8 Lessons I Learned From Leading a Remote Team | Entrepreneur

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I’ve held leadership roles at 2 fully remote companies: Square and FutureFund, the free fundraising platform for K-12 school groups that I founded.

But there was a big difference between these two organizations: Square became remote during COVID-19, whereas FutureFund started out fully remote. Here’s what I learned from Square’s transition and applied to my current venture.

1. Not everyone can work remotely

Square had 12,000 people who were all hired to work in an office. But not everyone who’s hired to be on-site will be equally successful in a remote context.

“If you can do it in the office, you can do it at home” isn’t always true. Some people don’t have the right environment. Others may miss the social aspect of work because when they go fully remote, they lose their social life. Lots of people build their entire community around their job.

That means you need to ask specific questions when you interview candidates that tell you how prepared they are for remote work. These might include:

Do you have a quiet place to work?
Do you have pets or children that are going to create complications?

2. Founders need an immense amount of trust

Most managers say they don’t micromanage — but if you pay attention to their behavior, you’ll notice that they count butts in seats, watch when people arrive and leave, etc. It makes sense to be invested in the business (nobody 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 make the most of remote work—even when they occasionally fail. This may involve giving up some control, but don’t be scared. As I’ve written elsewhere, it’s a calculated risk that often pays off.

3. Your technology has to 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’s off-hours, it results in lost time and money.

Embracing 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 delayed. For example:

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

4. Learn the legal implications of hiring in certain areas

At one point, we hired a single contractor in Washington — but because of this, 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 go, we had to charge sales tax for the next two years.

This happens to large companies with distributed workforces all the time — which might help explain why some high-profile business leaders have made a point of overseeing hiring at their companies. But you don’t need millions of customers for all those taxes to add up, so it’s worth being careful no matter your business size.

5. Know how your people are doing emotionally

I used to just be able to walk into work and notice if someone had a problem — then we could talk through it in the moment. But when you don’t see people daily, you aren’t there to observe their behavior. That means you have to get good at asking questions.

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

Once I knew this, I made her position full-time, but the issue would never have been identified if I hadn’t started that conversation. Check on your people.

6. Proactively bring others into your work

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

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

Start bringing ideas that aren’t fully baked to people who can help with them. Otherwise, you might waste time thinking about an idea that isn’t viable or can’t be completed without someone else’s perspective.

Bottom line: don’t be afraid to ask for input — even though it can take more effort to reach out remotely than to tap someone’s shoulder in an office.

7. Make your company’s goals clear

Every office I’ve ever been in had a few key numbers or metrics up on the board. Visual indicators in the office motivate people and guide their priorities, but they’re completely absent once you leave the office.

When you’re remote, you have to communicate your mission statement and company 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 organization’s success.

Sharing this information on a regular basis makes sure your employees don’t forget the “why” of what you’re doing together.

8. Bringing people together in person still matters

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

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