8 lessons from my fourth year as a product manager

Elaine Chao
8 min readSep 14, 2020

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As for many people, my 2020 did not go quite as expected. The sudden appearance of a novel coronavirus that sparked a global pandemic cut all travel and public speaking, forced the tech industry to a surprising shift to full remote work (a move that my cats absolutely adore), and shifted what felt like a metric ton of work priorities. Large parts of the past year felt like trying to turn an oil tanker on a dime.

However, despite the challenges, my fourth year as a product manager was filled with a surprising number of growth opportunities, largely thanks to the aforementioned chaos and (on top of that) stretch assignments. I worked on multiple initiatives in parallel, some of them cutting across almost more teams than I had fingers, which had me regularly engaging with coworkers from other geographies. I worked on surfacing and addressing systemic, architecture-level problems as well as user-facing features. I coordinated closely with other product managers at Adobe across a highly complex technical stack, working as hard as I could to influence priorities. And while I flailed at some and succeeded at others, going past my comfort zone continued to give me the opportunity to grapple with larger problems with less concrete solutions.

One key difference this year was the introduction of a new key member of my network of team members: a program manager. Having a program manager almost completely dedicated to my cross-team and cross-organizational initiatives helped me begin to leverage others to scale my impact. While last year was all about executing and learning how to scale on an individual level, I actually had a dedicated collaborator this year who was independently focused on ensuring that our key partners were in lock step with us for our larger features.

As I look back on the posts I’ve made over the past four years about product management, I can almost see how the experiences of the past year — everything from organizational changes to rapidly shifting priorities to changing market pressures — have changed the types of lessons I’ve learned.

#1 Shift the conversation to people growth, not just execution path

The collective trauma of COVID-19 spurred an immediate series of conversations that just came down to: “Is everyone okay?” For myself, it initiated a series of conversations where I asked my engineering partners for an emotional temperature check, both for themselves and for the team. These conversations helped me to figure out how I could best support our engineering organization as we shifted to full remote work. (As a side note, most of my teams were already partially hybrid remote, which meant very little process change for the team for the day-to-day.)

In recent months, as the entire system equilibrated and things started to seem more “normal,” these temperature checks have begun shifting toward more people-focused conversations. What are people working on? How does this contribute to their growth? What type of engagement and visibility do they need in order to feel included and challenged? This shift from simple execution path (how do we get from A to Z) and to the people who form the organization seems like a critical shift to have made. I’m planning to explore this a bit more in the upcoming year.

#2 Change processes to fit the needs

During the course of the year, I shifted from 2.5 teams to many more, sometimes fluctuating between 4 core teams and 9 core teams I was the product manager for. This was on top of the partner engineering teams I consulted with, often giving feedback on initiatives on a regular basis.

While I could make most of the standups with my two teams during my third year as a PM, this process didn’t scale when it came to more than two teams. As a result, I ended up having to prioritize activities that would bring value to the team, including collaborating with partners in marketing and on core services and storage. I shuffled my engagement with the engineering teams to ensure that I was able to be available for the important things.

This ended up looking like:

  • a weekly, half an hour “office hours” with key technical staff from a particular initiative in order to discuss burning questions that needed my feedback (with my partner designer for that initiative)
  • a weekly 1:1 meeting with key engineering managers, directors, and architects with whom I didn’t have regular meetings already
  • an ongoing commitment to respond to Emails and comments on JIRA tickets, and scheduling a conversation if it warranted deeper discussion
  • ensuring each set of features had a clear synchronous kickoff meeting and a review of requirements and designs, and
  • attending retrospective meetings and, when possible, planning meetings for ongoing work
Two women sitting together at an office looking at the same computer. They face away from the viewer toward a window.
Delegation is largely a partnership, and I’m profoundly thankful to work with a program manager who complements my skill set.

#3 Delegation is an art, not a science

With the introduction of a program manager came more opportunities to delegate. This process of delegation, though, ended up being a long series of experiments to figure out what worked for me and for my program management partner. In this way, it was more art than science, as we didn’t have a prescribed set of work for me to pass off to her.

