Etsy Lessons

During my four and a half years at Etsy, I learned a ton, from a ton of people. Honestly, the lessons are innumerable, and I’m forever indebted to this crew not just for letting me learn and grow there, but for all that they taught me. Here are just a handful:

Management and leadership

To be clear: I absolutely paraphrased all the quotes below. It’s safe to say that my memory is terrible, but that these lessons (or how I interpreted these lessons) have stuck with me and made a huge impact on my leadership style.

Teammates are forever

I learned a ton of management and leadership lessons from my manager, Jason Wong, during the years that I worked with him in his role as Senior Director of Infrastructure. I cherish those years for many reasons; Jason grew me as a leader by investing in me, giving me messy and unscoped problems to solve, allowing me to fail and learn from failing, and consistently believing in my potential. Jason is a great example of actively working against the typical grains of unconscious bias, like promoting men based on potential but women based on experience, and he instituted many processes that I’ll take to my next role to correct things like the wage gap, and rates of promotion for underrepresented groups in tech.

His management philosophy is to optimize for long-term work relationships. He treats you as a teammate not just for this job, but for the rest of your career, whether or not you work at the same company. As I said goodbye in one-on-ones with my team, I stole this page from his book. I’m here for my team, not just here at this role, but forever, supporting them and championing them in any way that I can.

Light up dark places

John Allspaw, former CTO, was famous to me before I went to Etsy. Imagine how floored I was when I arrived to interview and John bumped into me in the hallway in between meetings and said, “Lara! I’m so happy that you’re here to interview with us. We are very lucky.” How did he even know my name? How did he have any idea who this random person in the hallway was?? His attention to individuals, their stories, their families, their quirky traits, makes such an impact. I always felt like he genuinely wanted to make me feel welcomed and supported, even before I started.

John’s most impactful lesson to me was both a selfishly flattering one, and one that I’ve already used with other people. I was in between roles and managers at Etsy, trying to figure out that intersection between what work was needed and what I wanted to be doing and learning. John said to me, “you’re a light bulb. You shine brightly, and your work and your presence helps others do the same. It’s my job to move light bulbs into places that need more light. It’s not just about the work you do as an individual; it’s about who else you’re lighting up around you.” That’s the role of a good leader—to figure out where to place the light bulbs.

Rethinking diversity quota-filling

Kristina Salen, former CFO, generously mentored me once a month for about a year before Etsy started down the path to IPO. Kristina is the kind of leader who both focuses on individuals and how she can support them and give them room to grow, and actively sponsors them behind the scenes in ways you have no idea. I have no idea how I got so lucky as to get time on her calendar when I was just an engineering manager at Etsy, but I went to our one-on-ones prepared with humblingly-newbie questions for this incredibly badass woman leader. Her time spent with me is why I spend so much time talking to and mentoring women and nonbinary people who are early in their careers.

Of the many embarrassingly novice questions I brought to these meetings, I asked her once how I should handle invitations where it’s clear that they’re asking me because I’m a woman. My instincts were to be dismissive of these gigs, to be offended that I was just being asked because they’re filling a quota. She totally rocked my world view by responding, “Why would you say no? This is your opportunity to have another soapbox. This your opportunity to go and do work that helps other women. This is an opportunity to show up and blow everybody out of the water. And you need to take these opportunities so that you can continue to bring up other women behind you, too.” Mind blown, I left that meeting with an entirely different framing of the work that I could do in the world, and released the judgment and frustration I had about those invitations. It’s on those of us who have these opportunities to take them, to leverage them, to use them to grow so that we can have more opportunities to help others in the future.

Feeling shaky as a leader

I’ve had the privilege of knowing Vanessa Hurst, an Engineering Director at Etsy, since before she came to Etsy. (She’s a badass, look her up.) There was a time when I was feeling particularly shaky, unleader-like, unsure of myself, unsure how to move forward. She told me, “you are like a bridge. You’re solid, and stable, and capable. But even the strongest bridges need flexibility to be strong. They need to waver and move to do their job.” This idea of being something that still needs to waver a bit, to shake a bit, in order to not fully break, has stuck with me ever since. I’ve repeated this to other leaders who were in need of reassurance when they felt like they shouldn’t feel anything but static and firm.

Tactics

Management and leadership philosophies are cool and all, but they’re nothing without tactics to implement and live them. Here are some of the ones that both blew my mind, and proved to be super effective as I tried them out over time.

