The Startups Guide to Remote Teams

October 3, 2015

Featured in Mattermark G&A, Remotive, and Mattermark Daily

There’s a period in the lifecycle of building things where you go from side project to your main focus. Maybe you quit your job, or it simply becomes the thing that consumes all of your evenings. When you do, usually the first people you turn to are your friends which you may have already worked with. At this point things are pretty easy: everyone knows each other and there’s a lot of built-in trust that everyone will do their job well. However, before you know it you’re looking for more people to move even faster.

For those who live outside of very concentrated pools of talent like San Francisco or New York, getting access to the talent you need can be a challenge. You shouldn’t limit yourself to people who happen to live where you live. It’s 2015 and there are a ton of great tools out there to make a remote team work just as well as in-person! Refusing to allow remote work means leaving a lot of talent out in the cold. Many founders don’t want to allow remote work because there’s a huge trust and accountability factor involved. Hiring a remote worker means you’re likely working with people you’ve never met and only seen via Skype. Solving that basic trust factor in your interviewing process is best left for another article, but assuming you’ve gotten comfortable enough with adding remote members to your project, you’re going to quickly realize the process of getting work assigned and done is quite different than anything you’ve been exposed to. We’re going to help your remote team get up and running, and ensure smooth communication and accountability throughout. And we’re going to do it with just four tools.

WorkingOn is deceptively simple: all you do is type in what you’re working on. That’s it. It sends an end of day email (or Slack message) summarizing what the team worked on that day, and reminds everyone via email to tell what they’re working on.

Your team is on different schedules, leading sometimes very different lives, and probably in a different timezone. You need a daily accounting of what’s getting done.

Remote work shouldn’t mean “it get’s done when I get to it.”

Anyone committing to your project should have clear expectations of how much time they’re committing, and this amount of time should be expressed in terms of hours per day. Your project will develop a very slow tempo, possibly a fatal one, if you allow work to be completed on a weekly basis. Introduce this tool as one you use to make sure those daily committments are being met (or at least are trying to).

It’s likely the people you’re working with will have their own preferences. You should consider not using Trello or similarly robust tools because the time investment of creating, managing, and teaching the flow of your various cards and tasks just isn’t worth it for a small team. You have other things going on in your life. When you sit down to do work for your team, the process of updating them on what you’re doing that day should take less than 30 seconds. WorkingOn let’s you do that. Plus, its integrations areawesome.


For most small teams, the free version should do just fine.

As your project gets further along, you’ll want to start defining progress, planning ahead, and making sure it’s getting done in a timely manner. For larger projects and teams, tools like Trello and Asana really are wonderful. But if you’re just getting started you’ll want something light enough to get that accountability and planning you’re looking for without having to spend too much time just to learn and teach it.

Wunderlist is dead simple to pick up and with broad device support, it’s about guaranteed to have its beautiful design shine on multiple devices you own with its super-fast sync.

Your Virtual Office: Sqwiggle

If you don’t use Sqwiggle, I would say use something else like it but there is nothing else like it. So just use Sqwiggle. The thing that makes Sqwiggle different from Google Hangouts or Skype is that Sqwiggle is just like poking your head into someone’s office: anyone from your team that’s online on Sqwiggle is reachable with one click. You don’t wait around while they accept or deny, you’re just together in a video chat right away (there’s a busy mode to prevent this behavior, but you should discourage your team from overusing it!).

This is a really important difference. You’re used to a video call being something you set a time for, get ready for, and wait around for. When you’re working remotely it’s to your benefit to have your teams preferred communication be as similar as possible to how you would work in real life. People usually prefer personal interaction, despite all the time we spend staring at our phones. If you and another team member are both working, there’s no reason not to pop into each other’s office for whatever you need. Sqwiggle is the office, and with one click you can pop in and have a quick chat.

In fact, with Sqwiggle in mind you should come up with a communication heirarchy for your team. This is simply an ordered list that establishes how you should reach out to someone among the different methods at your disposal. For anything beyond what should just go in a chat message, consider putting the most personal ones at the very top.

Once a week, get everyone on Sqwiggle for an all-hands meeting and update (this requires the premium plan).


It’s extremely important in the early stages to keep all of your work in one place that’s easy to organize, navigate, and pull up wherever you are. Quip is like a shared, always up-to-date, real-time file cabinet.

Use this to get your launch plans organized and do some shared collaboration around your ideas. It has Slack-like chat so you can keep your conversations near your documents, and you can also comment within each doc as well so it’s always relevant. Plus it has robust offline support so you can still stay productive without a good Internet connection.

If there’s one thing you get from this, it should be that when building your remote team you should never “just wing it.” Don’t mistake the familiarity and ease with which you work with your friends for how it will be when you add strangers to the mix.

Making assumptions about how they’ll perform and operate can lead to hard conversations later on. Just winging it means that in your interview process you are unable to screen for the candidates that are comfortable working within your structure.

Whether you have just two people or ten, start using these tools today.Doing this from the beginning sets an expectation that everyone that comes later will feel they should follow. It will be clear to them that the founder(s) are holding themselves just as accountable and that it won’t be something you’re only expecting the new member to do simply because they’re the outsider. Plus, people are resistant to change.

The expectations you set today will stick around for a very long time.

We chose these four tools in particular because they enhance your work, not act as a drag on it. You’ll work better, keep the process light, and still be able to ensure accountability and transparency. At the end of the day, it means that if you’re up late at night then you’re probably building, not worrying why you haven’t noticed that your new remote member hasn’t done work in three weeks. Sign up for these tools, then get building!

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