Parting Lessons in Leadership

Parting Lessons in Leadership

Lessons in Leadership

Yesterday was my last day at Etsy. I’m leaving after over 1.5 years of leading the Maker Innovation/Pattern/Multichannel Services engineering team(s) through initial launch in April, 2016, through Pattern V2 launch in May, 2017 and through the dramatic organizational changes since. This is my attempt to document my time there and the lessons I’ve learned as a leader. Please note that the list is obviously incomplete, but are the concepts that jump out at me at this point in time in these current circumstances.


To set the stage, I’ll start by saying that Etsy was like no other place I’d ever worked, in remarkably good and surprising ways. This place had culture, personality, a strong mission and consistent, top-down values that were the real thing and not just corporate kowtowing. For a while, it was a an idyllic place where people loved coming to work and building things that had measurable, positive impact in the world; all while doing this with other smart people who held similar values. Perhaps in some way the idealism embodied in the corporate culture led to some level of blindness to the demands of public company overlords: shareholders and their rapacious appetite for infinite growth. But, that’s a topic for another post.


Though the following “lessons” aren’t things that I learned exclusively at Etsy, they’re principles that I think are universal to great leadership, and that were reinforced by my time there.

  1. You’re nothing without your people and that means it’s imperative that you take a personal interest and direct hand in developing their careers and helping them achieve their goals. Take the time to understand their motivations, aspirations and hurdles as input to help them navigate the arc of their careers. It is your job to provide this clarity. Their success is one of the true, key proxies of your own.

  2. Establish a credible & cohesive vision supported by strong, unambiguous communication and implemented with decisive action over discrete time horizons. Consistently missing any of these attributes fundamentally, and publicly, undermines your fitness as a leader. You may not have all the answers, but you have the visibility and position to inspire confidence or, failing this, to summon mediocrity and a slow death.

  3. Being a leader doesn’t mean you have all the answers—in fact you rarely do. Leadership means having the requisite humility, confidence and objectivity to recognize the individuals who do, and to marshal them together to address the task at hand. This is where the adage “first-rate managers hire first-rate employees; second-rate managers hire third-rate employees” strikes the greatest chord.

  4. It is better to be honest & direct than coddling. Often leaders are held back by a fear of delivering critical information, even if it’s what’s objectively necessary to drive needed change, because they are afraid of hurting feelings or harming their own positions. Treat everyone with the respect they deserve by being forthright in your dealings and they will (in most cases) do the same. Coddling only reinforces uneven power dynamics, learned helplessness and blind, ignorant followership.

  5. Establish a culture of empathy, collaboration and openness. Live and breathe the concepts of [mindful communication]({< ref “/posts/2017-09-29-Etsys-Charter-of-Mindful-Communication” >}).

  6. Don’t make things political. Rewarding unchallenging followers for loyalty and tenure is a recipe for bleeding talent and for creating a toxic growth environment. Most smart people I know won’t tolerate that bullshit (because they know it’s a strong signal of leadership incompetence) and would just rather take their skills someplace else where they can focus on the work and get rewarded on their merits.

  7. Communicate transparently, honestly, and with appropriate urgency—don’t just get ahead of the message, be the message. This overlaps with point two, but effective communication skills are such an important part of leadership, it’s worth mentioning more than once. Too many times I’ve seen weak leaders shine a spotlight on their own incompetence through incoherent messaging.

End Matter

There are obviously many more important lessons about leadership and management—these are just the things that stand out to me as I leave Etsy behind me. It’s been an amazing ride and I expect to learn more in my next chapter.