What I’ve found works best is if I have a clear idea of what piece of information I need to be able to make a decision, or if I have a decision that needs someone to execute on, particularly if it involves multiple teams. Then, in our regular 1:1s, I can get a quick download of where these initiatives are. By having her on the team, I’ve been able to focus less on execution and coordination, and instead invest my time in bringing unique value to the team.

#4 Try to find out core motivations

In addition to working with a large number of teams internal to my product, my teams also interface with a double handful of services, each with their own product manager. At the same time, I work with product managers across our larger organization to ensure that we have consistent experiences across multiple products. This means a lot of conversations and a lot of conflict.

The lesson I’ve learned here is to adjust all conversation to discovering and addressing the core motivations of others in the midst of these conflicts. What priorities do other teams have? Do mine align at all? Where do my initiatives fall in these priorities, and why? What do I need to do in order to change any of these priorities? By meeting the core need of both the product manager and trying to find a win-win solution for both teams, I can more effectively get solutions implemented.

#5 Summarize like your life depends on it

My value as a product manager revolves around building a narrative and ensuring that all of my partner teams understand the rationale behind a specific feature. This process helps people to link their work to an outcome that makes sense to them, regardless of whether or not the feature is user facing. Telling this story quickly and cleanly further reduces confusion.

However, the other aspect of summarizing actually comes in the context of trying to understand another person and their motivations, which can come up in any conflict. By summarizing what I hear the other person saying, I can not only bring clarity to a situation, I can also ensure that they feel heard and have an opportunity to clarify anything I might have misunderstood.

“Correct me if I’m wrong, but what I’m hearing is…” has been the catch phrase of the year, has helped me save a lot of time and confusion, and has often led to quicker alignment onto a solution.

#6 Manage risk at all times

As a product manager, this is hands down the most fluid market I’ve ever worked in, and quite possibly might ever work in. As a result, I’ve had to think of contingency plans (and contingency plans for those) and activate them at the last minute. I’ve learned to ask, “What are possible outcomes? What can we ask for? What do we need to make this succeed?”

I’m still learning about this, and there’s a huge amount of creativity that goes into devising solutions that might throw out previous constraints. It’s an exhilarating feeling to work in partnership with a leadership team that thinks broadly and creatively about the organizational challenges we have in place.

#7 Put on your own oxygen mask first

I think everyone agrees that this has been a completely crazy year from an emotional standpoint. Before I could care for others, I needed to remember that I needed to give myself some grace and tend to my own needs first before meeting the needs of others. This meant radical self-care, from extra sleep to exercise to phone and video conversations with dear friends. In times of crisis, our default should be to recognize our own signals of emotional distress and address them in healthy ways.

#8 Work your special sauce, but ask to stretch

Each product manager has their own strengths, and this was a year where I began to identify and cement some of the practices and attitudes that differentiate myself from others on my team and others in my field. However, I also know that this “cementing” runs the risk of my career being pigeonholed into a specific type of project I have the opportunity to work on. As I’m conscious of this, I’m working with my management chain to identify the next stretch assignment, something that will help me to continue this growth journey.

As with any year, there were successes and failures. Perhaps my solutions this year are a bit more elegant and the path to success slightly less circuitous in previous years. I’m thankful for a job that allows me to be imperfect. I haven’t nailed every presentation, nor have I always negotiated successfully. But every failure, every panicked day when I thought things were slipping through my fingers, ended up being a learning opportunity.

And these learnings stack up: every year that I’m in this job has been a series of lessons, both personal and professional, that I can build on and refine so that it becomes yet another tool in my product manager toolkit. I’m looking forward to what my fifth year of product management brings, knowing that it will be a road filled with excitement and grueling patches, requiring creativity, perseverance, collaboration, and joy.

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 by KOBU Agency on Unsplash

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Elaine Chao
Elaine Chao

Written by Elaine Chao

Principal Product Manager at Adobe. Also a martial arts instructor, musician, writer, volunteerism advocate. Opinions mine.

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