Accepting the feature wasn’t an easy decision[^1], but I eventually agreed after asking my super awesome partner PM and super awesome manager for their second opinion. The opportunity to talk about design at an org-wide level doesn’t come by often[^2], and I did feel thankful towards the faith our publicity and branding team had displayed in giving me this opportunity.

Whilst the final published post had to be condensed, the complete Q&A (with some edits for brevity and tone) can be read here 👇:

How did you get interested in digital product design?

This was accidental. I had grown up interested in web design and frontend engineering (thanks, Neopets!). After graduating, I got a very lucky start at Zopim, despite not knowing what exactly I was getting myself into. That experience and my amazing mentors there helped me gain a deep appreciation of the craft.

What is the biggest misconception about a career in design that you think others have?

1.) Designers can’t come from many walks of life.
2.) Design is easy.
(Completely cheating with 2 misconceptions instead of 1. 😬 )

I’ve known and worked with designers from diverse backgrounds—accountancy, law, design school, engineering, math, computer science, psychology, and more. Whilst my engineering degree does help me grasp software concepts more quickly, the role’s demands mean this advantage only goes so far. Being adaptable and quick to learn on the job matters more.

That said, whilst I think anyone can be a designer, not everyone can be a great designer. The best digital product designers have to juggle a lot: the actual UI/UX design, conducting research, managing complexity, focusing both on details and the big picture, collaborating with and influencing stakeholders, understanding business fundamentals, navigating technical constraints… The role is hard.

How would you explain your area of expertise in tech to your grandparents / kids?

“Hello, I make apps like Facebook / Roblox.” 😅

Jokes aside, I specialise in the design of enterprise applications. So, could I pitch it as “I make work software that help people do and like their jobs better”?

What is the most meaningful project you’ve worked on?

There are a few I remember fondly. In more recent years, it’d definitely be growing the digital product design function at CSIT, together with the rest of the Design Chapter. A big personal theme in my life has been “defying expectations,” and it’s been so fun seeing how the designers and the design function has grown here, even though there were a few “it’ll never work here” comments initially.

What is the biggest potential challenge / opportunity for the design team as you scale?

The design function right now can only contribute to a small slice of CSIT’s operations, because 1.) we’re a small virtual unit relative to the organisation, 2.) we’re a relatively young and still maturing competency. The downside is we’re not contributing as much as we should. The upside is we’re not contributing as much as we should. There is a lot of room for us to grow in both breadth and depth.

A major challenge is that mindset change required for design maturity takes time. On a day-to-day basis, it can feel like nothing is moving, though actually when we zoom out, maybe we’ve moved leaps and bounds. The designers here care a lot about the work and creating value, and it can be frustrating when there doesn’t seem to be progress. I think we need to train up our inner zen to keep going?

What’s it like working in a cross-functional team with engineers, product managers, etc.?

Better than sliced bread! 🍞

To me, engineering, product management, and design are different but equal weight inputs collectively increasing the likelihood that the “final” delivered digital product is effective, efficient, and engaging. We can’t do without any of the others.

I personally find the other functions also often have different thinking habits and mental models. Working with them helps me broaden my perspectives a lot. Case in point: two of my long-term mentors and close friends for >10 years are a PM and engineering leader respectively, and they still offer amazing guidance and advice even till today that are just… different.[^3]

AI: Friend or foe?

AI is a tool—tools can be either? As a designer, I think we need to learn the tool well, to shape it to serve as a friend?

(Sorry! Super boring answer =X)

What’s the best non-technical trait / skill to have for someone in your role?

To quote a design leader I really look up to: Compassion.

To add my own interpretation: Compassion doesn’t mean being a pushover or not holding people accountable, but it really means seeing people as people. We don’t put people up on a pedestal to the extent that we overlook their developmental areas, nor do we fail to recognize the dignity of others even if we don’t work well together. Compassion also means genuinely wanting to help the people we design for, and appreciating our collaborators and stakeholders as people.

I am human though, and often fail miserably in actually meeting this bar. As a mentor recently reminded me however, we’ll never be perfect, but we strive to get closer to it. This very desire to cherish compassion is itself precious?[^4]

What is one of the most surprising things that people know about you?

My age? 😝 Hmm… Most people can tell I am quite introverted, but most people can’t tell how much of an introvert I really am. I do actually like people, but my social battery drains faster than a first-gen iPhone streaming YouTube.

Do you have a special talent outside of work?

No. I am an incredibly boring and average techie / designer.

Name the coolest thing that you’ve done in your life.

Meh-cool: I was an adjunct lecturer at my alma mater for 8 years.

What I think is quite cool: Meeting my ex-students at design community events, and being told some of them picked this path because of the class I taught, and knowing that some of them are doing really well in their own careers.

I don’t think my lecturing / teaching skills were stellar, and it always feels like I’ve gained more from teaching than my ex-students did from me, but I still feel proud for doing this.

Your advice for those looking to join CSIT?

