In the startup world, personality types can become a prison


If you’ve been keeping your finger on the pulse of the startup world, you’ll have noticed that the topic of introverts in the workplace has come up a lot. In particular, many have been doggedly extolling the upside of being an introvert – headlines such as The Secret Power of Introverts and Why Introverts Make Great Leaders have been popping up across the web recently.

And then there’s also the bestseller Quiet: The Power of Introverts by Susan Cain that got the ball rolling.

Many of these articles have excellent arguments on why introversion has its benefits. The first article mentioned above, for example, has a section named “The hidden value of introverts” that reads like an advertisement for introverts (on behalf of all introverts, I thank you). Of course, the writer balances it out nicely by concluding that, well, it’s all “about balance”.

But let’s not gloss over the prevailing opinion, which continues to be that entrepreneurs need to be hand-shaking, party-loving extroverts in order to succeed. Many less outgoing people still believe that they can’t be ‘good entrepreneurs’, or even play a big role in a successful startup because they feel that they won’t be able to wheel-and-deal like the best of them.

The pressure to be more extroverted, as it is, doesn’t seem to be abating at all – this despite an increasing literature fighting against the status quo.

Is this debate ‘useless talk’?

The thing is, labeling oneself as purely an introvert or extrovert is fundamentally incorrect – unless you have a personality disorder, that is. The psychologist Carl Jung, who coined the terms ‘extrovert’ and ‘introvert’, reportedly said that there is no such thing as either, and added that such a person “would be in the lunatic asylum.” It is instead useful to think of human personality as a gradient:

In the startup world, personality types can become a prison

Simply put, humans are complex creatures, as are our personalities. It is all too easy to get trapped in a box of your own making by convincing yourself that you are one or the other in definite terms – and no, a personality test doesn’t prove anything definitively.

Experienced entrepreneurs know better than to pigeonhole themselves based on their personalities. Darius Cheung, a seasoned Singaporean entrepreneur, scoffs at the excuse that being introverted somehow diminishes your chances of becoming a ‘good entrepreneur’:

Startup people do what it takes to get things done, including switching personalities when the situation calls for it. If an entrepreneur says that [being an introvert works against them], he or she shouldn’t be an entrepreneur.

He has good reason for feeling bemused by this notion. In his previous startup, Homie, he was the team lead for marketing, sales, and fundraising. As such, he had to train himself to be more extroverted, which he claims was a step away from his natural personality.

“Entrepreneurs should figure out how to leverage on their strengths to overcome the weaknesses,” Cheung says. “There are advantages and disadvantages of being anything – Asian or American, rich or poor – but getting caught up with such talk is simply useless.”

Cheung considers himself to have a foot in both worlds today, depending on the situation.

Harder for some than others

Not everyone can adapt so easily. Programmers, especially, seem to find it hard to be vocal and outgoing in social situations. Winston Teo, a self-proclaimed introvert, admits that he is still getting the hang of making the first move to say hi at events – this coming from the organizer of Red Dot Ruby Conference 2014 in Singapore, a major event that brings together Ruby programmers from around the world.

Teo now runs a one-man consultancy called Jolly Good Code, but he previously worked at Neo, a product innovation company. When he was first offered the job, he was hesitant to take it on for one reason: they worked based on a process called ‘pair programming.’ He elaborates:

Doing pair programming means you have to communicate well, and explain your thoughts properly with your partner. So before I accepted the job, I actually thought hard about whether I would fit in or not.

It turned out not to be so bad for Teo – he stayed on for three years before making the leap into his own venture. In fact, the process of pair programming actually helped him to iron out his weaknesses as well. “Having gone through that, I would say it helped to transform me into an ambivert, where I feel more at ease in communicating my thoughts,” Teo says.

Making the necessary adjustments

Hearing these stories, it becomes apparent that being a full-on introvert simply won’t cut it in the startup scene. Since human personality is a continuum, it is entirely possible, and at the same time very useful, for shyer people to shift gears and take a leaf out of the extrovert’s book under the right circumstances.

“I don’t think being an introvert in a startup will kill you, but sometimes it pays to be vocal about your thoughts and feelings to your management to get something that you would like,” advises Teo. “Your management may not be able to guess what you need, so as an introvert one should learn how and when to ‘fight’ for your needs as necessary.”

Cheung thinks that the first step for introverts isn’t to ‘train’ to be extroverts, but to make a simple decision to get what needs to be done, done:

For example, usually introverts tend to prefer not to talk to people. But as an entrepreneur, it should not even occur to me whether I prefer to do this or that – if my job needs me to go talk to people, I will go talk to people. Of course, if it doesn’t, then it would be perfect.

