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Travel Guide for The Office Road Warrior

Business Travel Tips

A while back, during a particularly busy travel time for my job, I posted a few of my own travel tips for people who work while living out of airports and hotels weekly. To my surprise, this post got a lot of attention and feedback—bringing me to the realization that there are a lot of people out there who might benefit from some tips to make frequent business trips just a little more bearable. Here are some tips based on my own experience and the advice of fellow road warriors about staying connected with your team using some Microsoft tools many of us already have access to.

I have been traveling out of state for the last few months training end users on Microsoft technologies to ensure a successful post deployment adoption rate within corporations. I’ve spent most of this time in hotels and airports hopping from one city to the next. As a marketing director, it can become difficult to keep myself–and my team–focused on the short- and long-term goals and of our department while traveling regularly across the country.

My saving grace has been Microsoft Teams.

First things first though, even the best technology cannot save you from having a bad trip if you don’t prepare for the other aspects of your trip, so let’s dive into some general travel tips I’ve utilized over the past year!

Some people love traveling for work–I am not one of those people.

I have a family, house, car, friends, responsibilities, and a host of extracurricular activities I miss when I am traveling for work. However, I am devoted to my organization and its success–as I’m sure many of us are—and I’m also dedicated to the relationships PEI has with our customers. No matter what industry you are in, travel is sometimes part of the game, and it’s important to build your own travel guide to keep yourself organized and sane.

Here are a few of the things my travel guide has helped me accomplish:

  • Increase my productivity while decreasing my travel time
  • Lower stress that comes from traveling
  • Stay connected with the office and stay aware of important details
  • Keep myself and my team organized on internal and external projects
  • Strengthen team members’ relationships and trust within one another
  • Build a better understanding of and stay on top of client needs

The list goes on, but the important thing is finding what works for you. I’ve broken this travel guide into the stages of traveling to help you find relevant tips as you progress through the traveling process. Feel free to comment below so we continue to build this guide together!

Stage One: Pre-Flight / Packing / Booking

Rewards Credit Cards or Programs

Depending on how you pay for travel expenses like plane tickets and lodging, this will differ for some people. The bottom line is travel expenses are usually large ones, and you should collect the rewards for them.

If you pay for your own travel and are reimbursed from your organization, make sure you get a credit card with an attractive rewards program. I use the Chase Sapphire Reserve card because I earn 3x the points on all travel and food—my biggest expenses—and it gives me access to Chase’s discounted travel portal.

If you don’t pay for your own travel, you can still join the airline and hotel rewards programs. I am a Southwest and United rewards member, Marriot’s SPG program member, and Hertz rewards member–where I get points whether I pay the bill or not.

Attire for Business Traveling

Bring a bag for dirty clothing; they make smaller bags specifically for this purpose now, but any small bag will do. This keeps dirty (and possibly smelly) clothes away from clean clothing.

If you’ll be in a business formal environment, bring collar stays; these are magnetic collar inserts that keep your collar straight and tight.

Lastly, pack to dress appropriately while staying comfortable. They make khakis and shirts that stretch and breathe a bit. Since you’re already uncomfortable working away from home, don’t add to the stress by dressing uncomfortably.

Technology that Travels Well

Bringing a few compact pieces of technology can help you work better on the road.

  1. Mouse: Bring a small wireless or retractable-wire mouse. Working on a track pad of a laptop for days can get very frustrating, especially if you are doing design work.
  2. HDMI cord: this will allow you to hook your computer up to hotel TV’s/monitors for more workspace.
  3. Phone holder for the car: While renting cars and driving in unfamiliar locations, I am always using my phone’s GPS to get me where I need to be. Instead of having to frequently look down and risk an accident, a phone holder can make navigation safer. I recommend a holder that’s both easy to install and uninstall–like the kind you can clip onto the vents.
  4. Over-Ear Headphones: These will allow you to block out any unwanted sound when you are working or traveling.
  5. Wireless Hotspot: Portable, battery-powered wireless devices make a huge difference when trying to work in airports or other places with unreliable wifi.
  6. USB Cords and Dongles: Bring more of these than you think you will need! You have so many things that need to be charged when you are on the road and not a lot of downtime; it’s nice to be able to charge them all at once.
  7. Portable Charger: these are always nice for ensuring your devices never die. You want to get one that can completely charge your phone multiple times. Often times our phones help us get where we need to go in unfamiliar places and if your phone dies, you may end up stranded.