🤔 I’m not sure if I have advice specific to CSIT… (or if I’m even qualified to give advice?) Well, here goes anyway: Everyone has environments they thrive and don’t thrive in. If you’re someone who can wrangle complexity quite well, I think CSIT might be a good fit? The problems the org deals with can really be quite gnarly.

See you around? 😃

[^1]: Ugh, the spotlight! 😬

[^2]: Erm. We’re a team of 9 in an organisation of definitely >9

[^3]: Second case in point: I would not have accepted this feature if not for advice from two non-designers.

[^4]: A very close second critical trait would be humility?

Huh. Curious.

Being a (somewhat reluctant) leader and female in tech, such feedback is concerning. Do I exhibit behaviour that prevents healthy discourse? Do I not consult people sufficiently before making decisions? Do I give the impression that I’m not listening when people talk?

And yet.

Feedback has to be taken in context. Who is giving the feedback? Why are they giving the feedback? What is the behavioural change they want to see? How does me being “less strong” benefit them? What examples can they cite, with regards to my character being too strong? Is this consistent with the feedback I get from others?

Also, since when has strength in character actually been something we need to fix?

When we reframe “too strong”, does that also not mean being assertive, honest, and decisive?

Very curious.

Which is it? What’s going on?

I’ve had a history of been overly self-critical, and dismissive towards my boundaries. And yet, having recently read “Leadership and Self-Deception”, I’m also concerned if I am too focused on self-justification, and thereby perceiving ill intent on others.

What are my intentions when I question such feedback? What were my real intentions, during instances that led others to give me this feedback?

Work is hard. Relationships are hard. Where in the spectrum on truth are we, and how can we tell?

Cue mystified look. (。_。)

2 years ago, people asked if the designers were here to help “draw the UI” and “pick their app colours.” 2 years in, a few colleagues still ask for the same favours and we’re definitely not yet at a Level 5 design maturity, but hey! There are now a lot more people who know drawing UI is not our main job, and even proactively reach out to ask “How can I get a designer on my team?”

Does small celebratory dance. ヾ(･ω･*)ﾉ

So… how did we get our design team off the ground? Here’s our story.

Start here: Research and understand the landscape

Starting up a design team isn’t revolutionary. The difficulty always lies in designing the first steps to get started, appropriate to the organisational context. For designers, our design research toolbox can be put to good use here, to first understand the landscape and eventual value the design team can bring.

In our case, our research was a combination of very informal stakeholder interviews, a lot of casual coffee chats with stakeholders, and sometimes asking to be allowed in as an observer to product ceremonies.

The findings were… not too surprising. Essentially, design understanding was very low. Design work was mostly ineffective, not reusable, inconsistent, and often not even recognised as design work. There was no formal process to support design efforts. Design tooling was inconsistent across teams.

Designers were far and few, and though they were incredibly passionate, most designers were junior or mid-level, still requiring a lot of guidance. Product managers (PM) and engineers were often actual doers of the design work, a somewhat unfair situation for them since this was not actually their core responsibility. Management and user support for design was uneven—a few were very supportive (which explains how I could even land a job here), most were ambivalent.

And yet, research also revealed that there were actually also many opportunities for design to become a valuable partner to product and engineering.

The biggest unfulfilled potential we immediately saw for design was in facilitating coherency—CSIT had many enterprise products across many distinct workflows. There was need to ensure that information architecture and experiences across products were harmonious and purposeful, so that users could work effectively and efficiently across all these products. The unintentional lack of dedicated design bandwidth had prevented design from stepping up to this challenge. Could we ever get design to a state of maturity where we could deliver this value of facilitating coherency? What would come after for design?

Starting state?→Better understood. (•̀ᴗ•́)و ̑̑

Desired end state?→Vague, but there’s something there. (•̀ᴗ•́)و ̑̑

Steps in between?→Oh-kay… (ಠ.ಠ)

Many roads to maturity: Identify where to play and your starting strategy

After understanding the landscape, figuring out how to move ahead can still be quite daunting. Where do we even begin?

For us, we started by breaking down what makes up a design function, and then tried to design appropriate and coordinated strategies for its constituent parts accordingly. Building on the Design Management Office concept by John Devanney, we defined our design function to be these 3 pillars:

• Practice of design on digital products
• Platform on which design is done.
• People practising / enabling design.

With this breakdown in mind, we could begin thinking about where exactly to play. Should we split our resources across all 3? Work on 2? Focus on 1?

The answer? It depends.

If our team had more resources, maybe pursuing more pillars would accelerate design maturity more. If our tiny design team was mostly experienced designers, focusing more on the Platform and Practice pillars might have been a good choice.

For our team, we decided on the following:

• Practice: Only focus on a few projects, and try to ensure design work there was done well, without trying to contribute to product strategy or coherence, yet.
• Platform: Only invest to the extent necessary for our designers to function.
• People: Support our designers in making good impact on the projects we were assigned to, using those opportunities to also level ourselves up so that we can make greater impact down the road, and to also begin nurturing the community around design.

It was not simple translating research to these choices. In short though, we essentially balanced resource constraints against the highest value we could generate towards design appreciation.

