2017 in Review: My First Full Year in the Silicon Valley

2017 marks the first full year I’ve lived in America since college. It has been one crazy year – writing this took almost a week. Here’s my 2017 in review: 5 meaningful things areas of work, challenges + learnings, and hopes for 2018. I’d love to hear about your 2017 too!

  1. Engaging on the global stage: Technology and public good 

2017 started off with the Consumer Electronics Show in Las Vegas, where I was part of a Supersession panel discussing how cities should capitalise on the sharing economy to improve public transportation.

Not many know that this website www.techandpublicgood.com has its roots in CES. Walking around the exhibitions, I understood first-hand the quantum leap in technological progress enabled by data, computing resources, ubiquitous connectivity and algorithmic progress.

CES

I left CES feeling strangely disconnected. Over the December ’16 holidays, I had read Hillbilly Elegy, a story of middle class decay in America, and had been reflecting on my roots in social, educational and welfare policy. Questions, to which I had no easy answers, became fodder for articles on www.techandpublicgood.com

In total, we have had over 40,000 readers in the past year, including republications on sites such as Smart and Connected Cities and GovInsider.

2017 also brought opportunities to engage with these issues on the global stage.

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At the Singularity University Global Summit in August 2017. Video here.

From January to December, I spoke at 15 events, including:

Artificial Intelligence and Social Good” at the AI Expo in SF;

The Future of Smart Cities” at the WorldsFair Nano,

Self Driving Cars and Society” at AI By the Bay,

Data and Networks in Smart Cities” at Smart Cities Connect in Austin Texas,

The Future of Intelligent Mobility” at Innovfest Unbound in Singapore,

“Self Driving Everything: The Impact on Cities” at the Singularity University Global Summit.

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Facilitating a discussion with Feng-Yuan Liu (Govtech), Doug Parker (Nutonomy), Nick Jachowski (SWAT) and Xinwei  Ngiam (Grab) on the Future of Mobility in Asia. May 201

End-2017, I was appointed Faculty member at Singularity University, an amazing global community which is excited about using technology for social good. I like to think that by the efforts of us all, emerging technology will be used to make society just a little more equal, more cohesive, more inclusive of minorities than before.

What topics on tech and public good do you want to hear more about in 2018?

  1. Connecting with smart city leaders 

2017 also brought opportunities to engage inspiring thought-leaders at the intersection of technology and government. Many have become friends, not just collaborators. These included:

  • Smart city leaders in the U.S. (e.g. Seattle, D.C., Austin, Orlando New York, SF, San Jose)
  • Universities and non-profits examining technology governance (e.g. the Stanford Policy and Innovation Initiative, the World Economic Forum’s Center for the Fourth Industrial Revolution, the Global Foundations Challenge in Sweden)
  • Tech companies seeking to disrupt public services in transportation, healthcare, energy, etc, resulting in many link-ups across borders
  • A wide range of Singaporean leaders who visit the Silicon Valley periodically, including both our Deputy Prime Ministers and delegations from transportation, healthcare, defense, Singapore’s NSF-equivalent and so on

While a popular perception is that Governments are backward and arcane when it comes to emerging technology, my experience couldn’t be more different.

City leaders understand the huge potential of emerging technologies and their specific applications (e.g. AI and IOT applied to smart lamp-posts, self-driving cars, digital health) to solve existential governance challenges: improving outcomes for city dwellers while reducing costs and manpower, reducing traffic congestion as population explodes, moving healthcare systems towards disease prevention, rather than costly treatments.

However, there is tremendous uncertainty when it comes to adopting emerging technology in public services.  

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With my fellow panellists at Smart Cities Connect in Austin, Texas: Rosa Akhtavari (CIO of Orlando) and Kip Harkness (CIO of San Jose)
  • Which use cases are game-changing enough to justify the upfront capital investments?
  • If we need to develop public-private partnerships or purchase solutions from the tech companies, how do we reconcile the trade-offs in data ownership, privacy and algorithmic accountability?
  • How far ahead can we race with experimentation before some of these issues catch up with us?
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Singapore’s Smart Nation team had a deep exchange with Washington DC’s outgoing CTO, Archana Vemulapalli, in November. Smart cities need to find better ways of working together.

In the next 5 years, we will see many successes and failures in the smart cities space.

Failures will be hard for Governments to stomach because ‘losing’ public monies is always more galling than losing private investments.

Yet it is better than standing still. Like it or not, emerging technology is going to disrupt traditional public services such as healthcare, education, city management and transportation.

