6 Tips On Startup Leadership-1

Grab has grown a lot since I first joined. Back then, it was a small Series C company. Fast forward 9 months later, the company has grown multiple times in size, and the business is much more complicated. I’ve also recruited a small (but super awesome) team. So I’ve been learning about startup leadership, particularly in a rapidly scaling startup.

1. Be present and think lucidly

When I first started out in my role, I didn’t have a team for the first 4 months, and had to handle everything on my own. As the business scaled exponentially, I made my first hire, but initially continued to do almost everything on my own, until I became too busy and reactive. That interfered with my ability to think and often I wouldn’t be clear with what I needed, causing unnecessary confusion and stress. So I now have the basic principle #1 of startup leadership that even if 20 urgent problems were raining down on me at the same time, I am always present when my team needs to talk to me. Showing my team that I am engaged and can think lucidly about what they are discussing with me instills confidence that decisions are well thought-out and that I won’t be prone to judgment errors.

2. Step back and think strategically

Cute Weddell seal

In a rapidly scaling startup, there will be an endless stream of problems – people, technical, product, organizational, and operational problems. Whilst these problems definitely need to be solved, startup leadership requires the ability to penetrate the fog of a million operational and execution details and think on a more strategic and less tactical level. For instance, strategically I think about how we could do every single aspect of what we do better and how I could scale the effectiveness of the team, instead of only solving current problems. I’ve also worked and met with founders who articulate with authority and vigor a clear vision and unambiguous strategy to get there, and that is always really inspiring to me. Also, having recently read Elon Musk’s biography, I believe it is so important for startup leadership to have a compelling vision of what the company or team is trying to achieve. (Also, other inspiring startup leadership reads here!)

3. Hire for strengths


When I started hiring my team, I was clear that I wanted to build a team of people with personal and professional strengths that complemented my own weaknesses. I learned this startup leadership lesson also from Ben Horowitz, who taught me that a wartime CEO hires for specific strengths and not for all-roundedness, which is useless in wartime. So I was also super clear on the strengths I was hiring for. I recently did a Tetramap exercise, and found that my team of 3 actually has 3 out of the 4 different dominant elements amongst us. We are so well-balanced! I’ve found that my team works incredibly well together because we each have different strengths and weaknesses, and together, we complement each other and have managed to conquer and solve many problems together.

4. Groom the team to take over you

I will follow you..

I’ve learned one basic principle of startup leadership: to always be thinking about how to groom your team to take over you. I’ve seen firsthand how doing that frees leaders up to solve new and potentially more exciting problems. Also, the team becomes highly effective as everyone’s capacity and effectiveness scales together. To do this, I trust and empower the team and don’t micromanage them. I get comfortable that they might trip sometimes and plan what to do when that happens. But I believe that the team sometimes needs to trip a little so they could learn how to find their own way in things. So I start from the little tasks and give more and more as they start to demonstrate greater confidence in what they are doing.

5. Weekly 1 on 1s


This is one of the startup leadership lessons I learned which is so obviously helpful, I wish I learned it earlier. Simply put, 1 on 1s are regular weekly scheduled times with each of your direct reports, and it’s time for them to talk about anything they want – personal or professional, things that are going well, things that are not, and things that are bothering them. The idea is that there should be no surprises at the annual performance reviews, because my team gets (and gives me) one almost weekly. It’s a regular pulse check and helps me to course correct quickly in real time. Even though this is challenging given the many things that are going on, I try my best to keep to my weekly 1 on 1s with my team, and hear them out on what bottlenecks I could clear, and what I could do to help them to fly again. If done right, 1 on 1s really help to build trust and can be highly motivating for the team. Conversely, if we let problems and grouses go unresolved, over time, frustration builds and greatly hurts morale, creating bigger problems (and blowups) down the road.

6. Explain what’s going on

What are you staring at?

Every startup is chaotic. Every startup has a non-stop flow of problems to solve and priorities to choose from. So everything is always imperfect and there are plenty of elements everyday that could cause frustration to build up. By the time the frustration has accumulated, I have a bigger problem on my hands. So I’ve learned to listen for frustration. Then, I solve what can be solved. As for what I can’t solve, my startup leadership guiding rule is to not give false expectations and instead explain to the team what is going on, how we could do our best in that constrained situation, and lay out the plan or the next steps that are within our control. I’ve found that to be tremendously useful in helping to keep the team’s morale at a healthy level and avoid the buildup of negative emotions which could spiral out of control.

What startup leadership tips do you have? I’d love to hear from you!

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One thought on “6 Tips On Startup Leadership

  • October 8, 2015 at 16:33

    Your statement "Groom the team to take over you" strikes me a lot. I hope I'm wrong, but my experience so far is managers will usually put their own tasks as priority and only come to you when they really need your help. I also witnessed that some subordinates were remained clueless when the managers left. It will be definitely a great situation when the subordinates and the manager can progress together rather than uneven growth rate.

    Nice photos by the way. =)


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