As a team, we didn’t have sufficient experienced designers to drive Platform investments, and anyway, Platform improvements usually start benefiting designers first. Doing too much for Platform could even be seen as designers’ navel-gazing, and hurt our standing before we even had one. For Practice, since most of our designers were junior or mid-level, we would be taking too much risk by working high-complexity but high-impact projects. We also couldn’t take on too much work since we were a very tiny team relative to the organisation’s size. Hence, why not each take on a single product and try to do that really well? I.e. less, but better?

Our resources could then be focused on People: inwards on making sure our designers could deliver within our assigned scope, whilst improving our design skills simultaneously to deliver more impact in the future; outwards to begin building strong relationships with the community, so that future Platform investments and higher value Practice work could be better supported.

Focus on the People pillar it seems to be. (＠_＠;)

More thinking required: Translating to actionables, without losing sight of the bigger picture

These strategic choices were translated to more concrete actionables, which for us, manifested mostly in our design team setup and rituals.

Design teams can be centralised, decentralised, or hybrid/matrix. Since we decided to focus only on making the existing work better as a start, and on building strong relationships with the community, we supported and agreed with conforming to existing reporting structures, instead of pushing for designers to report into the design team. In CSIT’s case, this meant decentralisation, with designers reporting to product managers, alongside engineers also reporting to product managers too.

This choice has obvious downsides—designers might not be able to easily seek help or learn from other designers easily across their reporting lines, and we could prevent design from reaching its long term value of facilitating cross-product coherency.

To counter this risk, we negotiated for every designer to have 30% of their time, in the near term, ringfenced to seek and give support to other designers, and to learn from each other’s work. This 30% time was often spent on rituals such as regular bi-weeklys, design team exchanges, and even just time to meet and relax in a shared space.

For design’s longer term goal of facilitating coherency across products, a ringfenced 30% time would however likely be insufficient to counter the daily friction of product team boundaries and reporting structures. We therefore laid out strong recommendations that design should eventually be shifted to a hybrid/matrix structure in the long run instead of the current decentralised model, for design to overcome these hurdles and to better serve CSIT. It wasn’t clear when this structural shift might happen, but laying it out was also a reminder for ourselves—this is where designers shall strive to play in the long run.

Would all these preventive measures actually work? Only time could tell and only an agile mindset could help us pivot, if necessary. In any case, after all this planning, it was time to execute, to know how things will actually play out.

Time to get cracking. ┌(・。・)┘♪

Go forth, but brace yourself: The roads ahead are very bumpy, but the sights are worth it

And since then, it’s been almost 1.5 years of heads-down focus—our designers have been embedded into various product teams as planned, supporting their teams ship better work with good design, participating in design team rituals, and just working hard to demonstrate design’s value in our organisation.

Along the way, we learned many lessons and had to make a few course corrections. For example, despite the ringfenced 30% time, a few of our junior/mid-level designers still did not have sufficient support in their work, especially if they were in product teams more resistant to changing their ways. This happens in every organisation, but there was the need for the senior designers to step in to mediate or provide additional support, and the whole experience was definitely not pleasant. For me personally, this has been the most painful sacrifice of the journey thus far, and I often question if I had made the wrong choice advocating for the decentralised setup when we had so many juniors/mid-level designers. Perhaps we should have advocated harder for the designers to work in pairs as well? Perhaps we should have only the mid-level/senior designers embedded into product teams, whilst juniors supported their work?

Nevertheless, if we zoom out, our tiny digital product design team has still delivered a lot. On the whole, the team has accumulated many small successes and wins. We’ve built up some processes and resources to make our work slightly less manual and tedious, though more can be done. Our designers have slowly but visibly leveled up, product partners generally understand and trust us more, and stakeholders are starting to demand more from design. We also managed to get design formally recognised as an equal vocation to product management and engineering.

And there have also been many emotional ups too. The same engineers assuming designers were there to “draw the UI” are now also the same who tell us “wow that research session was super helpful for me” and “hey we should do more user research on this thing.” That’s progress.

So… this has been our story so far. There are many things we could have done a lot better, but I think we’ve also got some things right. And this story will continue, hopefully with a continued upward trajectory. Moving forward, we’ll start scaling a little bigger—still mainly focused on supporting our designers to ship good work where they are, but now with different tactics—the senior designers should step back from their product teams to support all other designers and their teams more, so that we build up more wins. We’ll also start facilitating some collaboration for designers working on related products/journeys.

As the journey continues: Seeking exchange of ideas and travel buddies

Coming back to “why would you want to work in in a defence-related government agency?” — the story thus far has been precisely why I joined CSIT. For me, it has been a tremendous growth opportunity to help establish and grow our design team. The “business” we’re in, as a government agency contributing to our nation’s security, adds on to the difficulty of the challenge, and yet also gives great meaning to all the work we do here.

