Ways We Work: Working From Wherever

by Emily Powers & Craig Bryant

Craig Bryant, Founder and CEO of Kin, and Emily Powers, Director of Operations and Finance at Fresh Tilled Soil, have joined forces to uncover the mysteries of the modern workplace. The following is the third chapter of an eight-part series featuring some of the greatest debates, struggles, and solutions surrounding how we work. Check out the entire series here.

Working remotely isn’t a recent innovation – the earliest documented examples of telecommuting stretch back hundreds of years, but over the last twenty years, the concept of a distributed workforce has evolved into a mainstream organizational design that helps companies hire talented people wherever they’re happiest.

The remote workplace of today is the product of technological advances, employee work/life values, and companies doing whatever they can to hire the people they need to succeed. Smack dab in the middle of it all is a growing collective of companies like Kin and Fresh Tilled Soil learning the in’s and out’s of building a resilient distributed workforce.

In this week’s article, we take a look at remote work from three vantage points. First, Craig shares some key organizational factors that make the fully-distributed workplace of Kin and its sister-companies, We Are Mammoth and DoneDone, possible. Then, Emily drills into Fresh Tilled Soil’s approach to a mixed-location workplace. Finally, we wrap up the piece with a list of the business-critical tools companies like ours use to keep these modern workplaces afloat.

WAMDunKin: Three companies, thirty people, seventeen states.

Five years ago a team member at Kin’s parent company, We Are Mammoth, had a dilemma. She loved her job but wanted to move to the west coast. The question for our business was, do we want to say goodbye to an exceptional team member because she didn’t want to live in Chicago anymore? We mutually decided she’d become our first remote employee in what would ultimately become a fully distributed company, the experience of which I documented on the We Are Mammoth blog.

Our shop isn’t a collective of freelancers. We’re full time employees working on big projects that require synchronous teamwork. This gets challenging with everyone communicating via glowing rectangular screens, and it’s taken a few years to find the right recipe of people, process, and technology to keep our thirty people humming along across four time zones and seventeen states.

Who are you remotely?

About a year ago, I made peace with my business partner’s decision to hire a new team member without having ever met the candidate in person. His reasoning was that ninety-nine percent of our work interactions are done remotely so, for some positions, it was more important to hire based on the “remote” version of the person than the “in-person” version. It’s still a strange notion for me. I’m one of five team members who still live in Chicago and I never moved away from our headquarters, so I’m one of the last people to have fully transitioned to our distributed work culture. You read that right: The CEO of a distributed company has taken a very long time to get used to working remotely.

Many people aren’t prepared for the unique challenges of remote teamwork. We pitch working “wherever you’re happiest,” but maintaining a clear division between the job and non-work life is challenging. Many folks work too much and have a hard time disconnecting at the end of the day. Others are too easily lured away from work by life outside of their home office.

Remote teams also can’t depend on the built-in social cues that help foster team culture at onsite companies. We don’t have body language, team lunches, or serendipitous hallway conversations. So, one of the biggest success factors in a remote employee is how well he/she can create a sense of “being there” in a time of need via the tech tools and processes we’ve established. Remote team members need to over-communicate to establish their “presence” – the digital equivalent of being at your desk, in your office, available to collaborate or, likewise, heads down working on a complex task. It takes practice to get it right.

Remote Operations for remote employees

One of the greatest compliments for our operations team is when new hires report feeling dialed in to the company’s community. That experience is by design and something the team still strives to improve with every new hire.

Working Remotely

Employee experience at remote companies needs explicit planning because it simply doesn’t happen by itself. Picking up paychecks, chatting in the kitchen, getting a computer fixed, or dropping by a manager’s office are just a few opportunities for an employee and employer to connect at physical offices. None of these exchanges happen incidentally at remote companies – but they’re important to employee engagement and organizational health.

Teams that get together stay together.

We’re social creatures and we often solve problems best when we’re together in the same space. For really important team events or work that simply can’t be accomplished remotely (design sprints, client meetings, for example), we get folks together at a mutual location – usually our Chicago office. We do this on an entire-company level once a year, but we also encourage teams to get together during the final sprint of big projects where morale, support, and in-person communication is mission critical.

