The (Initially) Reluctant Manager

It’s hard to believe, but today is officially my 4th anniversary working at MailChimp HQ here in Atlanta. Before that, I spent a year working remote, so I’ve actually been with the company for over 5 years now. In that time, MailChimp has more than septupled in size, we’ve been through 3 major redesigns, and we just moved into a rad new office at Ponce City Market. Until recently though, my primary responsibilities remained the same. I’ve had several management opportunities over the years, but always slipped back into writing code and looking for ways that I could improve the UX of our product myself. That all changed in November when I finally accepted a formal leadership role, managing my fellow front-end developers. It wasn’t an easy transition but I’m finally starting to feel good about calling myself a manager.

Let go of what you know

My initial approach to management was totally backwards. My goal was to spend as little time as possible making sure everyone had things to work on so that I could get back to what I did best. I probably spent about 6% of my time communicating with my teammates and the other 94% building, tweaking and troubleshooting. When it came time to delegate tasks, I found myself trying to wrap my head around everything that needed to be done as if I was going to handle it myself. All of my direct reports are brilliant front-enders who are amazing to work with. It wasn’t that I didn’t trust them to figure it out themselves, I was just reluctant to hand over responsibility.

It’s not about the tasks, it’s about your team

About a month or two in, one of the devs told me in a 1-on-1 meeting that the things he felt like he would normally get to work on were getting passed to other people and that he wasn’t getting assigned enough to do. “I never really found myself in this position with (our previous manager)”, he said. That conversation was a wake-up call that my approach to management was making me a terrible boss.

Fortunately, MailChimp started an internal training program for new managers to teach professional communication and leadership skills. In 8 half-day classes spread out over a month, I got a crash course in topics like mentoring, coaching, delegation, collaboration and influence. Between those lessons, books like Michael Lopp’s Managing Humans and following folks like Cap Watkins who took a similar career path, I started to see that my position wasn’t unique.

Instead of trying to keep people busy, I now strive to keep them excited about their work. Rather then assigning things to the person who knows a part of the app the best, I want to encourage that person to share their knowledge. The less of the legwork I do when assigning a task, the more they know I’m relying on them. People who feel both valued and relied on, do better work.

Management is an art and a craft

myteamWhile I still try to stay in the code, I’ve embraced the fact that serving the team is my number one responsibility. I finally spend more time guiding work than doing it myself and I still feel like I could devote more time to my team. In Outliers, Malcolm Gladwell talks about the “10,000-Hour Rule”, that it takes roughly 10,000 hours of practice to achieve mastery in a field. I might be a master at front-end development by now but management is a completely different field. If I’m working 40 hours a week and only spending 50% of my time managing, it’ll take 10 years to become a truly successful manager and leader. I’d definitely prefer to get there faster.

Managing people isn’t for everyone. It feels good to be good at something and if you love doing that thing, you can still progress in your career without managing others. If you’re getting nudged toward management though, it’s probably coming from someone who thinks you’re capable of it. If that’s the case, don’t hold off as long as I did. Being a manager is humbling, it’s rewarding, it’s terrifying but it’s a challenge that I’ve really enjoyed taking on.


  1. Jason,

    Thanks for opening up and sharing your thoughts about this. I think many people in our industry struggle with this. So many of us like the work we do that it is very difficult to think about giving up a big portion of that to step out of our comfort zone to lead others. It is so good to see the process in your life and for you to take the time to share that is going to be valuable to others. Thanks.


    • Thanks for the encouragement, Jeff. I was almost as reluctant to write about being a manager as I was about being one. I doubt many of us start out our careers aspiring to manage others but we all want a boss that understands what we do. Something has to give.

  2. Are you writing a book? The name of the book is “the all of beautiful web design”, I am your reader, I am from China. See the url in this book. But the website does not have any blog about web design.

    • Hello Zoey, I believe the 3rd edition of The Principles of Beautiful Web Design was recently translated into Chinese. If that’s what you’re reading, thanks! I wrote the 1st edition of The Principles of Beautiful Web Design way back in 2007. I was doing a lot more designing and writing about web design here on my blog then. These days I focus primarily on product design and lead the UX Dev team at a company called MailChimp. When I do post here on my blog, it’ll probably be more about front-end development, UX and managing teams. Sorry if that’s disappointing.

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