Are you part of a design team yourself? We’d love to chat and hear your story too because there’s still plenty for us to learn. Otherwise, if you’re a designer who loves working on complex enterprise apps or even teaching others about design—we offer valuable front-row seats to observe how a young (but talented) design team could scale. Join us if this sounds up your alley? ←⁠(⁠>⁠▽⁠<⁠)⁠ﾉ

Post-article credit, featuring many heroes

This was not a journey designers could have embarked on alone. Here’s an incomplete list of thank yous and credits that we therefore think is essential to include:

• Members of CSIT senior management for being true sponsors and supporters, as well as our various design champions.
• Ee Kwang for his co-stewardship in this journey, and our team of extremely lovable designers.
• Our product team partners and peers for their understanding and willingness to experiment.
• The users of our digital products, for their patience and support as we strive to do better.

A version of this was originally posted on the CSIT tech blog. Thanks to the CSIT design team and ex-colleagues from SP Digital XD Team for reading early drafts of this.

“They should change the app this way.”
“It looks way too cluttered and there is no white space.”
“Things have no consistency! It’s so messy. What do they think they‘re doing?”
“This company should allow us to have this functionality. How hard can it be?”
“Why can’t we just follow best practice?”

And building and designing digital products does initially seem easy, when they get started. Just follow this design process—empathise → define → ideate → prototype → test…

… and then user feedback actually starts coming in…

… and hey! They sound like the exact same criticisms.

How hard can it be, indeed? 😇

It’s easy to learn, hard to master.

We’re all mostly blind to our own flaws, as well as flaws in the things we build. For all the semesters I’ve taught—the same students initially criticising apps for being cluttered and inconsistent in their UI are typically the ones making the same mistakes in their own work. Most of the fresh designers I’ve mentored often start out fiercely condemning work done by others, sometimes demanding an impossible perfection with zero trade-offs, until they also get their hands dirty and realise how difficult it is to balance all the demands.

I’m often asked if there are any good design training courses we could send engineers/PMs to, so that they are able to be self-sufficient and independent if they’re not able to hire a full-time designer. To be honest, design’s basic toolbox is pretty easy to learn, so most training courses should suffice, as long as they cover the fundamental thinking models and skills (e.g. research!). I do also think it’s great for more people to learn some digital product design skills. But as with many things like sports or music, design is easy to learn, and hard to master.

This digital product design thing is really hard.

Having designed for a couple of years, I’m fairly confident that most of the stuff I work on aren’t too crappy. However, I’m also fairly confident that almost everything I’ve worked on is also a long way from being good enough.

Design is a craft. Craft work, by their very nature, takes years to master. For digital product design, the craft involves not just understanding the digital landscape, but also understanding complex human systems around the products we’re building—how digital systems influence and are influenced by the human systems. Almost every designer I’ve met have realised (or likely will realise) at some point that to create bigger impact, we need to delve down the rabbit hole of nurturing human systems to support digital systems that support human systems. (Ha!)

Thus, being really good at digital design thus isn’t just about being good with UI or digital design best practices, but it’s also about being very good at influencing people, and making other things happen to support the delivery of great digital design. Digital is hard enough with the large variety of platform-centric and technological considerations we need to account for, but humans… oof! There’s basically this giant unseen iceberg waiting to snare anyone who thinks digital product design is easy and has sailed this way thinking “I could do this easily too!”

Be demanding, be respectful, be kind.

So… Want minimalist UI, but guided enough for folks to understand what’s happening? Pick your poison. Introducing a new simplified workflow, but dealing with a community who’s resistant to learning new ways of working? Great, now you have to work with these partners to help introduce these workflows—is your product team capable of the added resource needed to juggle that partnership? Wanting the most efficient UI patterns, but adding so many engineering hours? Oh wait, your main hypothesis isn’t validated yet, but could your poor UI patterns be fudging up your test results?

Courses and readings etc teach us the broad principles of how to navigate this messy world of digital product design. Personally however, I’ve yet to find a better teacher than years of experience (preferably with a good mentor / coach to help catalyse your learnings). And just as the design craft is hard to master, it’s likely that many crafts are also harder to master than it seems. Engineering is tough, product management is tough, being a good project manager is tough, marketing is tough, management is tough etc etc. What hidden icebergs lay out there? What’s something we’ve underestimated, with our ignorant hubris and pomp?

We need, and should, demand a lot of the work outcomes from ourselves and from others. The people we serve are demanding after all, and we should be demanding when being served so we can generally all strive towards excellence. Demanding excellence also drives the craft forward.

But it’s all way harder than it looks. So, respect the craft and the years makers typically sink into building up their craft. And be kind.[^1]

o(TヘTo)

[^1]: Also, to be fair to folks who think the craft is easy: we’ve probably all been there before as well, and just don’t have that awareness to appreciate the depth behind a certain craft.

Perhaps the more obvious answer would be that we work to create value, and exchange that value for money, to acquire the value that others have created with their work. This all seems well and good, but why does it seem like many of us dislike work and are miserable in our work?

