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Before you begin, define your legacy
#managing_yourself Begin with the end in mind
In 2005, I was a Director of Engineering at a 50-person start-up called Movaris - a title I fought hard to achieve. In a previous role at Saba, I found myself frustrated that I was deemed too young to be a Director there. My manager told me that I was talented and was producing more than other Directors were, but promoting me would raise eyebrows because I was so young. I was frustrated that age was somehow correlated to title and not merit so becoming a “Director” was something I wanted to achieve. Yet, when the milestone came and went, I asked myself an uncomfortable question: what have I accomplished?
It is tempting to measure your progress by the salary you earn, the titles you have, or the companies that employ you. I argue that real progression in your career is defined by what you do. Did you do something concrete, not subject to debate, and something you can be proud of? I couldn’t answer that, so I re-read the 7 Habit of Highly Effective People, searching for answers then.
One of the insights I gleaned from the book was habit 2: “Begin with the end in mind.” But how do you apply this habit in practice when it comes to managing your multi-decade career?
As a younger person, it was hard for me to imagine what I would accomplish when I was long retired 30 years from then. However, it struck me that I could potentially shorten the horizon by defining the beginning and ends by my time at a company. What if I defined my legacy before I started my next role? By understanding the challenges of the business and the position I was to assume before I start, and envisioning what my LinkedIn update (or resume back then) would read when I changed roles, I would have a template for how I would conduct myself at work that I hoped would define my time at the company.
I still wouldn’t necessarily know how my career will end, but if I accomplished my wildly important ambitions in every role I assumed from that day on, I would always be able to have an answer to the question of what I’ve accomplished.
It took me a while to understand this but your salary, your titles, and the companies you work for will come and go, but what you accomplish is in the history books. How history is defined is subject to much debate, but the only voice that matters in this conversation is your own. That career conversation you have with your manager, while meaningful at the moment, is not nearly as important as the career conversation you have with yourself as the CEO of you.
When I look back at my career, this framework has helped me in the following ways:
1. It provided purpose and focus on a daily, weekly, monthly, and annual basis regarding why I worked - both in terms of myself and the company.
2. It gave my teams a broad framework for understanding the motivations behind my decisions, even if they disagreed with them.
3. It gave me a framework for when to turn down new opportunities and when to decide that I needed a new challenge.
After 15 years of applying this principle with good results, I am convinced it works and I intend to use this methodology until the end - perhaps another 15 years or however my time as a technologist may end. I wanted to share this tip with you using my Upwork adventure as an example.
The Upwork Story
Upwork is one of the largest contractor marketplaces on the Internet that caters to professional work. Much like eBay, where I spent two separate stints, in Upwork, I saw a platform that allowed people to make a living. By working at Upwork, I leverage my work to create more work for people around the globe! My thought when I joined Upwork was that if I did well here, and the company did well, it would make a difference to other people in the world. My work would matter. As you can imagine, when I received the offer to join, I was elated.
Critically, the opportunity presented several unique challenges that I understood when I signed:
1. The engineering team was fragmented because it had only been one year since oDesk and Elance joined to form the new company - Upwork.
2. The combined companies each had aspired for over a decade to go public.
3. The combined companies were scrappy and fast but ultimately struggled with the expectations of providing consistent delivery and stability that customers expect from a company that managed over $1B in transaction volume.
These are hairy challenges that Upwork would want solutions led by their head of engineering. They also formed a template for me to define my legacy before I started work.
After my first day at Upwork, I defined three goals for myself that I hoped would define my time:
1. Unify the engineering organization.
2. Help the company go public.
3. Build a world-class team.
Unify the engineering organization
When two companies merge into one company with one platform, you hope that you get the best of both teams. In practice, it is much like combining two different salads in one large bowl. There were many pleasant surprises when the two teams mixed, but as one would expect, challenges were also present when the makeup of two teams were suddenly combined. Some roles become extraneous. The strengths of some individuals required them to be repositioned into new roles while others needed to be given more responsibility and be stretched. The gaps in these combined teams needed to be filled with outside hires who were neither former oDesk or former Elance employees, but like me, were Upwork-native hires.
It took more than a year to unify the team so that the notion of who was hired from oDesk and who was hired from Elance faded into a distant memory. Along the way, I made difficult and often unpopular decisions but the result was one engineering organization focused on the mission of the company.
In time, when I canvass the cafeteria, I no longer saw cliques of groups who sat next to each other because of which company they came from. Instead, I see healthy interactions between colleagues invested in the unified mission of the company. Being one team is critical. In the book Team of Teams, Gen. Stanley McChrystal describes the importance of trust in the composition of teams. Trust would have been impossible to foster in an environment where individuals felt they were part of one of two separate teams. Ultimately, unifying the team became a critical cornerstone to what we are able to accomplish.
Help the company go public
From the start, we faced existential challenges as a team. Our uptime when I started, may have been acceptable if we were still doing $500M in volume but they were no longer acceptable for a unified company facilitating over $1B in transaction volume. The challenges were in some ways magnified by the mission of the company. If we were a photosharing site, people may not get the immediate satisfaction of sharing their pictures. However, we were a marketplace and if the site were down two people who could have helped each other at that moment in time may never meet. Those relationships, and the opportunity cost, were costly to our customers and the company since much of the business happens through recurring relationships and continuous spend.
