My First Career Lesson

Catherine Ye
6 min readMay 30, 2021

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Prelude

Through my career in Tech, I’m very fortunate and thankful to the opportunities of working with and learning from all shapes of talents in the industry, especially in software engineering. These experiences shaped how I work and my own career. The most valuable parts of these experiences are oftentimes the lessons I’ve learned. As time went by, I came to realize that the lessons that I’ve learnt the hard way don’t have to be like that. If someone had explained it to me earlier in my career, it would have saved me many detours. This realization has grown stronger and stronger as I’ve worked with more and more engineers over time, who are at very different phases of their career. So, here I am, starting my space on Medium, to share with you the hard and important lessons that I have learned in my journey. Hope my stories will save you some detours in yours.

Where to start?

Among all the topics that I can think of, I’ll start with a story that has had a very long-term influence on me. I consider it my first career lesson, and one of the most important ones. It took me several years to unpack this one-line comment. And now it has become one of the most frequently used pieces of advice that I share with others.

The first career lesson.

Let me first share a little bit about myself. How I was before starting a professional career.

I was a “model student” in school. I always listened to my teachers, followed the rules, gave all my best in homework and tests, even acted as a “teaching assistant” to many of my teachers since elementary school. My school experience taught me — the good work will show for themselves.

When I started my first job as a new grad at Google, I carried on this mindset. I thought as long as I worked really hard and delivered the best result, such great work would be recognized and rewarded — that was my master plan on how to build a successful career. I know. It’s laughably naive..

In my third year at Google, my promotion application was denied.. My confidence in the “master plan”, in myself, and in Google’s recognition system started to shake back then. “Why on earth do others not understand or see my great work?!” It is so frustrating when someone gives their best, yet feels that they’re not recognized or their hard work went into the void. I asked for a meeting with my Engineering Director and wanted to find out about the “why’s”. I can’t remember the details of that conversation after all this time, but I walked out of it with this one line carved into my mind -

“Good work doesn’t speak for itself.”

I was simply shocked.. What do you mean good work doesn’t speak for itself?? Good work is good work! — I didn’t know how to process these words the way they are put together. Period.

Since that incident, I’ve been searching for the answer to my million-dollar-question — “how to make good work speak?”. Turns out this is a very long path, on which I spent the next decade. I still don’t think I’m a master. But, oh boy, have I learnt about the meaning behind this seemingly very simple line.

Now that I’m on the opposite side of the table, I ended up sharing this same advice to my team a lot, with hopefully reasonable explanations and examples that can help them grok it much faster than I did.

The simplest way to think about “Good work doesn’t speak for itself” is that people need to speak for it instead — If you don’t speak for your good work, then others wouldn’t know it. The “speak for it’ part needs to be built into our “muscle memory”, just as how doing designs, coding, testing, etc. are natural parts of our day-to-day work plan — it’s much easier said than done!

How does one speak for their work then? Here are a few key questions to think through, applicable to both individual contributors and management. Take myself as an example, once I have solid answers to these questions, I’ll be able to speak for my work in various contexts, by mix-matching or prioritizing different parts of the information depending on the occasion and the audience.

Question #1: Why are you spending time solving this problem, and why NOW?
Answers to this question would explain whether you’re prioritizing and solving the right problem(s) for your team, your organization, and your company. It is important to make sure you don’t spend time on problems that don’t matter to your organization in a meaningful way.

I see everything in relative terms — priority, importance, urgency, impact — you name it. For example, in the middle of building a feature committed to external clients, an engineer decided to include a large code refactoring, because the code was hard to reason about and error-prone to make changes in it. However, because it’s a large refactoring, it ended up costing an extra 6-week in delivering this pre-committed feature to clients, which further caused the clients to scratch and rebuild their plans and timelines. While one may argue that this is good engineering work because the code quality is much better now, it is much harder to speak for this “good work” in the context of the customer relationship and trust issues it has caused to the company.

Alternatively, this engineer could have taken notes (e.g. commenting in code) on where the code suffers and a rough refactoring plan while working on this new feature. After the feature is delivered, they can bring up this issue and the refactoring proposal to their team and manager. This conversation would help the engineer engage whether this code problem is truly impactful to their team. With the team and management’s buy-in, they can explicitly budget cycles for the refactoring without impacting other commitments. The exercise of raising problems and proposals itself is part of speaking for one’s work.

Question #2: How does one convince others that their work is great?
While thinking through the first question above — why am I solving this problem? And why am I doing it now? — oftentimes we would have landed at the goals to achieve at some point in that thought process. Explicitly connecting the outcomes of one’s actual work to the pre-defined (even better pre-communicated and agreed-upon) goals is a frequently used method to articulate why the work is great.

Ideally, both the goals and the outcome of one’s work are measurable, often by metrics, e.g., business metrics, product/user metrics, system/technical metrics. Metrics help us build the most straightforward illustration and visualization of the deliverables and impact.

In some cases, it is hard to build quantitative measurements, e.g., metrics. Story telling becomes more important in these cases. Some frequently used methods include before-and-after comparison, anecdotal evidence, user testimony or stories.

Regardless of the approach, the key is to speak to the impact and outcomes.

It’s not uncommon to hear engineers speaking about their work by stating actions. Actions can be recognized by sentences that start with a verb. The actions are useful to understand project progress, for example, but they are not useful when the goal is to articulate how or why the work is great. Great work delivers great impact, thus the key is in articulating the impact.

Question #3: Who would care about your work?
In any organization, there must be someone who cares about your work (if you’re not solving a problem that someone cares about, please go back to question #1). They are your stakeholders — the set of people whom you need to communicate with on a regular basis; keep them informed on what’s happening, how things are trending, challenges encountered and how you plan to resolve them. They are the crucial set of people who can champion for you, and testify to your great work. Yes, it’s not enough for you to speak for your good work alone. You need supporters and stakeholders to speak for it as well.

Please don’t use these questions as a checklist, in the sense that — I have got the answers to each question, so I’m good. These questions are meant to help you synthesize what information is useful to share and who are the most important audience to share with. Mastering that, you’ll have a strong representation of your or your team’s great work no matter who the audience is!

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Catherine Ye
Catherine Ye

Written by Catherine Ye

A technologist, leader, engineer, and mentor. Stripe, ex-Google.

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