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Human Resources & Payroll

What Road-Tripping Across America to Meet Customers Taught Me About Being a Better Leader

My road trip, which involved visiting 11 cities in 10 states over a two-week period, provided the opportunity to hear firsthand from small-business owners about their goals, values, challenges, and triumphs. It reinforced my commitment to engage with ...

Joshua Reeves Gusto RV 1  59a9a48d579a3

Republished with permission of author.
This article was originally published on Entrepreneur here.

If the recent HR crises in Silicon Valley have taught us anything, it’s that leaders should take a more hands-on, thoughtful approach to crafting their company cultures. CEOs and business owners can start by seeking out humbling new experiences that connect them more closely to why their companies exist in the first place — to empower their teams and serve their customers. That realization inspired me to shadow my teammates across the company, and more recently, to drive over 4,000 miles across America in an RV, meeting small businesses along the way.

My road trip, which involved visiting 11 cities in 10 states over a two-week period, provided the opportunity to hear firsthand from small-business owners about their goals, values, challenges, and triumphs. It reinforced my commitment to engage with customers in-person on a regular basis and left me with some important lessons about how we can improve our product and service.

It also gave me a chance to step outside the Silicon Valley bubble. I was born and raised in the Bay Area, and while I’m proud to live and work here, travel can always offer a unique new perspective and this is powerful. For example, during my trip, I saw firsthand how small-business owners take pride in how they take care of their employees and serve their local communities. They are passionate about the problems they’re tackling and business is all about people for them. It became clear to me that Silicon Valley companies can learn a lot from small businesses. If startups focused more on people, instead of numbers such as headcount, funding, growth, and valuations, we would all be making better products, building better cultures inside our companies and creating stronger communities.

That’s why I hope more entrepreneurs escape their routine and venture out to gather additional perspectives. Before tackling a road trip of your own, here are a couple of recommendations about how to make the most of the journey:

Be humble.

Remind yourself that the purpose of the trip is to listen and learn from customers. Don’t show up and expect things to revolve around you. Instead, ask what you can do to help. Also, be sure to provide them with advance warning of your arrival and work around their schedules, while using their time wisely to find out how you can better serve them.

Do it yourself.

A road trip like this can easily become an overly polished, expensive marketing stunt if you get caught up in projecting an image of your company rather than just being yourself. We kept the trip authentic to Gusto by driving a rented RV ourselves, which I slept in, and spending responsibly. Instead of hiring a professional driver or photographer, I had a few colleagues join me, and each of us wore many hats on the trip. My chief of staff and I drove the whole way. Get back to basics and make sure you play a part in the planning rather than having everything done for you. The results will be more meaningful that way.

Don’t play it safe.

Be sure to visit places that are very different from where you live in order to meet a diverse set of people and understand multiple viewpoints. If you live in big cities like Boston, New York, San Francisco and Seattle, this means focusing on smaller cities and towns across America. For example, our trip included stops in San Luis Obispo, Calif., Amarillo, Texas, and Little Rock, Ark. Also, don’t spend too much time in your RV or motel. Get out and walk around — you can meet customers or prospective customers anywhere. We spent an entire afternoon in New Orleans just walking around, and ending up meeting nearly a dozen business owners who used Gusto, just by talking to locals and asking them how they found out about us (it was frequently through word of mouth).

Go all in.

For me, it was impossible not to have a good time given how interesting the people were and how passionate they were about their businesses — the passion was infectious! But, it was also important not to do other work while on the trip. Be sure to block a set amount of time to dedicate to your trip and trust everyone back at the office to keep the trains running on time.

Be open to serendipity.

Although it’s important to have a thoughtfully prepared itinerary for your trip, leave room in your schedule for chance meetings or events. In our case, we met an amazing nonprofit organization called Urban Promise in Little Rock because the business owner heard we were going to be there and tweeted at us to see if we wanted to meet up. We had a chance to meet some of the students in the program, and the business owner even took us on her favorite hike in the area.

Getting outside of your comfort zone and walking in other people’s shoes can help you become a more effective leader. In growing companies, there are always a million to-dos and it can feel like it’s impossible to set aside this amount of time. But, even if it is for a few days, the experience can be very meaningful. And remember, there will always be a million things to do — that’s what it means to have a high-potential company. What matters most is being intentional and deliberate about how you spend your time. You’ll be surprised by the valuable insights you can glean just from meeting different types of people and having candid conversations. While you’re on the journey, you might also learn a great deal about yourself as well.


Joshua Reeves is the CEO and co-founder of Gusto, a maker of payroll and small business management tools.