It’s 2014. I had been assigned a new role to lead transformation efforts in one of Singapore’s largest government agencies which oversees transport.

I was fresh from a one-year work attachment at IDEO, in San Francisco USA, a global leader in design thinking for innovation. No one in the service had done that before; design thinking was a rare skill back then. I was brought in by the CEO and I loved his vision of transformation (“a more people-centred organisation”). I would belong in the corporate group, driving change from the centre and with the very top. I was full of the Silicon Valley optimism and energy, raring to go with so many ideas, and with full confidence because I had trained with the best in the world. I would showcase how design thinking can create innovation in my organisation.

8 months later, I wanted to quit.

I was simply getting nowhere. This was a very complex organisation, with many different operational departments and objectives. It was the single largest employer of engineers in Singapore. When I tried initiating transformation projects, every department gave me the dreaded brush-off: “That’s such a great idea but now is not a good time.” I was frustrated with the organisation, I blamed its culture and its management. I blamed my boss (my direct reporting line, not my CEO) for not supporting me. I was leading my team around in circles. I dreaded going to work every day, trying to swallow my shame and inadequacy. I’m not as good as I thought.

You must understand a few things. Firstly, it was the only time in my life I wanted to quit a job. I’m not a quitter by nature – stubbornness has a lot to do with it. Secondly, it was not that straightforward to just ‘quit’. I was part of the Administrative Service, a scheme for grooming future leaders for the public sector. One gets assigned posts to any agency, and one does not simply ask for a new post like changing seats in a plane. To ‘quit’ means going to the assignment department (within the Prime Minister’s Office no less), tail between your legs, having to explain yourself and beg for a new post, which may or may not happen. It’s a career-killer for sure.

My boss sensed something was off. He summoned me into his office on pretext of a mid-year check-in: Yeah, breath of fresh air! New perspectives! Great energy!

“But what?” I said. “Just tell me the But.”

“But my senior management colleagues don’t trust you.”

BAM.

Weirdly enough, I was relieved. My boss was an old-timer in that organisation and could read his colleagues like a book. I finally understood why I was hitting so many brick walls.

People feel like you are using them for your own agenda, my boss further elaborated.

And he was absolutely right. I was insensitive to the keen pressures they were facing – fixing problems of the train system, hello!! – uninterested in their objectives and struggles, and ignorant of their daily operations. I saw other departments as means to my own end. I basically said to them: let me use you as my demonstration tool, to show everyone the great things I can do.

I will always carry this a-ha moment with me. It has formed my first principle of Systems Thinking.

Want to create enduring systemic change? Then Leave Your Ego Behind.

Everybody says, “Hell no, I don’t bring my ego to work. I do what’s best for the organisation.” I can bet you they are lying, or are at best completely self-unaware.

Here’s what I observed of high-performing executives in general. They have aced 15 years of academic life by having all the right answers, then another 10-15 years of professional life on the fast-track because they work hard, are always prepared and always meet (or exceed) targets. Pretty much like me.

Then one day they get thrown into a complex problem or a complex system like my organisation, and it’s a punch in the gut when they cannot solve it. Again, pretty much like me.

Why are system problems so bruising to the ego? There are 3 reasons.

The first is that the key trait that made them successful all their lives is precisely the one thing you cannot do in systems: winning. There is no win or lose in systems, there is only constant improvements in the health of a system over time. There is no “check-the-box-and-move-on” sense of finality; it’s a series of loops to test what approaches work, adjust and test again when circumstances change. People who are used to winning find this aspect of systems really frustrating.

The second is control. High performers have a preset idea of what it means to win. There are grades to achieve, benchmarks to set, targets to hit. We are taught that the first of 7 habits of highly effective people are “Begin with the end in mind”. This implies that if you are smart or organised enough, you can map out a linear cause-and-effect from your goal and work your way there. Systems, with all the glory and goriness of human complexity, do not work like that. They are entangled spools of unknown or unseen cause and effect. I’ll talk more about that in future posts.

The need for control leaves you boxing from your own corner, unable to zoom out and see other perspectives and objectives at play. It blinds you to the real state of the system, and instead you see it not for what it is but what you wish it to be (this is my second principle, also more on that in the future). It leads to a misdiagnosis of what you need to do to change the system.

I am your cautionary tale. I had one preset idea of winning (“showcase my design thinking skills”), I tried to shove that down peoples’ throats and failed to empathise with their needs. Then I diagnosed the problem as others – bad management, backward culture.

(To be clear, I know now the problem isn’t with the management nor the culture. In fact, this organisation has consistently scored the highest in employee surveys on the sense of mission, amongst all government agencies. The management, once you get to really know them, are lovely sincere people who are trying their best. Yes they have their quirks, but who doesn’t?)

The third reason is how winning is equated to self-worth. Psychology books will tell you that the genesis is from childhood, that being good at something or pleasing others was how we learnt to gain love at a young age. This notion is reinforced through the admiration of others through our professional accomplishments (made worse by social media). This sense of self built upon success is fragile, and we would do anything than to have our self-worth threatened.

Thus typically successful people often feel like they are bashing their heads against system problems like a brick wall. In short, there is a lot of pain.

In case you are wondering, I did not quit.

Luckily it was not too late to course correct. Once I knew the problem, I corralled a few of my team members to brainstorm how we could win the trust of the rest of the organisation. They had been in the organisation longer and had great insight into the needs of departments and the personalities involved. We designed a project plan that consisted of only stakeholder engagement and enquiry – our goal was simply to understand, nothing more. This is my second principle: see the system for what it is, not what you want it to be.

When our conversations led from a place of curiosity and empathy, people started to open up. Soon we were running several transformation projects in collaboration. Not all projects were successful, of course. What I remember most were not the projects themselves, but the amazing feeling that I got when someone’s eyes lit up when something I suggested hit the spot. The mutual feeling of excitement and possibilities is a beautiful thing.

My team and I ended up doing several things we could be proud of. A group of pioneers were sent to Stanford d-School for training - many of them have been promoted to senior management and are now using design thinking to engage the public. Permanent design thinking capabilities and processes were instituted within our design and engineering department. Many of my original team members are still there in this organisation today, leading large numbers of staff through project-based intact-team training. I’m so proud of what they have achieved, the honour is theirs alone.

As for me, I gained more from this organisation than I gave. I gained one whooping lesson in humility. I remain to this date deeply grateful for the grace and patience my colleagues and collaborators have shown me.

To help you exercise my first principle in Systems Thinking, I simply offer one question for you to ask yourself:

“What if my objective did not exist?”

Asking this questions your fundamental assumptions, opening up a world of possibilities that you had not considered before. It forces you to consider other values pulling the system in various directions. I challenge you, in the absence of this pre-conceived notion of success, to paint 3 new and different versions of success – the more visual the better. Mood-board it, draw on post-it notes, use cut-outs from magazines; hell, use AI image generators if you want.

Whatever you do, however you do it, just leave your ego behind.

Till next time,

Agnes