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Your First Business Trip

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My friend is about to go on his first work trip. I started writing down some of the lessons I learned from work travel over the years for him and figured it might have broad enough utility to share here as well. While I have by far logged the most miles on the road with RedMonk, many of these lessons (especially around expensing) were things I picked up in previous jobs.

in-flight photo of airplane wing overlooking mountains

Read your company travel and expense policy, and follow it scrupulously.

Understanding your company’s expense process is integral to successfully navigating work travel. (RedMonk’s policy is “be reasonable,” but most workplaces have a bit more structure to their travel and expense rules.) Be sure you read your workplace’s policies carefully and understand what is expected.

Know about per diems (this is where your company will give a set rate per day to cover your expenses; if you spend less than the per diem you can pocket the difference, and if you spend more you are responsible for the overage) vs. expensing (your company will cover your incurred expenses.) Most of these early tips will focus on navigating expensing.

Know what is and is not covered if you are expensing things to your company. Most companies will have dollar limits on how much you are allowed to spend for certain things (e.g. $X for dinner, etc). There are often other rules beyond dollar limits. It’s different everywhere, so know your company’s specific policies. For example:

  • I worked at a place where lunch couldn’t be expensed but breakfast and dinner could. (I think the idea was that on a regular workday you’d be responsible for your own lunch anyways, so they weren’t going to pay for it on the road. The rationale was arcane but the rule was real, so you still needed to know it.)
  • I worked at a place where that capped the amount you could tip at meals, otherwise the difference came out of your pocket.
  • Alcohol is often prohibited from being expensed.

Know when you are expected to use the company card vs. your own. Some companies prefer things to go on the company card. Some companies demand that things go on the company card, and won’t reimburse you for anything else. Some companies expect you to put things on your personal card and then will reimburse you.

Be extremely careful putting things on your own credit card. In the best case you are floating the company money; in worst case, if something happens with the reimbursement, any spending on your card becomes your expense entirely.

Know who pays for the company card. Some companies pay it for you, some companies have you pay it and reimburse you. Know that just because it’s a “corporate” card doesn’t remove you from liability.

Read your company travel and expense policy, and know that you can sometimes ask for exceptions.

This next part is going to be workplace dependent, so try really hard to stay within policy on your first trips while you’re getting the lay of the land. But in some organizations, it’s good to understand that the travel policies are not written in stone.

Sometimes there are last minute travel requirements where flights will be more expensive than the guidelines state. Sometimes the only flights within budget are onerous from a schedule perspective, and you can ask to take a route with fewer layovers / at more convenient times. Sometimes the only hotel within policy is in a far-flung or unsafe part of town, and you can petition for different lodgings.

If you are having a difficult time getting flights and hotels to fit within the recommended limits, talk to you boss, outline your rationale, and see if it’s possible for them to approve exceptions.

There are policies that are more absolute than others; flight and hotel bookings tend to be areas that have more wiggle room if you can show logistically why the in-policy options don’t work.

Be organized with expensing and receipts.

Early in your career you should be very careful about picking up anyone’s expenses but your own. If you are out with your colleagues, you can either

  1. all pay separately, or
  2. have the most senior person of the group put down their card for the entire tab.

The idea is that the top person should be justifying their spend to the person above them. Imagine a scenario where you and your boss go out to eat and completely disregard all the expense policies, and then your boss has you expense the meal so that they can approve it without anyone seeing all the misspent money. Having the most senior person present submit the report helps limit moral hazard for the company.

Always ask for an itemized receipt.

You can jot notes on the receipts to help you with expensing later. (For example: you can write yourself a quick note about the context of a conversation if you took a client out to eat, if you grabbed a coffee for you and a colleague you can note which employees the expense was for, etc)

Keep the receipt, but take a picture immediately. (If your company has an app like Expensify you can take the photo in the app and then finish filling out the expense details later.) It makes things easier on your future self if you make it a habit to quickly snap a photo as part of the process of putting your credit card away. And just might save your bacon if you happen to misplace a receipt along the way.

Bring an envelope in your laptop bag for receipts and store all your receipts there. It’s fine to stash them in a wallet during the day if you’re running around, but then every night in the hotel put your receipts away. Think of it as part of the process of making sure your phone and laptop are charging. Charge your shit and make sure you’re saving the shit you’ve charged.

Don’t let expense reports linger, ESPECIALLY if your company needs to reimburse you for spending on your personal card. I often make it a goal to work on my expense report at the airport waiting for my flight home so that I have all the logistics of the trip tied up before the trip is over. (This is admittedly aspirational, but seriously, be on top of it.)

Navigating your destination.

Look up your destination before you go and use Google Maps to download an offline map just in case you have issues with your cell service when you arrive. Have screenshots of any confirmation numbers you might need for the same reason.

