Newsletter 89: on becoming an effective operator (in Southeast Asia)
A question I like to ask during interviews is, “what’s something that’s easy for you to do but hard for others?”
The alternative to this question, and the more cliche version, is “what is your superpower?”
To discover mine, I asked the same question to ~ ten people who knew me well or had worked with me for at least two years. The results were quite interesting. People who used to report to me talked about clear communication. On the other hand, people who managed me directly had a different insight. They were confident that my ability to get shit done was my superpower. As I reflected on the answers, I realized both replies were accurate. In the eyes of my management and investors, my ability to execute and get shit done stood out. In turn, that translates to clear communication as I start delegating tasks across the organization.
An awareness of your superpower helps you build a career moat. In my view, working towards creating such a moat can help you accelerate your growth. Regardless of age or experience. So I find it valuable to ask yourself:
If you were given 10,000 hours to master a skill, what would it be?
Many people expect to have a superpower that consists of one core skill. While that’s true for some, life taught me that most people find their moat at the intersection of a few complementary skills. That brings back the question of do you want to be a specialist or a generalist? Either approach can work. But the one thing that remains consistent is how you must be good at something. You can be excellent in a niche skill like UX copy and thus be a specialist. On the other hand, as a generalist, your superpower would most likely lie at the crossroad of a few skills.
In my case, I am not the best operator, writer, or product person. But combining all of that creates a unique superpower that’s hard to replicate. Yet, let's go back to the question of where I would invest 10,000 hours in mastering a skill. The more I reflect, the more I am confident that mastering the craft of operating well is my answer. So today, I am diving into what it takes to become an effective operator. The lessons I learned the hard way. The mistakes I made. The struggle it takes to maintain a high-performance culture in your team at all times.
Becoming an effective operator
Over the last few years, I have invested a lot of effort in becoming a good operator. I might have reached 10,000 hours already; who knows. The process includes a variety of steps like studying great people by reading many excellent books about their lives. But most importantly, learning the hard way through first-hand experiences and building companies.
Looking back, my move to Asia was one of the most impactful steps in becoming a good operator. Living in Southeast Asia (SEA) exposed me to some of the most significant leadership challenges of my career so far. On the one hand, I managed some incredible people, but on the other, the talent was truly asymmetric.
Some people were brilliant and driven. Others could not reach their full potential just yet. Most often, the first group consisted of people who were fortunate enough to come from wealthy families. Such people studied at good institutions, traveled the world, and had entrepreneurial parents. Yet, at the same time, those people had daily exposure to true poverty and the poor infrastructure in emerging markets. The combination of experiencing both worlds kept them hungry and ambitious.
On the other side of the spectrum, I met people who were not fortunate enough to experience all that. To study at good schools, travel, or get exposure to entrepreneurship early on.
As a result, every Asian startup I worked at, had a mix of both groups. An incredible talent who did not need much guidance to do great work. At the same time, I led kind, hard-working, and ambitious people who needed much guidance to reach peak performance. Witnessing that dynamic taught me again and again about the importance of clear communication and keeping myself organized. That was the only way to remain effective in such a dynamic workplace.
The next thing that taught me how to operate well is the fast pace work environment of startups. I have worked at big and small startups for the past eight years. It goes without saying that new ventures are messier than established organizations. As a leader in any startup, you face hundreds of burning fires across the organization daily. Therefore, your ability to a) prioritize and b) swiftly solve the most critical problems determines success. In turn, that forced me to embrace fast execution and work on my communication while keeping myself organized.
Lessons learned as an operator
The following are my most important learnings as an operator so far:
Scarcity brings focus — a rooky mistake I made as a leader in Asia was to overhire several times. Salaries in SEA are pretty low compared to developed markets. It’s easy to fall into that trap and hire more people than you need. But the more people you hire, the less time you have to do actual work. The bigger the team, the more your job becomes to manage people’s problems. Small groups result in a scarcity of resources. In turn, that forces you to prioritize better. To think deeply before each significant decision. In small teams, it’s obvious who does excellent work and who is a passenger, which allows you to keep the talent bar high.
Demand great work at all times — people are very good at bringing you problems and excuses. When you are building something new, the whole world seems to be against you. Suppose it was an easy task; someone else would have solved it. Yet, it is worth taking on complex challenges precisely because they are hard. Solving complicated problems leads to an asymmetric upside. So learn to push hard and demand great work no matter the resistance you naturally face. To strike a balance, you need to be firm but supportive. In my experience, one-on-one meetings with your team help. Use such meetings to listen attentively and then quickly resolve bottlenecks. Having said that, some cultures may require a lot more hand-holding than others. That’s fine; your leadership should continuously adapt to the local culture. Yet, that should not slow you down; plan accordingly and keep the bar high.
“Turn up the heat in every interaction and ask uncomfortable questions. Some of the questions I repeatedly ask:
Can we re-frame this in terms of the customer’s problem?
What’s the soonest we could get this done?
What would you need to get this done tomorrow instead of next week?
What would we need to do to get twice as many customers? Ten times as many customers?
How does this relate to our goal? Is this the most important thing we can do for our goal?
What’s most important? What do we really need to get right?
What could we cut, even if it’s painful?”
