Leadership, Management, Startup
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Hard Learnings of a Young Tech Startup Founder on Leadership

I share these musings not as someone who knows it all, but just as someone who, under the intense pressure of running a startup, had to face all these dilemmas and muster all I know and have seen about what good leadership is like to run my team – where my legitimacy and career were at stake, where the livelihoods of all my teammates who have bought into my vision and strive with me tirelessly were at stake, and our mission was at stake.

I share these in humbleness for you to point out what perspectives I might not have considered – and if I may, help someone who have to face similar challenges in the future have a starting point to reason through these.

Running one-on-ones – but how can I even make my team members comfortable to share feedback on others and receive feedback positively in the first place?

Andy Grove (former Intel CEO) and Ben Horowitz (former CEO of Netscape and highly-respected VC) can’t understate how important it is for managers to run monthly one-on-ones with team members. How else would a manager know what problems and opportunities for improvement there are in the company, otherwise? The challenge though, for one-on-ones to be successful, is in creating an environment where my team members feel safe to freely share and be open to receiving feedback positively.

When I was in David Sng’s team back at SGInnovate, David always made it a point to start the one-on-one meeting with asking “How can I improve?”. It takes a lot of humility and courage for a leader to ask that question – I look back at the months when I conveniently ‘forgot’ to run one-on-ones, and they almost always corresponded with periods when I was incompetent in leading the team the month before – I knew I was doing so badly as a manager, I wanted to avoid asking that question my team members would be expecting me to ask.

But starting the one-on-one with that question does all the magic. It immediately communicates to my team member that I recognise I’m not perfect, and there is no unreasonable expectation for them to be. It creates an environment of safety where it tells them “hey, we are all imperfect humans – so just as I trust you enough to ask you to help me improve, we are all here to help you improve too.”

Lack of charisma, or servant leader?

During the first few months of running Nurture.AI, in our one-on-ones I would often get feedback from my teammates that I need to work on being a more charismatic leader, and someone even mentioned he’d rather that I be more “alpha”. Now, that’s something I certainly have to look into – I’m certainly not someone people would call a ‘natural born leader’.

Growing up as a self-absorbed but loud weirdo, I was bullied and ostracised throughout primary and secondary school. Not the most conducive growing-up experience for building one’s confidence, eh? I would stutter in my speeches even when I was heading up an international conference, and be preoccupied with thoughts about what people would think of me whenever I said or did anything.

This led me to reflect on what it means to be a charismatic leader. Charisma is only positive in that it draws people to believe in and follow a leader. But that effect of charisma is short-lived, if the leader doesn’t couple that with authenticity in caring for the best interests of those he leads.

It might take me much more time before I can dazzle crowds with my charm, or even carry myself with such certainty and confidence in both myself and the directions I give. But that charisma is only a means to the end of influencing positively – I’d rather focus on meditating daily upon whether I lead with conviction on my values not opinions, and with genuine care and concern for my teammates, holding their goals, aspirations, and personal growth close to my heart. That’s the only responsible thing to do towards people who have entrusted me with their faith.

A for-profit company which tells employees to “Make everything you do an act of love?”

At some point, every company would need to go through an introspection to define who we are, why we exist and what values we stand for. 2 months ago, our team at Nurture.AI had exactly such a conversation, on what values would govern a company we’d be happy and fulfilled to work for. The team voiced out values and norms like open communication, mutual respect, competence, judgement-free… and we soon filled the entire whiteboard.

As I heard each and every value put forth, the term “love” kept ringing in my mind. When we love someone, we communicate feedback openly to her not to put her down, but in an encouraging manner to help her improve. We treat each other with dignity and respect when we love them. We choose to be competent in our work when we genuinely love the people we serve. And we lovingly restrain from judgement when we acknowledge that we are grossly imperfect ourselves.

That day we decided to set Nurture.AI’s value statement as “make everything you do an act of love”. In a competitive business environment, with bottom-line pressures and investors’ interests to account for, does this make sense?

At Nurture.AI we ensure this value statement goes into even our daily stand-ups. At the stand-ups we share “Yesterday I was to loving towards _______ by doing _______, today I plan to be loving towards _______ by doing ______, and you can be loving towards me today by __________” Having this open reflection forces us to reflect daily on who exactly were we lovingly towards, and whether they would indeed feel loved through what we did. Each piece of code we write, each email we send (or missed out on replying to) has a real human at the receiving end of value, whom we are committed towards loving.

It’s still early to say, but my conviction is in this leading us to create true value for our users, turning us into a sustainable company that caters to both our investors’ interests and bottom-line in the long-run.

Being vulnerable openly, but giving feedback privately

When our team ran a Team360 review where each team member would write structured feedback for each and every other teammate, being the one who’d compile all the feedback anonymously for each person, I was the only one in the team who’d have full visibility on who the authors are – even for feedback directed at me.

So how then do I ensure that my team trusts I won’t abuse that visibility I have and would earnestly work on the feedback given to me? I realised probably the best way to do that, is to openly publish all the feedback I receive. As a leader, my responsibility to the team denies me that privilege of having critical feedback given to me being kept private – by being held publicly accountable to work on feedback given to me, the team can trust that I am sincere about wanting to improve through receiving feedback.

That privilege of privacy should be extended to the people I lead though, when giving the feedback publicly doesn’t contribute to the sole purpose of feedback helping the team member grow. It is a way of treating the team member with respect and dignity, acknowledging that all of us have our egos which we seek to protect so dearly.

Am I being adaptive, or fickle-minded?

As a young startup, the direction we are heading often changes quickly, sometimes even on a week to week basis. There’s an analogy explaining why startups have a chance of beating and disrupting big corporations – that of a startup being like a speedboat which can adapt quickly in response to opportunities and obstacles, while a large corporation with its bureaucracy is like that of a big ship which takes a longer time to steer course.

These direction changes have occasionally made the team lose faith in my leadership, leading them to question whether I have any clarity on the direction I’m leading the company on. One week I emphasised to the team on the need to simplify and declutter a page, and the next I suggested feature additions to the same page.

As I reflected upon this, I came to this conclusion – there might not be much consistency in direction during the early stages of a company, but there can be consistency in having a reasoned (mostly based on data from users) process for making these decisions to change direction that are well-communicated to everyone.

As emphasised earlier, I am still early in this journey, and don’t have all the answers. Let’s make this an open conversation on authentic leadership to learn and grow together from our collective experiences.

With much love,

Yap Jia Qing

Originally posted on Facebook on 10 March 2018

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