Your choices for ground transportation will be heavily dependent on your destination and what you’re expected to do on your work trip, so definitely ask your boss if you need to rent a car. I tend to favor using ride share and public transportation over having to drive in an unfamiliar place, but this is all going to be subject to your preferences and logistics.

When I’m walking or taking public transit in an unfamiliar city I tend to do a “one headphone in” approach, which allows me to get walking directions without constantly looking at my phone while also leaving me the ability to hear and be aware of the environment around me.

Pack well.

Don’t check a bag. You don’t want the bag to get lost, you don’t want a situation where your colleagues are waiting for you at the baggage carousel, you don’t want to be lugging that much stuff. Don’t check a bag.

Avoid roller bags if you can. Consider a backpack/shoulder bag (like the Patagonia MLC) or a nice duffle instead.

The bonuses of a soft-sided bag are:
– You can almost always shove a duffle into an overhead even if space is tight. This is not true for roller bags.
– On the days when you have to run from meetings straight to the airport, it’s nice to not have to have a giant suitcase with you. It’s also nice to be less conspicuously touristy if you every have to navigate public transport or walk around on your way in/out of a city.

Plan the outfits you pack around your shoes. Shoes are the clunkiest/heaviest thing to pack, and you want to avoid having to pack multiple pairs if you can help it. Try to pick a color family for your trip so that you can get multiple uses out of shoes, jackets, etc.

It’s good to check the weather of your destination city, but alas there is no good way to check the ‘HVAC weather’ of whatever meeting room / conference center you’re going to be in: pack layers.

If you’re unsure of the dress code of the event you’re going to, ask a colleague or your boss. If you’re going to a conference, you can also try looking up prior years’ events to get a vibe from the photos. If you really have no clue, when in doubt default to dark wash jeans (or slacks perhaps; this will be industry dependent) and a button down.

If you’re going to be traveling often, invest in duplicates and just keep a toiletry bag packed and ready to go. If you’re packing for a one-off trip, spend the most time reviewing your packing list in the toiletry section; this is the place where I most frequently forget things.

Your laptop bag should have:
– Charging cords / power bricks for all your electronics
– A backup USB battery pack
– Headphones
– A small notepad and a couple pens
– Travel-sized tissues
– Travel-sized ibuprofen
– A Band-aid
– Chapstick
Shout stain wipes – seriously these are magic
– Your receipt envelope
– An extra $20 stashed somewhere just for emergencies
– Pandemic additions: an extra mask and hand sanitizer

Hotel tips and tricks.

The first step to getting settled in a hotel room is to find the outlets AND MAKE SURE THEY WORK. Speaking from experience, it is so crushing when you think you’ve plugged your device in for the night and then wake up to a dead phone because you needed to have a switch flipped somewhere to send power to the outlet. Power is the lowest level of Maslow’s hierarchy of travel needs.

For phones in particular, pack a backup power cable so you have one for your hotel room and one for your laptop bag. Given that outlets are frequently in an inconvenient place, consider having an extra long phone cable for the hotel. (Just like toiletries are the things I most frequently forget to pack, cables are the easiest thing to leave behind. Check outlets diligently before leaving.)

Hang up your clothes ASAP to try to prevent wrinkles. If anything is hopelessly rumpled coming out of your bag, iron it now before rather than in the morning. Don’t rely on the “hang it up in the steam of the shower” trick; if whatever you are attending is deserving of an in-person trip, then it is also probably an occasion that deserves an ironed shirt. I know. It sucks. But do it anyway.

Bathroom counter space is really variable depending on your hotel so consider a toiletry bag that can hang from a towel rack.

It’s hit or miss on whether or not you can expense cash tips, but you need to do it anyway to be a good human. Bring small bills so you can tip in and around the hotel. If you want your room cleaned daily (I tend to just do the “do not disturb” sign for my entire stay, but again this is all your preference) consider tipping daily rather than all at the end, just in case there are different cleaners each day.

Check out some other travel tips and gear guides if you want more:
– Steve O’Grady: 35 Things That Make Travel Suck Less
– Steve O’Grady: Five Travel Mistakes I Never Should Have Made (a good read if you’ll be traveling frequently)

One comment

  1. Good post. Here are a few things I would add.

    – Depending on the company, expense limits may be as much cultural by team as mandated by a central policy. I’ve never had a real issue but I think I’ve had a pretty good sense of what was OK vs. what was skirting the line outside of explicit company policies.

    – I like the Osprey Porter 42(?) travel backpack. Anyway the smaller one. Actually like it better than the Patagonia MLC (which I also have and used for a number of years).

    – Even if you end up using some extra cables/toiletries/etc. create a few travel kits that have all your miscellaneous travel stuff and keep it in either your carry on or some other handy container. (My toiletries are just in the TSA-compliant ziplock.)

    – What’s this “iron” of which you speak? 🙂

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