Everything You Need To Know To Become A Remote CEO

Even CEOs need to break from the daily grind of office life every once in a while. Here’s how to do it without letting your business fall apart in your absence.

Everything You Need To Know To Become A Remote CEO
[Image: Flickr user rabble]

It has been three months since my family and I returned to the U.S. full-time after our two-and-a-half year trip sailing the world.


During the trip I continued to run my business from the boat, with quarterly trips back to U.S. soil to meet with clients, and prior to the journey, I spent close to five years preparing my financial services company to function in my absence.

When I returned, I expected to just walk right back into the firm where I left off, as if almost three years never happened. It didn’t turn out quite that way, and there are a number of things I’d do differently.

Prior to my departure, we spent years preparing for my firm to thrive in my absence by setting excellent systems in place for managing our clients. We had made services more efficient, had proper incentive plans, and hired great employees to work with our clients in my absence.

During the journey, I also flew in for regular meetings with clients. I was concerned with maintaining great customer service in my absence, and that became everyone’s primary focus. But we were so busy with client meetings that I didn’t even have time to have lunch with my employees, let alone evaluate the latest software or business process.

By focusing so much on our customers, I didn’t invest as much in three key areas: employee morale and development, software upgrades, and marketing. I’ve since learned that whenever you are away from your company for extended periods of time, it’s vital not to neglect continuing to work inside the business. Here’s why:

1. Technology gets outmoded

Computers and software need updating and workflows need to be constantly updated and improved.


For me, the biggest advancement has been the move to cloud computing, which has drastically changed the landscape of how different programs can share data, allowing for increased productivity. With new software comes new workflows and processes, all of which take time to implement–but the benefits make it all worthwhile.

2. Employees need performance reviews and check-ins

My team did such a great job that we didn’t spend enough time talking about their needs as employees.

The entire company employee structure became stagnant, with no real job promotions, advancements, or discussions of career goals–but they weren’t in the same time warp as me.

3. You cannot simply show up in the office and turn on the marketing

While we still had good organic growth with new clients, our marketing was non-existent for about a year before the trip and the entire time I was gone. In hindsight, it would have been simple enough to maintain some visibility within the community so that we would not be starting fresh upon my return.

So, what are my next steps?

I am going to spend one year redesigning the structure of the business itself before I restart the marketing campaign. While we did not lose clients as the result of my trip, and we even continued to grow with new clients, it will probably take one or more years to get the business management and marketing back up to speed.


Departing a financial services firm to sail the world in the middle of the Great Recession is incredible proof of concept that with the proper planning, any business owner can better leverage their company. I accomplished what I set out to do: I enjoyed an incredible time with my family and fulfilled one of my life’s goals. The time I was able to spend with my children was truly priceless.

However, now that I am back, I do have a little bit of rebuilding to do. I think of it like maintenance on a house: If you just do a little bit constantly, there are never really any big projects.

Sure, the house never falls down, but the deferred maintenance does build up over time. I would have been better served to take an extra day every quarterly trip back to the U.S. and perform more home maintenance.

Scott Leonard, CFP is the founding partner of Redondo Beach, Calif.-based Navigoe, LLC, a wealth management and investment advisory firm, and is author of the new book, The Liberated CEO (Wiley).