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Engineers who look up
The value of curiosity and initiative
Most people are not curious. When engineers are not curious, they look at their screen and don’t go from their desk to understand anything beyond the code they are writing and planning to write.
The best engineers I have met aren’t necessarily the most technically minded. They are the ones who look up from their desks.
Looking up means understanding the meta-problem and considering the nontechnical factors behind technical decisions. Engineers are system thinkers by practice, but the success of a project as a whole often involves a wide variety of factors other than technical choices, which means that engineers are often not looking at the whole system when making decisions.
I’ve noticed three main ways engineers look up.
Looking up when picking. For many engineers, choosing the company you work at is often more important for your career than the quality of your work. Similarly, understanding the financial implications of your stock package is often more important than the amount you negotiate for in your financial future. Most engineers are largely ignorant of these types of dynamics and have, at best, a surface-level understanding of the situations they get themselves into. Engineers who look up understand the importance of picking and think hard about these factors when making choices.
Looking up when operating. Many engineers are considered good when they can think out the technical implications of their work, and many excellent engineers can think of interesting technical expansions that would improve their product. However, very few engineers actually think about why they are building what they are building. They don’t consider which variables are important and often ignore non-engineering considerations. Their energy is infectious and drives other people to drive forward projects. Engineers who look up seek out non-engineering factors and lead even when it is not in their job description.
Looking up at the business. Products solve problems or bring joy. Many engineers are excellent at solving the technical barriers to their problems. But very few take the time to understand the business reasons that led to the problems they are solving in the first place. That means that incentives of the actors at play, what people are actually paying for, and deciding which businesses to even go through are almost always considered as outside the purview of engineers. Engineers who look up ask questions about the business and then build with those questions, and not just technical ones, in mind.
Someone I know got advice from a mentor of his on the difference between staff engineers and principal engineers: principal engineers can be given a task and then scope and execute entirely on their own. You can just press play. While I don’t want to go against this particular individual’s view (who will remain nameless but is highly distinguished), this is not the same as looking up. Self-scoping technical tasks is not the same as understanding that task’s “why”. The ultra-skilled domain experts are still necessary (too many opinions will create a black hole) and worthy of respect; looking up, however, seems rarer. You must be technically strong to look up, but looking up is less about skill than choosing to leave the matrix to ask your own questions.
Every time I have seen a skilled engineer who looks up like this they are successful. Here are three real-life examples from friends of mine (with key identifying details ommitted).
Picking. One engineer thought long and hard about their first job out of college from a prestigious engineering university when the cloud was still in the early days. They realized that the introduction of the cloud introduced certain security challenges regarding access and became one of the first employees at a big, now-public company. When they decided to move on to their next adventure, they thought about the new security challenges from the expansion of the cloud and the cybersecurity challenges those introduced. They then became one of the first employees at another cybersecurity startup. At the first company, they learned what CIOs and CSOs care about, became better at building products in a secure way, and learned how to navigate the engineering challenges of scaling technical teams and brought that knowledge to their new company. The second company was acquired at unicorn status.
Operating. The next engineer was the first outside engineering hire at a privatized open source SaaS startup that is now a unicorn. The space was not yet settled, with other startups pushing their product based on competing open cores. The engineer asked a lot of questions about when their company’s open core would come out with its major new version because many features were stuck in limbo. They realized this had become a meme and that all of their company’s efforts would be a waste if their core was not the one that won, and that the only way to win was to put out a major new release that addressed all common feature requests. They made their case to the CEO and took on the initiative independently to push the new version out even though they were not a manager. The new version came out and the other companies in the space are now the walking dead.
Business. One last engineer was the first technical hire at a first-of-its-kind company in fintech that is now valued at near-decacorn status. They were not content to just build features. They took the time to understand the business just as well as the CEO, understand competitors, understand other companies in the space, and even talk to customers to learn what their real problems were. They came to understand what they felt were deficiencies in the business model of a whole class of fintech startups and saw an opportunity to build something new. They founded their own startup that is doing very well.
Good founders look up in all these ways, but looking up does not necessarily mean you will become a founder. Founders have a personality type that requires grit and initiative, and entails an appetite for risk and responsibility. Looking up means you have those personality traits, but not necessarily to the extent needed to become a founder on your own.
Looking up is so important because often the most important factors for success are not technical. Engineers who look up are arguably more impressive than the absolute wizards. Not because they are “better” but because they seem to go on to do the most interesting things.