Why are so many of us stressed when we work? I'm certainly not immune to it — there's stress that I could be lettings others down, that I'm not doing a sufficiently good enough job, that my skills are no longer going to stay relevant to generate more and more value in the long run. There's stress from the identity tied to my work — if I'm no longer able to generate large and increasing amounts of value despite spending my time at this work, can I still call myself a designer? Am I able to continue teaching design craft? Who then, would I be? And then there's stress from the interactions with others at work: the competition over scarce resources to make our work more "valuable" to exchange for more… identity? money? Stress from being unable to influence someone to collaborate with me so that I generate more value… At the end of it all, is the value I'm generating as a design actually valuable at all? Does it have any meaning?

Does it necessarily have to be like this though? What are my core human needs being undermined, such that I have such responses? How could our work structures and systems be changed to overcome these, or is it a matter of the structures and systems? What role do I have as individuals to short-circuit these responses?

🤔

Tiny note to self: Don't take things too seriously, and don't forget to have fun at work.[^1]

[^1]: Just in case, don't worry — I do actually like my work at the moment. It aligns with how I think I've been pretty good at creating value, is challenging and lets me learn new things, and I have wonderfull colleagues. Just wondering, as usual.

Seize the day. Live in the moment. Yesterday's the past, tomorrow's the future, today is the gift. That's why it's called the present.

Plan for your future — invest in your finances and skills. The magic of compounding interest is truly the eighth wonder of the world! [^1]

In the long run, we are all dead. [^2]

We are each infinitesimally small in the grander scheme of things, whatever this scheme might be.

I've always found it an interesting conundrum—to enjoy the current moment, or to strive a little harder so that the future will be… a brighter one? Nicer one? Better one?

Of course it'd be easy to say we should find enjoyment in our current striving too, otherwise the future's not worth striving for. But that's not always how it works, isn't it? Our daily lives will be full of things we won't be too excited about, but have to get around doing, so that the future self won't regret it.

How would you live if you have 60 years left? Spend that time sorting out finances and investing well, so that you could retire well? Ensure that we eat healthy stuff every day so that 60 years will actually come to pass?

What if it's just 30 years?

How about 10?

How about a year?

2 weeks?

1 hour?

Thinking about our mortality is terrifying, is't it? Yet… doesn't it make us thankful?

There are so many sights and sounds to be seen and heard, so many more experiences to be felt and lived. However, what great fortune it has been, to have already seen and heard so many sights and sounds, to have felt and lived so many experiences.

If we definitively knew the amount of time each of us have left: Which relationships would we invest more love and time into, which would we mend? Which relationships would we stop? What life's calling would we now pursue, and which busy work would we ignore? Would we dare pursue our dreams more boldly, or decide that these are meaningless ambitions—a mere distraction from the meaning we give to our lives?

How much control do we have? How hubristic and cavalier it is—to pretend that we're able to plan our way through it all? Yet, how conceited and complacent it also is—to pretend that without planning, we'd be able to meander our way across?

So much universe, and so little time. [^3]

¯\(ツ)/¯

[^1]: Actually… not a quote by Einstein. [^2]: Probably by John Maynard Keynes, in A Tract on Monetary Reform. [^3]: Definitely by Sir Terry Pratchett, in the Last Hero.

I had my first phone around 15 years ago, a little later than a few of my peers. After the initial excitement, I'd always somehow mildly panic whenever I received a text message. [^1] It annoyed me at times—like I'd now had to put away whatever it was I was engrossed in, and now had to attend to the notification. In college, a friend scolded me for being annoyingly uncontactable and replying to her messages 2 days after she sent them. [^2] My mother would say the same, "You own a phone, mostly to irritate everyone trying to contact you."

Interestingly, the "contactable" aversion has clearly changed over the years. Whilst I still like to occasionally ignore messages and definitely forget to reply as quickly as most people expect, my responsiveness to messaging has gotten better.

Is this "better" in the grander scheme of things though? Who is it "better" for? Me? The sender? Do I actually like being so responsive? 🤔

Experimentation Time

I do still need my phone, for navigation, calculations, photos of beautiful scenery, music and such. I still want my phone too. Messaging can be enjoyable, especially with friends overseas, sometimes simply to tell them they're still on my mind and to appreciate that they hold me equally dear. When I come across something funny or interesting, it's nice to be able to share that with a friend in hopes they'll enjoy it too. Likewise, it's a delight to receive similar content from them. With some friends, we write essays to each other over text, on topics ranging from philosophy to the best movies to watch, and we probably won't want it any other way.

But… do my friends really expect instant replies, to warrant my frequent unlocks and high screen time? 🤔

In the recent few days, I've started muting my phone and switching off messaging apps on my personal desktop. Similar to email—I've marked out designated times to check messages and bulk reply everything in batches.

So far… no one has complained, yet. Including my mother.

What a difference it has made though! Simply within the recent few days, I've been able to concentrate on tasks at hand better and to sense the world as it happens around me. My thinking seems a little clearer, and my chosen focuses in life are brought to the forefront more often.

Hello, uncontactability

Obviously, this hasn't been a very scientific experiment, nor is this as well-researched as Nir Eyal's Indistractible. Perhaps I've just been more conscious about my mind's wanderings after realising the huge amount of time I've spent on my phone. 🤷‍♀️

That said, there doesn't seem to be any major downside of using my phone less. I'm also reminded of why I secretly love long-haul flights—airplane mode and a legit excuse for being uncontactable for long periods of time.