When you disagree with someone

I learned a number of things from observing Andrew Morrison, a senior staff engineer at Etsy, navigate really sticky technical arguments with others. I can’t remember where I first saw him use this tactic with someone who held an opposing viewpoint: he’ll say, “On a scale of 1 to 10, where 10 is caring really strongly, and 1 is barely caring, I’m like a 4 on doing it this way. What’s your number?” Sharing with a number how much you do or don’t care about a direction makes it easy to pull back and realize that you probably don’t need to spend a lot more time arguing. Or, if you both care deeply, switching to numbers quickly diffuses it from a heated discussion, and you can often move the conversation to a different venue or find another way to navigate it. I’ve used this countless times over the years and it REALLY helps.

Help someone grok your new idea

I can’t remember which engineering manager first said this to me—if you’re out there, tell me. :) “The first one to draw a visual for everyone, wins.” Though this is half-sarcastic, it’s absolutely true that if you can draw a diagram or another visual as you’re trying to communicate something is a really helpful exercise in sharing information with others. I’ve seen this work for underscoring how a reorg would help, how we should implement caching differently, how you prioritize work, and so many other critical things you’d want to communicate to someone else.

Rules without rules

Paloma Medina, the person who started the Learning and Development department at Etsy, taught me a million things while we worked together. I could probably write an entire separate blog post about the things she taught me about enacting change in an organization, handling difficult conversations, giving feedback, coaching others, and brain science. But one of the earliest tactics I learned from her was about how things worked in the anarchist camp she used to live in. She taught me that even in anarchist communities, there’s clear order. There may not be “rules”, but everyone knows what’s cool and what’s not. She helped us implement some of the anarchist meeting facilitation methods in our Engineering Manager Roundtable a long time ago, and it changed my life.

The tension between transparency and chaos

Mike Brittain, current interim CTO, was my first manager at Etsy. Like all the other people mentioned in this post, I learned a ton from him over the years, but one of my biggest takeaways was something he hasn’t explicitly talked about, but demonstrates consistently in all of his emails and words at big meetings. Watching him in this interm CTO role is like a masterclass in what it looks like to lead with as much transparency as you can legally and safely can without causing chaos. I gotta tell you—it is NOT EASY finding the balance between keeping it real and keeping people safe. He’s one of the bravest people I know, even while he’s under tremendous pressure. In even the toughest emails he’s had to send, he does three things:

  1. Communicates, succinctly, what his core message or ask is. He avoids using business jargon. He gives timelines. He says what he means and doesn’t faff about. Sometimes it’s bad news, or representing the business line, or making a difficult request. But he is always clear about it.
  2. Acknowledges how you might be feeling in hearing this message. So many people, in hearing bad news, just want SOMEONE in leadership to acknowledge how hard it feels for the recipient. Mike consistently does this.
  3. Shares his own understanding, thoughts, or feelings about the message. He does this with aplomb and never undermines the message. He might acknowledge that it’s hard, or give his own impression or reinterpretation if it’s warranted or otherwise unclear. He takes whatever the business line is and turns it into something that he owns, with his own voice and words.

I learned from Mike how to use humane words and not business lingo, how to avoid sounding like a bureaucratic asshole as much as you can (and that is TOUGH to do once you’ve hit director), and at the same time acknowledge how we’re all feeling and how you get it.

Career direction

Like Kristina, former CEO Chad Dickerson gave me the gift of monthly mentorship for a period before they both became swamped with pre-IPO work. One of my (again, embarrassingly novice) questions to him during this time was - how do you know what your next role should look like? I was feeling unclear in where my career path was taking me, and it felt like I should know what I was aiming for instead. How do other people know what to build toward, I asked.

Chad told me that as you grow in leadership, what you do next will become clearer closer and closer to when it happens. He reassured me that you don’t need a ton of clarity about the future way in advance. That’s just not how it works, especially as you advance in your career. You should be putting in the hard work, trying new stuff out, and of course it’s still a good idea to have goals and dreams - but he reassured me to release this anxiety of not having a clear direction. He compared it to when he realized he might become CEO of Etsy when he was still the CTO; when you get really close to the next thing, it’ll become increasingly obvious and clear, often right before you shift gears.

I’m so thankful for my years at Etsy, the amazing people here, and all that I’ve learned from them. I’m excited to be one of many to go out and make the world more like Etsy.

Lara Callender Hogan

I'm a VP of Engineering and the author of Designing for Performance, Building a device lab, and Demystifying Public Speaking. Follow me on Twitter, read my blog.