10 Ways We Make Our Business Trips Successful

By Devon Drennan on October 22, 2014

Recently, my co-worker and I had a whirlwind trip of meetings on the west coast. 4 days, 12 meetings, and even one conference. Working in business development, these trips are crucial.  

It’s crucial to meet face to face for partnerships to flourish. Photo credit: flazingo_photos via photopin cc

But how do you create trips that are affordable, productive, and successful? Years of successfully traveling on a startup’s budget has taught us a few things. Here are some ways we make it work:

1. Choose your event

Our trip out west was based around a conference. The conference was important but also created an opportunity to meet with potential partners in the same area face-face. Whether you’re going away for a conference or an overdue meeting, build your calendar around one event. 

We aren’t out west too often, and it’s a unique opportunity to cultivate relationships. So we maximize our days: breakfast, lunch, and dinner meetings. We even used breaks between speakers at conferences for less formal chats. 

Each hour is an opportunity when you’re on a business trip. Make the most of it. 

2. Traveling as a group? Communication is key

It can become pretty awkward when you have to ask a potential partner to reschedule after you’ve confirmed a meeting. You don’t look organized, and they don’t feel valued. Not great. 

But, traveling with a colleague meant I wasn’t the only one scheduling meetings. We kept ourselves organized with constant communication. As I’m tentatively creating a meeting, I can quickly pull up Google calendar to see each of our schedules. Just to be sure, we confirm with each other a meeting time works before we reach back out to the other organization. 

3. Smart business travel means cutting costs

We’ve got years of experience on trimming expenses while traveling. Photo credit: manoftaste.de via photopin cc

As a startup, we don’t have big coffers for luxury travel. As soon as we know that we’re going on a trip, we start scoping for flights. In this case, we booked our flights two months out. We use a lot of the sites people use as consumers: Priceline, Hotwire and Kayak. 

Some of the cheapest flights get in at odd hours. This time around, I got into Dulles at 1:30 AM (shout out to my wife for the late night pick-up). By taking the late flight, I was able to travel across the country for $400.

You may lose a bit of sleep, but your bank account will thank you later.

4. How we get great hotels and rental cars for less

Another way we cut costs is by choosing certain things blind. That doesn’t mean pin the tail on the donkey blind. But some sites, like Expedia, will show hotels and car rentals without brand names. We can get hotel rooms and rental cars from great companies for far less. 

If you’re willing to compromise on times, and willing to let go of brands, you can make a business trip for far less. 

5. Schedule in buffer time

Okay, if you really want to, you can get places quickly. But even a crazy driver still took 24 minutes to drive around Manhattan. Even if you’re only in one city, it takes time to get around, especially if you’re moving during rush hour.  

Thankfully, you don’t need to be in a city to test out how long it will take to get from place to place. If you’re going to a 9 am meeting, check out how long the drive will be on a similar weekday morning. It may only be 15 miles, but rush hour or an accident could suddenly leave you needing an hour to budget.

Yes, every hour counts on business trips, but so does arriving on time. 

6. Invest in meeting prep

With all the meetings set up, now you gotta roll up the sleeves and do the prep work. 

To get started, we think big. First, what’s the objective of the meeting? Make sure your whole team is on board for 1-3 objectives. Then, how are you going to get there? Work out the strategy and tactics you’ll use at the meeting. Next, do your homework to ensure you know as much as possible about your meeting contacts in advance.

To wrap it up, you’ll decide the materials you’ll need. Whether its tech, a power point deck, test it out as well. In our case, we needed to ensure that all our devices worked, and to double check at the location that Wi-Fi works.

So what does all this prep mean time wise? For a one hour meeting, I spend on average 2-4 hours prepping for a meeting. Some meetings are similar, and will only need slight tweaks, but some need to be built from scratch. 

Being diligent and doing your homework ahead of time will ensure you put your best foot forward.

7. Plan on taking notes

Whether you use your phone or a notebook, notes will help you remember what you need to do after the meeting. Photo credit: Symo0 via photopin cc

While often in these meetings you’re trying to persuade, influence or sell something, you also need to listen. This helps you understand where the other person or organization is at. Plus all those deliverables? They are way easier to remember if you have a chance to write them down.

That’s why we went west as a duo: one person can be the main presenter and the other can take notes (and give their voice a rest). 

Sometimes though, you can’t tag team a meeting. In these cases, I always give myself some time after a meeting to take down notes. Writing down everything while it’s still fresh is crucial for follow up and long term nurturing of the relationship. 

8. Follow up

Sometimes business development can feel like dating. You’re trying to woo a potential partner into thinking you have value. If you’re lucky, they’ll even meet with you in person.

The worst thing you can do, even after a great date? Not following up, or waiting too long to follow up. 

No matter how long your trip is, there will be emails, phone calls, and other business that you couldn’t get to while being away. Still: follow up quickly. Send out an email thanking them for their time. Show them you’re thoughtful, considerate.

If your meetings went well you should have deliverables to give them. Perhaps they had further questions about your product or about technical issues that you need to get more insight on. This work continues the momentum of those meetings, and deepens your relationship.

Following up quickly with thanks and providing deliverables soon afterwards doesn’t just build up your to do list. It builds trust, and shows you can talk the talk and walk the walk. 

9. Accept that there will be hiccups

No matter how many times you practiced, how much time you allow for travel, or thoroughness of your notes, something is going to fall apart. 

In our case, we needed Wi-Fi for a demo. It worked in the lobby, but when we got to the room? The Wi-Fi was unreliable and made GoCanvas seem slow. So while I was working on fixing the technical issue, Andrew was able to keep the conversation going in another area until we could get it working.

No matter what, keep your objectives front and center in your mind. It’ll help keep you focused, and able to remember what matters: not a perfect meeting, but getting your point across. 

10. Give yourself space to recharge

Working yourself like a dog means you need to take a break. Photo credit: Pauls imaging via photopin cc

When I was younger, I’d fill my days to the brim. I’d return exhausted and in need of major alone time. But these days I have family I’m coming back to. I don’t always get that alone time buffer the way I used to.

To prevent burn out, I allocate time while on trip for myself. On good days I’ll hide out in the gym and start lifting real weights. 

Not everyone loves weight lifting. But carving some time out each day to have your time to recharge. Some people love having a beer, others a book, or catch up with friends or family. 

A little bit of time for yourself will help you unwind after a long day, and help you prepare for the next day. 


Ensuring successful business meetings requires a lot of attention to details before, during, and afterwards. But doing these ten things, especially 5-8, ensure our trips are worthwhile. Anything you felt I missed? Leave me a comment below!

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