So… I guess this will be my new pattern of phone usage for a while more. In other words, if I don't reply to you, it's not you. It's me. ❤️

[^1]: I still panic when I receive phone calls. Some things never change, I guess? [^2]: Which… to be fair, was entirely justified because we were supposed to be rushing a project together and I had just disappeared on her.

As an extremely introverted human with occasional tendencies towards mistrust and struggles with self-esteem, I am very lucky to have met quite a few amazing folks with whom I can click with, and who surprisingly also cherish the moments we spend together. To be able to talk about nothing and everything, to want to jointly share and create new memories, to share mutual trust that someone will have your back, to be with each other through happiness and sadness, to know you're accepted as is and to return that acceptance for whomever they are…

What bigger joy could there be in life, than to have part of the meaning of our lives defined by these relationships?

Life, you have been kind to me. Thank you.

(✿◠‿◠)

What’s the best thing a manager has ever done for you?

The best thing a manager has ever done for me? 🤔

Perhaps not just one thing, but the best managers I've had…

• Gave me the job which effectively started my entire design career, even though my portfolio was so crappy I probably would not have hired myself.
• Patiently listened to my rants when I was still an immature and entitled brat.[^1]
• Openly and genuinely celebrated the growth I had.
• Taught us that work should be fun too.
• Let me fail when it was low stakes so that I could learn the lessons that needed learning.
• Magically knew how to place me on projects I was oddly suited for and loved.
• Reaffirmed my capabilities and gave me a huge confidence boost by telling me they really needed someone with my skills on the team.
• Recognized that women did face more unseen hurdles at work, asked about the obstacles we faced, and apologised for not having realised our struggles earlier.
• Kept reminding us how to live more balanced lives.
• Stayed present for me when I was going through a hard time.
• Honestly told me I deserved more pay for my achievements and skills, despite whatever the company was telling me, and then fought for that pay increment to happen.
• Gave me the brutal feedback I always needed to hear so that I would stop banging my head against the wall — including how I probably would thrive elsewhere other than the company we were working for.
• Gave me full autonomy to lead a large area of work.

… and the list goes on.

Management is tough, but I've mostly been incredibly fortunate to work with mostly great managers. Looking back, how did your managers help you? Looking forward, how can we pay it back, and how might we pay it forward? What are we doing today to help perpetuate all these?

[^1]: Probably still one today though.

My motivations were simple — job interviewers often questioned if I had enough UI design capabilities to cope with most digital design jobs. 🤷‍♀️ People weren't questioning if I could do other designery things, so… why not try just creating pretty interfaces to serve as a portfolio if needed?

Takeaways

Besides building out a portfolio — I actually learnt a lot and had fun during the challenge. Sure, some days were hard, especially when my main gig needed more attention. It was also quite humbling, because I did struggle, and realised that UI design really wasn't my strongest suit. The interviewers were right!

Hustle if you want to get better! Do side projects! Contribute to open source! Volunteer!

No, wait! Encouraging them discriminates the people who don't have the bandwidth to take them up! We're encouraging people to get caught up in the rat race!

At the same time, it got me thinking — was this considered taking part in "the hustle"? How did I find bandwidth to do one (meaningless) UI every day? How do others find time for other projects? Should we be encouraging this across the industry?

What if the best spot on the hustle continuum is different for everyone? What if we could just celebrate folks doing the best they can within their circumstances, without judging others for choosing what is best for them? Accepting that some folks may not have time, and the others may simply enjoy pursuing side projects? Could those with bandwidth seek to find causes to support those without? Indeed, those who can't hustle may not be able to advance as quickly, but aren't we also collectively not advancing as quickly as we could if we stop those with resources and bandwidth from hustling and pushing themselves to the best of their abilities and resources?

I'm proud of the results of this daily UI side project though there's tonnes of shortcuts everywhere, but I wouldn't say this is must-do for everyone. Again, the conclusion is… I don't have a conclusion.

Alice: Would you tell me, please, which way I ought to go from here?
The Cheshire Cat: That depends a good deal on where you want to get to.
Alice: I don't much care where.
The Cheshire Cat: Then it doesn't much matter which way you go.
Alice: ...So long as I get somewhere.
The Cheshire Cat: Oh, you're sure to do that, if only you walk long enough.”

— Lewis Carroll, Alice in Wonderland

A colleague and I were recently discussing what metrics or measures we should look at to understand how our product was performing. Usage? Engagement? General sentiments? NPS? A challenge the product team encountered was that they had instrumented our product to great detail, and were collecting lots of metrics and quantitative data, but no one was looking at them and no one knew what to look out for.

This struck me as a case of "If you don't know what question you have, any answer works."

Questions are hard

People often assume that the hardest part of design research is executing the research itself. I've generally found this not to be true. Helping people find / frame the questions they really should be asking often seems harder.

