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50% Of The U.S. Workforce Will Soon Be Remote. Here's How Founders Can Manage Flexible Working Styles

This article is more than 5 years old.

When most people think of remote workers, they probably picture someone lounging in their pajamas and taking a call every so often.

The reality is usually very different.

It’s less about wearing whatever you want and more about having the freedom to work in a way that allows you to produce your best work. That can mean waking up at 6am to connect with international teams or scheduling time to recharge when juggling a 12-hour work day.

While it’s not really the norm for a cofounder to be working remotely, more people—particularly in the blockchain space—are embracing flexible work styles. It’s becoming a more accepted framework. That’s a good sign because it shows the industry is willing to evolve, especially since freelance workers are projected to be the majority of the U.S. workforce by 2027.

At my current company, Chronicled, we have access to talent all over the world. Even though our headquarters is in San Francisco, I have team members in New York, Los Angeles, Tokyo, Vancouver, Hanoi, Katmandu and Kiev.

Personally, I moved back to Brooklyn about a year ago and have since worked remotely from there. But it comes with its own set of challenges and benefits, especially as a cofounder.

Here’s how to manage yourself—and your team—when working remotely:

Set the stage for being away from the office.

Remote work has to be part of the company culture.

If you just offhandedly tell people they can work from home a couple days a week, a lot of people simply won’t do it. They don’t want to leave the office if they think teammates are going to be there, working and interacting without them.

And simply spending a day or two outside of the office is actually counterproductive. The New York Times reported that employees who spend three to four days working off-site feel the most engaged with their teams.

In my situation, I’m remote and so are the rest of my direct reports. That’s a large part of why it works. They aren’t all sitting in an office together somewhere while I’m halfway across the country.

You can run into trouble if half your team is coming into the office every day while others are working remotely. It’s easy for people to begin feeling left out.

To keep the balance and make everyone feel included, you have to create an environment where flexible working is valued.

An easy way to instill that attitude is by asking people to share what they’re able to do because of their flexible work schedule. Travel stories, speaking engagements, time with the kids—it all promotes a sense that working remotely is a normal and positive part of the company culture.

You can also ask everyone to share their typical work hours and out of the office time. This helps eliminate miscommunications and makes it easier for the team to stay in touch. Otherwise, you’ll create needless tension and roadblocks—and your team will struggle to reach their true potential.

Stay fully connected to the team.

The options we have for connecting and communicating are astounding. You can be emailing, texting or Slacking people every day to stay in the rhythm of the business.

My team uses these platforms, but we also have bi-weekly leadership meetings to report in and provide status updates. There have even been jokes about getting a robot with a screen on it, so people can call in and zip around the office and see everyone.

Even with all of that connection, it’s still beneficial to visit the office every so often.

Things are changing very quickly, and even being with your team in-person one week every month helps make sure you know what’s going on and where everything is headed.

When you’re not catching up face-to-face, you can use tools like Slack to stay in touch, ask quick questions, and get the answers you need to stay productive. If you want to collaborate and work on a document in real time, Google Docs allows everyone to jump in and make changes to a shared document as needed.

And the pool of project management tools for remote workers has been growing rapidly. Tools like Asana, Jira, Trello, and Basecamp are all options for letting remote employees manage their own tasks and getting insight into what others are working on.

No matter what industry you’re in, chances are good there are tools and tech available to help you manage remote workers.

Know yourself and your team’s capabilities.

Freedom to make your schedule doesn’t always equal freedom of time. As an entrepreneur, that schedule often means 8 a.m. to 8 p.m., or 24/7.

When I started my first company, I quite literally lived in our office (I lived in our DUMBO loft). My second company was entirely distributed, and I adjusted to working on my own terms and using my time efficiently.

But not everyone is wired to work remotely. Some people do their best work when they have a structure imposed on them, and it’s important to remember that.

There are a number of assessment tools you can use to gain insight into the working styles that are best for you and your team. Some, like the Myers-Briggs Type Indicator and the DiSC Profile, give an in-depth analysis of your behavior, personality, strengths, and weaknesses. Others provide a quick snapshot, like this personal productivity quiz from Harvard Business Review or this work style test from Psychology Today.

Even if you understand the preferred working styles of your team, you still have to be aware that everyone will adjust differently. Some may need more help than others when learning how to manage a remote role.

Set boundaries and buckle down.

Working too much, not too little, is a fairly common trait among founders and leaders.

When I first moved from San Francisco to Brooklyn, I really enjoyed the three-hour time difference. But soon enough, I began scheduling east coast calls in the morning and meeting with people in NYC. And that meant my work schedule began to stretch. Instead of working from late morning to 8pm, I was working from 7am to 10pm.

Doing that consistently wears you down. You have to set boundaries and provide yourself a healthy structure within which to operate.

For instance, try using Monday as a day purely for working—no phone calls. It’s a way of focusing on projects that need a higher level of concentration without all the interruptions.

Blocking out time for certain projects, setting limits on “email time,” and breaking up the workday are all tricks you can use to work more efficiently from home. If you’re waking up, rolling out of bed, and immediately hopping on calls, that’s going to affect your quality of life.

Co-working spaces are another option to consider if you need to add some structure to the remote life. WeWork is the best known of the bunch, but there are other options like ShareDesk, Croissant, and WorkFrom to choose between. And a quick search of any metro area will likely turn up several independent coworking spaces.

One of the easiest ways to set the stage for your remote team is by offering to cover the cost of a coworking space for those who like to get out of the house and see other people during the day.

Working remotely can be an amazing experience. You just have to consider the reality and complexities of doing it before you begin.

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