Governments need to get their foot in early and help make self driving cars, AI, IOT and digital health work for the widest range of city-dwellers possible: not just those who can afford it.  

  1. Building a community among Singaporeans-in-technology

A group of 16-year old girls visited the Silicon Valley in October. They met big names, inspiring founders, judges and venture capitalists. I hosted one of their final sessions, and a question left me ruminating for months. In gist: “many Singaporeans think that living in the Silicon Valley is so much better than living in Singapore. Why are you such a huge champion for Singapore?”

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Hosting a group of 16-year olds visiting the Silicon Valley as part of their school trip

Over the course of 2017, I’ve met over two hundred Singaporeans living the Bay Area. Sure, many reflect on the better career opportunities, weather, outdoor activities and family time available in the Silicon Valley (compared to Singapore).

But I also frequently get asked (1) What’s happening in the tech scene back home? (2) Is there a way to contribute? In a short digital survey conducted at one of my Singaporean-in-tech events, data showed that over 70% wanted to contribute to Singapore even though they might not be ready to move back

In 2018, I want to reflect on what it means to be a country in this digital, globalized age. Perhaps countries will no longer define themselves by their borders but by their people. The Singaporean diaspora is spread all throughout the world, many in highly influential positions (we have CTOs all over the valley!). How can we involve them in our country’s future?

I am also interested to explore who is in this overseas Singaporean tech community and how to engage them in a way that is suitable to their needs and preferences. Case in point: in July this year, Jacqueline Poh, our Chief Executive of Govtech Singapore, spent six weeks in the Valley and wanted to host a dinner with Singaporeans in tech. By then I had met dozens of Singaporeans living in the Valley, but very few women. “How many Singaporean women-in-tech do you think there are in the Valley?” I asked some friends who had been around longer. “5? 10? At most 15 perhaps. Don’t get your hopes up”; most replied.

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Our first Singaporean women-in-tech gathering in July, which sparked a community of volunteers!

Within an hour of posting my invitation on Linkedin, we had reached full capacity of 60 Singaporean women. Data scientists, product managers, investors, software engineers, product and growth marketers showed up in full force. In past events, women formed at most 5% of the attendees – why?  

Singaporeans living in the Valley: how would you like to engage with Singapore’s tech scene more? Singaporeans at home: how would you like to engage with fellow Singaporeans living in the Valley?

  1. Exploring issues facing women and other workplace minorities

2017 was the year that gender-based harassment and discrimination exploded to the public eye in the Silicon Valley. Personally, I also came to identify with the experiences of minorities, upon entering the technology sector as a non-engineer and moving to America as a foreigner in the Trump era.

I’m curious about the experiences of women, and other minorities, in the workplace.

October: Women’s Forum in Paris

An opportunity to explore these issues deeper came up when the Women’s Forum for the Economy and Society sponsored my trip to Paris to share about how technology can keep people in work, and to participate in their Rising Talents program for women leaders under 40.

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I had an amazing four days engaging with women who are doing ground-breaking work, in big tech and start-ups, legal advocacy for girls in war-torn countries, healthcare providers in underserved communities etc. My experience and reflections on womens’ and minority issues here.

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With my co-panellists at the Women’s Forum: May Busch, Heather Cykoski (ABB), Christele Genty (Google) and Elisabeth Moreno (Lenovo).

November: Singaporeans-in-tech: Panel and Dinner 

In November, I led a group of amazing volunteers to organize a panel and dinner with Singaporean women-in-tech, who shared their career journeys in the Bay Area. Our event was over-subscribed by both men and women, Singaporeans and non-Singaporeans. The panel was honest, thought-provoking and inspiring.

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From L-R: me, Yen Low (Netflix), Aihui (Edgilife), Joo Lee Lim (GIC), Aakriti Agrawal (Blend)

A memorable moment was when I asked the panellists which Singaporean mindsets which helped and hindered us in the Valley. Aihui Ong, founder of Edgilife, shared how her Singaporean comfort with multiculturalism subconsciously shapes her hiring decisions – Edgilife is one of the most diverse start-ups in town (represent!)

Yen Low’s dogged Singaporean attitude enabled her to acquire data science skills and become a respected member in a male-dominated field at Netflix. Aakriti and Joo Lee shared the challenges of breaking into a market where they had no prior networks, plus tips for putting yourself out there and developing a ‘personal brand’ – something many of us did not have to do in Singapore (in fact it can be frowned upon in Singapore).

I could almost hear a sigh of relief from the audience (and certainly myself) when these accomplished women shared their experiences so candidly.

