9 lessons from my 5th year of product management

7 min readAug 30, 2021

I wasn’t quite sure the purpose of writing about my journey in product management when I first started with my six-month reflection. As I write my sixth post at the five-year mark, I realize that I had unintentionally started a series of time capsules that served as a journey that others could follow. In the past year, I’ve referenced these posts more than any of the other resources I’ve written about product management, as aspiring or new product managers inquired about the process I went through in my transition from engineering to product. And while I generalize and process specific situations into broader lessons, these posts still serve as a reminder to myself of both the highs and lows of those particular years. (I’ve listed them at the bottom of this post for easy reference.)

This year was my first full year under a new manager, my first full year working with teams abroad, my first full year working virtually, and my first full year of mentoring others. The entire year was in the backdrop of an incredibly fluid world, with the ebbs and flows of a global pandemic and massive shifts in the American political landscape.

If my fourth year’s theme was growth, my fifth year’s theme was endurance. While I had a couple of surprise initiatives during the year, the vast majority of it was pushing toward a larger goal in partnership with some centralized teams. This initiative has taxed me in a way that other projects with fewer dependencies haven’t.

It’s hard to think of growth when you’re in the middle of chaos. However, the martial way relies on growing with intention. That means consistently asking: what do I need to practice? What do I need to learn? Where are my gap areas? Do I know what I don’t know? What foundation do I need today in order to push toward my goals for tomorrow? What can I ask for that will help me toward my goals? In which direction do I want to grow? I had a surprising number of opportunities this year to push the conversation in this direction, and have some new paths open to me as a result.

#1 Listen to your body and choose rest

After a full year of working remotely and split between local and international teams, I found myself shifting into a slightly slower pace of life. I’ve spent a lot of my life working hard and playing hard, but now I’m spending more time just making life work around me instead of always pushing hard toward some goal.

Waking up a couple of hours ahead of my natural body clock and making critical decisions early in the morning, followed by hours of back to back video conferences and sandwiching Emails in the few minutes in between, leads to a different type of exhaustion than I had while making a long commute into the office. As a result, I’ve found myself spending more time on the basics in order to maximize my energy. I’m okay with temporarily putting aside some of my personal pursuits in order to optimize for the long haul.

It’s not to say I haven’t done anything creative — I’ve edited music videos, written music, and written words — but I don’t drive myself as hard toward deadlines and give myself plenty of wiggle room to simply allow those to be restful activities instead of must-do deadlines that add stress to my plate.

#2 Say yes to opportunities to stretch you

At the same time, I’ve been saying “yes” opportunities that are slightly outside of my comfort zone. One of the things I did this year was to apply to internal opportunities for mentoring and growth, including the Adobe Women’s Executive Shadow Program and a separate training program for Asian American leaders. Both of these required additional time on top of an already packed schedule, but saying “yes” meant investing in myself and in my career.

As a result, I was able to spend an extraordinary amount of time being mentored by someone who worked in a very different business role, reflecting on my role and my opportunities with an outsider’s lens. I also got some keen insight into how I can better position myself for future success.

#3 Own your failures

As a recovering perfectionist, one of the hardest things to deal with are your own failures. I’ve had plenty of missteps this year where I’ve had to eat crow and accept the fact that I messed up, sometimes badly. I’m thankful for the grace my colleagues extend to me on a regular basis. But the responsibility I have after making a mistake is to reflect and commit to growth instead of avoiding the discomfort and the potential to make the same mistake again or, even worse, perpetuating a broken system instead of trying to make it better.

#4 Hold space for imperfection

When you’re surrounded by high-performing people, sometimes what needs to be done is a reassurance that “not your best” is more than enough. In the midst of India’s Delta wave, what our colleagues needed most was the reassurance that they would not be perceived poorly for attending their family before their work duties. As a leader, I took it upon myself to frequently tell our team that it was expected that family came first, and to work with less-affected colleagues in other regions to lighten the load on the team.

#5 Sometimes, the problem isn’t yours to solve

I’ve had to fight the temptation to own every problem that comes my way. Working with partner teams often means influencing without having any direct ownership, which is incredibly hard when you’re just used to having full responsibility for things.

Sometimes, the best you can do is help others understand where you’re coming from and sell them on solving your problem for you. Sometimes, all a partner team needs to know is what matters to you, so that they can choose to be a part of a solution. And sometimes, you can support others in their goals without owning the result.

#6 Help others find their special sauce

One of the amazing things about product management is that there are many different ways to be successful as a PM. I’ve encouraged others to find out what their “special sauce” is as an individual and to leverage that with their team. By valuing each person’s contribution, we’re able to hold space for people of many different modalities and perspectives to work together toward business success.

#7 When possible, quantify the risk

Communication of risks, particularly when it comes to big projects, is sometimes more of an art than a science. However, one of the things that I learned is that sometimes, the tradeoffs are best communicated when you communicate things in hard numbers. What are the tradeoffs? What do we get or what do we lose? By quantifying the risk, you help the people around you align around what the team needs to do.

I’m still working on doing this consistently, but it’s something I’m learning to leverage as a part of my communication patterns, particularly to executives.

#8 Ask for what you want

I grew up with very clear instructions to keep my head down and accept whatever life threw at me. If I worked hard, my parents claimed, good things would come. As a result, I didn’t learn how to ask for what I wanted in order to help my career growth or help me increase my impact, until much later in life.

I’ve been practicing this skill over this past year, advocating for a new team member to take over some of my responsibilities in a different geo, asking for opportunities to practice skills that will help me grow into the next level of responsibility, and seeking advice and input into my own growth as a product manager. As a result, others have known more clearly how to assist me in being successful and have worked to open up doors for me.

#9 Build up others’ reputations

One of the great pleasures I take is helping others to understand the value our colleagues bring to the table. Whether it’s highlighting work that a partner team is doing or helping one squad understand what another is doing on my own team, I’ve explicitly practiced the art of highlighting the strengths of the people I work with to others. It’s part of the process of creating a work environment where everyone’s contribution is appreciated.

Five years is a strange interval; it feels both an eternity and yet a brief drop in the ocean of time. If I think about these five years against the backdrop of decades spent on other activities, like martial arts and music, it seems like a flash in the pan. And yet, five years is long enough to feel like you’re beginning to master a skill.

Photo of the ocean from near the surface. A clear sky is overhead, and the water ripples in the foreground.

The best way to describe how I’m feeling right now is how I felt immediately after getting my first degree black belt. For most people outside martial arts, a black belt is the pinnacle of martial arts achievement. But for people inside martial arts, a first degree black belt means that you’ve managed to learn the basics well enough to be safe while on the mat, no matter what happens. It says very little about how much you’ve mastered any other skill. As a result, a first degree black belt enters into the world with a very keen understanding of what they don’t know, and have learned a process through which they can pursue a lifetime of self-driven growth.

And so here I find myself, at five years of product management, realizing that I have so much more to learn, but that the journey continues every year I continue along this path.

Here’s to five years down.

But there’s much more to come.

Elaine is a senior product manager at Adobe. You can find her on Twitter at @elainecchao. All statements in this essay are her own and do not reflect the opinions of her employer.

Photo: “Ocean Ripple” by Matt Hardy on Unsplash