Spotting a Leader

Chia Jeng Yang
Messy Problems
Published in
3 min readJun 24, 2019

There seem to be a few recurring signs I have come across when finding out interesting people who could be the leader in their fields. These seem to be, among others, 3 key indicators that we can see in the people around us.

Intellectual curiosity

Intellectual curiosity is a good flag to notice. A leader needs to be able to have a meaningful conversation with all functions within his scope of responsibility. Changing industry trends, strategies, and improvements in technology and knowledge mean that a leader constantly learns. Learning is a painful process. The best learners are not the ones who are the most dedicated to their field, but rather those who are genuinely interested in the process of learning, self-improvement and constantly changing the way they think.

Intellectual curiosity can be glimpsed in a variety of ways. Some of the ways I’ve noticed include an enthusiasm to discuss a technical, academic or political point. A dedication to listening and asking intelligent questions. The ability to uncover deeper principles beneath seemingly trivial issues. With a genuine thirst for knowledge, the process of learning, and for projecting what comes next becomes easy. This is ideal for leadership situations where the organization has to make a decision in new situations or where data is hard to come by.

Expertise in multiple fields

It is hard to find somebody with concentrated expertise in one field. It is even rarer to find somebody with expertise in multiple fields. Typically, this is indicative of mental flexibility and capability to understand different foundational principles.

Expertise in multiple fields can be seen in a few ways. In my opinion, the fields should not be derivative; for example, an oceanographer with a concentration in hydro-dynamics. Rather, I think of the lawyer who wins hackathons, the doctor who directs stage plays, the engineer who writes treatises on Kant. These are the individuals who are more accustomed to bringing different, even contrasting principles under a single mind. This is ideal for leadership situations where understandings and priorities between different functions in an organization have to be bridged.

Action-oriented Contrast

The outgoing academic. The intellectual sportsperson. The creative programmer. The contrast typically indicates flexibility and self-awareness.

The key difference here is personality and attitudes rather than simply expertise. This is generally backed by a personality or desire to fulfill a typically missing attitude among his or her peers. On some level, it includes an ability to grasp an emotional flexibility to embrace an idea of ‘well-roundedness’. There are individuals who are more accustomed to stand out and add value in situations not normally encountered by their peers.

Action-oriented Contrast can be hard to assess if not in person. However, there are some interesting signs that may stand out on paper. I knew a nuclear non-proliferation diplomat turned emerging markets startup guy. Here, expertise and personality contrasts may overlap where certain expertise demands certain personalities. This is ideal for leadership situations where entrenched industries require a fresh attitude from knowledgeable insiders.

The underlying principle is principled flexibility. I am curious to know what you think are some of the signs you see or look out for. How do you display this in your own life? Let me know.

Chia builds interesting projects and works closely with early stage (Pre-A) founders. Previous work here: http://chiajy.com

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