School of Rock in LifeSG

Frankie Chew
LifeSG
Published in
4 min readJun 14, 2021

Growing LifeSG

Some of you may know that LifeSG was formerly known as Moments of Life, an app for new parents that aimed to transform the way people interacted with the government. With the success of Moments of Life, the next logical move was to replicate that success for more people, and in many other areas of life in Singapore. The challenge? We had to do it concurrently.

From the very start, we knew that if we wanted to expand our success, we needed to do more than just expand our team. To stay agile as we scale, we also needed to reorganise and operate very differently from before. And that was how we became the first in GovTech’s Digital Design and Development (DCube) to split into multiple development squads working on a single product.

As usual, if you’re the first to do something, you’ll be the first to fail. We went through the cycle of experiment > fail > learn > repeat. This cycle may sound crazy, but it’s the same process we all go through when navigating a new stage of our lives, whether it’s living together with a new spouse or caring for a newborn. In fact, we also go through the same process when we’re playing a computer game for the first time. We’ll always have to adapt and learn from what doesn’t work, then try again.

If you’re a gamer, you’ll know that every game has that final boss, the one that’s most challenging to beat. In expanding LifeSG, our final boss is toxic competition. It’s when team members start seeing themselves as ‘I’ and ‘You’, instead of ‘Us’ and ‘We’. When individuals start vying for personal recognition rather than contributing to the team’s success. That’s when we know we’re in trouble.

Building relationships

The strategy we formulated to defeat toxic competition was to make it easy for everyone from different squads to come together, forge friendships, and develop empathy for each other. After all, we’re all part of the bigger LifeSG team. To do so, we were very mindful about two things.

The first is to create an environment that’s safe for everyone to voice diverse views respectfully. There will always be occasions where we’ll have to agree to disagree, and accept the collective decision that has been made by the team. But what’s more important is that everyone in the team knows that their opinion will be heard and considered before an informed and calculated decision is made. This is known as psychological safety, and is embraced by many organisations.

The second is to create opportunities for people from different squads to work with each other. We encourage people to move between different squads, to get exposed to different contexts of work, and discover how other teams organise themselves. For example, our support team is made up of representatives from different teams — and this rotates every sprint. This practice goes against the philosophy of many organisations who believe that a close-knit team is able to work more efficiently.

Our perspective is different. We believe that each individual will learn and grow faster by working with many people and personalities, and this growth helps them contribute better to any team they are a part of. While it can be awkward working with new people all the time, we’ll eventually get comfortable with being uncomfortable. When that happens, we’ll always be able to contribute, no matter where we go.

The night Mama gave birth to School of Rock

LifeSG’s School of Rock was created as a result of the opportunities Mama saw for people to come together. Mama is one of our leads that has been through the phases of growth and has always been looking after our people, including those not under her direct care. She proposed for both our squads, ‘Back to School’ and ‘Rocket’ to come together to overcome a challenge where they temporarily renamed themselves ‘School of Rock’. Other than triggering laughs from those of us who are old enough to have watched the comedy, the name also suggested the strength of people coming together, growing each other’s knowledge (school) to overcome hard problems (rocks). More importantly, it’s a sign that our strategy works.

We may not have Jack Black to rock the stage, but we do have many other superstars who are willing to experiment, fail, learn and repeat. And that’s how we roll.

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