Hearing from fellow Singaporeans helped many attendees normalize, rather than personalize the uncomfortable experience of being a foreigner who needs to ‘break into’ the prevailing culture. Dozens sent me private messages afterwards to ask if we could have more of such conversations in the Singaporean community, and volunteered to help put more events together.

December: Asia Society Women’s Leadership Breakfast

December rounded off with an Asia Society womens’ leadership breakfast, where I had the opportunity to discuss issues facing Asian women in the Silicon Valley with Shie Lundeberg (Google), Shirley Ma (McKinsey), Tina Lee (Mothercoders) and Katie Benner (New York Times). Another eye-opening conversation, another set of inspiring women.

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The minority experience is one of constant reinvention, and defying – even overcompensating for – stereotypes. It is never quite feeling like an insider. I come out of 2017 much more aware of the responsibilities that majorities have in making workplaces and common spaces inclusive, and the responsibilities of minorities to support each other in a way that does not become exclusive or incendiary.

  1. Pursuing my passion for coaching

Finally, I enrolled in an 8-month coaching certification program in 2017. Though I’ve done this informally for many years, a personal goal is to master the art of helping people become more effective in achieving their goals. A workplace relationship they want to improve? A difficult conversation with their boss? Managing a major transition healthily? Fixing communications breakdowns? Becoming the boss for the first time?

Coaching is about creating that safe space for someone else to explore different perspectives, widen their options, and stay accountable to committed actions. I don’t know about you, but I find that the busyness of adult life makes it difficult to break out of old patterns, even if they are inhibitive to our professional and personal goals. Developing a coaching relationship is one solution.

In 2018, I’ll be writing more on the topic of coaching and leadership, building on these three articles that I wrote in 2017.

As part of my course I’ll also be taking on coaching clients starting in February, so do get in touch if you are interested!

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With my coaching Learning Group: Mahesh (a Paypal engineer), Deborah (an Episcopalian priest), Oliver (an actor and facilitator), PK (a sales consultant) and David (a Chief Compliance Office).

Challenges in 2017

2017 has been one of the most exciting and challenging years of my career to date. I’ve learned that I enjoy the ‘start-up’ life: experimenting, iterating, pivoting, and finding that elusive ‘product market fit’.

However, like any start-up, work is fraught with high highs (the market is responding; this is what is needed!) and low lows (what am I even doing?). I’ve learned to follow my convictions, amidst the many confusing signals about what I ‘should be’ or ‘should not be’ doing.

Fortunately, I have amazing, progressive bosses (Kok Yam and Chee Khern) who have given me so much latitude and trust. This is definitely NOT a traditional Government posting. I also have many, many brilliant, supportive co-workers across the Singapore public service who are just a call away (shout-out to Daniel Lim, Feng Yuan,  Mark Lim, Jacqui, Pui San, Rebecca, Shi-Hua, Chor Pharn, Titus, Kai Jit, Yang Boon, Simon Phua, Victor Tan, Stanley Leong, Lynn Khoo, Kenneth Teo, Melanie Tan, Heng Jie, Brandon, Sidra Ahmed… the list goes on). My husband, who is doing a PhD in statistics at Stanford, has also been an incredible support at work.

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End-of-the-year sunset in Southeast Asia

Nevertheless, I’ve realized that the extrovert in me needs a team in the same geography to be collaborators, sounding boards, and ultimately to start scaling up. Thankfully, I’m expanding the team in 2018, and plan to work much closer with other teams in the Bay Area!

I also need to work on pacing myself better in 2018. In my impatience to adjust to a new job, new country, new baby, new home and new community, I ended off 2017 very tired.

Thankful for some much-needed down-time by the ocean, with family!

Bring it on, 2018.

I enter 2018 with a mood of curiosity.

How can I serve the world, and my local community, in 2018?

Which direction should http://www.techandpublicgood.com take?

How can we shift the relationship between tech companies and Governments from defensive regulatory battles to co-creators of a more inclusive equal, and cohesive societies, assisted by technology?

How should countries think about their economic strategy in a digital, globalized age, where physical borders matter less and less?

How can we build workplaces and common spaces that are inclusive of minorities?

There is so much more to learn and contribute to the world. There are so many more relationships to build and deepen. I’m excited.

I’d love to hear about your 2017 and your hopes for 2018! 

 

 

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3 Tips for Middle Managers in “Day 2” Organizations

with my team at MOE, who taught me so much about leading well – I’m still learning!

