confidence and authority

• Practice ending sentences cleanly without filler words like "and yeah" or "that's it"

Public Speaking Moments

Work trips often include:

• Round-table sharing sessions

• Presenting to the group

• Answering questions in front of everyone

Use these as practice opportunities to improve your public speaking skills.

7. Self-Reflection Questions

Use work trips for professional development by asking yourself:

1. What do you want from working at this company?

2. What do you want to work on personally/professionally?

3. Rate yourself as a team member (1-10) - and why?

4. Who is your mentor, and how can you find one if you don't have one?

Setting Goals for Growth

Consider creating both short-term and long-term professional goals during your trip. The change of environment and reflection time can provide clarity on:

• Where you want to be in 3-6 months

• Your career trajectory for the next year

• Skills you want to develop

• Relationships you want to build

Final Thoughts

Work trips are paid appearances—you're representing yourself and your company. While they can be exhausting, they're also incredible opportunities for relationship building, skill development, and career advancement.

Remember to stay present, be professional, and view the trip as an investment in your career. The connections you make and skills you develop during these intense few days can pay dividends for months or years to come.

Want more career and workplace advice? Listen to Guyset - A Guy's Guide to What Should Be Talked About, available on Apple Podcasts, Spotify, and wherever you get your podcasts. Have a topic you'd like covered? Email josh@guyset.com or Dm @theguyset on Instagram

If I missed something or if you have any other questions, let me know and I'll do a follow up or just answer you directly lol.

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See you guys next Tuesday.