Leif Singer - iDoneThis

Since beginning as a weekend project in 2010, productivity app iDoneThis has grown an enormous cult following and has helped people complete millions of tasks. Its small global team supports clients ranging from individual freelancers to industry giants like Uber and Zappos.

Pajamas talked to Leif Singer, head of product at iDoneThis, about remote working at a small company with outsized influence.

What does your company do and what do you do there?

Every evening, iDoneThis sends you an email that asks you what you got done that day. The next morning, we send a digest of what everyone on your team got done the previous day to you and your team members. We have a web UI and a Slack integration as well, but emails are how it got started. It's a great replacement for daily standups, keeps a history of what a team has achieved, and in general improves asynchronous communication among team members.

I work on the product, i.e., I figure out what we should be building by talking to users and looking at analytics, and then draw out a map that will get us there. I'll also do development when there's time.

How many people are on the iDoneThis team now? How many people work remotely?

Walter (CEO) and Rodrigo (CTO), the two founders, are in our New York office. Our customer success engineer Chad is in Wisconsin, our developer Francesco is in Italy, and I'm in Germany.

How do you keep everyone feeling connected?

We use iDoneThis a lot, obviously. For more synchronous exchanges, we rely on Slack. Both are great for building some camaraderie through fun posts, emojis, animated GIFs and so on.

We also regularly have one-on-ones via Hangouts. While text-based media do help us feel connected, I find that a call between two people that is perceived to be ephemeral lets you communicate even more freely. There's just no chance of someone reading the transcript later and misunderstanding something. They're very time-intensive, though, and require us to find a time that works for both on the call, so we're trying to keep them to a minimum.

iDoneThis started out as a remote team, but now has an office in New York. Your site says you operate the same as when you all worked remotely, so why get an office? What does the physical space provide your team that you didn't have before?

Actually only the two founders are in New York! As the founders they need to communicate a lot about high-level things like long-term company direction, hiring, or strategy. I think it's very helpful in that situation to be able to just have a day of facetime. Other days they work from home, though -- when they have tasks that require less communication, but more focus.

As a team, what are the biggest challenges you face working remotely and how do you overcome them?

Time zone differences definitely have the strongest impact. Scheduling calls can be very hard when I'm in UTC+2, Walter is in UTC-4, and a customer is in UTC-7. Resisting the urge to work in the evening -- when half the company is wide awake and getting things done in their afternoon -- can also be a challenge.

With kids it's very common to have many small emergencies that would be much more annoying if we were locked away in an office miles away for hours each day

How do you deal with clients? Is it a help to have employees covering more timezones or a hindrance that you have more moving parts to take into consideration?

We're lucky in that we have a SaaS product where most customers are fine with support via email. I can imagine agencies and the like will find it more challenging to work with clients they'll have to keep in close touch frequently.

That also means that the support requests we receive don't have too many dependencies -- most can be addressed by whoever is awake. We do have a dedicated customer success engineer, though, who keeps on top of everything, takes care of most requests, and assigns customer issues to others when he thinks someone else might be able to solve the problem more efficiently. In that sense, it can be beneficial when someone who's just waking up can take control of things the previous "shift" was just working on.

We've never perceived our different time zones as a hindrance for support, though. It either doesn't matter because things can be worked on asynchronously, or it's beneficial when issues are passed from one shift to the next.

What are the biggest benefits for iDoneThis of being distributed?

For the company, we've felt the greatest benefit so far when hiring people. The accessible talent pool is just so much bigger!

For employees or me personally, I love the flexibility. Except for the two founders, everyone in the company has a family with at least two kids -- and with kids it's very common to have many small emergencies that would be much more annoying if we were locked away in an office miles away for hours each day. Just being able to make an appointment at the dentist and such without having to coordinate too much with others is a big improvement in quality of life.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

If you want to go remote, commit to it fully. Have everyone work remotely ... even if they really aren't. That is, even when a part of your team is in an office together, use the same communication channels the remote part of the team uses. If you don't, the remote people will easily feel disconnected from the rest of the team.

Walter and Rodrigo work from the office a few days a week -- but they still use iDoneThis and Slack. We can see in the chat when they go out for lunch together. That may sound trivial, but it actually gives us a better feeling of what's going on with whom.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

At least one of the founders has a regular one-on-one with every employee once a week. A huge part of that call is just talking about out how everyone's doing, both professionaly and personally. We want to identify problems before they occur so we can help remove them.

Anecdotally, it seems like remote work is most popular among software and web engineers. What about software development do you think lends itself so well to distributed teams?

The artifacts we create in our work have always been virtual. Inside the computer. We never really had a physical workshop where the apprentice could watch the master create a new sword, table, or painting. So right from the start, software engineers had to find ways to work together on these pretty much non-existent things. This necessity, combined with the engineering knack of always trying to improve the current ways of working, I think had a great influence on how we work.

Have everyone work remotely ... even if they really aren't. That is, even when a part of your team is in an office together, use the same communication channels the remote part of the team uses.

When the Internet appeared, it was mostly open source projects that showed us how to work together from a distance. As people who might have grown up with open source started their own companies, their prior experiences shaped the way they wanted their own companies to operate.

Other industries I think never had that much exposure to both these constraints and opportunities -- so they're less likely to trust the practices that enable remote work.

Describe your personal work environment.

I still do some research on the side, so I can sit in an office in the university I worked for while I did my PhD. If I didn't have that I would probably have gotten into a co-working space. Having a place to go to every morning and some people around there is very valuable. And a necessity with kids at home.

How do you manage work/life balance when working from home?

I try not to work from home. I leave home in the morning and return to have dinner with my wife and kids. The hours between 6pm and 9pm are sacred family time. I'm usually able to stay off work in the evenings, but sometimes this one bug I still wanted to fix or this one email I still wanted to write draw me back in.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I mute all notifications when I'm trying to focus, when I'm trying to plan or build something. I prefer silence to music when working and feel very bad about not fitting the developer stereotype there.

When I'm communicating, I try to do it in bigger chunks of time. For example, email -- I do it once in the morning to get through everything, and then again in the afternoon. Having other people push tasks onto your plate while you're in the middle of something is just too hurtful to productivity.

We use iDoneThis to keep track of what we're getting done every day, and for me personally measuring my own efficiency revolves around that. When I leave work, do I feel accomplished for the day when looking at that list? Usually the answer is yes. If I don't for several days in a row, I know I have to change something.

What are some of the tools you couldn't live without as a remote company?

iDoneThis for asynchronous text-based communication. Slack for synchronous text-based communication. For video calls we currently use Hangouts but don't feel very strongly about that.

What advice would you give to a company heading down the remote working path?

On a high level I think just being aware that you need to have a remote strategy is important. Don't assume that things will work the same as in a colocated situation. Don't assume that it will just work. Try to communicate more than you'd actually need to. Commit fully, or not at all.

Josh Catone
Josh has been the Content & Community Manager at feedly, the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWrite, and the Lead Blogger at SitePoint.