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Hello! What's your background and what do you do?

I am the engineering lead for the data platform team at Cimpress, a globally distributed team of 40 people. For those who hear it for the first time, Cimpress is a global leader in the mass customization industry, investing in and fully owning companies such as Vistaprint, National Pen, Pixartprinting, WIRmachenDRUCK, and many more.

My education was in Media Technology and Design, learning from a broad range of opportunities like video editing, 3D modeling, photography, web design in its early days (the decade before jQuery), and also a bit of software engineering.

Leaving university, I embraced software engineering. After a quick detour in consultancy, I was the CTO of a small startup building image recognition software for manufacturing purposes. After that, my journey at Cimpress started, about 10 years ago. Initially in manufacturing, taking on lead positions in a variety of projects to automate and improve production processes and expand Vistaprint into new geographies. In 2019, I got the opportunity to become the engineering lead of the Cimpress-wide data platform team, with the main challenge to turn an operations-centric team into an engineering team.

The team I’m part of is collaborative, innovative, and benefits from diversity. The 40 members are based in India, Czech Republic, Spain, Switzerland and the US, and come from even more diverse backgrounds - their experience, the many languages they speak, their personal and professional background, their interests, and notably their unique personalities and perspectives they bring to work every day.

How was your transition from software development to management like?

I prefer to say that I’m not a manager, but still a software engineer. But my recent commit history looks sad and tells me otherwise. (I still keep Visual Studio Code open in the background, just in case.)

I think a lot of becoming an engineering lead was organic. As the CTO of the startup in the early days of my career - yes it was tiny, but still - I was taking on various roles in parallel, from managing a remote team to project management to customer engagement to product roadmap. The opportunities at Cimpress matched my diverse skill set well, requiring technical excellence as well as a product mindset and execution focus. Over time, a completely different and new dimension was included in my responsibilities: Career management. This challenged me to look at the human challenges of projects. It pushed me to become a thought partner and coach. To whine and laugh together, and sometimes walk through some deep troubles high up in the escalation chain.

The real change in my mindset and the way I operate started about 3 years ago. I completely changed course on the information I consume and topics I learn. I left behind technical books, and started concentrating on how to make technology teams better. I learned how important it is to align teams, that is, being effective instead of efficient. I started to understand incentives of individuals and teams that lead to different priorities and perspectives on the same problem, and is often referred to as “politics”. Besides theory in the books, articles and tweets I inhaled, I had many opportunities to experiment, fail and luckily also succeed at times.

These days, I have evolved into being able to put my many thoughts into words, leading to clarity. The patterns that I repeat with my team, and often share with other leaders in the organization are technical (and drive for the right long-term investment), organizational (and are focused on a team-first approach), or align culture and mindset (helping to transform teams).

Let me dive deep into team transformations, a topic I’ve been thinking of more deeply. Team transformation to me entails a complete change of the incentives a team has, the skillset that is valued, and the leadership you take on to help everyone go on this journey. I’ve written a longer blog post a while ago that dives into the difference of operation teams vs. engineering teams. The essence of this article highlights how the very same people act differently depending on what management values. Once you know where you want to go with your team, change your behavior every day. Change how and what gets prioritized. Change what gets recognized. Change what’s valued. And live this everyday yourself. Your team will initially be puzzled, but most will follow within a few weeks.

Back to your question: As the biggest take-away, the transition to becoming an engineering lead has definitely made me get better at being able to phrase abstract thoughts into something that creates clarity for the team.

What does your day-to-day work look like, and what motivates you to do it every day?

They vary from day to day, and change in phases. I’d say I typically have a heavy few weeks before the quarter starts, thinking and discussing about the products, the quarterly and longer-term roadmaps, iterations on team collaboration, and other aspects to continue building the data platform team. So those are 2-3 meeting-heavy weeks.

Then the big relief. I see execution - delivery of something. That’s when all those architecture and trade-off discussions happen. Aligning with my passion to discuss and think about technology, often followed with an opportunity to do hands-on coding.

My coding has changed. While I initially worked on the heart of a product, I don’t have the flexibility in my schedule anymore to go deep for a couple of days on a specific issue. I’d be a blocker on a feature delivery given my other responsibilities. So I take on changes around improving security, operations, reducing error rate, or complex situations that require infrastructure changes that not everyone is familiar with.

My motivation is looking at how much can be changed in a short time, how people are motivated to deliver, and simply how much we can deliver with 40 people if we’re fully aligned.

What are the biggest challenges you've faced so far? What did you do to overcome them?

I’d say those are two areas.

First, challenging situations in career management. For example, if an employee is under-performing or not a fit for the team. I still struggle a lot. With the related talks and measurements, and simply to be anxious of the employees future. Fortunately, it's been a fairly rare situation, and everyone has found a spot where they are happy and striving. By having had respectful conversations and by giving support in the most difficult situations, I've found these relationships are stronger on the other side.

Then, it’s about transforming teams and mindset. It’s simply a clash of two or more world views. There’s no right or wrong. So it’s opinion against opinion and very little progress. And everyone gets exhausted. As previously mentioned, the books and other information I started to consume over years has helped me to identify pain points and create clarity in conflicting situations.

What has been the biggest surprise so far? Something you didn't expect?

The big differences of world view across the organization, but also within the team.

There is a good part of different views and perspectives. The one that leads to a diverse point of view, meaningful discussions, and eventually a grumpy “disagree and commit”. But there’s the other one, that still surprises me -- how a top-down strategy can be interpreted so differently and leads to repetition at every layer simply to somewhat align.

What's the best advice you've received about being a manager?

Listen more, to name a classic. I’m still struggling with it. Getting better. Thinking more how I can coach more, give more room.

However, to me, there’s no single single piece of advice. It’s being persistent. My persistence of reading daily for the past 2-3 years. About philosophy. About adopting habits. About understanding oneself better. Then about products. And eventually about what makes organizations tick.

What do you tell developers who are considering making the switch or new to the role?

I try to convince them they shouldn’t do it yet. They should remain technical for longer. Increase their influence. Invest more into product visions. Or architecture. Explore opportunities before committing to a role change. It’s for sure the hard and long path. I believe a well-earned, naturally evolving path often fits technologists better, earning and growing into a new role with different tasks, rather than doing the switch from one day to the other and being surprised by the unforeseen challenges.

Final call to action! Where can we go to learn more about you?

You can find some of my thoughts on my website at https://thoean.com, follow me on Twitter at https://twitter.com/thoean or find me on LinkedIn at https://www.linkedin.com/in/thoean/.

And if you’re interested in joining our central Cimpress Technology team, or one of our 10+ businesses, get started at https://cimpress.com/careers.

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