How We Made Working With Remote Teams, Work

Darren Lee Yong
Coffee With a Side of Thoughts
4 min readMar 7, 2020
Photo by Yusuf Evli on Unsplash

3,248 km—That’s the distance between my Engineering Team based in Taiwan and us, the Product Team in Singapore. We’ve been working this way for a year and during this span of time, we shipped products that positively impacted our users and delivered results. We did great work.

But let’s keep it real. It wasn’t easy. Remote work arrangement posed challenges. And it’s inevitable for some teams or members in any organization due to business operations or circumstances. Having worked with a remote team the past year, I learned valuable lessons and appreciate my colleagues even more for their patience, resilience, and kindness.

Media Richness Theory—Can’t believe what I learned in college is put to good use!

Not being in the same physical space affected collaboration. I can’t go over to my engineers, tap their shoulders and ask them tech-related questions (let alone coffee). Or vice versa for design. We couldn’t have face-to-face conversations, the richest form of communication. We’d rely on Computer-Mediated Communication such as video conferencing and workplace messaging apps like Slack as our alternatives.

Just like any relationship, both parties have a part to play in effective communication, engaging one another, and finding out how we can help one another grow. Here’s what worked for us, what didn’t, and how we made this relationship triumph.

What worked

We were fortunate to be in the same timezone. Regardless, we still had to be considerate of time and boundaries. Instant responses are not expected as schedules can be different. So, how do you know when? Use judgement. If someone’s DM was lost in an onslaught of messages (as it always does on Slack), we’d send a reminder ping. And if we’d like to discuss something more in-depth, a video conference meeting can be scheduled ahead of time. Turn that front-facing camera on, show that beautiful smile, and make sure to listen actively when someone’s speaking.

Being detailed in written communication was also effective. One example was when we introduced a template for writing tickets on JIRA, where details were explicit (a single-liner on context, design specs, requirements, edge cases, metrics, acceptance criteria). At the same time, an open culture for questions and further clarification was encouraged. We noticed less doubt on supposed tasks and it was a lot more smooth-sailing!

Lastly, we hold regular retrospectives as a way to address issues (processes or technical) faced in a past sprint/project, brainstorm improvements, and assign owners to follow-up. This worked better instead of bottling up issues and letting it snowball.

What didn’t

Explaining huge complex concepts was inefficient. When I was going through the design for a flow last year, my engineers would be lost in the sharing. I don’t blame them. Looking back, the 1-hour session was overloading them with information. Yet, in attempt to solve this gap, we scheduled even more design walkthroughs. Without a doubt, it was ineffective. Everyone was frustrated and it was a waste of time.

How I felt. Wanted to chew heads off. Can’t. Photo by JESHOOTS.COM on Unsplash

At that time, I was using Sketch and only designers had access to viewing the design. Everyone else couldn’t see the changes when they want to. They couldn’t study it ahead of time and understanding it in an hour’s brief was hard (Gee Darren… No one has photographic memory 😠). And then we discovered Miro — a digital canvas where design could be uploaded to and anyone could access it. We experimented Miro with the team and it was a big success! Everyone loved it. They could see the big picture (visibility) and can study the design in their own time (context and prep time). We have since moved to Figma which worked wonders as well. In essence, show. Don’t tell.

Another challenge with remote arrangement it that it requires more effort for communication and bonding with the team. Especially when you don’t see them in person and instead through a screen ~90% of the time. As such, there’s increased chances for miscommunication even when intentions are good. Hence, the Product Team would visit the Engineering team in Taiwan once in a while. Additionally, we stay connected via social media to see life from their perspectives and know what they’ve been up to.

The Alpha team — so grateful working with this bunch the past year. Although not everyone is in the same team now, I wanna wish everyone the best in their future endeavors.

Remote arrangements aren’t easy. But with an open-to-learning mindset, we overcame challenges that enabled us to grow and develop better collaboration skills.

Coffee for thought: What are some ways to foster collaboration across remote teams? What worked for you?

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