Everyone wants it to be “Day 1”
Jeff Bezos’s 2017 letter to Amazon Shareholders had some piercing insights about running a “Day 1” organization. He doesn’t exactly define Day 1, but the concept is clear when he describes a “Day 2” organization: “Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.”

There are many gems on running an innovative organization, but I’ll highlight two:

  • First, a Day 1 organization never lets itself be owned by process. Processes exist to serve an outcome – following the process should never be the outcome. “The process is not the thing. It’s always worth asking, do we own the process or does the process own us? In a Day 2 company, you might find it’s the second.”
  • Second, a Day 1 organization masters the cycle of rapid decision-making, prototyping, failing and trying again. Jeff urges his people to take action based on 70% of information they would ideally have, and to be willing to disagree and commit (rather than disagree and grudgingly assent): it’s helpful to say, “Look, I know we disagree on this but will you gamble with me on it? Disagree and commit?” 

I recently shared a part of Jeff’s letter on Linkedin, and the responses suggested two things:

  • Many look upon tech companies like Amazon with envy, because their organizations seem so “Day 2” in comparison
  • Most (if not all) of us want our organizations to be “Day 1”

What if my organization is already Day 2?

What do I do if my organization is already Day 2? This question is important to the area of “tech and public good”, the subject of my blog (www.techandpublicgood.com).

Why? Because the main reason organizations (Governments, civil society and private sector alike) fail to harness technology – or for that matter any type of innovative practice – that will clearly improve their customer experience and operations is internal resistance. In other words, it is because they are in “Day 2”.

It is often not deliberate resistance. It is a slow, painful death, precipitated by adherence to process and status-quo practices, and a lack of clear ownership for the outcome.

When it comes to building innovative organizations, “it’s about the people, it’s really not about technology” – I can’t agree more with Greg Godbout, co-founder of 18F, who said this in a recent Harvard Business School interview.

People matter, and in my experience, the level of innovation in an organization depends on the behaviours of middle managers. Middle managers are some of the most powerful influencers in an organization – they set the tone for their teams’ culture, and can almost singlehandedly dampen or stimulate innovative behaviour among a large majority of your workforce.

Forces that make middle managers susceptible to “Day 2” behaviours

Unfortunately, I have noticed that when people transition from “team member” to “middle manager”, gravity seems to pull them towards being “upholders” rather than “innovators”.

This could be the result of coping mechanisms to deal with increased responsibility. When promoted from member to manager, one takes on a multitude of new objectives. In addition to the original objective they were hired to achieve, they have to help their team navigate relationships with other departments, obtain resources and gain the confidence of their bosses, manage HR issues, and prioritize their team’s bandwidth. Email load triples; more time is spent managing upwards, downwards and sideways; the appetite or bandwidth for innovations gets lost.

I worked in 5 teams as a member and middle manager over the years, and have seen the following traps among leaders:

  • Falling into a “process-orientation” in their leadership style to cope with volume. Simply ensuring that process is being followed can give some comfort that the team is on the right track, without having to commit too much mental bandwidth. There’s limited upside, but also limited downside.
  • Defining success by whether everyone (bosses, team members, fellow managers) is happy, and hence failing to challenge the status quo.
  • Feeling de-motivated. I have had friends lament that when they became middle managers, they felt removed from the real groundwork, but not high enough to influence decisions. They lost their motivation to challenge the status quo.

Three Important Questions for Middle Managers (and their bosses)

It would be a natural point for me to go into how an organisation should select, train and reward middle managers. In the past, such articles have left me feeling validated but disempowered, as it leaves the action to the organisation – and who knows how long it will take.

As middle managers, we have agency. I’d hence like to address middle managers who are aware that they are in a Day 2 organization and are possibly perpetuating Day 2 practices. What questions can you ask yourself, and have conversations with your boss and team about? Three tips:

First, where exactly am I creating new value for my organisation?

This seems like an obvious question, but we need to be very ruthless in holding ourselves to an answer. “Keeping the peace”, or “making my boss and team happy” are bad answers that busy people can easily default to.