Sam Gerstenzang
Build trust — to add to my previous point, managing teams across cultures is tricky. For example, most Southeast Asian cultures are not terribly confrontational. In turn, you need to create a high level of trust for people to open up and share their thoughts. Whenever someone opens up, reward that behavior. Praise them for having the courage to speak up. Be open about how you make decisions and the tradeoffs you have to make. In turn, a shared understanding and safe environment will inevitably build trust. Another successful tactic I discovered was to immerse yourself in the local culture. That works only if you show an authentic desire to learn the local way of living. Appreciate the local food, drinks, habits, and language. Invest time in getting to know people. A high degree of trust will naturally follow.
Nothing is “not my job” - do whatever it takes to help the business succeeds. If the activity pushes the company in the right direction, get it done. Ignore your seniority or job description. You will be rewarded with trust and accountability. As your reputation in the organization compounds, you will stumble on plenty of valuable opportunities.
Align incentives — Start by studying the principal-agent problem. A principal is a founder, i.e., the owner. In contrast, the agent works for the founder—an employee. The founder’s incentives are different than the ones employees get. The business's success aligns quite well with the founder's success. In turn, the founder wants what is best for the company. At the same time, most employees care about what will look good to the principal. What will make the most friends at the office? What would keep their workload manageable? The whole concept of the principal-agent problem is about aligning incentives. Agents will always find ways to hack the system if your incentives are poorly designed.
Fast is as slow as we go — if a decision is not permanent, move as fast as you can. On the other hand, take your time if a decision is permanent. That’s why VCs take their time in making decisions. Because they make just a handful of investments annually, but as a business owner, you must make hundreds of decisions daily. The faster you move, the better. Making a decision is not easy, but in my experience, a wrong decision is better than no decision. That’s because motion leads to feedback and learning. Overthinking leads to procrastination.
"A principle for writing, investing, and life in general:
It is much easier to notice when something is working than to predict ahead of time if it will work.
Take action, make many small bets, and run lots of quick (but thoughtful) experiments. Then, double-down on the winners."
James Clear, author of Atomic Habits
Write things down and overcommunicate - every call, meeting, or quick interaction needs a summary. Writing things down brings clarity to all parties involved. It’s hard to distill and synthesize long discussions. Yet, it will help you reduce the number of misunderstandings. The bigger the organization, the more critical it is to overcommunicate. The same logic applies to setting goals. Once you select a goal, make sure to restate it again and again. Your objective is to ensure the team thinks about the goal daily when making the thousand invisible decisions. Whenever you set new goals, make sure to a) communicate them consistently and b) ask how every initiative contributes to the core goal.
Give credit where credit is due — a lesson I learned at Greenhouse is the importance of giving credit to people. When someone does a good job, say it out loud. Then repeat it in public. Respect the craft of your team and show appreciation on every possible occasion. Couple that with a willingness to jump in and act as an owner of your colleagues’ outcomes. Giving credit and supporting them without taking credit will build a great deal of trust.
Give away your legos — sometime back, I read a great article on the importance of giving your legos away when the time comes. The metaphor goes in the following way. Working at a fast-growing startup feels like you are building a large and complex tower of Legos. As you add more people to your team, you must learn to trust the newcomers to handle your Lego tower. The feeling will be unnerving. After all, what if you are better at building that tower than the new employees? Handing over your job and projects you most likely created from scratch is tough. You have to trust new people with something you care about deeply. It’s completely normal to feel conflicted. Yet, the only way to grow is to give up your legos and move to build the next, even more, giant tower.
“If you personally want to grow as fast as your company, you have to give away your job every couple months.”
Molly Graham
Become antifragile — when setting a high bar for your team, you will inevitably create stress in the work environment. Having stress is not necessarily a bad thing. There are different types of stress. Healthy stress will push you to do incredible work. In the process, achieving results, you did not think were possible. Other types of stress burn you out and cause health problems. Avoid the second type but nurture the first. You need to become the kind of person that gets stronger from hardships.
A calendar speaks more truth than a to-do list — to be truly effective, you need to manage your calendar well, which includes activities like:
Constantly push back on requests for meetings on half-baked ideas.
Closely monitor where you are spending most of your time VS what are your current objectives.
90% of all meetings can be 30 min long (or less), so schedule shorter appointments. It forces brevity across all participants.
Block time in your calendar for deep work.
Understand when you are most productive. Then, push the most challenging problems to that time of the day. For example, I am most productive between 9 and 11 am.
Allocate 10 to 20% of your time on recruitment. The search for great talent never ends; your calendar must reflect that.
Schedule 1:1s with your direct reports. The frequency of the meeting depends on how well aligned you are. In my opinion, a bi-weekly frequency works best when things are going well. Otherwise, meeting weekly for 30 minutes is a great starting point.
At the end of each week, plan the following week. Then at the end of each day, review the activities for the next day against your objectives.
The pursuit of becoming great in operating requires a constant process of tweaking, iterating, learning, adapting, and growing. To reach peak performance, we must constantly ask ourselves and the people who work with us what we can do better? Stay curious, learn from great people, and push what you think it’s possible. There is no end to it. You may feel frequent dissatisfaction with how things are done around you, but happiness requires struggle. Be grateful for that, as it gives you opportunities to grow. Everything has its price, and operating well is not an exception.