Luggage: Suitcase, Backpack, Computer Bag

Travel as light as possible. If you can avoid checking a bag, do it. This will prevent you from spending more time at the airport than necessary. Also, get yourself a solid computer bag or backpack with multiple pockets that is organized. I personally travel with an Osprey Carry On & Thule Computer Backpack.


Keep a fully assembled toiletry bag ready to go at any time. Depending on the complexity of your hygiene routine, this is not always possible, but for the frequent business traveler, this can drastically reduce packing time while ensuring you have all your essential products with you each time you leave.

One item commonly forgotten in the toiletry bag is medicine. This is one item I cannot travel without because I am somewhat of a hypochondriac. The more you travel, the more you come in contract with germs and illness. You will get sick more often. Having medicine with you to combat that is important!

The last thing I recommend is to bring a tiny lint roller. Nothing is more frustrating than having to find tape before heading to an important meeting because your outfit is covered in your dog, cat, or hamster’s hair.

Prepare to Stay Connected with Mobile Apps

When traveling for multiple days a week, there is usually very little downtime for opening your laptop and working productively. Download the Microsoft Outlook and Microsoft Teams mobile apps before you head out to the airport. These will ensure you can respond to emails and work remotely anywhere.

With the Outlook app, you have your email at your fingertips as long as you’re in a cell phone service area. Make sure to update your email signature from your application settings to match your work desktop application signature. You want to avoid sending emails that end with “Sent from Adam’s iPhone.” Although these tell people you are out of office, they aren’t as professional.

The Microsoft Teams app lets you stay connected to your team and attend conference calls as well as make and receive calls from your work phone number. The application is very user friendly and ensures you aren’t missing anything while on the road. With Microsoft Teams’ mention (@) functionality and Planner integration, you can be pinged with important updates as well as follow the progress of your team throughout the lifecycle of projects. It also allows you to answer work calls on the road without the caller knowing they have reached you on your cell phone. With Microsoft Teams Meetings, you can easily drop into scheduled meetings and participate instead of trying to find the dial in number and only having access to voice capabilities.

Stage Two: At the Airport

Airport Security: TSA Precheck & CLEAR

As many of you know, airport security is a complete toss up; one day there is no one there and the next it’s an hour wait for screening. Having both TSA Precheck and CLEAR makes you the fastest person through security without having to work for the airlines.

Here’s why: if you are lucky enough to be in an airport that has both, the lines at CLEAR are never longer than 2-3 people, and if you have TSA Precheck, CLEAR will put you in front of the entire TSA precheck line too. For those who only have TSA precheck, the lines are continuing to grow as the service gets more popular.

Attire for Flight

Dress to fly comfortably. Sometimes keeping a spare pair of comfy jeans or nice sweats in the car you can throw on before you head to the airport can make the difference. Also, remember you are going through airport security, so a shirt or top with tons of zippers or pockets will lead to longer wait times.

GPS & What to use it for

I’ve already mentioned a phone holder for your car while using your phone to navigate. However, your GPS is useful for more than just finding your way from location to location. Use Google Maps to search for specific locations around the airport–bars, restaurants, hotels, etc. This is how I pick where I eat every meal. Everything is rated by distance from you, reviews, star rating, and price level.