In the midst of our organizational turnaround in 2016, which involved massive investments in R&D, training, and process improvement engineering we also found ourselves, like many other sites, at war defending cyberattacks. The breaches that occurred that year leaked nearly a trillion username and passwords on the Internet which inspired legions of account takeover attacks from criminal organizations around the world who blindly tried usernames and passwords against everyone. We didn’t do anything wrong, but the secular security trend meant that Upwork and major websites across the Internet were forced to fight.
With so many challenges happening at once, I was tempted to reframe my goal to "help the company go public - without getting fired first." Luckily, as one team operating in unison, we eventually prevailed. It wasn't until the third year on the job that I was able to spend a national holiday undisrupted by some sort of site event. It was the sweetest Christmas ever.
By 2018, the site had managed to gain a full three 9s in availability and the business was growing quickly. Despite the rocky years before, the company went public and I managed not to get fired despite several of my self-reviews in my performance review package urging the CEO to do so.
When the company went public, I had been up all night with several dozen engineers and engineering executives monitoring the site for potential issues. Together we were stationed at our headquarters in a war room. I didn’t even know when we started trading because we were so focused on keeping the site up. When it was over, and things settled. Matt McDonald, my long time consigliere across three adventures and now current head of engineering at Upwork, said to me - I’m sorry you couldn’t be in New York.
I wasn’t. Perhaps in a moment of bravado, I told him there will be another time when I will get to see another company ring the bell in person but that time wasn’t now. Truthfully, I’d spent 4 years hoping we would get here one day as a company. There was no place else I wanted to be.
Later in the day, exhausted, and rambling I gave a toast:
Hi guys. What an amazing day! I want you to know that I’m so happy to be here with you right now. You know, an IPO is so rare that most people may never experience this so my one pro tip is for you to take a moment and really soak this in. Hug your coworker, shake hands, do the high fives. I walked up to I* and K* today and shook their hands to congratulate them and they looked at me like a weirdo. I’ve gotten precisely zero hugs so far. Really try to lock this moment in your mind. When things get bumpy, I hope you can draw strength from this moment and remember what we stand for, but know that the best is yet to come.
I want to thank our customers. When our customers do well, we do well.
I want to thank those colleagues including our distributed team who’ve been with us for years through good times and bad. Your faith in the business never waivered, so thank you.
I want to directly thank all of you for your hard work these last few years. The road is hard but the victory is sweet!
Cheers to you!
Build a world-class team
I probably should have thought this one through before I set this as my goal. What is a world-class team? I’d been on some legendary teams in the past, but I don’t think they considered themselves world-class at the time. Really, do folks at Facebook, Amazon, Netflix, and Google walk around telling people - we’re world-class? It’s probably an unachievable goal but one worth striving for.
After the IPO, I realized I needed to change gears and shift my focus inward. So much of our engineering culture, was driven top-down. Perhaps in the early years, it was a necessity. In times of struggle, you need someone decisive to make the calls, even if they were often wrong but one person, or even a group of very smart people, can’t possibly out-think hundreds of people. I realized that the time had come for me to double-down on my belief to empower individuals across the organization.
In my final year, I:
Created a bottoms-up proposal process so that any person in the organization could propose a change and have some guarantees that the engineering leadership team would review the proposal thoughtfully.
Solicited weekly feedback on what issues individuals were facing and held my leadership team accountable by calling out every issue reported directly to me. These included broken builds and even individuals not responding to each other’s tickets.
Solicited weekly feedback on who did good work that week and wrote a weekly memo recognizing those heroes. I was often surprised by how much good work was done every day. Writing that memo was the highlight of my week, every week.
Cleared my calendar and opened up office hours to the entire organization. For my co-workers that seemed to struggle, I coached them privately regardless of organization or level.
As time went on, I realized that slowly, I had less and less to do as decision-making became more distributed. From time to time, I would sense trouble and try to assist in taking over a stray team here and there. I felt useful in those moments, but with each passing day, my relevance seemed to fade. I attended operations meetings from time to time, but more often than not, I worried that my opinions were being over-indexed. It’s easy to be lulled into a sense of comfort. You work with people you like, you’re part of something meaningful, and your colleagues respect you - what more could one ask for?
For me, I wanted my work to matter and I was at a loss for what I could do next. It felt that I could leave tomorrow and things would be fine. In my 20 years in the industry, I’ve resigned every position only once transitioning into a new role with something lined up. Until Upwork, I had never written a good-bye note. However, such formalities are unavoidable when you’re the head of engineering. I spent days responding to notes wishing me well, but eventually, they stopped and life moved on.
It had been days since I had written an email leading to my last day, but my final note was my weekly recognition email. I wouldn’t have ended my last communication with the company in any other way - by taking the time to recognize my colleagues. My quiet ending at the company, only made it more apparent to me that it was time to move on. Perhaps the definition of a world-class team I was seeking all along was whether or not my presence on the team even mattered. Would the team perform inspiring work, when my time was a distant memory? I would never know unless I left.
Define your legacy today
While our performance is constantly being judged in the workplace, in the end, the only performance review that counts is the one you give yourself. There is a fun scene at the conclusion of the Back to the Future trilogy, where Doc Brown explains: “Your future is whatever you make it. So make it a good one!”
A subtle but important observation I’ve long made about those films is that all of the action happens in the present, because only in the present can you change your future. Every plot point in the Back to the Future series happened because something in the present changed the future. Do you want your future defined by haphazard chance or will you choose to define your future today?