Working Remotely in Startups Teams

We have teams based in different places. It’s how we roll at HealthCare.com. Of course, I would prefer to all be in the same place but then again, I would prefer even more working remotely with the team we have. Thankfully, everyone is mostly in the same time zone, which significantly eases the coordination challenges. Plus, many of us have been working together for multiple companies. This history, plus the trust that we can build a consistent culture and produce in our various hubs, allows us to operate with these constraints.

I’ve been working with remote teams for over 8 years now. In my first start-up experience with BrokersWeb, our technology and operations team was mostly in Guatemala while the US team was in Miami and Palm Springs. (Despite being in resort towns, we did actually do a lot of work and built a company and team we were all proud of.) I co-founded my previous company, ContactUs.com, with a partner based in Chicago. In my current company, HealthCare.com, I lead the team from New York while most of our people are in Miami and Guatemala. I keep doing it, sometimes unintentionally. Thankfully, it’s kept working.

I’ve picked up a few things along the way on what have worked along the way. It’s a set of tools or processes we use to either simulate being together, or to minimize the disadvantages of not being in the same place. Here are some of the things we do:

• Slacking. Use Slack, which is built for teams. Specifically, use the desktop and mobile apps of Slack. Whether you’re remote or not. There’s a reason it’s had ultra-fast user growth. While chat is almost as old as the internet, Slack is different in that it is built for organizations. Plus it is device-agnostic. It archives conversations. It makes it easy to create evergreen channels. Uploading attachments and images is seamless. If you’re at an online company. You’ll find yourself sharing screenshots a ton. The other benefit for remote teams is that it’s your defacto indicator of presence.
• Screensharing early and often. Skype works well for 1-on-1 conversations. We use UberConference for multi-person conversations. If a picture is worth 1,000 words, a screenshare is worth even more. (Side note: I don’t know why we don’t use Google Hangouts more, especially since we’re already on Google Apps. But I just like UberConference.) For advanced users, try Jing for recorded screenshares. You end up with a nice link to a cloud hosted mini webcast like this one. For videos under 5 minutes, Jing is free.
• Having a real conversation. If after a few rounds of back-and-forth chats or emails there’s still confusion, getting on a the phone (or doing a voice call on Skype) to have a conversation. There are inherent inefficiencies towards not being in the same place. Don’t let the confusion snowball. When working remotely, you can’t see in the other person’s eyes whether they are comprehending, and the other person can’t see into yours. (Certainly you can do video calls, but if I had to choose between a screenshare or a video call, I’d prefer the screenshare.)
• Scheduling “Work Sessions” with your teammates. These sessions are more than check-ins or information downloads. They aren’t just talk. These are calls focused on doing some form of work together. Come into the work session with an agenda, goal and checklist. Have a Google Docs open that all participants in the work session have open and expect collaboration from others. While it’s obviously a lot easier to do this in person, this is a great exercise for remote teams to do regularly. It helps the other person you work with know how you’re thinking about the things you’re working on real-time, and vice versa.
• Training everyone on the team on how to initiate, schedule and moderate meetings. Everyone in the team, even the most junior should feel comfortable doing this. I view it as an important skill-set, and it reinforces proactivity throughout the organization. The importance is even higher in remote teams.
• Scheduling recurring one-on-one meetings with the remote people you work with closely. I’m not proposing that people schedule a meeting just to have a meeting. Instead, make sure the meetings are productive and efficient. They are the best forum to get through lists of items you need to cover. Making sure agenda topics are prepared on both sides in advanced, and put them on a shared screen during the meeting.
• Using an extra computer monitor. This is a personal preference. I believe it helps me to keep my communication software live in one screen, while I work in the other screen. ALT + Tab is the alternative when I’m not at my desk.
• On group calls, encouraging full engagement for all of the active participants. This means no multi-tasking. If a call is important enough to schedule into your calendar, it’s important enough to be fully-engaged. (There will be some calls when you’re not an active participant, so sometimes multi-tasking if OK. But be sure to mute yourself so no one can hear you typing. And try to to join to many calls that you’re not an active participant on.)
• Using some kind project management software. We use Trello. Not only does it help you get things done, it also help communicate. Both passively (enabling others to be able to following), but also directly through topical conversations inside of cards.
• Using real-time collaboration software. We’re a Google Apps user as a company. So this means using Google Docs and Google Sheets when you’re working on a document that will eventually be shared and eventually be collaborated on. (I know Googlers would just prefer you use it everytime, instead of MS Office, but old habits die hard.) It’s important in how you use it. Use the commenting features built inside of Docs and Sheets. Make sure to tag someone in the comment that you want to direct the message.
• Traveling. I know it’s an investment in time. And an investment in, well, money. And money is a scarce resource that needs to be used wisely, which is why I didn’t put this one up higher on the list. The reality is that startups, especially in the early stages, can’t afford to travel as much as bigger companies with a budget. However, every time we get back from a physical meetings. Psychologically, because there’s scarcity in face-to-face time for remote teams, you tend to use the time really efficiently. And nothing beats the informal, impromptu conversations that come up.
• Training and onboarding new people. When you have a remote employee, you have to commit to spending significant time together during the onboarding process. If you don’t make the investment upfront, the employee’s future productivity and happiness is at stake. Despite being remote, we’re able to minimize this issue because our teams are built around locations. But to the extent that a new employee will be working significantly with teams in another location, that’s where the investment in being together will pay off.
• Being available. It’s really difficult to be a 9–6 job for remote team members who work often together. This is the case when I’m working with each of our team leaders. Since I’m a remote employee work primarily with people not in the same place, I have to be flexible and available. It’s too difficult otherwise. I know it sounds rough, but this is the choice both the employee and employer makes. It’s our job to set the expectations upfront, and make sure our people buy in.

I’d love to hear back from others who have done this (including my own team), about what hacks and practices they use to improve the way they work together.

photo credit: True phone via photopin (license)

Appendix:

While there are obvious challenges, but I wanted to highlight some less subtle ones I face all the time.

• Limiting the kinds of people you can bring on. Being remote makes it extremely difficult to train inexperienced people who aren’t working alongside experienced ones. In fact, I really wouldn’t even try it. It’s hard enough onboarding a remote, experienced new employee, to understand your business objectives, processes and KPIs and buy into the company culture. For inexperienced hires, I’m certain there are good people out there with the raw talent to succeed, but unless they are in an office environment and both actively and passively learning from others, it’ll be hard to make it work in our remote team. Experienced hires who bring in a directly-translatable functional or technical expertise is another story, and those are the ones we’re more open to.
• Reading emotive states in people. I know this sounds like psychological babble, but it’s important. If a team member is frustrated, or if she’s excited, it’s difficult to read it. But it’s important. Since it’s difficult to read, then I would recommend that we be more open to asking the other person.
• Losing spontaneity. When all of the conversations have to be actively initiated, it’s hard to get the kind of insights that might come along by, say, getting lunch together. Only solution here would be to open yourself to those creative moments. Schedule those one-on-ones. When someone gets excited about an idea, do your best to get momentum on it quickly.