How do we ask the right questions in product development? How do we know if the question is right? I am not 100% sure either — but I suspect it stems from the confluence of who we are serving, what needs they have, and what mission this product has. It also stems from the clarity we currently have about all three and the stage of product development we are in. There also seems to be some element of intuition involved, which is what I've personally relied on most of the time. How do we duplicate that intuition, and help more people ask better questions? [^1]

Hoarding answers until questions emerge

That said, as the Cheshire Cat says in Alice in Wonderland: "You're sure to do that (get somewhere), if only you walk long enough."

There seems to be criticism against research theater in design circles — doing research for the sake of doing research. At the same time, I wonder if questions can also emerge the more answers we collect? Isn't there a parallel we draw from our own lives? We explore and try various things, most of us aimlessly [^2], and some of us eventually understand our purpose or meanings through the various explorations or answer-collecting activities we conduct. The more explorations we perform, the more knowledge we have, the more curiosity we have as a result of this knowledge. Isn't this also the basis of insight synthesis — we explore, and discover emergent patterns we would never have thought of asking?

Conclusion?

Our answer to life, the universe and everything is 42. But what is the question? Why is this the question? To what extent do we need to dive into the question? Some questions also seem unanswerable or not useful to me (E.g. What is the meaning to life? [^3]), but how can we tell?

Thanks to my colleague who triggered these thoughts, and for humbly reminding me I have no answer to anything. 😵

[^1]: On that note, how do I know if I am asking the right questions here as a researcher? Oh dear, down the rabbit hole we go~ 🐇🕳️ [^2]: I knew I was aimless, at least. Envious of all you people with a clear purpose in your lives. [^3]: In no way am I saying this is a stupid or useless question — I agonised about this, and decided that I don't have an answer nor is it likely that I will find an answer. However, considering I am already alive, this is simply not a useful question for me, and thus it might be better for me to ask "How should I create meaning in life?" If you have an answer however, I'd like to hear it!

Different core purpose

Surprise, surprise! While designers are expected to conduct research at some organisations, there is a reason why we hire dedicated researchers. 🤦‍♀️ This was a major "Duh!" moment.

The two roles do overlap a lot — both need to care for the users, to understand them well, to zoom in and out, and to think strategically about work. Nevertheless, the major difference is that designers and researchers operate dominantly in different parts of the product development process. Researchers learn on behalf of the organisation — acquiring knowledge for the organisation to make better decisions. Designers ensure the learnings get translated into meaningful decisions and actions.

One learns and recommends, one decides.

Zoom in, zoom out 📷

As a result of the different focus, I realised I was also working at a different zoom level as a researcher, as compared to my time as a designer. Researchers seem to spend more time at the big picture view naturally, as compared to designers.

This could perhaps be exacerbated by the fact that I was the only researcher for my business vertical. Nevertheless, when thinking "what is the most valuable knowledge to acquire for the organisation for the time and resources I have?" — the answer is usually "what are the larger bets this organisation wants to make, or should make?" Highest bang for buck, no?

In contrast, as a designer — to ensure that what we ship is of sufficient quality, our focus is a lot more in the tactical and operational realm. Product details mattered more, and since I worked on the product daily — it just made sense that I owned the tactical and operational research, as opposed to researchers who may not need to know the finer details of the product to go about their research work.

Inclusion into decisions

A common observation I've heard from other researchers is that sometimes they feel left out of product decisions, or that insights don't make their way to product decisions — which is sad, considering that researchers gather knowledge precisely for better decision making.

After working as a researcher for a while, I realised this was true… for a certain degree of truth. What I experienced wasn't a case of people not believing insights, or not wanting to be inclusive in decision-making. Rather, because research insights from the dedicated researcher usually mattered more in longer time horizons, it naturally took longer for the knowledge generated to make it into the roadmap. Insights were also at a higher elevation level, so how these insights translated into product decisions were not always immediately obvious, and at times a little abstract. As the "knowledge-finding" person now — I also knew too few product details to make great impact for every single product decision, as compared to the "crafting" designer person who literally decided how the product should work. It would have been a waste of my time and the team's, to pull me into every single tiny decision.

Operating cadence — alongside product teams or not

At some places, both designers and researchers follow the cadence of the product teams. I tried doing the same, but quickly realised that this was more natural as a designer, but did not make sense as a researcher. Again, as the "crafting" designer, roughly following or being aware of the product team's timelines helped ensure that I could be involve in all shipping details, and that folks could always find me for any decisions. As a "knowledge-finding" researcher, I couldn't always control research timelines — matters like research recruitment usually did, and this rarely matched up with the cadence of the team. Because I was also usually running ahead of teams in what I was researching, again, I wasn't blocking anyone from proceeding, so timelines were my own responsibility.

Perception of expertise and role

Before taking up a role as a researcher, I had imagined there wouldn't be much difference between my research skills as a designer as compared to a researcher. 🤔 Just spending different proportions of time on research, no?

