Photo: Getty Images
Cover Photo: Getty Images

In her search for a new team of leaders to helm and scale her 14-year-old jewellery business, the Singaporean founder gains five non-intuitive insights that would help anyone on their own high-stakes search

In my previous articles from this feature series for Gen.T, I talked about why I chose to put my company Choo Yilin on hiatus and when I realised it also needed new leadership to scale. Once all of this became clear, I made plans for the search.

Just like so many events that had occurred during my entrepreneurial journey, there was no precedent I could draw on. 

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I’ve put together a list of five tips that helped me to navigate what I consider to be the most significant, high-stakes search of my life. 

You may not be looking for new owners to your company, but chances are you will be embarking on your own personal high-stakes search. Perhaps you’re fundraising or looking to change industries while being your family’s primary caregiver. 

Or maybe you’re debating which new city to relocate your family to, and need to reconcile multiple considerations like your children’s schools, career prospects and other never-ending lists of requirements. 

Your high-stakes search is uniquely yours, but I’ve found that the five tips below can shape how we think about our journeys. So I hope they will be helpful to you as well in some way.

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Choo Yilin founded her eponymous Singaporean jewellery brand in 2009 (Photo: Darren Gabriel Leow)
Above Choo Yilin founded her eponymous Singaporean jewellery brand in 2009 (Photo: Darren Gabriel Leow)

Tip 1: Define your non-negotiables  

The most important first step I needed to take when I embarked on my search for a new leadership team was to define what I was looking for. More often than not, we have a sense of what we want, but we’re not always conscious of it. 

I found that in order for the search to be effective, especially if I was going to be engaging my networks to assist, I had to make my company’s needs explicit. 

For some, the creation of this list is a short, fast and immutable process. But that’s rare. 

For most, articulating our needs is usually a long, slow and mutable process. So if you’re sitting in front of your laptop, with your brain doing pretzels, you’re not alone. 

For me, I found it helpful to speak with trusted associates—fellow entrepreneurs, investors and executive coaches who would have valuable insights and networks. Through their supportive but sharp questioning, the list that I was building of what would serve Choo Yilin best started to evolve. 

This helped me realise that the conventional route of hiring a professional CEO through headhunters wouldn’t be suitable for us. What we need is the infrastructure and global networks that would allow Choo Yilin to navigate the inevitable growing pains of going global. 

In an ideal situation, Choo Yilin would be partially acquired by an institutional buyer who understands and respects the nuances of building a luxury brand globally and digitally. The buyer would believe in our story, DNA and value. After all, Choo Yilin needs stewards who can grow the company but also preserve our distinctive identity. 

Even as it is important to have a structured, disciplined approach in this search, we also need to leave room for serendipity

- Choo Yilin -

Tip 2: Process, discard and integrate 

Even as I spoke to different people, each time learning something new, there was a surplus of data. In some instances, the advice was contradictory; in others, there were many insights but they couldn’t come together in a coherent, actionable narrative. 

This is to be expected, and it’s part of the process. It may seem like an obvious point to make, but I only realised now that it is virtually impossible for people to offer an opinion or piece of advice that isn’t shaped by their own experiences. And if you consider what their experience is, you will realise that it can never be fully applicable to you. 

So it is crucial to distil the universal wisdom of each of our human experiences and take only what’s relevant to you. 

I wish that there was a neat template I could share with you on how to do this, but I do not. But remembering the first tip above will be helpful.

As an example, a friend of mine who is an entrepreneur in the AI space recently shared how she wondered if she was going down the wrong path by pursuing the projects that she did. Her choices were relatively unorthodox compared to what others in her industry were pursuing, which led her to second-guess herself. 

But we realised that she shouldn’t be competing in the same space as them. By almost every measure, she was different from many of her peers—she was female, in her mid-30s, Asian, a mother of two children under the age of five and the primary caregiver of her family. And these experiences give her a perspective distinct from the traditional players in her industry.

The real question was how would she leverage these differences as strengths to distinguish herself and stand out in her field.  

So being aware of who we are, what we want and the lens through which we see the world will help us decide how best to process and integrate feedback. 

Tip 3: Build a community  

An associate who has led several tech startups once told me that in high-stakes searches, be it Series A fundraising or negotiating an M&A (merger and acquisition) exit, it’s important for founders to build a strong community around them. 

She first advised me to “get used to hearing no”.

Then, she said in order to do that with equanimity and find the emotional resilience to pick yourself up again and again, I would need the right support. 

The most successful and emotionally resilient people I know have either deliberately or intuitively built a support community for themselves. They lean on their communities across various parts of their life—from personal matters such as navigating parenting and familial challenges, to professional matters such as achieving ambitious career goals. 

The community that you build will be unique to you, and it will consist of people who will provide you with support in different ways. After all, no single person has the bandwidth or the skillset to cover all of the areas you will need support in. 

If you would like to map out the types of support you need and who you think can provide them, see the chart below. It is based on Ascend from Harvard Business Review’s mentor map, with some of my own tweaks.

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Illustration: Raphael Quaison
Above Illustration: Raphael Quaison

 Tip 4: Express intentional gratitude 

I found it important to acknowledge those who had helped me along the way. I wrote personal thank you notes to them. Sometimes, I sent gifts. 

This is because a human’s journey, like a company’s, is impossible to be done in isolation. Everyone exists in a community, and acknowledging and honouring the relationships you build with its other members is key. 

This exercise also instilled the discipline in me to deeply reflect on the progress I had made and the advice I had received, rather than focus on the distance I had yet to cover. 

Neuroscience has increasingly demonstrated that gratitude has a multitude of benefits, not least of all influencing a person’s nervous system to become more emotionally resilient. 

Tip 5: Prepare for planned serendipity 

Even as it is important to have a structured, disciplined approach in this search, we also need to leave room for serendipity. 

It is equally about being flexible and responsive to change and seizing the opportunities that unexpectedly arose, as it is about acknowledging that a large amount of anyone’s success can be attributed to goodwill and grace. 

Part of the search requires consciously creating conditions for serendipity to happen for the stars to align. If not, you’re closing your eyes to what the future can hold, and limiting your and your company’s potential to grow in unexpected ways.

So with that, my search for a new steward and a new home for Choo Yilin continues.

A journey of planned serendipity. 


Choo Yilin is the founder of her award-winning eponymous fine jewellery label, which specialises in jade and is modernising this historically significant gemstone for the 21st-century audience. She sees herself as a storyteller, but instead of words, she uses gold, diamonds and Type A jade to tell these important tales rooted in heritage and history. Connect with her on LinkedIn, especially if what she’s written resonates with you.

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