What are your objectives and how are you adding to them? As a middle manager, you have a wider scope than a team member, and your value could come in a variety of forms, including:

  • Taking ownership of an issue that falls between departmental lines. Take on the “start-up cost” until everyone is on-board. For example, put together a short think-piece that outlines the issue you want to tackle, and why it would be beneficial all around if different teams to got involved. Use it as a starting point to rally people across departments, and eventually bring it to upper management for endorsement and resourcing. When I became a middle manager, I realized I was uniquely positioned to take the lead on such issues, as I had greater ability to cross inter-departmental lines.
  • Examining a process that does not work, and proposing an alternative. I read this lovely article on Linkedin about the prevalence of bad systems, and why they are allowed to persist. The problem is that bad systems often end up in a kind of corporate Bermuda Triangle — no one really monitors them; worse, one is empowered to change them when the need arises.” When you see a stupid process, don’t let it pass you by. I once had a boss who had this mentality of fixing bad systems. I admired her deeply. Our department had to manage hundreds of event invitations to our Ministers. For a long time, one person oversaw all these events because it was “the only way to not drop the ball”. It clearly drained her. My boss, our “czar of bad systems”, developed a tracking list which could be rotated among 3-4 people on a weekly basis, spreading the task around and allowing us to monitor follow-through far better than before.
  • Work on a development plan for your team members. HR is not a “good to do”, but an essential objective that should take up a middle manager’s work time. Everyone does it differently, but I had monthly check-ins with each team member, where we discussed where they needed to be challenged, or supported. I kept a file on their work record, training and future job aspirations. It certainly came in handy when I had to argue for their promotions and opportunities.

“But I don’t have the time!” So true. Something has to give. Most of your bosses will have a vague idea of what is important in your job (they’re too busy thinking about their own jobs), so you have to tell him/her. Proactively engage your boss on the 2-3 pieces of value you want to deliver, and why you think it is important. Use it as an opportunity to talk about what you will not be dedicating much bandwidth to i.e. I will not be responding as fast on x, y, z issues, or for x, y, z issues, my team members will report directly to you. If you are working for a boss worth his/her salt, you are guaranteed a good conversation and probably a green light. You will definitely feel more motivated.

Second, am I creating a team in my own image, or does each individual feel empowered?

Usually, people are promoted to management positions because they did well as a team member. The result can be a narcissistic impulse to make your team members perform in the same way that you do. It is also a key source of overwork – vetting and thinking about everything each team member does. I encourage middle managers, especially new ones, to break down their management job into at least two roles, and define their value differently for each.

  1. Roles where there is a legitimate need to uphold standards. In my experience, issues that fall into this category have included managing external relationships (such as a foreign university pulling out of a partnership with a Singaporean university, with implications on our students), sensitive complaints (such as allegations of sexual harassment by a Professor or teacher), or a reply to the Minister on a key policy issue (to ensure we make the best use of the Minister’s time). These are areas where a middle manager’s experience must be applied to help the team member make the right proposal.
  2. Roles where you provide one perspective, but let the team member fly. However, there are also issues where the team member should be allowed deep ownership. Proposing an overhaul of the preschool sector? Revamping communications materials for Principals following a policy announcement? Please proceed. I’ll give you my perspective, but it is up to you what you propose to our boss. In one of my favorite jobs, my bosses were very conscious about giving us autonomy. Ministers and even the Deputy Prime Minister would call the “lowest level” staff directly, and we never felt hesitant to make our arguments.

Again, be clear to your own boss how you see your role in the different projects under you. It helps to be transparent with your team members about this too, so that they can hold you accountable if you become a micro-manager or if you’re not providing enough guidance. I’ve treasured the times my team members have said “hey Karen, we need to talk about your involvement in this project.”

If you get this right, you will also be better able to manage your time. Type 1 issues will command more of your bandwidth than Type 2. Ultimately, you want to train your team to the point where your role is largely Type 2. The more your team can fly, the more bandwidth you have. Both you and them will feel more motivated when you have that autonomy.

Third, how often do I disagree and commit, compared to having my team disagree and commit?

In his article, Jeff Bezos gave an example about how he strongly disagreed with a team’s proposal, and though their discussions did not change his mind, he committed strongly to their proposal. I was impressed – in typical organizations, the bulk of “disagreeing and committing” is by team members, not team leaders.

As middle managers or leaders of any form, we should ask ourselves how often we disagree and commit to our team members, compared to the other way around. It is a reflection of how empowered our teams are (and hence how well we are using the precious human resources we hire). It is also a proxy for how innovative our team’s culture is.

Conclusion

If you feel like you work in a “Day 2” organization, I believe you have the agency to bring about change, and I hope that by reflecting on these three questions, you will have some idea of how to push your team towards “Day 1”. I write about this as a fellow learner in the journey towards good leadership. Many of these lessons were the result of making painful mistakes, observing others’ strengths and weaknesses, getting feedback from my bosses and team and reflecting deeply on my own practice of leadership. I would love to hear your experiences as well.