No one else seemed to see it the same way. 😅 Right from the get-go, it felt that people now saw me as the "research expert" even though I had basically honed all my research skills working as a designer and was just as good as the team's designers in conducting research. Interestingly, because now I did have a lot more conversations around research, it felt as if my research skills were slowly being sharpened over time just by taking up this specialist role.

On the flipside, I realised that my role came with lower expectations for exploration and play. Research is serious business, whereas design involves pushing the boundaries, lots of creativity and experimentation. One is a straight-laced professional, the other is the explorer. Was it because of our mental associations or stereotypes with the words "research" and "design"? 🤷‍♀️

Everyone's mileage will vary

I do suspect that the differences in my experiences for both roles were also greatly influenced by the organisation culture and the environment. Design / research maturity and size of the teams also likely played a part. What I did take away is realising the importance of dedicated researchers — the difference in vantage point and long-term focus can really be valuable for organisations.

Personally for me, working as a dedicated researcher has helped me appreciate the depth of specialist fields associated in product development, and in fact helped me reaffirm my fondness of working as a designer — not because it is "better," but simply because it suits my personality and impatience better. How different is it for other researchers and designers? At different seniority levels, is there convergence in responsibilities? Given the differences, how should the two roles best work together? 🤔🤷‍♀️

When was the last time you sat by yourself? No book, phone, schedule, to-do list, thought, worry, judgement? Just listened?

Earlier this week, while waiting for an appointment I was an hour early for, I found myself sitting at a stone bench near the appointment location, with nothing to do. It could have incredibly boring, but it was a lovely day out and there was a nice good breeze. I decided to put my book away and just listened to everything happening around.

What I found was a good reminder that waiting can also be a much-needed pause, that life happens even without our participation anyway, and that we can find peace everywhere.

So… When was the last time you sat by yourself?

( ◡‿◡ )

[^1]: Her mother said no. 👍 for great physical distancing consciousness.

A sabbatical? When?

After leaving my previous role as a product designer at Zendesk, I decided to take time off, and promised myself to head back into tech only when I felt ready. This ended up becoming a 5-ish month sabbatical from Dec 2018 to ~May 2019. The decision was driven by the fact that I’ve always found long breaks after immensely restful and rejuvenating, instead of short breaks interspersed throughout the year.

What do you plan to do?

Quite surprisingly, and perhaps sadly, everybody who learnt that I was going on a long break asked “What do you plan to do? What’s next?” Almost everyone seemed universally surprised when I sheepishly grinned back and said “I honestly don’t know.” Some people expressed envy, some started telling me about their past experiences, some started envisioning what they would do if they were in my shoes.

🤷‍♀️ Oops.

Did you actually do anything then?

I ended up saving the world!

😶

Well… Obviously not. 😅 In the end, my time was mostly split across:

• Getting many hours of 💤
• Waking up with zero plans on most days and trying to figure out what I should do that day
• Sitting around and writing / reading / arguing with myself (in my mind) / people watching / staring into space
• Creating this site with Gatsby (which I’m pretty proud of, considering how rusty I am in coding. I taught myself enough React for this to be functional!)
• Cleaning and decluttering my house (definitely nothing to do with Mari Kondo, though she was all the rage at the time of my sabbatical)
• Taking my mum to a vacation
• Walking around Singapore a lot
• Meditating (almost) daily
• Exercising a lot more
• Meeting up with a lot of friends
• Spending time with my wonderful nephews
• Landing the job I’m currently have at SP Digital

How was it then?

The sabbatical seemed to take off my blinders.

The reactions I received were surprising, as mentioned. Taking a break for myself seemed almost an act of bravery and courage? How would I fill up all my time? How do I deal with questions? How do I cope with the voices in my head when there’s no busywork vying for attention?

It was all very curious. Why is taking a break for ourselves such a big deal? Why do we seem worried about not having anything “productive” to work on? What constitutes “productivity”? What does this reflect on us?

Many hidden anxieties and questions did surface during my break. Far from being terrified and disoriented by them, the sabbatical provided me ample space to be curious and to accept each of these anxieties kindly. Eventually, I actually felt that I could better align my personal values to the design work I wanted to do.

Many peers also asked where I’d be travelling to. There was a sense that I needed to travel, without which I would not be doing my break justice. 🤔 Why? While I did eventually plan a short vacation with my mum overseas, most of my thinking and relaxation was done in Singapore. No nature / beautiful sights / new environment needed. Just lots of peace and quiet. This made me wonder—was I similarly imposing judgement on others on how they should live their lives?

And… so on and so forth. I could go on about the takeaways. Perhaps I might write more intimately about other findings when I have sufficient courage to put so much online. 🤷‍♀️ In a nutshell though, taking a sabbatical was one of the best things I had ever done for myself so far. It’s hard to justify and measure, but I actually felt that I was advancing my skills as a designer / researcher mentally, psychologically and emotionally, through understanding myself a lot better and seeing how my skills could be utilised in service to others.

Do it again?

I would definitely love to, if the conditions are right. To be fair, being able to responsibly go on such a long break is an immense privilege, one which I was very fortunate and grateful to have. 🤷‍♀️ We shall see.