Traveling takes a lot of time though, and time is what engineers and design folks need the most of, so we use travel only when we know it’ll facilitate productivity long term instead of tiring folks out even more.

Different states = different employment laws and taxes

Every state has its own set of rules to follow when it comes to employment laws and taxes, so things can get complicated.

Our companies’ teams are in seventeen states, which means we have a lot of tax obligations and, to boot, we need to be mindful of state-specific employment laws. For example, California and New York are at the forefront of employee and family protection, while Illinois is pretty lax about employer obligations. So, what’s an Illinois-based company that has employees in NY and CA to do?

While it’s our desire to always have our team’s best interests at heart, it’s hard to stay on top of every single combination of federal and state law, especially when they’re changing so rapidly these days. Luckily there are accountants and employment attorneys out there to help us stay on the right side of the law. Getting started early with corporate taxes each year is a great idea, as is finding experts who regularly publish new mandates and laws, such as payroll companies.

Work where you’re happiest, but stay happy.  

Embracing a distributed workplace has been one of the most important economic opportunities our company has pursued in its first ten years. What technology has enabled companies like ours to do is to hire the best people wherever they’re happiest, and the growing familiarity with the model means less friction with clients and talent alike. It requires extra discipline from every team member and some out of the box organizational thinking, but once everyone is rowing in the same direction (CEO included!), it’s truly a liberating way to work and live.

Mixed-Terrain: Fresh Tilled Soil’s everywhere workplace

Fresh Tilled Soil is a majority co-located company that flirts heavily with being distributed. We are a team of 27, with 2 fully remote, 3 majority remote, and the remaining 22 operating from our Watertown office but working from elsewhere frequently, at their discretion. It’s safe to categorize us in that awkward middle ground between co-located and distributed.

Let me tell you, these are dangerous waters my friend. In a co-located company, everyone is always on site collaborating, joking, and talking about their weekends around the water cooler. In a successfully distributed team, there is time allocated for these same exact interactions to occur online. In the awkward middle land where we sit, remote team members are certainly a part of working meetings and collaboration during video conferences and chats, however, they are often missing out in the bonding, sharing, and joking that occurs in between meetings. If someone tells a funny joke in the office that makes everyone crack up, is someone then going to run to their computer to make sure that joke hits Slack for the remote folks? Likely not, and that’s not okay.

At Fresh, we have one huge, nagging factor on our side: I myself am one of those 3 majority remote team members. This means I feel every single flaw in our remote inclusion culture first hand. Here are a few examples of ground-rules we’ve established to support and include those working remotely:

  1. We don’t ask questions: If someone makes the choice to work from home, we fully trust their decision and carry on.
  2. If the run club heads out for a run from the office, all remote team members are encouraged to get some fresh air at that same time.
  3. If we head out for a company hike, remoters are encouraged to take one too!
  4. When we arrange for our masseuse to come to the office, we offer our remote folks a massage at their local spot as well.
  5. Technology is everything: We’ve researched an upgrade to all our conference room cameras and mics to make any remote participants feel like they truly are in the room and at the table.
  6. We fly our remote team members out approximately once a month to get face time with the team.
  7. We make sure everyone who works from home (even occasionally) has an equipment set-up that is equally as effective in the office and at home.

Emily’s take on maintaining professionalism

When I speak to friends and family members about the fact that I work from home four days a week, they are just flabbergasted. They think it’s just the greatest thing in the world that I can “roll out of bed, grab some coffee, and sit down to work at the kitchen table in PJs.” In fact, if you Google image search “working from home” this is the very first result you’ll find. This could be my type-A roaring its ugly head, but this is not how I operate, and it’s not my recommendation for others. This PJ-laden stereotype has wreaked havoc on the image of working from home. In my experience, there are a few keys to successfully working from home (or anywhere really).

Mental prep

I still wake up at 6:00 every morning to get in exercise, coffee, breakfast, and time for personal emails (not work emails), just as I did in the days when I was commuting. I think we are so much better at mentally preparing for getting out the door. However, these morning routines to prep your brain for the day ahead are critical whether you are hitting the road or staying put. For some people it will be meditation, a cup of tea, or rolling around on the floor with your kids and/or dogs. Make time for whatever sets your head straight for the day ahead, and do not start working before it’s time!

