1. What have you found most challenging as a CEO or executive of a large enterprise?

People often talk about the volume of work; and it’s true that it can be challenging. But what makes it especially difficult is the need to stay in touch with the nitty-gritty detail of what’s happening, and the simultaneous need to adopt and retain a strategic, holistic viewpoint. Both take a lot of time and attention, but constantly zooming in and and out, from micro to macro, requires a particular mental energy. The two are such different mindsets that switching is both difficult and draining. - but it is necessary. One way to try to reduce the challenge is, of course, is to try and segregate the functions - for example by distinguishing carefully between operational and strategic meetings. But it’s not really entirely possible because the two perspectives feed off and enrich each other, and the interplay is rich. It’s one reason why we need to choose the teams that we have around us so carefully - so that the different people can play different roles by virtue of their natural default styles.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

Well, I started here at UWCSEA as an inexperienced teacher, in 1995; left at the head of Department in 2001 and worked in several other schools worldwide. Wherever I went, there were so many aspects of the school I missed; and I worked hard to try and live up to the values and Mission wherever I was. But I was absolutely delighted to see a second UWCSEA Campus open, and to re-join as a senior leader in 2011; the second campus aspect made it feel like coming home, while also doing something new. Looking back, it seems to me to be the combination of long-term institutional knowledge and the varied experiences elsewhere that have been really valuable to me professionally.

3. How do you structure your work days from waking up to going to sleep?

I’m not sure this is a great question, because so much depends on one’s family situation, or on the specific times of the year, or stages of organisational development. But at the moment I can say that I try to get 45 minutes of exercise during the week when I get up at 5:45; and generally get to work around 7:15. From then on its conversations, meetings, wandering about school, with slots blocked out for specific projects as needed. I try to be responsive to emails; I know that’s not very fashionable and I often read that one should never be driven by them, but it seems to me that if people are aligned by a Mission and Strategic Plan, and they need something, then a quick and helpful reply is very much in service of that Mission and Strategic Plan. And it helps me stay in touch with the nitty-gritty day to day operations,, which is so important. This means that there is often a fair chunk of time needed in evenings or weekends, to think through strategic matters, or read an important book, or write an important paper. That’s the price of the work; but I feel blessed to be in a role and organisation where I have some agency, in a profession where there are built-in slow periods across the year.

4. What’s the most recent significant leadership lesson you’ve learned?

I have three mantras that I recite to myself almost daily. They are timeless, and they are broader than leadership; they’re old and cross-cultural wisdom: It’s not about you. This too shall pass (the good and the bad). Everyone has their own stuff going on.

5. What one book has had the most profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I think it’s Leadership on the Line by Linsky and Heifitz. What I love about this book is the way it foregrounds the leader as a flawed person doing difficult things to the best of his or her ability. It’s rather different to so many books that really describe leaders (perhaps implicitly) simply as loci of technical skills, or repositories of strategies to be operationalised in ways that maximise shareholder value, or some other such abstract goal. I’ve always felt that the leadership literature tends to ignore the person, with all their worries and failings - but this book addresses it. There’s no one story I can tell here, but the book has given me a useful framework to understand my own reactions in complex situations. I re-read it every few years.

6. How do you build leadership capacity in a large enterprise?

So much is contextual, but I think the main thing is related to the previous answer. See the leaders as people; with their own hopes, aspirations, strengths, weaknesses, dreams and complexities; and know that as humans they created and are created by the culture in which they exist. So work with them to create an organisational culture that nurtures and inspires. If you can get that right, and critically, if the organisation has a compelling Mission, then leadership capacity will be ripe for growth. Then there are a million tools and protocols that will work; but it is the broader matrix of articulated and enacted and constantly communicated values and aspirations that created the soil in which capacity will grow and people will flourish.

7. If you had to pick just one story, what would be the most meaningful story from your time as a CEO or executive of a large enterprise so far?

Wah, so many lah! I suppose one thing I was especially touched by was what happened when I thought I would try an internship programme for our Grade 12 Alumni, to come and spend more time at the school after graduation. I was a little unsure if it would work, thinking who would want to spend even more time at school after just finishing K-12 education, especially when our students have so many options available to them? But I was overwhelmed with the number of applicants - far more than we had anticipated, and when the (small) budget ran out, they wanted to come for free. And when we interviewed the prospective interns, what we heard what just how happy they had been at school; how inspired by their teachers they had been; how they wanted to give something back; or how they wanted to learn more about being a teacher; or just wanted not to leave but to be in school for longer. Now, I’m always mindful that families don’t always give me the unfiltered truth about their experiences - but here was a wonderful affirmation of all the massive work we’d done over the years, to build a positive, enriching and inspiring culture. It’s a warm glow of satisfaction when this happens.