8 Lessons I Learned from Leading a Remote Team

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I've held leadership roles at 2 completely distant companies: Square and FutureFund free fundraising platform for the K-12 school groups I founded.

But there was one big difference between these two organizations: Square became remote during COVID-19, while FutureFund started completely remote. Here's what I learned from Square's transition and applied to my current venture.

1. Not everyone can work remotely

The square had 12,000 people who were all hired to work in one office. But not everyone who is hired to be on-site will be equally successful in a remote context.

“If you can do it at the office, you can do it at home” is not always true. Some people don't have the right environment. Others may miss the social aspect of work because when they leave completely, they lose their social life. Many people build their entire community around their work.

This means you need to ask specific questions when interviewing candidates that tell you how prepared they are for remote work. These may include:

Do you have a quiet place to work?
Do you have pets or children that will cause complications?

2. Founders need a huge amount of trust

Most managers say they don't micro-managing — but if you pay attention to their behavior, you will notice that they count the backs of the seats, watch when people come and go, etc. It makes sense to invest in the business (no one works harder than a founder), but you also need to hire people you can trust.

Hire trustworthy people, then give them the freedom they need to do it most work remotely— even when they occasionally fail. This may involve giving up control, but don't panic. As I've written elsewhere, it's a calculated risk that often pays off.

3. Your technology must work

Remote work is only as efficient as the technology that connects your team. If someone comes in at the start of their day and needs help from someone who is out of hours, it results in wasted time and money.

hugging asynchronous communication helps avoid this. If you want to hire the best people in the world, their time zones won't always overlap, so you need processes to prevent people from getting stuck or late. For example:

Project management software to track tasks and deadlines
File sharing solution
Virtual collaboration and meeting tools

4. Learn the legal implications of employment in certain fields

At one point, we hired a single contractor in Washington – but because of that, all of our customers in that state had to pay sales tax because we were considered Nexus in that state. Even if we let them, we still had to pay sales tax for the next two years.

This happens to large companies with a distributed workforce around the clock – which may help explain why some high-profile business leaders have pointed out employment supervision in their companies. But you don't need millions of customers for all these taxes to add up, so it pays to be careful no matter the size of your business.

5. Know how your people are doing emotionally

I used to be able to come into work and notice if someone had a problem – then we could talk about it in the moment. But when you don't see people every day, you're not there to observe their behavior. This means you have to be good at asking questions.

Here's an example: at one point, we had a part-time employee who was responsible for our sales leads, but I saw that there was a higher than expected volume of customers. When I checked in to ask if she was still working part-time, she revealed that she was working beyond the scope of her agreement to stay on top of things.

Once I realized this, I made her position full-time, but the issue would never have been identified if I hadn't started that conversation. Control your people.

6. Proactively bring others into your work

Water cooler talk is important. It is good for sharing ideas and expanding the mind. Brainstorming doesn't happen in isolation, and solutions don't come from sitting behind a desk.

You often learn what other people are doing through impromptu conversations. Some companies mandate work hours because they want to restore that kind of synergy, but there are other ways to achieve it.

Start bringing ideas that aren't fully fleshed out to people who can help with them. Otherwise, you may waste time thinking about an idea that isn't viable or can't be done without someone else's perspective.

Bottom line: don't be afraid ask for data — even though it may take more effort to reach out from a distance than to tap someone on the shoulder in an office.

7. Make your company's goals clear

Every office I've ever been in had some key numbers or metrics on the board. Visual cues in the office motivate people and direct their priorities, but they are completely absent once you leave the office.

When you're remote, you need to communicate the company's mission statement and goals clearly and often. Try this:

Provide regular updates on key goals during company meetings.
This helps unify people and make them feel invested in the success of the organization.

Sharing this information on a regular basis ensures that your employees don't forget the “why” of what you're doing together.

8. Meeting people in person is still important

Being remote doesn't mean you never see your colleagues. Get together once or twice a year to make that physical connection with people. This helps you get closer to your team and build real relationships, which also means more trust and synergy at work.

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