Greg Sherwin is a Senior Principal Engineer at Farfetch, a global technology platform for designer fashion, connecting creators, curators and consumers.
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1) To kick things off, could you tell us a little about your career background and current role?
My short, semi-humorous answer is that I am a recovering engineer. That reflects a career trajectory that expanded from a more reductionist scientific problem solving approach to one that is much more systemic, pluralistic, humanistic, and, well, messy. Instrumental to that has been learning to live with the uncertainty and complexity of the world as opposed to pretending it doesn’t exist.
In less poetic terms, I first worked at academic research labs and attended grad school in the applied sciences. A real pivot came when I caught the very first wave of the consumer Internet while working at a particle physics research center, which launched the first Web site in the US. This led to many years of leading technology and product teams at various San Francisco/Silicon Valley startups — some that grew big, many that failed. Each providing plenty of lessons.
Today I am a senior principal engineer at Farfetch, where I co-lead a core digital experimentation team at the intersection of technology, data science, emergent learning, and organizational culture.
2) What does a day in the life look like for you? Can you take us through a recent workday?
Thursday morning I joined one of our experimentation “communities of practice” rituals: an experimentation peer review session. Various product owners from across the company (located in London, Lisbon, Porto, and Shanghai) presented their insight-based hypotheses, and the community provided feedback on how we might better design their experiments and what metrics we should use to measure success.
After a brief standup with the product development team that builds our central experimentation tools, I collaborated with an engineering lead on a “Design Improvement Proposal” for a new service. We’re planning a universal service for remote feature configuration — to better manage software feature releases with more detailed activation and measurement controls.
This effort was later informed by asking detailed questions of an experienced native mobile app development team, who described how they experienced governance shortfalls with a similar service in the past.
After reviewing and commenting on a few proposals from other principal engineers and replying to a handful of Slack messages, I finished the day reviewing a research paper from AirBnB on estimating biases over a portfolio of feature changes made as the result of online controlled experiments.
3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?
My current role allowed for some flexible or remote working, but COVID-19 suddenly made working from home mandatory. Lockdown considerations aside, I’m rather adaptable and I’ve managed to establish a good routine from home. But when I first went all remote, I took fewer breaks, didn’t do enough to have lunch in a different room or chair, and poorly separated my work and home lives at the end of the day.
We humans depend on cognitive rituals that transform our role identity and focus when we switch into the different operating theaters of our work, home, and family lives. A surgeon scrubs up and follows ritualistic protocols to prepare them for life-and-death surgery, which is a very different operating theater from helping her six-year-old daughter with her homework. I’ve found it essential to acknowledge these boundaries when all of our lives are compressed in a single living space under quarantine.
Fully remote work, however, is not my ideal. I look forward to flexibly returning to the office, even if office life will have to be different from before. Despite the parade of tech companies declaring the death of the office in favor of remote-only work environments (and what Naomi Klein has called the Screen New Deal), there’s a lot to company culture, creative collaboration, serendipity, and non-verbal communication where digital-only connections fall flat.
I’ve led globally distributed Agile teams going back as early as 2008, when I ran sprints between engineering teams in Palo Alto, CA and Gurgaon, India. Even back then, in addition to weekly face-to-face video meetings, we championed a best practice of having at least one team member intermingle in person with the other office at least once every three months.
The interpersonal dynamics of a remote team change immensely once you break bread with each other, and sustaining that dynamic requires actively nourishing it. Zoom fatigue is a product of trying and failing to recreate that through a screen.
To quote a famous Peter Drucker line, “Culture eats strategy for breakfast.” Many organizations new to fully remote work are currently living off accumulated social capital that will need to be replenished. Otherwise they risk becoming farms of virtualized, transactional mercenaries with little or no distinguishable culture.
These organizations will be easy prey to competitors with stronger cultures, especially when success is defined more by learning how to collectively do things differently rather than just repeatedly doing the same things more efficiently from home.
I get the sense that some have lost patience living with the natural uncertainty of our times. Hence some businesses are trying to prematurely force acceleration to a post-COVID future in order to fabricate a false sense of security and predictability. But I fully expect this to become a classic, unsolvable Polarity Map problem for businesses: a series of opposing waves driven by management and business culture that alternately lean towards and away from remote work. We should all expect to ride out these waves in the future.
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4) What does work-life balance mean to you and how do you work to achieve that goal?