Physical prep

Yup, I’m going to tell you to get dressed. I’m not telling you to put on a suit, but I am telling you to get dressed as though you were going out into the real world. And this is not just for those of us who video conference all day long and need to keep up appearances, this is for everyone.  There is something about showering and dressing that flips a switch in our minds, it tells us we’re prepared for something, it provides a clean break between not working and working. Again, this is key for the mental prep.

Claim your space

Make sure you have a clean, well-lit, designated area where you do work. For those who video conference, be sure you have a simple, professional background (yes, we can see the piles of laundry you wish were invisible).

Having a completely separate space will also provide that clean break from not working and work. You enter your “office” in the morning and dive into work, head out for lunch, dive back in for the afternoon, and get the heck out when you’ve wrapped up for the day. I make a strong point of closing my computer and immediately leaving the house for a hike or run when my work day has ended.

Claiming and defending (yes, put up a sign if needed) your space should also limit distractions – discouraging pets and random drop-ins if these are big distractors.

Looking for inspiration? Design company Hanno is 100% distributed and has always been that way. They’re very open about their workplace culture and requirements, and have made their company “playbook” accessible to anyone interested in how they’ve built an amazing design team that spans the globe.

The Tools of the Trade

Communication tools are vital to establishing a successful remote working culture. Every single member of your team needs to be fully informed of the ongoing company minutia, regardless of their location. There should be no barriers to communication whatsoever, and it should be easy. If you have even one team member (or client for that matter) who’s remote, you need to take a serious look at how supportive your remote working culture is. A wise colleague from Four Kitchens (a fully distributed team) once said, “The moment one person goes remote, the ENTIRE team must go remote.” When they hired their first fully remote employee, all meetings became Google Hangouts. That’s right, even with 15 people sitting in the office next to one another, everyone got in front of their computers to meet on Hangout, so everyone in the entire company had the same working experience. Now that’s leveling the playing field!

The following is a list of tried-and-tested tools we recommend to build a supportive work-from-anywhere culture. If you’d like a more extensive list, check out The Next Web’s list here.

Messaging

Messaging is vital for super quick back and forth communication. It’s also great for building company culture and morale through joking and play. Kin recently moved to Slack from HipChat because team messaging is business critical and HipChat’s service didn’t reflect that. A vast majority of team communication happens via Slack, and it’s an incredibly useful tool to get caught up on past project conversations – it’s like a transcript of a project’s team collaboration.

Video Chat and Screenshare

Nothing can take the place of face-to-face conversations when time and tone matter most. Since we can’t meet face-to-face on a whim, video chats and screenshares play the role. Kin uses GoToMeeting for extended-team meetings because their video streaming quality is superior to most other solutions. For smaller 1:1’s or project team video chats, Hangouts are the go-to because it’s so dang easy to fire one up. Fresh uses Zoom for 95% of meetings, occasionally throwing in Hangouts here and there for the remaining 5%.

Operations Software Apps

We’re fortunate to work in an industry where most everyone is accustomed to interfacing with their employer’s operations via software app. The key to these apps, like Kin and DoneDone, is to ensure the experience using them is productive and memorable. There’s a quick slide into wasted resources if these online tools aren’t more efficient than simply rolling up the sleeves and doing things manually. You can find a webapp for just about every single operational function from hiring, to performance management, to to-do lists, but here are a few we recommend:

In closing, working from wherever is fast becoming the norm. Keeping your company running smoothly regardless of where your team is located is possible with a great deal of planning and consideration including: Crafting a culture and expectations around how to work remotely, dedicating resources to the technology and tools necessary for keeping the team in close touch, getting your legal ducks in a row, and understanding that once you’ve successfully distributed your team, you still need to bring them back together pretty regularly to enjoy one another’s company.

About Fresh Tilled Soil

Fresh Tilled Soil is a Boston-based user interface and experience design firm focused on human centered digital design