8 lessons I learned from leading a remote team

I have held leadership roles at two fully remote corporations: Square and FutureFund, the free fundraising platform for K-12 school groups I founded.

However, there was a big difference between the two organizations: Square went remote during the Covid-19 pandemic, while FutureFund began completely remote. Here’s what I learned during my Square transition and applied to my current enterprise.

1. Not everyone can work remotely

Square had 12,000 people, all employed to work in the office. However, not everyone who is hired on-site shall be equally successful in a remote environment.

“If you can do it in the office, you can do it at home” is not all the time true. Some people don’t have the right environment. Others may miss out on the social aspect of labor because they lose their social life by completely distancing themselves. Many people build their entire community around their work.

This signifies that during job interviews with candidates, you have to ask specific questions that may mean you can determine 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 would cause complications?

2. Founders need a lot of trust

Most managers say they do not micromanage – but if you concentrate to their behavior, you may notice that they count butts in positions, watch when people come and go, etc. Investing in the business makes sense (no one works harder than the founder), but you furthermore mght must hire people you’ll be able to trust.

Hire trustworthy people, then give them the freedom they should make the most of remote work – even if they fail sometimes. This may mean losing some control, but do not be afraid. As I’ve written elsewhere, it’s a calculated risk that always 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 starting of the day and needs help from someone who is after hours, it’s a waste of time and money.

Using asynchronous communication helps avoid this. If you need to hire the best people in the world, their time zones don’t all the time match, so you would like processes to stop employees from getting stuck or lagging. For example:

• Project management software to trace tasks and deadlines
• File sharing solutions
• Tools for virtual collaboration and meetings

4. Know the legal implications of hiring in certain areas

At one point, we hired one contractor in Washington, D.C., but because of that, all of our customers in that state needed to pay sales tax because we were considered a nexus company in that state. Even if we allow them to go, we’d still have to charge sales tax for the next two years.

This happens all the time in large corporations with distributed workforces – which can help explain why some influential business leaders supervising recruitment in their corporations. But you do not need thousands and thousands of consumers for all those taxes so as to add up, so it’s value being careful no matter the size of your online business.

5. Find out how your people are doing emotionally

I used to give you the chance to simply come into work and notice if someone was having a problem – then we could talk about it in the moment. But if you do not see people every day, you are not there to look at their behavior. This means it’s good to learn to ask questions.

Here’s an example: At one point, we had a part-time worker who was responsible for our sales contacts, but I noticed that a larger than expected variety of leads were coming in. When I checked in and asked if she was still working part-time, she revealed that she was working outside of her contract to remain on top of things.

When I discovered about this, I took her position full time, but the problem would never have been identified if I hadn’t began that conversation. Check on your people.

6. Actively involve others in your work

Talking about a water cooler is necessary. It’s good to share ideas and expand your mind. Brainstorming doesn’t occur in isolation, and solutions don’t come from sitting behind a desk.

You often discover what other people are doing through impromptu conversations. Some corporations set working hours because they need to reclaim this type of synergy, but there are other ways to realize it.

Start pitching ideas that are not fully fleshed out yet to individuals who will help with them. Otherwise, chances are you’ll be wasting time considering about an idea that won’t feasible or that cannot be implemented without another person’s perspective.

Bottom line: do not be afraid to ask for input – regardless that connecting remotely may take more effort than touching someone’s shoulder in the office.

7. Clearly define your organization’s goals

In every office I’ve ever been in, there have been a few key numbers or metrics. Visual indicators in the office motivate people and set their priorities, but once they leave the office they are completely absent.

When you’re employed remotely, it’s good to communicate your mission and company goals clearly and ceaselessly. Try this:

• Provide regular updates on key goals during company meetings.
• This helps bring people together and make them feel invested in the organization’s success.

Sharing this information commonly will ensure your employees do not forget the “why” of what you do together.

8. Bringing people together in person still matters

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