One of the greatest myths that frequently quashes the desire of introverts to make the leap into entrepreneurship is surely the notion that extroverts own the startup world. While extroverts do tend to get most of the attention, Teo believes that through good old-fashioned hard work, less outgoing people can make a name for themselves as well.

“I don’t think introverts are overlooked. If they are doing good work, word of them will spread too,” he explains. “Their names might not appear in established publications, but within the appropriate circles, they will definitely still be well-known and respected.”

Kristine Lauria, who plays an active and visible role in organizing grassroots-level startup events in Singapore, believes that there is room for anyone in the startup ecosystem – regardless of their personality:

Some positions – such as sales, business development, and management – may be better suited to those who enjoy social interaction, but for every job it’s important to be able to understand what others are working on and communicate your role, timeline, and deliverables in the process.

As with Teo, she thinks that one’s reputation plays a far more important role than his or her appearances. “The tech space is still small – particularly in Singapore – and your reputation is very important. It’s definitely more important than if you’re introverted or extroverted,” she explains. “There are so many technical founders that may not be well known but are incredibly respected for doing great work.”

She brings up the example of the team, who as a team of introverts were still able to raise a substantial amount of funding and do great work.

It seems that face-time and public recognition may not be as essential as one might believe to the success of an entrepreneur – and Cheung agrees wholeheartedly with this sentiment. When he first founded TenCube with two partners, Rishi Israni and Varun Chatterji, he was the face of the company most of the time.

“Today, they are both running successful companies themselves as well,” he says. “It didn’t matter that they weren’t the most public-facing members of the company back then.”

The funny thing is, those who are the most vocal or active in the social scene may not even be extroverts at all, as Lauria can attest to. “I’m not shy by any means but I am – perhaps surprisingly – much more introverted than extroverted,” she reveals, and adds:

I find it super draining to be surrounded by people, and need to recharge with a lot of alone time. I thrive in small groups where I already know everyone and don’t need to take pains in figuring out the social dynamics. Conferences kill me.

Goh Yiping, CEO and co-founder of ecommerce portal AllDealsAsia, is similarly outspoken about topics that she feels passionate about. However, in an MBTI personality test that she took recently, her extroversion won introversion by a mere 1 percent.

“I think, when it comes to business, I use my extroverted side more. In my personal and private space, I am more of an introvert – I generally shy away from parties, big gatherings and often enjoy time alone to reflect and unwind,” she explains.

Introverts are great workers, too

Thus far, the game still seems to be slanted in favor of extroverts – much of what has been said points to examples where introverts need to be more extroverted. Does introversion bring anything at all to the table?

If you’ve been paying attention so far, you’ll know that the answer is a resounding yes. Cheung goes as far as to say that introverts make better entrepreneurs:

They tend to be more introspective people, and they are very good at inspecting and challenging the status quo in a way that is insightful and uninfluenced by external forces.

The conditions for introverts to do their best work, according to Lauria, have to be just right. For example, while she enjoys working in co-working spaces and coffee shops for the action and buzz that goes on around her, when it’s time to get down to work, she keeps her earphones on to signal that she’s busy.

“Sometimes I go a whole day with my earphones in with no music playing,” she comments.

Distractions, in the form of conversations and meetings, seem to be the number one productivity killer for introverts. Lauria agrees. “I really don’t like working where there are constant meetings and interruptions,” she explains. “I need to bunker down and concentrate on my work. I find a day of meetings to be my least productive.”

Roger Chang, CEO and co-founder of Singapore-based Pirate3D, agrees that working conditions are enormously important for introverts to do their best work. The Pirate3D team endorses flexible working arrangements, and keeps meetings short and sharp – or scraps them altogether.

The layout of their office also facilitates both collaboration and concentration. “We have a section upstairs that is usually quieter and good for focused work, while downstairs is a sitting area that fosters discussion and collaboration,” Chang explains. “Balance is key, as you will definitely have both introverts and extroverts in your team.”

Seeing success in a startup

Having a team with a broad range of skills and styles is critical to the success of a startup. “Everyone needs to find a person to complement their skill-set,” Lauria confirms. “For example, while I can throw a killer event, I suck at getting sponsorship! That’s why partnerships are so important.”

Individually, however, perhaps the best thing for those who want to achieve even a modicum of success in entrepreneurship is to play to the strengths pertaining to their personality type, but at the same time not be afraid to work on their weaknesses as well. Break out of the ‘boxed-in’ mentality, and you’ll be surprised by the results.

An earlier version of this article first appeared in the Tech in Asia Emag, which is exclusive to our Insights subscribers. Find out more about TiA Insights.

Editing by Terence Lee and Steven Millward
(And yes, we're serious about ethics and transparency. More information here.)

Read More