Stage Three: At the Hotel

It’s important to remember that when you are traveling for work, you are not working at all hours. You can have time to yourself to let loose, explore, or just veg out. Below are a few things that you can do outside of your work hours:

At the hotel: Almost everyone has a subscription to Netflix or another streaming service. I always bring a device loaded with hundreds of my favorite movies that I can toss on whenever I want. Many people travel with books or a tablet for some quiet time. Some people bring games with them as well–whether it be something on your device or a portable gaming system like a Nintendo Switch.

Outside of the hotel: Get out of your comfort zone and take some time to explore where you are. Check out some of the local restaurants around town that look good. Maybe there is a sporting event or a local site you want to check out. Just because you are traveling doesn’t mean you can’t have fun. Last month while traveling throughout Texas, I hit a famous BBQ restaurant, visited The Alamo, and tried indoor skydiving–all in different cities.

Exercise: this will help with stress. I don’t expect people to try to hit the gym regularly or run miles on the treadmill, but ANY exercise is good for you. Walk around more than you would, take the stairs, or do anything to get your heartrate up a bit. It is easy to fall into bad habits when on the road.

Stage  Four: Post Travel

Dry Cleaners

I am an advocate of dropping off all dry-cleaning off immediately. This avoids massive piles that build up over time and running out of clothes for a trip. While you don’t get a volume discount at the dry cleaners, you will save yourself quite a bit of time as well as the panic of having to go back on the road tomorrow and realizing you have nothing to wear.

In-person Team Meetings

When you finally do find yourself back in your home office, I know it takes some time to decompress and get your feet under you. I caution people to not take too long before sitting down with you team. If you’ve been utilizing Microsoft Outlook and Teams, you shouldn’t be out of the loop. Getting face time with your team is important to show them you are still on top of everything and regrouping to get any questions answered you or they might have. I like to personally meet with my team the following day after I return.


Uber / Public Transportation vs Rental Car

This really depends on your geographic location. Major cities like New York or LA aren’t great places for renting cars. I would suggest Uber or exploring public transportation there.

However, for more suburban areas, there are a number of benefits to renting a car. In the long run it will end up being cheaper, and there is nothing worse than feeling like you are stuck at your hotel for the week because you have no car. Being able to run out to grab lunch, a drink, or other necessities is a huge advantage. Also, if you are renting, I suggest considering an upgrade. The comfort level gap between driving a decent car versus driving the worst car on the lot is massive.

Cell Phone Data

If you are traveling regularly, you must have unlimited data. You will be on your phone a lot. Also, many carriers have plans to allow your phone to turn into a hotspot. Take advantage of that; wifi is key to the traveling business jockey.

Mobile Airline Apps

Download the applications of the airlines you fly. This will make getting in and out of the airport faster and ensure you always have your mobile boarding pass. For iOS users, drop your mobile boarding pass into your Mobile Wallet. This ensures you’ll be able to get it even if you have no service.

Hotels & What to Ask for

As I mentioned before, I use Marriot’s SPG rewards program. The nice thing about this program is I have specific requests saved for every hotel I stay in. I like a king bed on a high floor away from the elevator. This takes some experience of living in hotels to really know what you prefer.

Most Importantly, Stay Connected

This is my guide for the traveling office road warrior. Comment below if I’ve missed an important step in your travel preparedness practices!

The real trick to being productive on the road is finding what makes you comfortable and doesn’t throw too much of a wrench into your life, whether it’s personal or business.

Staying connected is the most important piece of advice I can give.

It is easy to lose yourself on the road, but utilizing Office 365’s complete tool set is how my organization ensures that every employee, no matter where they are or what they are doing, is always connected and collaborating.

Microsoft Outlook keeps us connected to our email (our lifeblood) no matter where we are. Microsoft Teams keeps us connected to our departments and helps us manage, track, and organize our schedules and tasks all while keeping the lines communication flowing. What I truly love about Microsoft Teams is the consistent chat, where I do not have to be present within a conversation at the exact time to come back and go through it.

I am continuing to add to my list with every trip and am truly interested in learning other travelers’ tricks. Comment below on what you’ve learned from your trips!

Adam Lee, Director of Marketing

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