My definition of work-life balance includes an equilibrium between inhaling and exhaling. Of working on focused tasks with efficiency and making space for very human and inherently inefficient creative work. Of positively impacting my work and coworkers while actively on the job, but also creating separation so that I may seek stimulation and challenges in life more broadly. Personal development at one creates fertile ground to better nourish the other.
I’m most successful at this when I can regularly switch off work, or switch away from a work mindset, to spend time researching, learning, exploring, and otherwise living “life” — typically during evenings and weekends. But I also have a decade-long habit of daily hikes of an hour or more, ideally in nature. Having that quiet time reconnecting with the primacy and wonder of nature speaks to my soul. But it also creates space for big ideas to generate and sink in, distractions to subside, and creativity to flow.
5) In the past 12 months, have you started/stopped any routines or habits to change your life?
I’ve become more receptive to what I am feeling while simultaneously observing, and tempering, my reactive instincts. Although I started practicing this long ago, it’s only in the past 12 months that I feel I have become particularly good at it.
Out of necessity, really. Internet economics have booby-trapped our digital lives. We are immersed in minefields optimized to trigger us into autonomic responses rather than thoughtful, deliberate ones. Social media thrives on this. Much of our news feeds us an IV drip of fight-or-flight adrenaline, whether it’s COVID, Donald Trump, or what’s on the menu this month at the Internet Research Agency. We’re constantly being trolled into reacting. Giving in to that siren song only leads to mental and emotional exhaustion.
I have also been focusing more on our causes leading us more than individuals — a kind of analog to seeing the forest for the trees. While I appreciate the unique gifts individuals bring more than ever, I’ve become quite skeptical of leaderism. I see examples of it everywhere.
Human history is rife with stories of the hero’s journey, but there’s also a certain unhealthy cult worship and savior mentality that comes with that. Not to mention a perception of leadership being as much about entitlement as it is about positive social outcomes.
While it’s great to have good role models, you can’t lose the perspective that all humans are fallible. Loving the person also means loving them for their imperfections. It’s not only the most humane thing to do, it’s a more sustainable strategy in a world that’s defined ever more by relationships within interconnected networks rather than any individuals.
6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?
I know podcasts are quite the cottage industry now, and they offer a listener intimacy that’s hard to replicate digitally. And they are fun to do. But I’d be lying if I told you they don’t feel like listening to someone else’s voice mail. Not really my thing.
As for favorite books, other than the classics they tend to change faster than you can publish this interview.
But one of my favorite newsletters on technology, strategic trends, and the future with more of an arts & culture bent is Petervan’s Delicacies from Peter Vander Auwera. It flies under the radar of most newsletter readers, but it’s one of the best. It not only consistently extends my analytical left brain but also more of my right brain with how I feel and experience the future.
7) Are there any products, gadgets or apps that you can’t live without?
At the risk of sounding like a Luddite, I’m relatively gadget-free save for a semi-modern smartphone and a laptop. And don’t get me started on smart speakers and AI voice assistants. Surely Generation AA will leave me in the dust in this regard, but too often I find myself attempting multi-part exchanges or pinpoint navigation that still clumsily breaks down with voice-activated systems. Thus I have yet to identify any real convenience worth their cost in surveillance capitalism.
One of my general rules is that if you need an app to do it, you’re probably doing it wrong. OK, I’m only partially kidding there. But I believe many technologies create as many problems as they attempt to solve, and there are a lot of solutions out there in search of a real problem. The millions of available mobile apps is a manifestation of this techno-solutionist culture.
The things worth most in my life are not the things that can be efficiency hacked, optimized, wired up with vanity metrics, and interfaced with a toddler’s busy box full of controls. An appreciation for art, culture, music, love, belonging, nature, and meaning would all be on a short list of things that an AI would throw out as pointless — and yet they all make my life most worth living. These are all things that don’t get better with a hamburger menu or by unlocking gamified achievement levels.
8) If you could read an interview about work-life balance by anyone, who would that be?
The ever-curious novelist and reflective soul that is Pico Iyer. I love his appreciation for negative spaces, for deepening questions and not just finding answers, and for the yin-yang of embracing both the dark and the light. He has an amazing sense of balance and of not running away from contradiction, which is more than relevant to a discussion of work-life balance.
9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?
It’s definitely not one size fits all. The whole concept of “work-life balance” is nonsensical to a lot of people: their work is their life is their inseparable identity. Which says nothing of the billions of people where entertaining the idea is a form of privilege to begin with. Work-life balance means something different to each of us, and even that can change over time.
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